I drafted a college entrance exam for my kid — not that I expected him to use it, more as a writing sample to inspire him.

“Inspire” is too strong of a word. “Get him off his ass” is perhaps more appropriate.

He’s finished his essays (which bear no resemblance to what I wrote). I thought I’d share this with you, just in case you can make some use of it.

Enjoy.

People have been questioning my judgment. Since I started applying to universities, it’s happening more and more. As I’ve begun to work on my applications and Personal Statement specifically, it’s happening every day.

Specifically, they’re questioning whether my choice of a career in computer science and engineering still makes sense in a world shaped by artificial intelligence.

The question usually comes with a sly smile: “Is Computer Science even going to be a real career by the time you graduate?” “Aren’t the computers pretty much thinking for themselves already?”

After several years competing in a national-level robotics league, I’m convinced that this question comes from a misunderstanding of what engineering actually is. It’s only without the hands-on experience I’ve gained from working in the field that one can arrive at the belief that machines can replace human creativity.

As a freshman, I thought engineering was mostly about building mechanisms and writing code. Over time, I learned that the hardest problems were rarely technical alone. They were human.

The design meetings for our robotics team were never linear or automated. AI tools could generate CAD sketches or analyze performance, but they could not replicate the collaborative process of deciding which problems were worth solving.

On competition days, unexpected challenges arose and had to be solved without consulting the computer. Parts became unavailable days or hours before deadlines. Robots that labored in the lab suddenly failed on the field.

As I took on more leadership responsibility, I organized brainstorming sessions, mediated design disagreements, and worked to ensure every teammate felt ownership of the robot. I learned that leadership is not about having the answers. It is about creating space for others to ask the right questions.

So now, when people question whether computer science is a wise choice, I have feel pretty good about my answer: Technology does not replace the need for human thinking. It raises the bar for it.

Maybe the right question isn’t whether computers can think for themselves. The question is, “Can I?”

This just in: The changes you want to make to your career do not have to be executed all together in one catastrophic irreversible cataclysmic fallen swoop.

Pick the job title you want for your next role and just “try it on for fit” at the top of your next resume. My new client delightfully supplied me with that phrase the other day and I love it.

Try it before you buy it. Walk into a meeting and say “I’m focusing on purpose-driven companies in my research.” If someone in the meeting says “Oh, are you?! Since when?” (which they will NOT) you can simply say “Since now, bitch. I’m trying it on for fit!’

Maybe that’s a bit much. But know that you are the decider about making changes like this for yourself. There is no gatekeeper or approver. You do not actually need to “submit changes” to LinkedIn first in order for them to be official.

If you’re looking to change direction in your career, it’s essential that your resumé and profile have the new job title at the very top. The title of your resumé needs to say the job you want, and you need to give the impression that you’re doing that job in your most current position as well.

Make the change to the title right now. Try it on for fit. Hit reply to this email and send it to me, we can start working on the rest together.

You’ve already got the impostor syndrome. It’s going to come in handy!

These are my two coaching ideas on the tip of my tongue right now.

For job seekers: Ask for the Job

The emphasis here is on job - not ask.

In your introductory email, you must be able to say “I AM A [insert job title here]“ The job title must exactly match the job role being advertised.

Do not fudge it. If the position is UI designer, say “I AM A UI DESIGNER” not graphic designer or UI/UX designer. Please do not ask the recruiter or hiring manager to select you over someone who introduces themselves with a title matching exactly.

When it comes time to interview, introduce yourself the exact same way. Say “I AM A SOCIAL MEDIA MARKETING MANAGER” or whatever the exact job title is. The most recent job title on your resumé should exactly match this title. You should fudge this, if necessary.

Otherwise you are asking the recruiter or hiring manager to select you over someone whose most recent job was the same as the role they’re hiring for.

And why should they do that?

For salespeople: Ask for the sale

Salespeople often spend so much time scrounging and hunting for business that they forget that the customers they are looking for are also looking for them, as well. These customers want to buy — they want you to be successful at your job of making the sale.

Clients will help you stop guessing and clear the remaining obstacles if you ask them for their help. Ask them sincerely, and you’ll often learn what it will take to get the job done. You might also learn that a deal that you thought was close just isn’t going to happen, and that can be valuable as well.

Here are some words I’ve used for this recently:

“Could you let me know specifically a price that would enable you to move forward with this immediately?

“If we were able to offer this at $X, would you be able to get us a purchase order by [DATE Y]?”

It’s not the colleagues you fear disappointing, or their hitched disappointments that would cut at you like a thousand paper cuts — each with a bit of citrus diplomatically applied.

It’s not the haters — your mortal enemies, nemeses since high school, sworn with the charge to undermine, obstruct, and interfere with your intent.

The haters all suck, there’s no doubt, with every cursed breath they draw in. And the disappointed all blow, it is certain, with every putrid breath they spit out.

I’m not here today to apologize for them.

Worse than worst

Because you — dear reader, you are much, much worse. And so am I. Like, ugh.

Why?

We shall forgive our imaginary enemies and the illusory disappointed for their chimerical grievances. Because, you know, they’re not fucking real!

We are real. Actually, we exist in the real world, which provides us with things like proof, evidence, corroboration, facts, friends, mentors, coaches, and therapists. I

And yet, we fill our own filthy, fetid minds with toxic ideas about ourselves— our limitations, our failings, deficiencies, and shortcomings.

We invent narratives to support this nonsense. For example: about past events which we endlessly replaying to concoct fouls, slights, and transgressions despite no detectable evidence of harm.

And then what do we do? We build our self-image mostly from this instead of what we learn from looking in the mirror, from the results we’ve gotten from our hard work, or from what we hear from the people who love us.

Jerks!

We have been worried since last Tuesday that the thing we said while trying to be nice to someone was taken the wrong way. There’s no evidence that it was, it’s just a thing to worry about it.

Meanwhile, it’s Summer! And probably one of our last, because the fucking planet is burning!

We are obsessed with these invented beliefs about how we are falling short or disappointing people. I call these anti-fantasies.

Welcome to my community of people who are obsessed with invented limiting beliefs about themselves. We’ll call it the Anti-fantifa!

Before we get started, any feedback on the name?

If it ever comes to the point where you are unwilling to do a thing that is expected of “leaders” or managers — remember this: It’s ok. You are not alone.

The first 39 floors of the building you are in right now are occupied by thousands of freshly RTO-d people who made the same decision somewhere along the line.

They’re good people, mostly. Salt of the earth. Respect!

As for you, maybe you don’t have to be in charge. Do you even remember how that came to be what you wanted?

Maybe you only want to want to be in charge. Maybe you just aren’t as ambitious as you think you’re supposed to be.

There’s nothing wrong with that. There’s nothing wrong with you.

I kind of like that about that about you, actually.

We all do.

Businesses are making cuts because economic conditions are tough. But cutting costs alone does not lead to growth.

Whether you’re a CEO, entrepreneur or a freelancer, the best strategy to ensure you’ll continue making progress — even against stiff headwinds — is by focusing on the things you can control.

I’m working with more clients than ever on sales, marketing, and revenue-generating operations. These skills are always important, but they’re essential during a downturn. Even if you’re a cog in a giant corporate wheel, be assured that your management is looking for a greater sense of urgency around revenue growth in .

👉 I provide sales coaching to help individuals, small- and medium-sized businesses optimize their revenue generation. If you’d like to have the PDF that describes how this works, just hit reply and ask.

Today, I’ll share some thoughts from this practice.

What are Sales Skills?

“Sales” — yuck. The term evokes things we all hate: Buying a car, or answering the door to an unexpected and unwelcome solicitor. It’s hard to see ourselves as someone who is good at sales but still the kind of person we want to be.

Here’s good news: The skills that made a salesperson great in the 1980s are not relevant in the modern world. If you always never wanted to be that kind of salesperson, or have that kind of business, you are alive at the right time. Finally!

A better term is “revenue operations” or “RevOps”. I love this term for all the work inside a company that relates to revenue generation. Its important because it acknowledges that most of the important sales work happens inside — and that has changed tremendously in the last 20 years.

Even for a freelancer, thinking about RevOps can change how you approach your business. In a bigger company, being mindful of RevOps will help you align your mindset with senior management and investors.

Science, riches

Your mental model of sales may be based on a caricature of a golden-throated Don Draper pitchman in a snazzy outfit, a loud voice, and whiz-bang demo or deck. Many of the archetypes for a successful sales performance are toxically masculine. Also I cannot find any evidence that they actually work. Cool!

I have also discovered this: good products made by good people sell themselves even when sold by salespeople who are objectively terrible at their job. Have you ever bought something from an objectively terrible salesperson? See, told you.

Thanks to the internet, it’s harder to sell a bad product at any price — even with the salesperson of the year — because there’s a better product with a worse salesperson just a click away.

So, what does work? Experimentation, trial and error, and measurement, repeated and practiced with discipline. This is a longer topic for a lecture or a workshop. I learned this from working for more than a decade at the biggest companies in the world — so you don’t have to. And I’ve read all the books on the subject at the airport bookstore.

The experts all agree.

“Hustle” is not a Strategy

In the academic world, the process I described above is called “science.” The knowledge gained from it over time is called “truth.”

Science allows us to determine what works, and what does not. It is, apparently, the only way of doing that. That right there is a pretty good argument for making it the basis of our approach to making money.

In many companies, scientific practices are rigorously applied in the product management, engineering, finance, and research departments. I have noticed it may be less often practiced on the sales team, which may rely on pressure tactics, pricing obfuscations, psychological stress, caffeine, and adrenaline.

