The last few months have been a lot. I don’t really know else to describe it. I was gearing up to write a long mid year update and then work got really busy. It took down most of a vacation; I pride myself on never cancelling vacations for work, but this one, I may as well have cancelled. And while it led to one of the most productive three months of my career (with two new investments) it also helped me put a lot of things into perspective. 

The first thing was a reminder that I spend more of my waking hours working than anything else, and I’m generally very OK with that. However, while interesting problems and liking my direct co-workers is important to me, being part of a system where autonomy is at the forefront and there is clear correlation between what someone puts in and what comes out, is more important. In the words of Pre “To give anything less than your best is to sacrifice the gift” and I saw many smart colleagues sacrificing the gift, I didn’t feel like now was the time to sacrifice the gift, nor do I hope I ever feel like it is time to sacrifice the gift.

Now that the cork is pretty far out of the bottle – here’s my Q1-Q3 update, with a reminder for what I was shooting for:

Professional

1. Get promoted or find a new job: My actual goal that I couldn’t fully articulate was to put the ball in my hands to be able to make a decision I was excited about, either taking a promotion or doing something new. With two new investments this year, I know I did enough for the first one (and was told so). But I was more confident going into the year I’d be better off finding something new to do. And investing in two awesome healthcare services businesses only strengthened my resolve to get direct operating experience. So when I found an opportunity to work with a CEO that a) I think can build a business and team to the same potential as the two companies I invested in this year and b) could benefit from my help in getting there, my main focus was how quickly I could get started. So the promotion, the year-end bonus, the carry vesting…all out the window. Maybe that will be a good long-run decision, maybe it won’t be. But rather than wait, or maintain the status quo, I can just do things, and not wait around.
2. Think strategically around mentorship / menteeship: Honestly – haven’t done much here (mostly because I had a view on the prior question and didn’t know what “board seats” I’d need to fill), but with the move to an operating role, I’m going to need to do this. Luckily I’ve worked with some great CFOs over the years, and I need to give some thought over the coming months as to where I need help (all recommendations are welcome!).
3. Apply what I know in a new (board) context: Now that I’m moving into an operating role, my role in the boardroom is going to be pretty different than it has been the last few years. However, I’ve already cleared with my CEO (in principle) my ability to sit on an outside board. So I’m hopeful that once the dust settles in 2026, I’ll be able to find an outside (likely search fund or similar) context to apply board skills. For now I’m going to rely on some light feelers, and hope that being responsive, intellectually curious, and with decent enough vibes means people will want to work with me.

Financial

1. Budget (for guardrails): I had a few good months here. But then quickly got too busy to think about how I wanted to spend money on myself, so I didn’t do it. I think this will evolve into me realizing that I can spend a higher percentage of my take-home pay on “normal” things versus making specific investments. Especially with the new job being primarily working from home, and the strong pull I’ve had to feel settled somewhere, that’s probably going to show up as leaning into a house a little more than I normally would want to. 
2. Get worse at the marshmallow test: Taking a new job where the upside was potentially large but “whippy” was honestly me eating a marshmallow or two. How is that possible? Easy. I realized 1) how important autonomy was to me and how draining it was to spend the majority of my waking hours in a system that was at odds with that and 2) I was at a place in life where I could honor some more of my values (pro tip – global cultural differences are real and worth thinking about when going to work for a foreign company) through how I spent my time. I’ve struggled a lot with honoring values historically because it was too open-ended and I’m not the kind of person who has a singular cause or mission they want to champion. Rather – I realized that at least right now, my mission is to 1) work with really smart, driven people 2) support great leaders in helping them actualize a vision in which they have the utmost conviction 3) work in a field and an organization where a human is at the center (not that I think all AI is bad, but much of it is bad for the world, many of the people driving its adoption are ill-intentioned and should be shunned. I have a long anti-AI slopification of society rant in me soon) and 4) do something that will enable me to simultaneously give my all, have a significant impact on outcomes, without sacrificing on other things that were growing in importance to me (where I lived, how many nights I was on the road). My hard decision wasn’t leaving my job (although it offered many interesting problems and some good people), it was what I was going to do after that. 
3. Simplify with tax advantages and index funds: One good thing about leaving financial services is the levels of restriction around managing your own financial accounts is significantly reduced. So now that I get to get rid of Interactive Brokers (seriously the worst financial company I’ve interacted with, all my homies hate Interactive Brokers, up there with SAP and Oracle as companies I’d be embarrassed to tell my friends that I work for) maybe I’ll get to figure some of this stuff out. Some of that will probably be “VTI and chill” too. But if anyone has anything more interesting than that or tips on how to do it, I’m all ears.

