Forty-two

Published: October 26, 2022

An introduction

Today I turn 42. (Sorry if you came here for a Hitchhiker’s Guide to the Galaxy reference; I’m a fan, but this post is purely personal, related neither to the book nor to pretty much anything else on this blog. This one’s just me, writing down things I’m thinking and feeling, for better or worse.)

Birthdays seem to fall in and out of favor with me, depending on my life’s trajectory at the time. In my 20s they were often unwelcome reminders of my continued failure to do anything with my life; in my 30s, as I found my way, I learned to savor birthdays, and see them as opportunies to reflect on growth, celebrate with loved ones, and look towards the future. (You know…kinda like a normal person.)

But between the birth of my son in 2019 and the beginning of the pandemic quickly following in 2020, I feel like my life has been in a sort of stasis for the last few years.

Or, maybe that’s not the right way to put it. Much has changed. But in many ways, it feels to me—as I know it does to many others—as though time has stood still for the last 3–4 years. The world changed; things about my life changed. But it doesn’t feel to me like I’ve changed—at least, not for the better. Certainly not in the way one might hope when looking back at the start of a new trip around the sun.

The biggest fight my wife and I had in the pandemic was at the start, maybe two weeks in. Both of us were sick of being at home, sick of having no space of our own, infuriated at the situation, and took it out on each other. Back then, staying at home all the time did that to us.

Now, this borderline reclusive lifestyle is our normal. We rarely go places. We see few people, and only infrequently. I haven’t eaten inside a restaurant or gone to a gathering of any kind—wedding, party, funeral, meetup, conference; nothing—since January of 2020. Our son only occasionally was sent back to daycare during the pandemic, and never full-time.

So in that continuous sameness, I’ve felt stuck for a very long time.

But yet, somehow, this also feels like the turning of an actual chapter. I don’t feel quite as frozen as I did turning 40 or 41 in the pandemic, one day bleeding into the next for months at a time.

If you count role changes, I’ve had three new jobs since my son was born. He’s grown from a newborn to an almost four-year-old with a mind very much of his own. He is a challenge and a delight (sometimes at once). I released two apps. We upgraded our house (“we” meaning “mostly my wife, whose eye for design and industriousness are both above mine”), sold it, and moved to a whole new city. We started moving into our new house 13 days ago (and with any luck, will be able to stop moving into it someday).

So maybe it’s that move to a new house, or the new city; maybe it’s something else; maybe it’s just naive optimism. But whatever the case, this year feels like the genuine turning of a page in a way the last few haven’t.

So, to commemorate that…I wrote this post. Part journal entry, part advice column, part observation, and admittedly, largely self-indulgence.

Read it if you like; take it as you will. It would’ve looked different a few years ago, and it will likely look different if I rewrite it in the coming years. Lots of it I haven’t really thought through deeply; all of it is contextual to me, right now.

Think of it as a sort of bookmark; let it be useful for what it is as long as we’re both here.

The inspiration

Chris Coyier is a colleague in the web space I’ve admired for a while. (If you’re not familiar, he’s the founder of both CSS Tricks and co-founder of CodePen).

Chris Coyier began a “40 for 40” series on his personal blog a couple years ago. Each year on his birthday, Chris posts a list of personal thoughts, beliefs, ideas, and things he’s learned. And while his words certainly carry far more credence than mine when it comes to finding success and building great things, I appreciate and admire his highly personal approach to blogging.

So in that spirit: I’m 42 years old today. With a hat tip to Chris’s series, here’s my (first?) entry. These are 42 things I think, know, or at least think I know.