It doesn’t take a radical reboot to alter that approach. It can be done the same way the coach improves the performance of any team, by working with the players, sharing experiences, drawing up plans, and calling the right plays.

When my clients apply a scientific approach it’s usually easy to find ways to make gains.

Here are three simple and concrete ways to combine measurement, trial and error, and repetition that can be applied to improve the revenue operations of almost any business.

1. Measurement and Attribution: Most people have heard this famous quote and it, like most, is total bullshit. The companies you are paying for your website and for your internet advertising want you to believe it! Well-run companies carefully scrutinize the return on investment of every dollar they spend on sales and marketing. Poorly-run companies do not. Even when it cannot be done with complete perfection, spending money with no attempt to measure the ROI is the very definition of superstition.

   84% of deals are won by the first vendor that a buyer contacts

2. Speed to Lead: There’s plenty of research that shows how important it is to quickly connect with a potential client. You do not need to read it, though. When you need a plumber or electrician, do you hire the one with the best website, or the one that calls back first? Still, when I ask clients how long it takes them to respond to a potential client in the inbox, I rarely get a numeric answer! Aim to respond to prospects in minutes, not days. In larger companies, here’s a tip from experience that works: Sometimes just announcing that you’ll measure a number like this is enough to make it go down.

   It’s easiest, fastest, and cheapest to sell more to the clients you already have.
   Next best, to sell to prior, lapsed clients.
   It’s hardest, slowest, and most expensive to win new clients

3. Revenue Sources: Most companies focus their business development efforts on finding new clients. For many, that’s where revenue growth has come from in the past. However, most companies will experience a stage where most growth will come from selling more to the clients they already have. You may choose to consider this approach when the economy looks a bit stormy. In any event, review on a quarterly basis whether you have sold as much as you can to every client who’s received an invoice. Send a pitch every year to a client who hasn’t received one recently.

Many of my other favorite tactics for revenue operations come from streamlining the sales process from quote to order: creating estimates, sending proposals, generating invoicing, optimizing collections, streamlining delivery, and so on.

If you’d like to hear more about sales coaching, just hit reply and ask for my PDF. It is suitable for you to forward around your organization.

I’m looking forward to hearing from you!

I know, I haven’t written in a while. But then, you haven’t written me either!

Actually, that’s not true. I heard twice recently from people who told me that my writing or workshops had impacted them. These were intensely moving and meaningful conversations. Keep ‘em coming.

If you have any more feedback like this, now is a great time to share (just hit reply and your message goes directly and only to me!) And negative feedback, too, or what you’re not getting that you really need.

💥 Welcome new readers! 💥 This newsletter has gained more new subscribers in the last 48 hours than in the past six months. You newbies too, are invited to hit reply. Let me know how you found me, and what you need to know, hear, or learn.

Come and join us in our very low-key Slack where we share links, ask questions, celebrate and support each other.

What’s Going On

I’ve been away from writing for a while beceause, perhaps like you, lately I’ve found it a bit difficult to feel inspired.

Giving career advice — especially on job search — is especially hard when it feels like most of things I have to say are things that people really don’t want to hear.

The job market is terrible. Recruiting, hiring, and management practices were already becoming increasingly inhumane when I started writing this newsletter. Since then, companies are setting fresh new records for stupid, abhorrent, and counter-productive hiring and firing practices at an increasingly grandiose scale.

My greatest fear is that our culture is changing in ways that emboldens and rewards unethical, crass, and unscientific people for their mushy-headed, feckless, and ultimately unsuccessful practices.

I’ve heard from quite a few people who are choosing to exit the professional workforce, resetting their careers, and their lifestyle. If you have the opportunity to consider changes like those today, I don’t think that’s an overreaction at all.

What’s Next

Going forward I’m going to limit my coaching for job search and career transition to existing clients and referrals. I’ll increase my focus on the topics that brought most of you hear in the first place: Business skills, sales, marketing, business development, and people management.

For those of your who are job seeking and in career transition mode, I’m going to repeat the most urgent advice I can offer:

1. Most of the billions of jobs posted on LinkedIn are, for a variety of reasons, total bullshit. Do not waste your time reading them, or worse, applying to them. Only apply to a job posting when both of these conditions are met: You’re a perfect 🦄 fit, AND you can find a referral, recommendation, or some other edge to move you to the top of the pile. Every person I talk to who has gotten hired recently met both of those criteria in some sense.

2. don’t waste time stressing about your profile. Just keep it simple. Avoid comparing yourself to other people whose primary accomplishment is having a nicer resume than yours. They are just as miserable as you — believe me. Ignore the stupid superstitions: resume gaps and background images and all that made-up nonsense that exists primarily to drive social media pageviews and the influencer industrial complex that nurtures it.

3. When many of my clients look back on their careers, they notice that they got most of their jobs through referrals, references, or introductions. Yet we find it much easier to focus on pursuing job postings then we do on cultivating our relationships with the people who might be able to help them. That’s strange, because the latter task is objectively much less despicable than the former! Here’s a tip: calling it “networking” makes it feel more like work.

Except for those at the top, the corporate world is pretty terrible. It’s an especially dangerous place for women, people of color, people with disabilities, chronic illness, queer people, and just about anybody else who isn’t a young, CIS white male. If you’re from a marginalized community and you need help with absolutely anything, please know that I am always here to help you. The cost of my fees will never be an obstacle.

Regardless of how you are situated, consider the suggestions I made when I launched Safe@Work — it’s the idea the newsletter is named for. Keep your professional identity healthy and safe from your corporate employer.

Diversify your career path, and have multiple paths for your professional development. Have a side hustle — ideally more than one. The best time to get that started was last week. The next best time is today.

What’s Next

See what I mean? Do you really want a career coach who believes that the corporate world is so unhealthy and dangerous as to be unfit for human habitation? It’s a like asking a paroled inmate to teach people how to break into jail.

If you’re looking for help negotiating a job offer, leveling up your business skills, developing your people management skills, or any of the other topics I’ve written about here, I’m available now for 1:1 coaching. You

Anytime you find yourself in need of help at work, please remember that I am always here when you need me. Drop me a line, or head over to Bizlet.org and book a free chat.

And stay in touch!

Low-key trauma is inflicted daily upon our working siblings, much of it by managers and management with the best intentions. This is for you, the leadership class. It might hurt a bit.

Y’all should know better, but you don’t. Managers get away with doing stuff that it seems like they’re supposed to, or saying things just because they sound official. We know it’s bullshit. Knock it off.

Hiring because they can

I heard a realtor complain about a property being listed “before it was ready.” They meant that the listing agent had only taken a few photos, and they couldn’t answer a potential buyer’s basic questions about the home. Everybody’s time was wasted, and the agent looked like a moron.

Eager managers often rush to start the hiring process before they’re ready, hastily whipping up ill-conceived job descriptions, failing to consult the rest of the team, and making a mess of the whole process. Eager hopeful candidates are interviewed by people who can’t answer questions about the role. Human resources isn’t sure who it reports to, don’t know what the job entails, or where it’s meant to be based.

Dozens of people have hundreds of hours of their time and energy wasted by an insincere company over an position that is unlikely to be filled. This is an abuse of power by people who have jobs and plenty of time to waste. They’re exploiting the inability of unemployed people to call them out on it. If you see this happening, be brave and call bullshit.

In the deep end

“Onboarding” is a neologism — a newly-invented word referring to how we ready a new employee for their service in the role. It resembles another recently-invented word, “waterboarding”, which coincidentally is a process also designed to be survived — but only just — by its victims.

Years of research, study, and consultants have generated reams of best practices, conferences, and training seminars about how to welcome new employees and train them up for success. After all of that, our corporate leaders, in their wisdom, have collectively responded “It’s on the intranet assholes, sink or swim!”

Managers spent ten interminable weeks interviewing candidates, boasting about their empathetic team spirit, will now unceremoniously dump a decade’s worth of forwarded email (with missing attachments and links to long-deleted web pages, of course.) Somehow you’re meant to make better sense of the poor shmuck who came before you.

When you hear the phrase “drinking from the firehose” you know you’re fucked. It’s another way of saying “we know there’s a better way to do this, we just don’t care.”

Good bad job

There’s no rule that says a performance review has to contain equal parts positive feedback and constructive criticism. Managers feel some pressure to make the review seem balanced. Often some effort goes into figuring out what kind of negative feedback to give an employee, so the manager can show that they’re being tough and “raising the bar.”

A really shitty thing that managers often do is dredge up minuscule errors or long-forgotten transgressions in order to fill out the “areas for improvement” section. Every manager knows that the employee will give about a thousand times more weight to each negative word as they do a positive one. As if they haven’t already replayed that moment a thousand times in their own mind!

Sadly, the real audience here is the manager’s manager, not the employee. So a little bit of blood must be performatively let.

Two ways for an emotionally intelligent manager to thread this needle: First, make absolutely certain that there is never a surprise in any performance review. Just write an email explaining why you chose to include each of the items you did. Be a boss and say something like “I included this because it’s helpful for me to demonstrate to my boss that I’m setting a high bar for everyone on my team.”

Another idea is to tie “areas for improvement” to the specific and literal promotion criteria given in your company’s guidelines for the employee’s job track as they become eligible for promotion. Show the employee that you’re thinking about their career progression as you do the difficult work of managing constructive criticism.

