Lessons I Had to Learn the Hard Way, 49th Edition
The Weekend Windup #24 - Reflections, Cool Reads, Events, and More
I turned 49 yesterday. Every year around my birthday, I take stock of what is actually working, what is noise, and what I’ve had to learn the hard way. This isn’t meant to be a “happy birthday to me” post, and it will be a bit different from my typical data/AI-oriented themes, but that’s for the better. The last few weeks have had some doozies, and I think we need a break from the typical “Joe Rant.”
A lot of people ask me for advice (career, health, life, etc), so I figure this is also a good place to lay out some notes, rather than repeat myself. There are lots of books from very smart people offering advice, with varying degrees of applicability to your life. What I’ve learned is no matter how much you read and get advice from others, you’ll have your own experience learning things the hard way. I guess that’s how it’s supposed to be. What I write here is only my perspective. Your mileage will vary.
The TL;DR for me right now is that life got better when I stopped optimizing for appearance and started optimizing for durability, focus, relationships, and real work.
I’m not sure how old you are, but let me start with the bad news. If you’re in your 20s and 30s, science shows that your worst years are ahead of you. If you’re in your 40s, at least statistically, you’re smack dab in the middle of this trough. This is called the “rush hour” of your life, usually culminating in your midlife crisis. It sneaks up on you. For me, it happened in my mid 30s. I was unsure of what direction to take my career, but I had a nagging sense that I was going the wrong direction - shitty bosses, pointless jobs. What motivated me was raising new children and feeling like I needed to do more.
Around ten years ago, I decided to make a change. I quit my job, went off on my own, and haven’t looked back since. I’m not saying this is the wisest thing to do, and you should do it only if you’ve got financial reserves and something to transition into. You might not be in a spot to do this for a number of reasons. But we had the financial means to make this move, I wasn’t getting any younger, and so it went. I’d tried to go off on my own a few times before, but it didn’t pan out. I realized that in those failed cases, I was impatient with the process, expecting things to happen immediately. Making a change like that requires more than just a simple ROI calculation. You need to realize you’re also changing who you are - your temperament, attitude…everything, really. That metamorphosis needed time to build, and by the time I was ready to really make the jump, I had changed internal self-talk and expectations so I knew I was ready. Again, your situation will be different. Whatever big decision you need to make, just know there’s never a perfect time. You’ll never be totally ready, but you’ll know it’s the right decision to make, and have enough trust in yourself to see it through.
Back to the midlife crisis. It does get better. For me, it got better in my early 40s. Today, the worst is behind me (I might also be delusional). Here are some lessons I learned the hard way.
Do More By Doing Less
We’re told that we must always do more. We need more projects, more money, more fancy toys to impress our friends who also accumulate more fancy toys to impress their friends. More this, and more that. Most problems in work and life are not solved by adding more inputs, commitments, goals, or complexity. Here’s what happens.
More projects can mean less progress.
More information can mean worse thinking.
More ambition without selectivity becomes fragmentation.
More money, more problems (so does a lack of money).
You need to cut out the things that aren’t serving you. Subtraction is an adult skill that you learn once you’re done saying “yes” to everything, and realizing the most powerful word in your vocabulary is “no.” The second most powerful word is “enough.” Know there’s an opportunity cost to every decision, and most things simply aren’t worth doing. Be very selective. This means understanding that:
Not every opportunity is worth taking.
Not every job is going to be perfect.
Not every smart person is worth working with.
Not every audience is worth chasing.
Not every expansion is growth.
No deal is better than a bad deal.
Say no to most things, and know when you’ve got enough. Striving toward goals (especially those put up by other people) can feel like chasing a mirage, because it is. Be clear on what you want, and be very selective with your choices and actions.
Energy and Attention Are More Important Than Time
People talk about time management, but the real constraint is energy, clarity, and attention. If the luxury were simply having more time, what would you do with it? How often have you been on vacation and seen the people around you staring at their phones? I’ve been guilty of this, staring at my phone and missing out on the places I visit. It’s a shame.
Back to the less-is-more advice, I’ve learned that optimizing my energy levels gives me the clarity and attention I need for various pursuits. A focused two hours beats a scattered ten.
People say that time is your biggest asset. It depends on how you bring yourself to the occasion. You can have all the time in the world. But if you’re wasting it, who cares? Energy gives you the ability to leverage your time wisely. Protecting energy is not indulgence. It is a responsibility.
On that note, what you pay attention to becomes your days, and your days become your life. Too much internet and doomscrolling make you reactive. Too many open loops destroy depth. The modern world is optimized to fragment you. This is why I like to unplug, read, write on paper (and now on a Remarkable tablet), and go for walks without my phone. Guard your mind more aggressively than your calendar. This will also increase your energy levels.