42 for 42

Being unafraid to ask questions is my superpower. If you’re also the person in the room who can raise their hand without fear, do it. Somebody else in that room probably wants to know the answer, too, but asking it might cost them more. Say the thing.
1. The surest sign of any toxic environment is that questions are discouraged. Questions are a form of honesty and vulnerability.
2. Oh yeah, I forgot to mention: this thing is gonna have sub-points. Probably a lot of them. What, you expected me to actually cram everything into just 42 list items? Come on.
Honesty always pays off more than any lie ever could.
1. A mistake handled well, and honestly, is often more valuable than something that went well in the first place.
Keep what you create. Don’t ever throw away something you made. No matter what you think of it now, you’ll want to experience it again someday, and see the old you through new eyes. Trust me.
If there’s one thing every successful person I’ve ever known has had in common, it’s endless free opportunities to fail. I wouldn’t call myself successful, really, but I’m doing pretty well I guess, and I’ve been shitty at everything I’ve ever done, often for years at a time. Being shitty at things, it turns out, is a prerequesite for being ok at things.
1. If there’s a second thing every successful person I’ve ever known has had in common, it’s luck. (Which, arguably, is the same as the first one.)
A willingness to say uncomfortable things, have uncomfortable conversations, and sit with uncomfortable feedback is a skill well-worth developing, and one that will be useful in every relationship you ever have, both personal and professional.

Bonus points if the uncomfortable thing is issuing sincere apology.
If you don’t feel like you bring much to the table, you’re probably just at the wrong table.
When a professional quotes you a number that sounds high and you think, “I could just do that myself,” just shut up and pay.

Every project has at least three unknowns: how long it will actually take; what unforeseen obstacles you’ll run into; and the mistakes you’ll make doing it yourself (that you might not even realize you’re making).

Most of the time, you’ll underestimate all three. But regardless, it’s three bets, and if you know anything about gambling, you know a three-bet parlay doesn’t pay off 85% of the time.
Believing something won’t happen is the first step toward ensuring it does. No matter how unlikely or far in the future it seems, it will arrive.
Learn what motivates you, if for no other reason than so you know what doesn’t.
1. If there is an amount of money that makes an unpleasant job enjoyable, I have yet to encounter it.
There’s no medicine like sleep. We like to think we’re smart enough to overcome our animalistic needs through intelligence or willpower, but at the end of the day, we’re just slightly sophisticated housepets. We need rest, water, nourishment, exercise, and sunlight, and odds are we won’t feel right if any of them are missing.
If you can only be good at one thing, be good at communication. A huge subset of problems boil down to communication problems. (In fact, I think a compelling thesis could be written that all problems—or at the very least, all business problems—are fundamentally communication problems.) There are very few things in life that don’t involve some kind of speaking, listening, reading and/or writing.
Don’t ask people what they believe. Believing is easy. Ask people what they’re doing about it.
1. This is a good question to ask yourself, too. (I do so far less frequently than I should.) We tend to give ourselves credit just for thinking the right things, even when we don’t actually do anything about it.
Be nice to people. There’s plenty to be cynical about in the world, but most people are just trying to do what they genuinely think is best. And in any case, being mean to them won’t change their minds.
1. If you need a selfish reason for this: being a jerk gets a door slammed behind you way more often than it opens one in front of you.
Your truest self is who you are to someone who’s wronged you.
1. (Don’t take this out of context, please; there will be people you’ll need to cut off, and that’s fine. But when you feel like going off on someone who deserves it, I think what you do with that right says everything about you.)
Always make time to play, whatever that means to you. Play around. Goof off. Play games. Play with ideas and concepts, or just play with whatever seems fun and/or interesting at the moment, even if that’s literally nothing. Play is the sneakiest gateway to learning and development, and figuring out what fulfills you most likely means figuring out what you consider fun.
1. Never be above making fun of yourself.
Everything in life is balance. There’s virtually nothing in this world that’s totally bad, or entirely good, either. Most things are a sliding scale of benefits and tradeoffs; bad when there’s too little or too much, good only in the range of just enough.
The difference between helping the user do what they want, and trying to nudge the user to do what the company wants, is the difference between good and evil software (and usually, good and evil companies).
HR is not your friend. Ever. The only reason anybody in HR will ever help you is if it helps the company. Don’t be deluded into thinking otherwise, no matter where you work.
Most things only matter as much as you decide they do. What you focus on, you give power to. “Nothing is as important as what you’re thinking about, while you’re thinking about it.”
Romance is fine, but don’t fall for the idea of soulmates, or that things happen for a reason. Both are self-fulfilling prophecies; it’s easy to retcon your own life to fit whatever shape you want, or to find a meaningful pattern in a smattering of chance and circumstance.

