I’m not big on the memorializing of celebrity deaths. There is enough pain and suffering with those I know personally. I normally say nothing and move on.

But damn. Kobe Bryant.

I remember watching him play in the McDonald’s High School All-American game before he was drafted. I remember him entering the league in 1996, right when my sports first love was moving from baseball to basketball. I remember his swagger. I remember him trying to take the mantle from MJ. I remember him doing it.

I didn’t know the guy personally. I have no idea whether he was a “good” guy. I can tell you that his determination to achieve greatness was insane. I never thought anyone would match MJ’s drive for greatness. But Kobe did. That is inspiring.

Kobe has been a fixture in my sports fandom since age 12. His myth and mystique color all my sports conversations, and even the way I think about life beyond sports. The stories are legend.

There are a few sports moments I’ve experienced that transcend whatever they mean within the game. Moments that left a mark. Moments I’ll never, ever forget. Kobe’s last game was one. It was the final day of the NBA season. I was flipping back and forth between the Warriors chasing an historical 73rd win, Steph Curry chasing yet another 3pt record, and Kobe’s last game. I assumed Kobe’s Lakers would lose a meaningless game, Kobe might hit one or two memorable vintage shots, and get a moving standing O and maybe a little speech.

You never could’ve convinced me that by the 4th quarter, I’d be completely ignoring the Warriors game, eyes glued to Kobe. I’ve never seen anything like it. No playoff contention. No records on the line. No bigger glory for a big performance. The man’s legacy was sealed. He didn’t come out and goof around high fiving everyone. He laced up and came out playing to win the game like always. But his teammates just wouldn’t stop passing it to him. They wanted the most they could get. And Kobe pulled out the most Kobe performance ever. What he did that night surpassed in my mind even his 81-point night years earlier. He was in his prime then. Feeling it.

His last game wasn’t Kobe feeling it. It was Kobe willing it. He looked so tired. He almost – almost – looked like he didn’t want them to pass him the ball. He was like a boxer in the final round, just trying to stand, summoning everything to throw a punch that looked barely strong enough. And the shots kept falling. Not only was he scoring, his team was pulling closer from a game they’d trailed and looked to be over. He. Just. Kept. Hitting. Shots. It was out of control. Every release was a cosmic spark. You could feel it in your bones. He ended with 60 points. At age 39. After a 20 year career. 60 points of pure exhaustion. Kobe gave every last drop his mind and body could possibly give as a basketball player.

Oh, and the most Kobe part of all? They won the game.

I’ve re-watched that full game a few times. And the highlights several times. And the final quarter many more. I’ll never forget that. There was something in that performance that rippled through the universe. It changed the nature of what’s possible. That game spoke to me on a deep level. It still does. Thank you for that Kobe.

When I yell, “Kobe” while tossing a wad of paper in the trash, it’s just a little different now. Something’s missing from the universe. A little piece of Greatness is gone.

RIP.

Sunday so empty

No fantasy or Lions

Why do I miss pain?

You can read this and all issues if you subscribe here.

(It’s $5 a month to keep me accountable and make it feel super exclusive only for big time ballers.)

Strength in memories
Identities
Now come back to me
As unity
The stuff that moved me
When I was young
Holds a power still
Can come undone
Objectivity
Is no option
This one life that is
Where I stopped in
Can’t get out of what
Gets inside me
Wired into systems
Can’t divide me
Into little parts
Cleanly broken
Instead I’m fused in
Things heard, spoken
From day of first breath
To day of death
An unfolding arc
That beckons breadth
Unseen not unfelt
This changeless core
Animated by
The call to more
So bring it home now
Place where it starts
Is where to gain more
Depth for new parts

I just talked to an entrepreneur friend of mine and he had a great phrase for what building a company is like.

Playing chess with the market.