Energy in, energy out.
Real Work Compounds. Performative Work Does Not.
As I’ve said before, there’s a lot of LARPing in the business world. Lots of people cosplaying business - getting promotions, moving up the ladder, working at a fancy company, winning “awards,” and other superficial and performative achievements. But this is not real work. There is a difference between looking productive and producing durable artifacts.
Do the work that compounds over time. Read books. Write articles and books. Generate new ideas and products. Build things. All of this work compounds over time. Your reputation will compound, too. On the other hand, shallow busyness and business cosplay do not compound. It’s a treadmill that makes you run faster and faster, but you’re stuck in place.
This goes back to when I took a bet on myself and left my job. I was tired of pretending to care about a job and workplace where I was phoning it in. I wanted to do real work in areas that I cared about. Years of real work got me to where I am today, and I still feel like I’m just getting started. You’ll know when you’re doing real work because it won’t feel like work. It will feel like your obsession and mission in life, and you do it because it’s uniquely you. At some point, you need to start playing your game, not the game dictated to you by others.
Your Body Keeps the Score…and the Upside
I’m lucky to have been an athlete all of my adult life - climbing, Crossfit, lifting, a mediocre runner, hiking/trail running, etc. Unbeknownst to younger Joe, that’s paid off big time! As I get older, I realize that aging well is not passive. You need to stay active, even if it’s just a daily walk (or whatever you’re capable of doing). Strength matters. Endurance matters. Mobility and recovery matter. Diet matters. You can get older and better at the same time if you train with intention.
On a personal note, I’m still feeling stronger, fitter, and more capable than many younger people I train with in the gym. It’s not a brag, and it’s also not luck (well, maybe it’s partly genetics). The real win is accumulating these gains over many years. If you’re younger, find a fitness routine you can do for years. It might be yoga, lifting, running, etc. But also learn areas outside your specialty and become a well-rounded performer. If you’re a runner, get stronger. If you’re strong, get endurance. All of these feed on each other to help improve your overall fitness. By the time you reach my age, you’re more likely in maintenance mode, trying to preserve whatever you’ve built over the years, as the inevitable decline of strength and power sets in. Decline is real, but so is staying active.
Relationships Are the Actual Scoreboard
Work matters, but it is not the final measure of…much of anything, really. While your friends and family might think it’s cool you’re successful at work, they probably don’t care as much as you do. And if you managed to be extremely successful, you might regret some of the things you had to set aside to get there, whether it’s time with your partner and kids, time with your friends, or time in your community. You won’t get these moments back. I know, as I’ve done it to myself, having missed key events in my kids’ lives to “go on a work trip” or some other lame excuse. To this day, these are the things I regret most. Because I’m a workaholic and have an insane travel schedule, I’m working hard to curb this behavior.
My lessons here are twofold. Presence matters more than half-hearted good intentions. Success that comes at the cost of your closest relationships is failure.
I’m sure there will be many more lessons in the years ahead. And I’m unsure if any of this applies to your life or situation. Again, I can only write from my experience and perspective. The only thing I can be sure of is that every year, I’ll look back on what I’ve learned, use what works, and throw away what isn’t serving me anymore. As I do, so you should do too with whatever you read here.
Have a great weekend,
Joe
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Cool Videos and Reads
In this conversation, I sit down with Tim Delisle and Chris Crane, co-founders of 514, to discuss bridging the gap between software development and data engineering. We cover their experience leading global data engineering at Nike and why software teams are increasingly taking ownership of heavy analytical workloads.
We also dive into how they are building the Moose Stack to give developers a local-first, code-first analytics experience. Finally, we explore how AI co-pilots are acting like an "army of interns" to fundamentally change how we write code , and why the "personal data lake" might be the future of privacy and local compute.
Check out 514 & The Moose Stack
Here are some things I read this week that you might enjoy.
Investors spill what they aren’t looking for anymore in AI SaaS companies | TechCrunch
JSON Documents Performance, Storage and Search: MongoDB vs PostgreSQL
Has the internet stopped producing mega stars?
Harness engineering: leveraging Codex in an agent-first world | OpenAI
A GitHub Issue Title Compromised 4,000 Developer Machines | grith
AI will fuck you up if you’re not on board
EBITDA adjustments are getting ridiculous - PitchBook
When Using AI Leads to “Brain Fry”
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I love the reflection, Joe. Once I stopped caring so much about what other people thought about how I lived my life, I actually started living my life. It's definitely easier said than done, but it's an actual practice, just like the internal reconfiguration that you have to go through when you finally go on the path less traveled. Happy 49th birthday. The big 50 is on the way :)
Amazing. Best thing I've read in a year, you're an inspiration.