It’s nobody else’s job, destined or otherwise, to make you happy. There is no meaning or destination other than what you choose. To believe otherwise is to relegate yourself to the role of a mindless robot, going where it’s programmed to go, happy when it’s programmed to be, with no choice or autonomy.

It sounds better the way they put it in romantic movies, but that’s what it is. Own your life. Choose someone who chooses you, because you know what? That’s better anyway. Don’t let random luck and circumstance own you just for some charming ideal.
Never burn bridges. But also, don’t put up with people who do.
Guard the times you’re alone with your thoughts. Drive with nothing on the radio; do yard work in silence; take walks without headphones; listen to the sound of the shower running. Distraction is mental fast food; the solitude of your own thoughts is sustenance.
Many victims of abuse (of all kinds) become staunch advocates for that form of abuse, believing it helped them somehow. (Apparently, our brains like us to believe that our suffering is not without reason.)

This is true anywhere there’s a power imbalance, so naturally, it’s rampant in tech. But no matter where you go, you’ll find people who think they’re benefitting you by passing on their trauma. Do your best to dismantle these systems if you can, but in any case, try to see the people perpetuating the system as victims of it.
There’s no such thing as lazy. A person you think is lazy is most likely just facing obstacles you don’t see, or forced to make tradeoffs you don’t understand. (There’s a whole book on this. I haven’t read it yet. But I still firmly believe it.)
Being a parent—especially to a newborn—is the hardest fucking thing on the planet.

Don’t get me wrong; parenting is incomparably rewarding, and my son is without question the best thing in my life. But being a parent is also on a tier entirely of its own as hands-down the most difficult thing I’ve ever done. (And I’ve only got one kid—and a pretty good one, at that.) Don’t judge parents.
Getting older is mostly great. Don’t be afraid of it, especially not in your 20s and 30s. You have only begun to become who you are. (Do take care of yourself, though.)
All experience is relevant experience. Don’t under-value yourself; all knowledge transfers. Being in lousy bands taught me how to be in front of people. Being a waiter taught me how to manage group attention and expectations. Playing video games taught me to keep trying. Working in tech support taught me to ask the right questions and give helpful answers. All experience is relevant experience.
With very few exceptions, the hard things to do are the best things to do, and eventually, hard things always pay off like they should.
Acquired tastes are worth acquiring. (Hat tip to Wes Bos.)
1. Every taste is acquired. We get it backwards and think we regularly consume what we like, but in reality, it’s the opposite; we like what we regularly consume.
  
  Some things just won’t be for you, and that’s fine. But odds are, if you aren’t into something, you haven’t given it enough of a shot yet (and conversely, whatever you like is probably just what you’re most familiar with). This is especially true of foods; picky eating is willful ignorance.
2. Come to think of it, most of my favorite things are things I didn’t like at first.
3. If you don’t like the way somebody else’s food smells, that’s on you, not them.
Say no when your gut tells you to. There’s massive empowerment in just saying no to things, and your gut usually knows when your head is trying to talk you into something it shouldn’t.
1. That said: learn the difference between your gut and just plain fear. Don’t listen to fear.
Don’t make people use their headphones. Use yours. Headphones are for people who want to hear their thing, not for people trying to drown out somebody else’s thing.
1. People who have the volume up on their personal devices in public are sociopaths.
You can’t change a bad hire to a good hire with policy. Make rules to protect your best people, not to mitigate your worst ones. You can’t fix people with documents.
Context is everything. There’s no advice that will apply in every situation, no move that’s always a good one, no evil that’s always bad, no truth that can’t be made into a lie by the air it’s spoken into. It always depends. Wisdom is knowledge + context.
1. That includes this list. Not all of it—or any other advice—will always apply to you.
Learn to question your feelings. The ability to think rationally and honestly about your own emotions, where they come from, and whether they’re genuine is a crucial and undervalued skill. Being able to acknowledge what we feel may be incorrect, misleading, or hollow is absolutely key (especially in a world where entire industries have been built on manipulating emotion).
The more wealthy a person is, the worse of a human they are. There’s some variability from person to person, of course, but no matter who you are, there’s only so much money you can accumulate before you start making moral compromises, and it’s probably a lot less than you think it is. (It’s way, way, way less than a billion dollars.)