I love this because building a business isn’t so much about right and wrong, luck or skill. The outcome is determined by a series of moves made in response to another player whose mind you can never read. There are causal chains, but they’re all theoretical. They assume certain actions by the other player that may or may not happen. In fact, it’s like a never ending series of chess matches against a rotating cast of random opponents, where moves that worked the first five times stop working the next, and patterns you learned change.

This framing reveals how hard it is and make the challenge exciting. It also depersonalizes it a bit. Of course you won’t get every move right or win every game. But you try to learn each time. Treating it like a game is a huge cognitive relief.

I grew up in a pretty conservative Midwestern protestant situation. I was homeschooled and church was a big part of our social life. There are plenty of things to mock and joke about in this milieu (and I do!) but there are some under-appreciated benefits.

There are benefits to not getting into sex, drugs, and partying as a young person, but that’s not what I’ve appreciated most. As time has passed, I’ve seen other benefits I didn’t think about at the time. I took them for granted and assumed they were omnipresent.

Those benefits are philosophical. Epistemological, not aesthetic.

While not ubiquitous in Christian upbringings, the particular niche of Evangelical Protestantism I came up in was very focused on intensive Bible study, theology, and examining questions of meaning, free will, good and evil. There was an expectation that you should be able to logically prove every belief, examine arguments against it, and wrestle until you had coherent, non-contradictory ideas. Discussing claims made in sermons and questioning their accuracy, alignment with scripture, or logical consistency was normal.

There was utmost respect for reason and analytic philosophy. Difficult scriptures were studied in depth, arguments on all sides examined, original Greek and Hebrew checked, historical context learned, and commentaries consulted.

I always enjoyed this. I liked studying the Bible and various theologians. I loved their debates and disagreements. I was fascinated by questions of fate vs. free will.

There was a sense in which we Christians always felt the need to, “Be ready always to give an answer for the hope that you have”. You didn’t just believe stuff, it was incumbent on you to really examine it and understand it, and be able to explain it even to antagonists. I remember diving into apologetics and preparing to be attacked from all sides by classmates and professors when I took college philosophy classes.

I was disappointed.

Everyone in the class was an atheist (this was the very early 2000’s, before the resurgence of spiritual interest common today), but reflexively so. It was a default setting. No one had any arguments. None of them seemed to have examined anything. And it didn’t seem to trouble them. I was looking for some fights! I wanted to challenge and be challenged. It was as if everyone – even those wanting to major in philosophy – didn’t much care to examine the most fundamental questions of being and existence and morality and meaning. They would laugh at or dismiss ideas sometimes, but freeze up if asked to explain.

This was a real shock to me.

I had one TA who asked any theists to raise their hand. I was the only one. Some people snickered. He said, “Don’t laugh. All the best analytic philosopher were theists. Aquinas would run circles around most of you. Do you know why? Have you engaged this stuff?” He was an atheist moving towards agnosticism, but he had mad respect for anyone who did good philosophy (I later discovered he became a Bhuddist and quit academia. He was my favorite philosophy professor, so I’m not surprised). There was one other philosophy prof who was a Christian, and everyone was afraid to debate him. I think he dreamed in airtight symbolic logic.

I didn’t realize at the time that the intellectual tradition I’d inherited in all those Bible studies and debates and books was straight from Aristotle. The more I studied the history of philosophy, the more I realized I wasn’t the one who was wacky or out of step. Questions of God and religion had been taken the most seriously by the most serious thinkers. The whole Protestant project was, in a way, a big philosophical “eff you” to those who said don’t think for yourself, just act out the rituals. It was a celebration of reason. (This is not to say Orthodoxy and Catholicism do not retain a lot of sound philosophy, or that Protestantism always does. All religion tends to have interesting ideas at its core, and devolve into a less rigorous social movement subject to capture as it grows).

I often wonder how people go about their lives acting on important core ideas and assumptions without seeming to have any interest in or feel any necessity to examine, define, and make logical sense of those ideas and assumptions. Being wrong is one thing. Being uninterested in examining tacit truth claims is another.