After coaching and managing people through so many wild and scary situations in my years, I’m a bit worried that my writing is starting to resemble a kind of corporate Kama Sutra.

It’s my account of all the ways us corporate types are getting fucked at work. Whether you are looking for a new job or ways to grow your business, I remind you that you must first love yourself before any employer or client will.

Just do it in moderation. And please wash your hands.

Today’s Book Club Book

The Kama Sutra — literally, “Principles of Love” — is an ancient Hindu text. It was first published in English fairly recently, in the grand scheme of things, in 1883.

It was written much, much earlier; perhaps hundreds of years BC. The text is probably the most-pirated in history.

It is terribly, tragically misunderstood, but aren’t we all. According to Wikipedia, the Kama Sutra “is neither exclusively nor predominantly a sex manual on sex positions.” So, displaying it on the shelf in the living room does not make you seem as edgy as you might think.

It’s a self-help book, really. In a mix of prose, poetry, and illustration, it reveals ageless manual of love and desire, relationships, and adultery, and how to do or not do all of those things the right and proper way.

It’s the BCE equivalent of “live laugh love” or perhaps “you cannot love anyone until you love yourself.”

Along with vivid diagrams of how to do both the right and proper way.

Survivors

Still here?! Fascinating choice.

Today, I wanted to share three important ways to avoid fucking yourself over. I promise: No pictures.

First: Expect less from your bosses. In the corporate world, participation in the management class is predicated on a simple trade-off. Managers are permitted to believe that they will enjoy some greater measure of stability than the people below them. In exchange, they tacitly agree to fire them stoically when asked, and to forego questioning the ethical or moral ramifications of the decisions made by those above them.

Every manager knows, or should, that their own interests will inevitably diverge from the team they lead. Hold this knowledge in the space between you and your boss. That way you’ll never make the mistake of expecting more from them than you should.

Negotiate

Please, please, please: Never accept the first offer. In any negotiation for a job offer or a business deal, if you accept the first offer, you are — with the rarest exception — a fool. The courage to negotiate is distributed unevenly and unfairly to privileged people who, shittily, need it least. Find one of us! Ask to borrow some privilege when you need it. Say “Hey, Mortimer, could you help me figure out how to handle this negotiation?”

A great way to lower the stakes is to find a way to respond to an offer with a question. Try this: “Thank you! Do you feel this is open to negotiation, or are these strictly the only terms you would accept?”

My friend, if you do not negotiate, guess what the person with more privilege will always end up with? And look how that’s working out for us.

The end

Finally, remember that none of us are getting out of here alive. One thing I have learned from 30 years in the corporate world is that there is no way to succeed at it. The most talented, successful, appreciated, educated people I know have been mercilessly shitcanned from billion dollar companies. They may have money in the bank, but no idea what to do with the rest of their lives.

Get in control of your career as early as you possibly can. The best time to start was years ago and the second-best time is now. Start a business, and fail. Start another business, and fail again. Diversify your sources of revenue. Take on partners. Invest in your friends’ businesses. Real estate? Freelance? Coaching!

What if you start an Etsy shop or a newsletter or an eBay store, and it never even makes enough to cover a bag of scones? Well, what if you don’t start that store, and somebody else does?

If you haven’t already, please get something started for yourself this year — before the year runs out. If you’ve already started your business, expand it. Launch a new product or service on your website. Try something new.

Don’t leave your career or your business in the hands of other people.

Fuck those guys, am I right?

Hi, it’s me! I wanted to say welcome to the many of you who have recently discovered the newsletter and hello to the new coaching clients who recently joined the practice. I’m so happy to have you all in our community.

Has everyone read How Coaching Works? How about Safe From Work, my piece on maintaining your identity during times of career turbulence?

The intelligent community

18 months ago I wrote The Opposite of AI. This was my reaction to the cultural paroxysms of dystopian AI panic gripping us last Spring. It’s aged well so I gave it a light zhooshing this morning.

The AI apocalypse breathlessly predicted by literally everyone has…well, not quite materialized. AI has not quite appeared in the skies over our major cities. It has not quite replaced professional people in every job. So, the difficult work of destroying our planet remains in the capable hands of us human beings. Who, as you all know are making slow but ruthlessly steady progress at that job.

Everybody get back to work!

Coaching

I would like to invite you all to visit http://Bizlet.org/coaching and consider the new and improved coaching subscriptions. Options now start around $350/month. I am here to help you with your job search, career change, freelancing, small business, agency, or any other career or business challenge.

I am looking for clients who may not have been able to afford coaching in the past. If even this lower fee is problematic, please let me know. I will try to find a way to make it work for you.

My best advice for everyone who isn’t getting coaching or therapy is in my essay titled Don’t Listen to your Therapist.

You really shouldn’t listen to me, either, or to your spouse, parents, or children about your career or business problems. You should talk to them.

I’m half-joking. You probably should listen. The most important thing for me, when I’m facing difficult problems, is to spend the time organizing my thoughts well enough to tell somebody about them. One way to do that is by writing about them (which I do badly here, and thank you for your role in that!)

I also learn so much, and you will too, from finding out how your ideas sound when you say them out loud. You need to start talking about the impossible, improbable, unlikely, and just plain irritating career and business challenges that you’re facing. It matters less who you talk to, and it matters more that you talk about it.

Are you waiting for the universe to deliver the perfect mentor, manager, executive sponsor, or coach to help you solve your problems? Please start talking to someone — anyone — about it instead.

Your hairdresser or barber is a great place to start. I started my career working for some years first as an assistant in a beauty salon, and then as a licensed cosmetologist. I consider myself empowered to assure you on behalf of all of the world’s hairdressers: they will not mind.

Have a great week. See you all soon.

“Networking”… blech! I am throwing up in my mouth already.

I hate this word because it describes a thing that you’re supposed to already be good at in order to be successful. It’s an idea about success that’s just another way of saying “be a white guy”. Ugh.

Anyone can develop these skills. Often the people who feel most averse to them are often the best at them. Some people find them more approachable when we call them “relationship” skills. So let’s do that.

Your relationships skills are more important than your resume. They are more important than your interview skills. For any business, your networking and relationship skills are just as important as your marketing materials, your website, and your newsletter.

Are you familiar with the stereotype of the well-connected under-achiever who fails languidly upwards on the strength of their connections, their family, or other unearned advantages? Let’s all be more like them!

Going far, going together

Coaching clients report they “just don’t have the relationships” they need to make relationship-driven career development or business development as easy as they would like. Really? No shit! Me neither!

Nor have I found my family name engraved on the walls of any museum or hospital lobbies. Nor are the likeness of my forebears etched into monuments littering our city parks. Nor have I inherited anything more precious than a few cookbooks, a predisposition to high cholesterol and addiction, and the ability to parallel park in a space slightly smaller than my actual car.

(If your name does appear on the wall of the museum or theater lobby, you lucky dog! All you have to do is write down the other names you see next to yours, track those motherfuckers down at the country club, and ask them for, you know, their money. Or ask mommy and daddy when you see them in the Hamptons, or when you visit them in prison or whatever. Now please get lost, your Tesla is blocking the bicycle lane.)

Look: almost nobody believes they have the “right” relationships. You might not have the ones you want, but you have the ones you need to get started.

There are many ways to do that. Here, I will propose one way to get started.

Make three lists of people

Sit down with your phone contacts and browsers logged in to each of your social networks: LinkedIn, Instagram — anywhere you have accounts.

Go through your contacts and make lists of the following people:

1. Everyone who loves you. Any amount, for any reason. No questions on this one — just make the fucking list.

2. Everyone you respect and admire. If these people are also already on the first list, great — leave them there.

3. Anyone who you truly hate and wish for some great evil to befall. This can be someone who committed a great sin against you, or someone who is merely too nicely dressed. Doesn’t matter.

Step 1. For each of the people on the LOVE list, you are going to write a short, thoughtfully-composed, well-written email. You are not going to use AI in any way for this message. It will just take a second. Here’s an example:

Maria, hello. I wanted to drop you a line and let you know that I am looking for new clients for my business. Here’s a link to my website. I know everyone is busy but if you have an opportunity to send any clients my way, I’d truly appreciate it. You’ve always been very supportive and I could use your help right now more than ever. Thanks so much!

Step 2. The RESPECT list. Write a short, thoughtfully-composed, well-written email. Let’s not use AI in any way for these messages, either. Each one will just take a few seconds. Here’s an example:

Albert, hello. I wanted to say how much I respect and admire your work on that project making little origami hats for your parakeets. I was really inspired by that! I told everyone at the office about them, and I sent some people to buy cat booties from your site. I am looking for more clients for my business, and I wanted to share my website with you. If you ever have need of my services, or thought to send any clients my way, I’d sure appreciate it.

Now, the HATE list. Actually we’re not doing anything with that list today. I just thought it might be cathartic for you to make a list of the people who have harmed you. Fuck them, am I right?

What are we doing

What’s the point of this? The point of this is to deconstruct the dark and mysterious art of “networking” into tasks like “making lists” and “writing email messages to people.”

How does this differ from the work that the best networkers in the world do? It does not. They do this work a lot. For the most part, we don’t do it at all.

There is no right way to do it. You have probably already figured out that it doesn’t matter if you make lists of people you love, respect, worked with, worked against, love, hate, are related to, play tennis with… What matters is that you organize your effort in a way that ensures you’re not unintentionally giving your future clients or co-workers the sad and chronic silent treatment.