Personal

1. Read 10 books: I don’t think I was on pace for this but then my new boss sent me a library (thank you) and I’ve read 2.5 new books in the last few weeks, plus a re-read. So now I think we’re tracking. And with the extra hour per day since I’m no longer commuting, maybe we’ll keep it going. I do have a lot of books I would like to read. Late summer / early fall was mostly re-reading / re-skimming a bunch of “find yourself / career transition” type books, and I don’t think re-reading should count toward the number. Next it’ll be re-reading this HBS classic. And since I get a couple weeks off in between roles, I’ll hopefully tackle a few of the books that I’ve bought recently but haven’t cracked, or the half-finished ones that are scattered around our house. 
2. Buy a house, to feel settled: This hasn’t happened yet, mostly because I thought there was a decent probability that we’d at least have the option to leave Colorado this year. And now that we have it, the obvious answer is “where are we going”. I don’t know yet. We’re trying simultaneously to not let “perfect be the enemy of good” while also recognizing that this is a big decision. Colorado isn’t totally out of the running – it’s certainly got its perks (the mountains in summer/fall, lots of sunshine, still somewhat decent value for money) and we’ve built some community here. However, culturally, Erica and I are better fits in the Northeast, our families and most of my friends are there, and I’d prefer to not have to get on a plane to see them. As much as I think airports are an underrated part of public society (no guns, and everyone has paid admission to be there which cuts down on anti-social behavior) I’d like to spend less time in them in the next 10 years than I have in the last 10 years, and that includes personal travel.
3. Visit a new state and a new NASCAR track: No NASCAR race this season (currently posting this while watching the season finale race). And my two favorite drivers both got eliminated from the playoffs a few weeks ago. What I didn’t anticipate this year was Brand New’s reunion tour. But what I really didn’t anticipate this year was their Denver tour dates falling on the same weekend of one of Erica’s cousins getting married in New York. So this goal morphed into booking a random weekend trip to see them in Detroit. Prior to this, my only trips to Michigan were airport connections, or to the Westin attached to the Detroit airport for United Road board meetings. I’m an atheist (probably not news to most of you reading this) and seeing Brand New after not thinking I’d ever hear them play live ever again was kind of religious. The closest experience I can equate it to was being visited by a dead relative in a dream. This band is at the top of the list of “got me out of some dark places over the course of two decades” and seeing them twice more was worth every penny. Also we’re going to New Mexico in two days, so we’ll get the new state after all.