I’m not looking down on people who are uninterested in or not conversant in inquiry into these things. I just don’t understand it. And because I value getting to the why of things, I am very grateful that I grew up in an arena that prized the most foundational questions, and expected one to be intellectually and morally accountable for their own beliefs – and comfortable being a bit of an outsider.

I must’ve seemed so weird. An early teen spending hours underlining, cross-referencing, diagramming, checking translations in my Hebrew-Greek keyword Bible, writing arguments and counter-arguments. Fortunately in my social circles, it wasn’t weird at all.

My brother just turned 38. He said getting older was more difficult at 35 and 36, but now he’s adjusted to it and doesn’t mind at all.

I’d never thought about this explicitly, but it felt true for me too. I’m 36. In my early 30’s, I still felt young and, like all the rest of my life up until then, never really thought about age. But age 34, 35, and 36 all seemed to be big turning points. Somewhere in there, framing changes. Nothing I do in my life from here on out has any additional value for being done “early”.

Of course we all love being thought highly of by others, but being seen as ahead of my peers by the outside world isn’t the real thing I cared about. It’s not just a sense of drive, speed, and trajectory. It’s a sense of freedom and looseness. Early in the game, you feel you’ve got enough time to pivot and make up for just about any crazy thing. There are infinite re-inventions and new directions. The course is so early that small deviations can result in huge changes in the long term.

Visualize it in a really practical way we’re all familiar with. Investment projections. You’ve seen those charts that show likely return at age 70 or whatever of $100 a month invested from age 20. If you don’t start until 30, the difference at 70 is immense. (At historical rates, we’re talking $3.9M if you start at 20, and $1.1M if you start at 30. Play around here if you want.)

Now apply that not just to finances, but everything. The later you go, the smaller the end of life impact. There is a sense in which leverage decreases as you age.

But that’s not all there is. Leverage also increases, because you begin every day with a larger accumulation of human capital than the day before. You have more to deploy on every move you make. You don’t start from zero. You don’t have as much time as when you were young, but you have more of everything else.

After turning 36 last year, and especially after moving into an advisor role for my first company Praxis at the end of 2019, I no longer feel pained by aging. I closed chapter one in The Life and Times of Isaac Morehouse (a running joke with my kids). Young man Isaac started and built a company, made a difference, overcome a lot of shit, had fun, and handed the reigns to the next generation. Medium-aged Isaac is just beginning. And he’s got all kinds of assets no young man ever could.

It’s a great feeling. I like aging. I like change, and I’m not super sentimental. No, I don’t like the increased need for body maintenance, but everything else about getting older is fun, or at least not unfun. I’ve more than made my peace with it.

At least for now. There’s probably a next tier, maybe when my kids start to leave the house and set off, where I’ll have to make peace with a new stage.

Titans versus Chiefs

Smart, simple, boring, versus

Complex, exciting

I recently ran a workshop for Praxis participants on job interviewing. It was so so. I didn’t do a great job and wasn’t particularly pleased with the outcome.

I used to do workshops like that a lot. And I got pretty good at them. It’s been several years and I only took about 5 minutes to prep, assuming I’d pick right up where I left off. But apparently, running a workshop is not like riding a bike.

It got me thinking about different types of learning, different types of know-how and mastery. It doesn’t matter how many years it’s been, riding a bike and swimming are no harder. You learn them once and the know-how sticks, without decay.

Why aren’t workshops like this?

It can’t be due to the physical nature of biking and swimming. Because basketball is not the same. Even if the form of a jump-shot stay largely intact (only if you put in enough reps when you learned, even then the form can start to decay a bit), the shooting percentage plummets after long absences from the game. It’s true, getting the percentage back up to playing-days average is quicker than originally getting to that average, but not very quick.

And language is not a physical task, but seems more like bike riding. I can’t speak Spanish. Until I visit a Spanish speaking country. Then the same proficiency (not very, but enough to get around) I first learned as a teen comes back in almost an instant, maybe an hour or two. Same for accents and impersonations and parts of songs. If I learned years ago, it never really decays. Worst case, I forget, hear it one more time, and it’s right back.