(There is, in my view, exactly one wrong way to network, business develop, career develop, etc. and that is cold calling. Applying for jobs, asking for business or any other kind of opportunity without trying to leverage a relationship is, in effect, a cold call. Ask yourself: How do you treat the cold calls that come to your cell phone or email inbox? How would you treat the same messages if it came from friends, family, or acquaintances? Set your priorities accordingly.)

I know you, and I know you have inhibitions to overcome in speaking directly to people — even family and close friends — and asking for their support. I love working with people on this. These steps can be taken in small, incremental, painless ways. This is really fun work because it starts to pay off in a very short time.

Remember that quitting is the only way to fail. All other paths — other habits and practices that put you in touch with people who can support your career and business growth — will eventually lead to success.

I’m here if you need me. Good luck!

I’m back to coaching, and it’s terrible.

Not the coaching, you twerps! I love coaching. I couldn’t be happier to be back in business with so many of you. If you’ve been thinking about coaching, or you’re a lapsed client and you want to get back in touch — just hit reply and tell me what’s up.

Times are tough! It’s more difficult than ever to find new jobs, plan career changes, and for people to sell themselves and their services.

I want to address how much harder it has become to apply for a job via postings on sites like LinkedIn and Indeed. A lot of these same issues apply to freelancers who are out there selling their services online.

It’s not you, friends. It’s them.

The Opposite of Emotional Intelligence

What is the opposite of emotional intelligence? Whatever it is, corporate employers have industrialized it, they have weaponized it, and they have turned it against careerists during the job search process.

They have aimed it at our amygdala when we are at our most vulnerable, when our sense of self is weakened, when the security of our families and our place in our community is in question.

And why? Why post a job for a position that don’t really exist? Why post a job description without a location? Why interview candidates three or five or seven times, then ghost them?

Because it’s easy! Because they can, without consequence. This is ignored too often, and it’s not a fun thing to say out loud: Companies are not interested in any solution that makes it easier for candidates, if that would increase the number of applicants. Every job posting has way too many applicants for the hiring manager to even review. Anything that makes it easier for applicants is a solution to a problem that companies do not have.

Employers do not believe there is a problem. They are on the winning side of a essentially unregulated marketplace. Regulators cannot afford to tamper with the underlying mechanism. Workers generally cannot afford to reject them, or speak out publicly against them, and won’t even when they can.

So, what can we do?

Stop applying to jobs

First, a quick experiment.

If you got your last job via LinkedIn’s “Easy Apply” feature, you have won a valuable prize. Please hit reply and send me an email to claim it. Seriously, let me know if you’ve heard of anyone who got a job that way.

Next: If you got a job post-pandemic from a “cold application” via any online job application, please hit reply and tell me your story. I am sure they are out there, but I haven’t heard one in a while.

In my professional career, every single job I have got came via a referral or some kind of personal connection. From memory (and you will correct me if I’m wrong, won’t you, darlings?) every one of my clients who have gotten new jobs during our professional relationships either got them via a referral, or they applied to a job and their application was supported in some way via a relationship or connection.

Anecdotally, relationships are the single most important ingredient in a successful job search — and that’s also true for sales and marketing of freelancers and small business. Everybody believes they don’t have the right relationships, and literally nobody has as many or as powerful as the ones they want, but you have the ones you need to put to work, and they’ll do the job harder and better than an AI-generated resume template.

The practice and discipline of networking should be the primary focus of careerists today. The conditions in the “job market” (and by this we really mean cold applications online) are so bad for the applicants right now, I’m advising people that they should not be “cold applying” on the job sites at all. Keep your powder dry, until you find an opportunity that’s supported by an introduction or referral.

Last week, a pal of mine pointed out that applying for a job on LinkedIn is the equivalent of getting a “cold call” from a salesperson. Sure, there’s a 1-in-1000 chance that you’ll be relevant enough at that exact moment… but probably not.

And what about the poor cold calling salesperson? We know that this insane, inane, repetitive process of cold applications is harmful to us. Even though it is not a reflection on our self worth, even though it does not indicate our actual value in the marketplace — it is harmful.

That’s why the framework I’m using with my client begins with cutting out cold applications, or reserving them only for opportunities that are unique or special in some respect. The rest of the energy goes to developing our network of relationships, and finding the best possible ways to put them to work from us. Another post on that topic is below.

Thoughts or ideas: comment on the post, or just hit reply and let me know what you think. Thanks!

I have a little news to share. I don’t want to give anything away, but if you have been waiting for the perfect moment to have that big career crisis you’ve been planning for a few years, this might be your moment.

Coming soon…

I’ll resume coaching and will begin accepting new clients, starting September 2024.

The Business Letters website has gotten an update. Please drop by and check it out. Give the new coaching plans a look. If you’d like to sign up, email me for a discounted rate. Just hit reply.

If you need choices or pricing options you’re not seeing there, please just ask. Nobody will be turned away for financial reasons.

If you’ve been missing me (and I know you have) perhaps you’d like to drop by the archives and read up on some of the newsletters I wrote last year. The full archive is free for everyone to read.

Using my very sophisticated mastery of digital marketing metrics, I have determined that my YouTube channel is the best thing on the internet that almost nobody knows about. That’s too bad, because it is totally amazing. Please enjoy it.

You’re also so welcome to join us in the Safe @ Work Slack. Even during my hiatus from coaching it’s been amazing to hear from clients, colleagues, and friends about their career victories and challenges. It’s a great place to learn from others or just to be reminded that you’re not alone.

That’s the most important message I wanted to put in your inbox today. Whether you want to become a coaching client or not, I am here for you. You can always hit reply to this message and talk to me about what’s happening. That’s what I’m here for.

Thanks for hanging in there with me. More to come in September!

I’ve been fighting with Long Covid for the last 18 months or so. If it’s a battle, it’s bitter, lonely one, with no beginning, no middle, and seemingly no end.

Compared to others, my experience hasn’t been that bad — no hospitalization, no chronic fatigue. Lots of people have it worse than me. I can still do nearly everything I want to do, I just can’t do it very well. It’s like spinning the lid open on a giant jar of ants that come along with me to every fucking picnic.

Particularly shitty is the liminal space it occupies in the popular consciousness. Most people won’t say that Long Covid is actually fake, but they sure as shit aren’t saying it’s real, either. I suppose this is what passes for good news: the media is eagerly reporting the revelation that Long Covid, you know, exists.

The boom and bust of hope and despair never gets old. About every three months, I will string together 7 or 10 good days and I’ll start to think — hey, that was some bullshit! Sure glad that’s over!

But then it returns. It arrives suddenly, like a falling safe arrives on an untidy sidewalk. Imagine falling asleep briefly during a terrible movie and then waking up with a very bad hangover. You’d feel cheated, wouldn’t you? If I’m going to feel this sick, shouldn’t I at least get to have a good time?

Well, What Have You Tried?

One of my many doctors asked me “Have you tried working a little less? Limiting the amount of stress, prioritizing your wellness and sleep?”

I replied “Have you tried getting your head reattached to your torso after it’s been removed by a nearsighted, colorblind, middle-aged white guy with a headache?”

Actually I didn’t say that, because I have exceptional self-control and, given the current economic conditions, it may be hard to find a criminal defense attorney willing to be paid in high-quality artisanal fonts.

This is my way of saying that I’m taking a step back from coaching and writing for a while. I am winding down my group coaching programs. For a little while, I won’t take on new coaching clients. I’ll be posting here a bit less frequently — lucky for you, more room in your inbox!

Oh, another lucky thing for you — my readers. I want to extend an invitation. If you want a little help dealing with what’s happening in your career right now, here’s an opportunity to become part of a community that I enjoy, and that I’ve enjoyed participating in over the past few years.

I’m inviting all of you to join the Safe @ Work Slack group. This is a community of my clients, colleagues, friends, lapsed clients, future friends, and vanquished enemies. Kidding — it’s all delightful people, and to be clear, this is a completely free thing — there’s no paid version of it.

As far as Slack workspaces go, ours is extremely low-key. We don’t see posts every day. A few of the channels are probably clinically dead and should be ceremonially destroyed.

The terrific thing about the group, though, is this: Every week or so, someone posts their resume (“How does this look to y’all?”), or an email they got from a recruiter (“What the fuck does this mean?”) or asks for some help or ideas from the group. And that’s when you’ll learn how amazingly kind, thoughtful, nurturing, and supportive the group can be.

I routinely have the sensation that I am not cool enough to hang out with these people. I honestly am not sure why they let me. It’s probably the fonts.

Anyway, I encourage you all to drop in and say hello. Ask a question or answer one. Send me a DM if you need some help with something. It might take me a day or two to get back to you, but I do try to reply to everyone on every thing.

In the meantime, if there is anything you’d like me to write about, this is a great time to send your ideas. If you’re reading this in your inbox, hit reply and let me know what’s happening with you.

I’d love to know why you started reading, and what you’re hoping to hear from me in the future.

Be well. I’ll see you soon!

The most valuable career and business skills I have did not come to me naturally. They came slowly, and with practice.

I learned them the way a child learns to walk — starting with a few wobbly steps, then by hurtling myself at the steepest or sharpest obstacles I could find.

The skills did not come naturally, or easily. In fact, some of them might not have come to me at all! I am still practicing, failing, learning, and repeating the motions that I know have helped me win the little victories I have earned.

Like you, I have aversions to certain things I know are good for me. Allergic might be a better word to describe how I initially felt about the business skills my mentors pointed me towards as I left behind my technical career and transitioned into business.