Health

1. Run a 1:30 half marathon or finish a full marathon: I initially drafted most of this from the plane ride back from Minneapolis, where I ran a marathon (a few days after giving notice at my job). I signed up for the race in early spring, had a couple solid months of training, and then the first paragraph (two closed investments and interviewing / trying to figure my career out simultaneously) got in the way. Before the race, I honestly don’t know when the last time I ran 10+ miles was. Maybe I had a couple of those this summer, I honestly stopped keeping track. To top it off, my typical pre-race anxiety mixed with my “holy shit I just quit my job doing the only thing I’ve done for 10+ years and now I’m going to do something else that I might fucking suck at what if I’m not good at it and what does that mean about me and my value as a person” anxiety, which meant I slept like absolute dogshit the night before. Generally, I would not recommend running 26.2 miles on (less than – I don’t care what the Whoop says) four hours of sleep, particularly if you have not run more than 10 miles recently. In fact – I think you will really struggle to find a training plan or a sane person that suggests this (unless its a bad AI-generated training plan, or you are fleeing something terrible / being chased). My strategy was go out calmly, sing out loud to myself / spectators / anyone else to mitigate my inability to pace, walk through all the hydration stations, and have a good fucking time until the pain made it a bad fucking time. As you can see from the below, the bad fucking time started around 30k / mile 18. I dunno whether “all bad things come to an end” but at least this one did, with the stated goal achieved. Next time maybe I’ll train with some level of structure / rigor / and maybe knock some minutes off this. Until then I’ll be happy with YOLO’ing a sub 4 hour marathon.
2. Make it social – run clubs, classes, etc: No new friends. At least not yet. But this is going to become more important as I shift into primarily working remotely. And while it’s going to be easy for me to use “we don’t know where we’re going to be long-term” as an excuse for not doing this tomorrow, the reality is that no one is going to give a shit if I stop showing up to a brewery run club a few months in because we moved to Maine or Virginia. 
3. Buy the gear: Well, we went to Detroit and Worcester for Brand New concerts and Minneapolis for a marathon. So I’m gonna count that as spending money to do things I really like. Maybe the racing sim and home gym will come in 2026. 

Social proof of poor sleep and poor life running decisions:

I don’t really know how to end this, except with three other quotes / moments that have stuck with me over the last few months, that are a bit of a preview for what’s up next. None of these are from a dead former U. Of Oregon runner. 

The first one is objectively true, and comes from an investor and operator I have a ton of respect for. In a conversation where I was weighing a couple of different career opportunities, he cautioned me “remember, you don’t get any points for degree of difficulty”. And this is true in the sense of plain dollars and cents –  needing to turn around a project-based business with no recurring revenue to make a 3.0x ROI is way harder than buying a company with recurring revenue that’s already growing 20% per year, and trying to do the same. So if the goal is to make 3.0x ROI, take the more certain path. Investing 101. 

But this took me to my second quote, which comes from JFK, when the US was trying to go to the moon (as an aside, I worry that the AI slopification of the world makes us significantly less audacious as individuals or nations, and when combined with the polarization of our times and how important the space program and a new common enemy were to a pretty culturally fractured US, this seems like a pretty terrible combo!). Dig back in your social studies textbook and remember “we do things not because they are easy, but because they are hard”. And life isn’t spreadsheet math, as much as I (and probably some of you) sometimes try to reduce it to that. So while I may be doing something “hard” next, I would much rather be actively making that choice, than weighed down by a system in which I become a passive participant. 

Lastly – I did spend two years in a Harvard classroom (graduates are required to remind people of this, it’s in the honor code, look it up. Quick aside – shoutout to the random older guy with the Harvard Law shirt at the marathon who must’ve been walking his dog and not there to watch the race. I ran off-course to high-five and yell “a fellow Harvard man” at this unsuspecting chap – I rode that high for a few miles. I went to the business school so I’m barely a Harvard grad, but it wasn’t totally stolen valor. Anyway, rarely do 90 people who earned their way into a Harvard classroom get stumped. But when a finance professor asked us what made options valuable, I remember a class of very confused but intelligent people. The answer was volatility. Options only have value when there is volatility. Maintaining a portfolio of options in non-volatile securities is a great way to incur transaction costs but not much else. So while I am not a r/wallstreetbets member (and if i get there please rein me in), one thing I will not do with my one wild and precious life is live in fear of the volatility that comes from doing something difficult but impactful, and aligned with my view of the world in which I want to live.

Tomorrow I’m going to turn in my laptop, close a chapter (a job), and potentially a book (a career path). Until next time.