I can’t spot an easy pattern in the, “Need to stay in practice to keep it sharp”, and, “Never really decays”, types of know-how (I’m not saying knowledge, because that seems more like info only, and I’m not saying mastery because I’m not a master at most of these examples). It’s like different kinds of know-how have different rates of entropy, and different refresh rates. It’s a lot easier for me to get back to up to snuff with running workshops than it is with basketball (even if I control for the physical decay of being slower with age. Shooting percentage alone is harder to re-acquire).

It makes me wonder about other kinds of know-how that I’ve never really ignored for long periods. What about social intelligence? What would happen if I was a hermit for half a decade? Would I lose my ability to work a room? How about writing? I’ve never not written regularly since I first learned. Is it more like bike-riding or basketball? If lost, how fast could I refresh and get back to where I am now?

I’ve always been fascinated with the process of learning, the act of creation, the art of obtaining tacit and explicit knowledge, the interplay of the conscious and subconscious in the brain, and the idea of “embodied” knowledge.

The more I think and dig, the less I understand the human brain (biologically) and human knowledge (epistemically and ontologically).

PS – It’s probably also true that I am not a perfectly accurate judge of my then vs. now skill levels. Self-awareness changes, and memory is imperfect. It’s likely I remember myself a better basketball player or speaker than I really was. It’s comforting to think after a lackluster performance, “It’s just because I’m rusty”, instead of “That’s about as good as I’ve ever been.”

The latest from my private weekly newsletter on building a startup.

Read and subscribe here.

I’m trying to get better at preparation.

It may seem weird, but prep gets more important the further I go in my career, not less. It’s true that with more experience winging it is easier. But it’s also true that with more experience there are far fewer low-stakes, dubious value activities.

I’ve gotten expert at saying no. That means the stuff I do is disproportionately high value, or high potential. If I’m going to do it it’s gotta be worth doing.

And if it’s worth doing, it’s worth prepping.

Even a 20 minute phone call is worthy of at least as many minutes of prep, background, research, outlining, goal-setting, and getting in the right frame of mind. Maybe two or three times as many.

I’ve only begun to realize this, and it’s a challenge. I’m a snap judgement gut based wing it kind of guy. But the prep pays. If I’m going to show up, I want to do it with intention and focus. I want to know what I’m trying to get.

I’ve been thinking recently about some of the jobs I’ve had.

When I was 15, at the start of the summer, I wanted a new job. I’d been bagging groceries at Harding’s Friendly Market during the school year, and wanted to make more money (I’d gotten a raise from the $5.15 minimum wage to $5.45/hour).

I scanned the classified section of the Kalamazoo Gazette, and found an ad for help on a housing construction crew. I called the number, which I’d later discover was the boss’s Nextel cell phone in a thick protective case that he kept on speaker phone hanging on his hip while he yelled into it, and could barely hear well enough to make out his few questions. He told me to come meet him onsite tomorrow in a new housing development.

I didn’t have my license yet, so my mom had to drive me there. I walked up and he seemed a little baffled at how young I was. He seemed to think it weird I’d want this job, and he tried to make it sound as crappy as possible. I told him I was really excited for it, but that I’d be heading to Mexico for most of the summer, and wanted it when I got back. Again, he seem surprised I’d be trying to secure a job for the end of the summer at the beginning. He seemed skeptical, but he said, “Call me when you get back. If you really want it, we’ve got a spot for you.”

I did.

The job was amazing. It was hard work and it sucked at times – framing houses in the middle of Michigan winter, climbing the icy OSB with questionable toe-board on a third story roof at an 8/12 pitch while carrying a nail gun with the air hose wrapped around your waste for safety – but it was pretty awesome too.