It took me a long time to overcome that avoidance. Today, I do some of these things automatically, without even thinking, and I can measure on a weekly basis the contribution they’ve made to my career development over the years.

There is one skill in particular is that I think are essential to practice for anyone who wants a successful professional career. These skills have two things in common:

1. Most people feel incompetent at them

2. Most are much better at it than they think.

Some things that seem hard seem much easier

I’d like to take a crack at sharing a few simple ideas about why these skills are important, and how you can practice them without turning your stomach.

Networking

The word networking is such a risible obscenity. It causes the eyes to roll right back, and a deep sigh to be exhaled by any noble person.

How do you perceive someone who claims to be good at networking? I know this one, because I am perceived this way sometimes. The word that comes to mind is douchebag. Or the more recent synonym, influencer. (If this is you, I’m sorry. I don’t make the rules.)

I am trying to eliminate the words network and networking from my coaching practice because it has such a strong negative connotation for so many of us. Let it go, my friends. Let’s all resolve together to never use the vile word again.

Instead, we will replace it with a friendly and benign word that has absolutely no challenging connotations whatsoever.

Relationships

As any salesperson will tell you, business is about relationships. You can take the work out of networking by focusing on the aspects of your business relationships that feel normal and natural to you. If you can get comfortable with this, you’ll develop a superpower that you can put to work in any career or business situation.

You can start by taking a moment and think about the important relationships that have impacted you and your career. Really, just for a moment, think back on the people at work who made the biggest impression, who hired you, promoted you, and have run interference for you in your business and careers.

Think for a moment about your relationship with your last boss. Ok, that was too long. But it’s significant that your relationship with your manager and your co-workers is likely to defines whether you enjoy or merely tolerate your work.

Think about the person who hired you into your first real job, or who gave you your first promotion. Think about the first time you worked as part of a team that gave you that amazing feeling of effectiveness and productivity. Remember some of the individual people who you’ve worked with that you would love to work with again.

Comfort and Authenticity

Why does networking feel gross?

One of my favorite clients used the word transactional to talk about the discomfort she felt when performatively reaching out to people to talk about her job search. She’s right. Know what else? If you’re subjecting yourself and other people to a conversation that feels like a pretentious, fake, or phony transaciton, it’s unlikely to be successful.

Think back on the relationships you’ve enjoyed with all of those amazing people from the previous paragraph. If you ran into one of them on the street and they asked what you’re up to, would it feel gross to say “Hey, yeah, I’m looking for a new job.” Probably not!

Business relationships are inauthentic, transactional, and gross when the friendliness is fake, when the social aspect is performative or obligatory, and when one person is trying to wrangle some uncompensated advantage from the other.

It doesn’t have to be that way. In fact, it’s ridiculous to throw the baby out with the bathwater. If you’re refusing to engage the people you know in the process of trying to grow your business or find a new job, it’s like you’re refusing to wash your hair because someone tried to sell you Amway shampoo.

The Real Deal

Every interaction you’ve had with someone in a career context represents a relationship. Every relationship has value worth assessing, cultivating, and leveraging.

Does it feel weird to talk about leveraging relationships? Do you feel bad about asking a friend for advice? A colleague for their opinion?

If you call it networking it feels bad as fuck! When I talk to my clients about this topic I am usually asking them to do an exercise like the following. Give it a try and see if it seems like something you can do without feeling disgusting.

Go back one or two years in your email inbox. Read through some messages and note the people you were interacting with at that time. Pick one or two of them who appeared not to hate you and send them an email.

The email can be incredibly straightforward and transparent. You can copy and paste this:

Hey [Name!] It’s been a long time since we’ve been in touch. I am looking for new clients for my design system consulting biz. I really enjoyed working with you at [Company] so I thought I’d ask if you could send any projects you come across my way. Thanks!

Another example:

Hey [Name!] I’ve just been updating my profile here and I remembered the great work we did together on [Project.] I just wanted to let you know I really enjoyed working with you. I’m looking for a new role so if you hear of anything that might suit me I hope you’ll keep me in mind.

Most people react poorly to the idea of doing this kind of relationship work because we are all inundated every day with spammy cringey garbage in our inbox, from people pretending to know us pushing some kind of crap at us we do not want.

Your own efforts to network with your colleagues do not have to be like that. If you practice being straightforward, transparent, and concise, you’ll find it easy to write the kind of messages that you’d be happy to get.

Boom! You have just been born. One moment you’re nothing, next moment — whammo! You’re a baby.

Nice going, baby. Congrats! Make sure to update your LinkedIn.

Before anyone can react or comment, babies becomes kids. A toddler becomes a tween. Adolescents become adults. Well, most do, eventually. Some faster than others and few as quickly or completely as we’d like.

The progression from infant to adult is a process of continuous change. You gain wisdom and abilities, empathy and patience. Your tolerance for alcohol increases, and for assholes as well.

You hope for fewer surprises as you grow older, but change is continuous and constant. Your tolerance for assholes, developed so patiently, suddenly disappears. Some abilities falter, while others are enhanced. You’re no longer confident you can select the appropriate emoji for any given circumstance. In the other hand, it takes a lot less time to figure out what to wear.

One moment you’re quite spry. The next, you’re unable to transition to or from a sitting position without emitting an involuntary sound. You tolerate surprises, revelations, improvements, and disappointments. You finally learn how to give a really good hug.

Throughout this lifetime of continuous change, is there anything that stays the same?

Space and Time

Time passes. The world spins. Borders change. Governments and markets and hemlines all rise and then fall and then rise higher than we ever thought possible before crashing down again. The motion is predictable, but takes us by surprise every time.

Technology inches ever closer to perfecting its terminal business of first compromising then destroying its creators. Young people become far smarter than previously thought possible, all while remaining way dumber that we can comprehend.

Our language evolves. Maybe devolves is the better word. It definitely involves everyone else in a global conspiracy against you, as the meaning of words suddenly change or invert without proper notice.

Your habits, your health, and your beliefs all change. You quit smoking, but took up daytime drinking to deal with the stress. You take up running to help you quit drinking, and that destroyed your knees.

You quit texting your ex, which is good because it makes your friends happy. You’re still talking to your ex’s mother, though, which gives your friends some concern. They wonder: Is that, like, appropriate? Don’t worry, you assure them, we’re all in a really good pace.

Throughout all this, is there anything about you that stays the same?

You might say your body stays the same, but you might not say that to anybody over 40.

Your cells are continuously, silently, imperceptibly being created and destroyed. Every cell toils to perform its assigned function while simultaneously creating the ones that will replace them when they die. They’ve automated their own obsolescence, like managers overseeing layoffs at a big tech company.

Did you know that the cells in your skin regenerate as frequently as every few weeks? The oldest cells in your body are in your bones — but even they last no longer than about 15 years. That means if you’re over 15 years old, literally nothing about you has stayed the same. If you’re not over 15 years old, this is not appropriate reading material for you. Please turn off your iPad and GO TO BED. Do not make us come up there again.

Does your family stays the same? You wish! Your family can’t even get through a holiday dinner without a divorce, disownment, or disinheritance. Your family is “related” to you, like the items on the right side of an Amazon product page. It’s an association of people with similar DNA, selected by nature over generations to ensure survival, perhaps, but not solvency.

If there’s consistency in your family, it’s that the net amount of disappointment and disapproval remains constant. It’s the conservation of discontent — familial sorrow can neither be created nor destroyed.

It surely doesn’t stay the same.

Same Shit, Different Day

Ok. So what does stay the same?

There is one thing that stays the same through the maelstrom of heartbreak, ecstasy, creation, and destruction.

That thing is:

Yep. The only things that I can depend on to remain constant throughout my life are the specific aspects of it that I choose.

The few things begun in relative youth that persist into old age — friendships, religion, hobbies, that outfit you will never fit into — they are all still there for the same reason: because you choose to keep them around.

You choose, select, or decide the things that remain permanent. Like that tattoo, your best friend Bertie, and the way you take your coffee. You decide which things are temporary, that you’re just trying on, like a borrowed outfit, a pilates membership, or that trial subscription to Paramount+.

Let’s say, for example, that I decide to abstain from couples yoga for the rest of my life. I create that idea, develop the intention, and I begin to align my behavior with it. I will not practice couples yoga today. I will not do it tomorrow, or the next day.

My behavior may stray from my intention. I accidentally relapse while wife and I vacation in Costa Rica. We practice two hours of utterly divine couples yoga at a seaside resort taught by a topless Swiss instructor with an eyebrow piercing which, weirdly, actually looks kind of good on them.

This changes nothing! I can go right back to abstaining from couples yoga when we get back to the States, because my intention is for my abstention from this practice to persist for all of my days.

What if, in a fit of ecstatic self-discovery, I decide to make a daily practice of couples yoga? What if I commit to maintain for the rest of my natural life? That’s cool too. What matters is that I’m deliberate about the intentions that I set to become my habit or practice. That’s how I define what aspects of my are essential to being me.

This is not really about yoga. It’s about your career. I will now get to that point, and illustrate how it relates to making emotionally intelligent career decisions.

Career Choices

My intention to preserve, promote, or propagate some aspects of my life determines which practices are likely to persist, survive, and continue no matter what else happens.

In my career, there will be distractions, interruptions, abstentions, abstentions from abstention, et cetera. However, outside actors cannot alter or influence my intention if I don’t permit them. That’s because I have made permanent certain aspects of my professional identity that I keep safe, through practices that are invulnerable to layoffs, firings, bankruptcies, distractions, and so on.