For the most part, wealth is exploitation. Maybe there’s a world in which that’s not true, but as long as we’re in this capitalistic system that pushes money inevitably upwards, wealth always has been and always will be exploitative on some level. The higher you get, the less you care. It’s pernicious, it’s intoxicating, and it corrupts everybody near it. There is no amount of wealth that will ever feel like enough to the person who has it.

I know this for lots of reasons. But the main one is: there are few big problems left in the world that money can’t solve, and wealthy people aren’t solving them. (In fact, wealthy people created most of them, and in many cases, continue to make them worse for the sole purpose of wealth.)

[Edit: please don’t mistake this for a zero-sum mindset. That’s wrong. I don’t believe in zero-sum, but capitalism generally does. The current system exists to make the people at the top many, many times more wealthy than the people at the bottom, even though nobody at the top works many, many times harder than the people at the bottom, and it’s next to impossible to generate wealth in ways that don’t take part in that exploitation.]
Growth is death. You can’t be everything at once. Embrace the idea that sometimes, you need to sacrifice parts of your old self to allow room to grow, and don’t be silly enough to think of those tiny deaths as being untrue to yourself, or giving up on your dreams, or some other such nonsense like that. Prune those branches.
Never have a serious personal conversation over any text-based medium. If the relationship and the conversation are both important, use your voice, or wait until you can.
If there’s one mistake I’ve seen everywhere I’ve ever worked, it’s cutting costs. Taking anything away from customers in order to pad your own bottom line, no matter how negligible or invisible you think it is, is the beginning of an inescapable death spiral.

I saw it in just about every bar and restaurant I ever worked in, I saw it in marketing and design firms that prioritized churning out maximum content at the minimal cost, and I’ve seen it in plenty of tech companies who have slowly and quietly stopped listening to what their users have to say to save a few bucks on infrastructure or whatever.

I’m sure it looks great on paper when you can say you saved the company x dollars by buying cheaper beef, or taking away employee benefits, or outsourcing to a foreign company, but the people paying you absolutely will be able to tell the difference.
Growth and profit are byproducts of success, not its definition. Making them the goal in itself is draining the ocean to catch the fish.
Listen to your support team, or whoever is closest to your customers. Make it somebody’s job to get feedback from users to the people making your product, and make it somebody’s job to make sure it’s properly recorded and prioritized.
1. If it’s not somebody’s job, it’s nobody’s job.
Religion is fine, but don’t believe anybody who says God talks to them. I’ve known dozens of these people throughout my life, and every single one of them, directly or indirectly, was just hearing what they wanted to hear.
Listen, and educate yourself. Listen especially to people who are different than you, who’ve had different experiences than you, and educate yourself on things outside your own bubble of familiarity.

I’m a very different person than I used to be, for the better. I once said, did, and believed things I now find shameful. I didn’t think I was racist then, but I was. I didn’t think I was sexist either, but I was. I only changed and grew through time, and education. I was lucky enough to have friends who made me sit with uncomfortable truths, and to go to college, where I was exposed to a wider range of experiences and learning than I would’ve encountered otherwise.

If you can only do one thing, for yourself or for others, make it education.