I began by mostly cleaning up stuff, handing the crew tools, and getting the lumber to the right place. I had some experience with construction, as my brother and I had spent a previous summer helping my grandfather and uncles build a house from scratch. But I had a lot to learn. Next, I was upgraded to making cuts for everyone. Guys would scream down over the blaring classic rock on the radio and through the Skoal or Marlboro in their mouths, “6 foot 45 angle 45 bevel” and I’d try to understand and quickly make the right cut on the right board and hand it up. At first I screwed up a lot. Wasting lumber is frowned upon, so for the more complicated cuts (places around the roof would often have strange connecting beams with different angels and bevels on each side), they’d toss down a scrap of wood with a badly etched drawing of what they needed.

Then I got to do the sheeting. Cutting and nailing giant pieces of 4×8 foot OSB board onto the frame of the house was super fun. The roof not so much. I’d stack two of them on one shoulder and carry up the 20 foot ladder. I think if I tried that today I’d probably die.

I’ll never forget in my third week when the crew had to all head out early, but the boss left me behind to finish sheeting and clean up the tools (which all had to be put away in a very particular way). He trusted me with a lot, and I was thrilled.

I made $8/hour to start, and got a raise to $9.50 a few months in.

The guys were crazy. They told stories over lunch – I’d pack peanut butter sandwiches and tortilla chips and water pretty much every day – many of them probably untrue. They were incredibly crass. They yelled everything. “Break time” (a 15 minute stop mid-morning) sounded more like, “Baaaayeeee Tiyeeeeee” screamed out in a sing-songy way. We started early, usually 6am when it was still dark, but also finished early. Usually 4pm. I worked three weekdays (went to community college the other two, something they all were impressed by and encouraged me in) and some Saturdays if there was work.

One time one of the guys went into the portapotty and another jumped on the lift truck and slowly drove it over and pushed the forks against the door until the portapotty was leaning on a precarious angle, the door pinned shut, and the other guy screaming obscenities inside. They left him for ten minutes or so.

Another time, one of the guys who was a big deer hunter went off for his daily retreat to the woods behind the house we were working on where he had a deer lick of some sort. He took longer than normal and I swore we heard some strange noises. Then he walked out, the front of his pants and shirt streaked in dirt top to bottom, panting like a madman (maybe that was all the Mountain Dew and Skoal), and said, “I got the fucker” his eyes crazy. We were confused. He said, “I saw him there and walked up behind him as quiet as I fuckin’ could and jumped on that fuckin’ deer’s fuckin’ back. He kick me off but I held his legs. Fucker dragged me fuckin’ ten feet before he got away.” He opened his palm to reveal a large hunk of fur. I’m pretty sure he was telling the truth. (I removed several “fucks” to keep it more concise).

We’d arrive at a new house when the basement had just been poured, with a blueprint and a bunch of lumber. The boss was some kind of savant at reading blueprints, and often knew just from glancing if the lumber order was off. One time the entire basement was poured an inch too narrow, so to stick with the prints we built the house hanging over the foundation half an inch on each side.

We’d work there every day and if we were in rhythm, we’d be done in two weeks and an entire house would be standing there all framed and sheeted. To this day, I’ve never found a kind of work with so much visual feedback and tangible progress. You literally saw walls and rooms and stories go up in a day sometimes. It felt awesome.

When I called the boss to tell him I was taking a new job (installing telephone and internet cables at businesses across the state with my brother…too many stories there for today) the crusty old probably-on-speed contractor cried on the phone and told me what a great worker I was. I was shocked. They mostly razzed me, though I knew they appreciated my hard work. It felt good.

I loved that job.

Getting good at delivering or receiving bad news dramatically raises the success ceiling.

Inability to give or get bad news is a big success limiter.

I’ll never forget the first time I fired someone. It was awful. I didn’t sleep well for a week. The second time was awful too, but I was able to sleep OK after just a few days. Since then, it’s been hard the day of the firing, but that’s about it.

Two things happened to make it less painful. First, I saw how quickly all parties recovered and had a happy next step. Much easier and quicker than you imagine. Everyone ends up OK. Second, I got better and faster at the delivery process.