I accomplish this by severing1 aspects of my professional identity from the parts that belongs to my employer(s) or clients. I ensure that I continually invest a fraction of my time and energy in practices that are not influenced or controlled by anybody else.

If the Soviet Union is reconstituted, if the wrong person is elected president, if the seas continue to rise so high that we all move to the mountains…

If I get fired from my job, if I rage quit my job, if AI makes talents obsolete, if my boss fails to deliver their promises for the third year in a row…

It’s my decision to cultivate a professional life that I keep safe and separate from my daily work, and I want to try to inspire everyone else to do this to. In my coaching, I sometimes call this the “Side Hustle” option or “Your Etsy Store” for a stakes-lowering example.

Personally, this newsletter fits in that space for me, along with coaching, some other writing, consulting, and my other side projects. For you it might be doing some freelance work, volunteering as a mentor, trying to professionalize your hobby. As long as it is yours, and you own it, you can make it temporary, or you can make it permanent.

I can try it on just for one weekend, like your my friend Ainsley’s hooker boots. Or I can tattoo it on in a rushed expression of misspelled inspirational mishegas.

Another great thing about setting your personal intentions is that they cannot be broken or interfered with by outside actors. Not even by a very good actor, like Julianne Moore.

Example: Let’s say I have decided that I am going to make my expertise in design systems a major part of my professional identity. I start investing some free time in writing, participating in communities, doing a little freelance work, helping a friend’s startup with their brand — whatever.

Let’s say my boss is the amazing actor Julianne Moore (who at 62 years old is starring in May December, which by the way was made for only $20 Million — less than 1/10th of a Hunger Game) and tomorrow, out of nowhere — boom! Julianne Moore fires me.

Fuck you, Julianne Moore! (Just kidding, I love you J.M.! She is also amazing in Sharper on AppleTV — totally transcendent, check it out.)

Anyway, let’s say I am fired from my job. Or, I’m not fired but my boss doesn’t respect my contribution, or even seem to realize that I exist, and relegates me to a stupid corner of the company. Or, let’s say the company has a shitty year and kills my main project which was my only hope at becoming a manager in this lifetime.

If any or all of those things go wrong, but I have set my intention to focus on I don’t know design systems. Even if everything else changes, my intention and focus stays the same. If I have gotten involved in a community online related to my intention — to my passion, talent, interests, goals, whatever — I might lose my job or my promotion, but I can keep that community. They cannot take it from me.

My job might change — I could lose it. My company could change — it could go out of business. The trajectory of my career could be interrupted. No matter what happens I get to keep the aspects of it that I created by and for myself. That’s the result of setting my intention to create and maintain those elements of my professional identify.

This is the single best thing you can do to keep yourself safe in our current cruel, despotic, demonically unpredictable working world: Decide on something about your professional identity that really matters to you. Set your intention to promote or at least maintain it, no matter what else happens at work.

The corporate world dazzles with false promises of success and safety. Perhaps now more than ever, more people are waking up the idea that corporations can’t be trusted to take care of us from cradle to grave.

They can’t be trusted for kindness, fairness, sensitivity, or generosity. There is no guarantee that they won’t take everything you give them for twenty years or more, then turn around and cast you aside without so much as a phone call.

Don’t trust a corporation to be kind to you. Don’t even trust it not to be cruel. If you feel apprehensive about starting up a regular practice of investing in your own professional identity, stop worry about how, and start worrying about when.

Some of the people suddenly laid off in the last few years have lost everything. But a corporate employer can’t take away what isn’t theirs. I want you to be one of the people who, if their job gets taken away, have something truly valuable that’s left.

No matter how much the world changes, that’s one thing you can count on to stay the same.

Somewhere my career took a turn, and now I work with letters. More specifically, for the past fifteen years or so I’ve been working with and for people who make type. On the inside, we call it “the type industry” but you civilians just call them fonts.

A remarkable thing about the type industry is that very few people know that it exists. I always knew fonts were a thing, I think, but I didn’t give them much thought until it became my full-time job to sell them. Today I run a company called Type Network, which offers type from nearly 100 independent designers all around the world.

Many of the people I work with have been involved in type and letters for decades upon decades. In type years, I have the accumulated wisdom and experience of a toddler, and with this topic I am rushing overconfidently towards a flight of stairs.

With sincere apologies to the many who are better qualified, today I will briefly summarize my views on a topic that fascinates me:

What are fonts? Where do they come from? And why do they matter?

The Basics

It’s de rigueur to argue about whether to use the term “typeface” or “font.” On behalf of the type industry, I assure you that it doesn’t matter what you call them. We’ll all be tremendously delighted if you call us at all.

The distinction is a bit like champagne vs wine — it matters most to people for whom you are wrong no matter what you say. Truly, there’s more than one right answer, but none of them will make your slides look less shit.

It does not matter what you call them, but what does matter is who. The fonts installed on your computer were designed and programmed by people who do so for a living. These people are called type designers. They’re often organized in teams or companies called foundries since the time that each letter was cast in molten metal.

Anybody can download an app and make a font. Anyone with enough tattoos and piercings can learn to pull an espresso but there is no comparison to one made by a professional with a lifetime of practice.

Fonts made by professional type designers are a similar. The fonts pre-installed on your computer, for example, were produced to an extraordinary standard of quality and subject to extraordinary scrutiny by the OS maker before they were put there. Commercial-quality fonts, like those offered for sale or subscription by Type Network and many others, are primarily created by professionals who have spent many years learning and practicing the craft before investing yet more years in the creation of their first commercial typeface.

Professionals at Work

There are very good free fonts out there. There is also fine coffee being served right now in a Starbucks inside a Target inside a shopping mall, somewhere in America. People who are passionate about coffee won’t buy it there, probably. Is it because they’re snobs? Maybe. You’re also more likely to find great quality product in an environment where passionate, trained, experienced professionals are at work.

There are far fewer of them out there than we should like. Have you ever met a type designer? I think I have met most of them and they are wonderful people with an eye for detail, and usually a great sense of humor about both the ecstasy and obscurity of type. I guess there are probably less than 10,000 type designers working full-time at their craft world-wide. I hope and believe that number will increase in the coming decade, as more programs graduate more talented young designers and craftspeople.

In my opinion, the relative paucity of the font workforce relates partially to the relative youth of the digital type industry. That’s another topic best left to others, but briefly, you’ll recall that type refers generically to movable letters used for printing in a press. This was pioneered by Johannes Gutenberg invented the printing press, enabling publishers to produce up to 3,600 pages per workday, which compares favorably to my average output one of about two every seven days.

Digital type — what we now call "fonts” — has only been a commercially viable endeavor since right around the turn of the century. There was no market for fonts at scale until after the Apple Macintosh was introduced in the mid-1980s, followed by another revolution instigated by web fonts and CSS around 2000.

If you want to complain that the type industry has not yet found its place on the modern internet it helped create, well, it’s nothing the other millennials have not heard before.

In the scale of historic figures like Gutenberg, it is astounding to comprehend the impact that digital type has had on our society. By the 1980s, thanks to the genius and labor of thousands of people in hundreds of companies around the world, the meaning of the word “publish” changed forever. With 500 years of aggregated of innovations stacked a mile high, anyone with a computer could make typographic choices specifically tailored to the brand, mood, or the needs of the reader.

They could do that. But mostly, they don’t. Mostly they use Helvetica.

Why Fonts Matter

Fonts matter for a number of obvious, prosaic reasons related to legibility, suitability to purpose, brand, and more. These again are topics best left to others.

Fonts matter to me for reasons that relate to how I approach my work, how I think about my readers or users, and the kind of person I want to be.

There are reasons that I think you should care about fonts, but almost surely do not. Today I’ll talk about those.

Design & Craft

For me the most important reason to care about fonts is related to the idea of craft.

Graphic designers, UX designers, editors, typographers, software developers, and even social media marketers all practice a craft. Mirriam-Webster defines craft as something “requiring manual dexterity or artistic skill.”

To me, another thing that defines a craftsperson is their tools. Here’s an example: I drink coffee every day, but making it is not a craft. I use a department store coffeemaker, and mass-produced brand-name coffee that’s ground in a supermarket coffee grinder.

Others who truly care about their coffee call may take a much different approach, especially including their choice of tools. A carefully-selected boiler, brewer, grinder, tamper… you get my drift.

Professional designers of all types exhibit a similar hallmark: they select high-quality, purpose-made tools made specifically for their craft.

(Another feature craftspeople have in common is rank snobbery about terms and terminology, history, ways and means of production. Each industry has it’s own terroir and each their own terroirists.)

I have noticed while working on motorcycles that I’m still a terrible mechanic even if I buy professional-quality tools. Good tools probably do elevate the quality of my work in some respects. At worst I am less prone to certain errors while making them. Many of you, I am told, buy professional-quality kitchen tools in an effort to elevate the practice of their culinary craft. Your sous vide machine won’t turn you into Harold McGee, but it also won’t burn your steak.

Fonts are kind of like this! Professional-quality tools elevate the work of every practitioner, from amateur to expert. You will rarely find a professional designer — even less likely a professionally-trained or celebrated one — using default system fonts, or free fonts they found on the internet. And if you do, you will surely find them telling everyone of their displeasure about it.

Read This

For me, the most important reason that fonts matter is this: almost everything I make is text. In terms of what the reader will experience, the fonts I use are the most important choice of tool I can make.