The only way to deliver news like that is to look the person in the eye and open the meeting with, “We’re letting you go.” No beating around the bush, no long setup. Say it. Own it. Be direct. Be clear. Be kind. Be resolute.

Delivering bad news sucks, but if you can get good at it, you will become so much more free and able to take on so much more leadership. It’s cleansing and relieving to be direct and honest and just say the thing they don’t want to hear when it needs to be said.

I’ve gotten better at hearing stuff I don’t want to hear as well. It’s much easier than being the one to say it, but it still takes effort to be detached enough to get the information and act appropriately without letting emotion run the show. (One odd fact is that people who are good at receiving bad news don’t make it easier on the giver. Fire someone who is clear, direct, gracious, and awesome about it and you feel a lot worse than if they respond like a petulant child!)

I sometimes get emails from strangers pitching and proposing various things. Some of them are open ended requests to talk about nothing in particular. I hate getting these. It’s a kind of bad news. Why? Because it puts me in a position where I have to do something I don’t like. If I don’t respond, I feel weird because I generally make a point to respond to everything earnestly. If I say yes, I’m lying. I don’t want to. And I have to take a call I don’t look forward to. If I say no, I have to deliver bad news to them.

The more Spock-like I’ve learned to be about getting and giving bad news, the easier it is. I don’t get bothered by the ask anymore, I just treat it as a fact. And I don’t fret about telling them no either. It’s an equally inoffensive, impersonal fact.

It’s amazing how much more can be done without fear of hearing or saying stuff that’s not fun.

It’s great to not have to think about things.

Most tasks in daily life are autopilot tasks. You don’t re-examine your core beliefs and the causal chain of dental hygiene every time you brush your teeth. It’d be exhausting if you had to.

Our brains are incredible at turning repeated patterns into unconscious processes. This frees up a lot of processing power for other stuff.

But what is that other stuff?

What if we’ve got a lot of latent brain power sitting around, waiting to examine, rethink, and get creative?

What if we’ve allowed almost everything to go on autopilot?

That’s the natural direction. Our brain tends toward autopilot, and if we don’t deliberately step back, we can end up feeling like our entire life is on a conveyor belt.

This causes a lot of stress. All the brain power goes to fear and hypotheticals, while all the action is done unthinking. This is not a good recipe. For example, I see people stress and worry about what job they want. They torment and toil over what their passion might be, why this or that job may not be perfect, what if it ends up sucking, etc. They burn tons of brain juice on fears and hypotheticals. Meanwhile, in the realm of action, they’re on autopilot. They format a resume of boring bullets, craft a generic cover letter, scan jobs boards, and send the same damn app to dozens or 100s of jobs. Total autopilot.

I love helping people get their careers started. It sets a tone for life. Beginning the job hunt on autopilot isn’t the foot you want to get off on! All that toothbrushing autopilot is freeing up brain power to be used on cool stuff like showing your skills and pitching people on working with you. So put it to work!

One of the reasons we built Crash is to help people overcome autopilot when it comes to finding and winning career opportunities. Careers are best approached experimentally, and with optimism. Don’t do stuff you hate, or suck at, or stuff no one is willing to pay you for. The rest is fair game. Pick a few big buckets, and then open up your creative brainpower to think about some cool, unique ways you can go about getting a shot at an interesting job.

Remember, only two things matter on the job market:

1. Your ability to create value.
2. Your ability to prove it.

Those things have 10x more impact if you’re not on autopilot.

Don’t limit the kinds of roles you can go after. Don’t put your brain to work only in the realm of analysis. Put it to action! Try some stuff. Learn. Experiment.

Ask yourself how you’d win a cool job with no resume, cover letter, or application. What could you come up with? Then go try it!

The first step to a great career first step is to switch off autopilot. It’s harder work, but more rewarding. It’s the beginning of the kind of adventure you want.

Flip the switch to manual. Go deep. Be creative. Have fun!