Fonts are a design tool — like an architect’s compass or French curve — that impart their quality to the product of their work. A shitty designer like me will not suddenly be a great one because of the font I chose. But I will might get a little bit better!

It’s possible for a total novice to get pretty decent design results with nothing more than a great font. And in competent hands, a great typeface elevates a good idea to a sublime effect.

Made by Hand

Today, virtually all type is made by hand using digital tools. I am not aware of any AI-generated typefaces as yet, but I am eagerly looking forward to ignoring them when they inevitably do come along.

It’s said that a camera does not take the picture, a photographer does. In the same sense, type designers use font design software to create type, but fonts are truly made by hand.

Photographers, too, spend just as much time editing and perfecting photos after they’re taken as they do setting up and capturing the shot. The same is true of fonts — drawing the shape of the letters is only the beginning of the work. If you start to pay attention, you’ll learn a fascinating thing about type: the space between the letters is as important — sometimes more important — than the letters themselves.

A couple more fun font facts: a typeface family is composed of all the related fonts in a typeface, including different weights like regular, bold, bold italic, etc. and widths like expanded or compressed. A complete family might consist of dozens or even hundreds of fonts. Because the work of designing high-quality type is so technical and meticulous, it could take a designer years to complete a family. A large project, like one that includes Asian writing systems, could take a team of dozens of designers many years to finish.

When I use a quality typeface in my work, every letter that appears in that work is influenced by decisions made by a trained, talented craftsperson who has not only considered the exact shape of every letter, but the shape of the space between them.

I enjoy knowing that when I make something like a proposal using a high-quality font, every letter I set has been meticulously crafted by someone who really fucking cares about what they’re doing. That’s a way for me to put my own kind of hallmark on the work I create. I hope it shows1 that I care about what I create, even if I’m working on something that requires a little extra effort to care about.

What Matters Most

I meet a lot of people who say that they’ve always been drawn to fonts, and that they’ve long appreciated the beauty, rhythm, and proportions of nicely-set text. I’ve also met people who’ve said they find it difficult to tell the differences between one font and another.

To me, there’s one idea about fonts that matters most. It came to me via a 2006 essay on web design but it’s taken on some greater meaning for me lately.

The world is text. Nearly the entire internet is text. Virtually every device you use displays text. Literally everything you read is text! Most user interface is text. A huge portion of the information available to us in the world comes to us in the form of text. You cannot do any of that without fonts.

If fonts only matter a tiny bit, they matter a tiny bit to a huge number of things that are tremendously present and significant in the life of billions of people.

I want to work on something that matters, and to me that sounds like something that matters a lot.

When I finally watched the movie An Inconvenient Truth, I was startled to hear Al Gore using the expression “boiling the frog” to describe the failure of humanity to act on climate change because we’re terrible at understanding subtle changes over time.

It’s a jarring and ridiculous phrase that conjures a ridiculous image, but the lesson the metaphor is trying to impart is an important one.

For those of you willing to admit never having seen the film, the expression refers to a legendary science experiment:

An unlucky frog is dropped into a beaker of boiling water. It immediately recognizes the peril, jumps out of the water, and so it survives! Another frog, even unuckier, is placed in another vessel of water. This one is slowly brought up to a boil. Because the change is gradual, the frog is unaware of its impending doom. It sits patiently as its circumstances deteriorate.

It is boiled alive, and it dies.

Out of Control

I have been thinking a lot about the frog as I record the many alarming ways that our working world seems to be getting worse each year.

More evidence rolls in of the growing rift in our culture between employer and employee. Every month it seems another record is set for most abhorrent method of layoff, worst manager behavior, most obscene abuses of marginalized people, and the ongoing deterioration of work-life balance.

I’m especially saddened when I talk to Americans who feel trapped in a shitty job situation because of our employer-based approach to health care. A friend with cancer described to me her discovery that while it is nominally illegal to fire someone for being sick, our system offers no mechanism to prevent it — only the opportunity for someone who is discriminated against to sue after they’re fired (but before they die.)

I have heard from several people recently who are subject to various forms of surveillance at work. You might find in your next job that your activity at your computer is monitored, and a little status icon displayed to your manager (and your colleagues!) that shows how ‘busy’ you’ve been in the last little while.

In a company famous for panopticon-like surveillance of warehouse employees and delivery drivers, you might think that the knowledge workers in downtown skyscrapers would be exempt from the same scrutiny.

Notice the two-way turnstiles installed recently in the building lobby and on each floor? What’s that about?

This innovation is necessary if you’re in the business of keeping track of people both arriving and leaving. We’ve been swiping in to the office for 30 years, but swiping out is a relatively new phenomenon, and it’s necessary if you want to keep track of who has truly “returned to the office.”

I snorted with laughter when a previous employer described this technology as necessary to ensure the building was completely evacuated in case of an emergency.

An emergency like what? A union election?

Doing It Yourself

Most of the people I talk to in the corporate world feel trapped by it, in once sense or another. Maybe you’re shackled to your health insurance, or the visa that allows you to stay in the country. Maybe it’s your only shot at paying off your student loans. Maybe it’s a standard of living you and your family are accustomed to. Maybe it’s what you parents expect of you.

If you’re taking what you need from the corporate world, I support you. I’ve been there. You’re certainly not alone.

The real danger arises from the illusion we’ve created for ourselves that our performance in this system is rewarded with some kind of safety or stability.

Every year it’s increasingly clear that it is not.

There’s only one group of people who are consistently enjoying more and greater rewards from this system, and those are the ones at the very top.

The best way I can think of to overcome this system — to beat the game — is by taking back as much ownership and control of your professional life as you possibly can. This isn’t easy for everyone, and I don’t mean to make it sound like something you can achieve at the drop of a hat.

It takes some grit, a lot of determinations, and the investment of a lot of time to build yourself an “alternative” career that’s not tied to a corporate employer. I had the benefit of various kinds of privilege to help me on my way — less than some, but more than most.

Creating your own professional identity doesn’t have to be an overnight transformation. For most people it won’t play out as a heroic entrepreneurial training montage. Almost anyone who can find a little bit of time each week to invest in themselves can start building toward a future where you’re not at the whim of an anxious executive trying to meet their quarterly targets.

Here are a few ideas:

• Start freelancing — just announce it: “I’m available for freelance.”

• Start writing a newsletter or an eBook on how to be amazing at what you do

• Get involved in the networking organizations in your industry

• Dedicate some time to coaching or mentoring people

• Commercialize your hobbies using Etsy, eBay, or Squarespace

• Sign up for expert networks like GLG, Coleman, or Alphasights

• Start writing a paper or presentation to present at a conference

• Ask your manager if you can get more involved in recruiting, training, or professional development programs

• Talk with the people you know who aren’t in the corporate world and ask them how they did it.

Most of the people I talk to already have an idea about what “side hustle” they’d pursue if they had the time. Put an hour for yourself in your calendar every week. Mark the time as “busy” and start investing that time in yourself each week.

If you’re feeling that your corporate career isn’t going to get you where you need to be, you’re probably right. From some experience I can tell you that feeling doesn’t get better with time.

Get yourself started today. The frog is not going to boil itself.

This week I’m obsessed with the word fingerless. It pokes fun at the difficulty that the current crop of AI image generators to render a convincing facsimile of the human hand.

I feel like I’m noticing more and more AI-generated images of people in poses in which the hands are hidden or obscured by a prop.

That would show that the AI is both aware of its shortcomings and is working hard to conceal it.

Sounds like management material to me!

Anybody Home?

I complained to a client a few weeks ago that the profile introduction they’d written struck me as a bit fingerless. They immediately confessed that it was AI-generated text, and I thought “wow, nice going Matthew, you just made two people and a computer feel bad.”

My impatient and cynical mindset is of someone who has spent years and years reading resumes and profiles by the thousands. I have spent hours upon days, months upon years scouring a seemingly infinite database, searching doggedly like a loyal St. Bernard urgently searching for candidates buried but not yet lost amongst an avalanche of thousands of irrelevant applicants.

Like the highly trained but moderately compensated service animal, I grew quite adept at this simple and repetitive task. I’ll bet anybody with experience recruiting for big teams in a large company has developed a similar sense of their own capabilities.

On reflection, I’ve come to realize that what I’m looking for boils down to two important signals — like the faint fog of breath or a pocket of warmth in the snow:

1. Is this resume/applicant directly and closely relevant to the job I’m hiring for?

2. Does this person seem interesting, cogent, thoughtful, and highly engaged enough to hang with our team of extraordinarily talented and slightly maladjusted weirdos?

Two things that anybody who has been a hiring manager will tell you:

1. The vast majority of applicants are not in any detectable way specifically relevant to the job, nor do they meet the stated requirements, nor is no apparent explanation for why they chose to apply to it.

2. The vast majority of applications do not indicate authorship by someone with a active human personality, humanity, emotion, perspective, or ideas. We spent millions on software that requires applicants to re-enter all of their resume data, when in fact it might have been more productive to administer a simple Turing test.

The Opposite of Artificial

The uncanny valley describes the idea that as a simulated person becomes more realistic, they are fairly unobjectionable until just before they become nearly-perfect, when they become completely revolting.

A low-fidelity simulation is easy to tolerate — like Robby the Robot or Optimus Prime. If the simulation is any better than about 70% it provokes a feeling of discomfort or revulsion — like the cats in Cats! or Mark Zuckerberg, for example.

Is it just me? I often perceive AI-generated text as landing with a solid thud deep in the bottom of the uncanny valley. It might be hard to find anything specifically wrong with it, but there’s usually not much right about it, either.

(If this reminds you of anybody you work with, try asking them to click on the stop signs in a picture. Let me know how that goes.)

When I read a resume, an uncanny simulation of businesslike copywriting is exactly the opposite of what I am looking for. I don’t expect divine prose, light comedy, patentable ideas, or even perfect typography.

I can even tolerate a typo or two — if I can detect some real meaning in what’s being said. If it’s a composition of meaningless buzzwords, unobjectionable jargon, and boilerplate bromides, I’m just as likely to bin it.

What is the opposite of the uncanny valley? It’s anything you create using the gifts your petite but powerful human brain so generously provides.

Yours might be better than most, or it might be a bit worse. It’s hard to tell from here. You’re smart enough to use a computer, that bodes well! On the other hand, you’re reading career advice from a high school dropout, so.

Never mind that! Here’s the good news: You don’t have to be smarter than all of them — you only have to be more clever than the AI they’re using to avoid the tedious task of applying for a job.

Outsmart the legion of robotic wordsmiths using nothing more than the power of your own human mind (and one to three nonfat lattés, but never after 4 pm.) In the process, you are supplying the hiring manager with canny signals that indicate you’re well-suited to the position, and that you are a sentient human being with human fingers and toes.

Here’s how to do that:

• Supply an interesting anecdote that relates your professional experience to the job you’re applying for. I often advise people to prepare STAR or PAR-format anecdotes in preparation for interviews. These anecdotes are also deployed to excellent effect in the About section of your profile, or in a cover letter when you’re looking to get the attention you deserve.
  Example: “In my role at Acme Corp, I led the team’s adoption of time tracking software that drove a 25% increase in billable hours. Your job posting mentions that you’re adopting new design collaboration tools, and I believe this experience will be relevant to that challenge.”

• Some more than others, but some AI is weak in understanding late-breaking news, developing trends, and recent events of significance. By incorporating these ideas into your writing, you’re showing both that you’re keeping up to date on the industry and thinking about how to apply that knowledge in your next role.
  Example: “The role mentions the importance of user research. I am eager to discuss with your team the very interesting discussion taking place in the Product community about the role of a dedicated product research function vis a vis continuous discovery practices popularized by Teresa Torres.”

• AI-generated text often seems to avoid taking an opinionated position and favors instead a dry, even-handed survey of a topic. This is exactly what I do not want from a job applicant. Instead, tell me what you believe about something that matters, tell me why it’s important to you, and why it should matter to me. Have the courage of your convictions, without being a total blowhard.

  Example: “I’m a perfect fit for a role in which people management is treated as a first-rate professional discipline, rather than the second job of someone acting as both player and coach. I am a leader who can be depended on to roll up my sleeves, and there’s ample data to show that people want a manager who takes that role seriously. I’ve worked in both environments, and I’d enjoy the opportunity to learn how you perceive the role of managers in your environment.”

There’s a satisfaction to ensuring that every message you send during your job search includes an ingredient that’s essentially you.

Even when it’s repetitive, making that effort is something to be proud of.

Many years ago Arthur Conan Doyle wrote:

This fucking guy.

The words flowed from Doyle’s pen into the mouth of Sherlock Holmes, who ruminated on the importance of making an honest living. Holmes believed that few things were more important than a reputation earned through tireless and honest efforts.

At some point, someone — a manager, probably — rewrote the slogan as “Hard work is its own reward” and now it’s something we hear all the time.

But Doyle never said that. Holmes never said it. Know why?

Because, reader, it is not true.

Your Best You

People describe their work as rewarding when they’re performing at the uneasy intersection of the upper-right quadrant represented in this crude diagram — doing challenging work that we enjoy.

I am generalizing, of course! I had a girlfriend who claimed to love doing mindless, repetitive work at the office. She did statistical analysis of quantitative market research — processing scanner data from thousands of supermarkets. Her definition of “mindless” may have differed from mine.

I do think there are plenty of people would love to have a job that yields neither much resistance nor surprise. Personally, I suck at that. I fail most often at tasks that should be easy, when I find it difficult for them to sustain my attention, even when not much of it would be required.

I do my best work against an unattainable objective that must be attained by no later than yesterday. From getting to know some of you, I’m certain a few can definitely relate.

People who I find intelligent and interesting often seem happiest at work when they’re doing something hard. They seem to want work that is fairly challenging and report growing disenchantment with jobs that fail to utilize their full potential. They want the opportunity to learn and grow rather than to coast.

So, work is its own reward when the work is rewarding.

Is yours?

The Year 2000 Problem

There’s a stereotype that the Millennial generation is lazy and selfish. This drives me absolutely crazy because it always seems to come from people who are remembering a time when everything was objectively worse for everyone on the planet.

I cannot think of anyone I’ve met in the professional workforce who I’d describe as lazy and entitled.

It’s not hard to prove that today’s workforce has higher expectations for their managers and employers than we did 50 or 100 years ago. The National Labor Relations Act (the “Wagner Act”) was passed in 1935 in response to systematic exploitation of labor by industry dating back to the earliest days of the coal era.

(The origins of the act date back to the Colorado Coalfield War which, in 1913, was spawned by deplorable conditions endured by fuel and coal workers. The uprising itself culminated in many violent incidents. Workers were murdered in droves by interests aligned with their employers. The NLRA became law over conservative opposition1 which complained bitterly about any rule that “unacceptably obstructed” the free flow of commerce and that ignored the “laws of economics” that would render the U.S. industry vulnerable to the threat of foreign competition.)

I think a big part of these complaints come from the idea that our expectations of the workplace are higher, even though the work itself may have gotten easier, or safer. This is, I think, confusing two separate but related issues.

The most discontent workers, I’ve noticed, often complain the most about the aspects of their jobs that are not integral to the actual work itself. I am less likely to hear complaints that the workload is too high or the job is too hard. It’s more common to hear from people who complain that they are:

• Not motivated, recognized, rewarded, praised, acknowledged, or even noticed.

• Operating in an environment that is carelessly and ignorantly unaware or even hostile to what they consider basic human values.

• Expected to make performative but meaningless displays of “engagement” in team-building or morale exercises (like returning to the office) while also being asked to ignore the greater risk that they’ll in so doing experience harm from sexism, racism, worker exploitation, and/or becoming complicit in dishonest, amoral, and illegal business practices in the name of creating shareholder value.

All of that is Tuesday in a big American corporation, but it rarely distracts from our cultural worship of the wealth they manufacture for their executives, managers, and shareholders.

Does Anybody Want to Work

So what about the Boomer’s lament: “nobody wants to work anymore”?

Well, it’s true. It’s true if “nobody” means “people younger than me” and “work” means “work in a dangerous factory environment like we all did after the war.”

Actually — they do want to work! Corporate parking lots are not crammed with the automobiles of people who don’t want to work. They are not clogging the busses, subways, and expressways every morning. Corporations are not algorithmically reducing pay, cutting benefits, and firing the 15% of their workforces that simply have no more fucks to give.

The companies are, or were, full of hopeful and ambitious people who suffered through inhumane and alienating recruiting tactics, survived layoffs motivated by feckless greed and avarice, and are slowly being forced to return to offices even in the face of stark evidence that this is against the interests of everyone but their landlords.

If there’s anything that sets apart the workplace culture of the younger generation, it’s the sudden ease with which they’ve arrived at this revelatory idea:

It does not make sense to entrust the trajectory of your career to a corporation that can scarcely be bothered to treat you and your colleagues like human beings.

One Last Fuck to Give

Nobody wants to work anymore. Not under deplorable conditions, for evil corporations, for hypocrites, racists, abusers, assholes, or Nazi apologists. (A weird apparent exception for an employer who is all of the above.)

Nobody wants to breathe second hand smoke at work anymore! Nobody wants to be exposed to carcinogens, or be forced by their employers to break the law! What’s the world coming to?

Nobody wants children to work in factories anymore. They’re always complaining, and they always want to be fed!

Women don’t want to do more work anymore for less money. Nope, not like they used to!

People who are not white, or not the same religion as you, don’t want to be excluded from the workforce anymore.

People who were born in a different country than you don’t want to be worked to death while enriching the country they nearly died getting into.

They never did. Okay, Boomer?

Here are a few ways to think about the ideas that have changed what it means to work in our increasingly dangerous world at work:

1. When you encounter someone whose ideas seem entitled, or fragile, ask yourself this: Is the problem that I wish these people wanted those things less? Or is the problem that I wish I wanted those things more?

2. If you’re leading a team that seems difficult to motivate or inspire, try asking them what changes you could make that they might appreciate the most. Worried they might ask for something you can’t deliver? Don’t fret! That’s easily resolved by simply re-inserting your head even deeper into the sand. if you aim carefully, you won’t even have to dig a new hole.

3. If someone makes a big deal out of something at work that isn’t important to you, try to remember this: You literally just said it’s not important to you, so why not just fuck off for a bit while the grownups talk. Thanks!

4. People increasingly report feeling their contributions are not noticed, their victories are not celebrated, and the achievements are not rewarded. Is this entitlement and fragility conditioned by the continuous expectation of gold stars and participation trophies? Perhaps. Are gold stars and participation trophies cultural adaptations that make us safer, happier, more inclusive, and productive? Damnit, also yes!

That’s all for this week, thank you for reading.

Join us next week, we’ll talk about what the type of water bottle you bring to the office says about you.