v27 - Becoming "Who I am"

Published on Jan 20, 2020

What is this?

I subscribe to Brad Feld’s blog (a VC in Boulder). One of my favorite things he does is start his new year on his birthday rather than on the calendar new year. He uses this as a time to set goals, review his previous year, etc.

I love this philosophy. The calendar new year is arbitrary in my opinion—how could we logically chose a single point on our path around the sun to be the “start?”—and it’s packed in with the holidays when I don’t have enough time to properly reflect and plan.

I turn 27 today (at ~10:20 pm). Below is a comparison of v25 Zack and v26 Zack (how I changed last year) as well as goals for v27 Zack (how I want to change this year).

v26: A Year in Review

v26 didn’t host any pivotal life moments for me (graduating from college, getting married, having kids, etc.), but I think I matured and evolved more in the past year than in any other year of my life.

The road was quite bumpy and I questioned myself a lot, which is unusual for me. I’ve always been an “old soul” who’s known what I should be doing with my life. I’ve blasted through life without looking back much, and for the most part, this has served me well.

“Not so fast,” said the universe…


In v26, I had to come to terms with my own limitations, both physically and mentally.

I’ve been lucky enough to never have a health problem other than a cold or the flu, but this past year I developed gastritis, which is like a rash on the inside of your stomach. It’s not a big deal and with some lifestyle changes it’s already gone away. But this was the first time in my life where I was forced to face my own mortality. I initially tried to fight this beast, but quickly came to terms with the fact that my body might not allow me to do whatever I want without consequences.

I also pushed my mental willpower nearly to it’s breaking point, which I wasn’t sure was even possible to do in v25, v24,…

I’ve always been the type of person who can sit down day after day and focus for long hours at a time. I enjoy it and this skill has made me successful.

My success has led to a plethora of opportunities. Opportunities are nice and I’m lucky to have so many, but I handled them poorly in v25 and the first half of v26. I get a lot of people who reach out to me because they want me to work on their projects. I’ve always responded to the best pick of the lot that I’m committed to my full-time job, but that I work at nights and on weekends on side projects and would be happy to take it on.

I genuinely thought all of the projects I chose to work on were fascinating, solving interesting problems I wanted to work on, and could blossom into viable businesses. It was difficult to say “no” to anything, but by saying “yes” to everything, I over-extended myself.

It sucks to turn down a good opportunity. It sucks even more to turn down ten opportunities. One of the most important things I learned in v26, though, was that I only have a finite amount of time in the day and that I can’t work on everything. In the past, I’ve always been able to squeeze a little more efficiency into my life and work just a few more hours to make things work. Last year I bumped up against my physical time limitations, which was stressful to try and keep up with (part of the reason I developed gastritis).

About halfway through 2019 I had to start “trimming the fat.” This meant cutting ties with several projects, a few of which I was working on with good friends. I was lucky that no relationships were damaged in the process, but it was painful. Both because it felt like I was abandoning people I cared about and because I genuinely wanted to work on all the projects. FOMO was real for me.

In v26, I learned to be selective about what I say “yes” to and to focus my time on 1-2 things that I want to do at an elite level rather than 5 things I want to do well.


Over the past ~5 years, I’ve developed a terrible habit of anxiety. A large driving factor of this is that I was juggling too many projects (most of them at night and on the weekends that led to +80 hour work weeks). I felt like I wasn’t giving anyone my best effort, but I wanted to give my best effort to everyone. I’d reached my limitation and I became more and more anxious trying to navigate it. Especially before I recognized what was happening.

Even outside of this specific experience, I’ve always been prone to worry too much. I show up to airports several hours before I need to, I meticulously plan out every detail of my life for fear of making even one wrong decision, and I always tend to focus more on what could go wrong than on what could go right.

In v26, I learned how much I can juggle while staying healthy/sane and that by focusing on the upside more than the downside, I take more risks, some of which pay off big time. Plus, it makes life more fun.


I’ve always been the type of person who likes to do everything themselves. This isn’t a control issue. I don’t mind giving up control and actually love working on teams. It’s more that I have so much curiosity about how everything in the world works, that I want to do things myself so that I can learn, explore, etc.

A combination of factors has helped me reach a tipping point. First, I’m making enough money now that paying the cost to delegate matters less to me financially. Second, I’ve explored so many things at this point in my life that the allure of doing everything has worn off to a more healthy level. And finally, I’ve seen the power of delegation first-hand and how much it can lever up my time.

In v26, I learned that I don’t have the time to be an expert at everything, nor do I don’t want to be. And by delegating, I can focus more on becoming an expert at 1-2 things I’m passionate about.


In v26 I was lucky enough to have someone who cares about me point out that I over-communicate. The emails, texts, slack messages, etc. that I sent were too long for most peoples’ attention spans and time constraints.

It took me a lot of work to dial back the volume of my communication, but it’s done wonders. Not only do I have more time, I feel like people engage more with me despite the fact that I’m telling them less.

In v26, I learned to look at situations through other peoples’ eyes and only tell them what they need to know. If they want to know more, they’ll ask. That’s a more engaging way to converse and it saves me a lot of time.

v27 Goals

Becoming “Who I am”

Instead of focusing on 5-6 projects, I want to focus on 1-2. I want to sacrifice my blood, sweat, and tears into them and do something great instead of 5 things well.

But I don’t want to work on just anything. I want to pour myself into something that matters and that I know has a high probability of payoff. This may take some experimentation with lower probability projects, but I’ll be quick to cut anything that doesn’t fit what I’m after. I only have so many years to work and live, and I want to do something significant in my life.

Predict less, focusing on understanding and navigating the present

The title says it all. I feel like in the past few years I’ve become a little obsessed with predicting the future. Not only have I determined that doing this is impossible, I’ve also realized that it doesn’t make me happy or successful to try. Instead of focusing on what might happen, I’m going to focus on what’s happening right now and optimizing how I react/adapt to my environment.

Focus on what I can control, frame goals/projects so that I control the outcome

Instead of worrying about factors outside of my control, in v27 I want to focus more on what I can control. What can I do each minute, day, week, etc. that will have a positive impact on my life. This means worrying less about what will happen in politics, the economy, whether projects at work will be successful in the market, etc. I can’t control them and spending time worrying about them or trying to predict what will happen is a fruitless endeavor, in my opinion.

In conjunction with focusing on what I can control, I specifically want to make sure I frame all of my projects and goals in ways where I’m in full control over the outcome. Make a million dollars, get promoted, launch a successful product, etc. are things out of my control. I can work to give myself the best chance possible, but at the end of the day randomness and a million confounding variables outside of my control will determine the outcome just as much as myself. If I frame my life so that I’m in control, I think I’ll live happier and with less stress.

Explore more ideas, people, and experiences outside of my comfort zone

I’ve always been an adventurous person, and I’m usually not afraid to work harder to explore something new. But in the last few years I noticed myself becoming more of a creature of habit.

I hate that! I don’t want to be comfortable, I want to experience!

So in v27 I want to re-embrace my own playfulness. I want to pickup books on topics I’ve never explored and written by people whom I might not agree with. I want to try foods, explore places, and meet people who are different than myself and my friends/family. I want to put myself in new situations where I’ll be forced to learn and grow.

I made this change in my life a few months ago, and I’ve already seen a huge difference. My wife, dog, and I are now officially traveling for a year in Europe (while I work remotely) starting in October 2020, I’ve read books I was sure would be stupid, but some of which have already changed my perspective on life, and I’ve embraced my curiosity in the small things in life. This comes in tandem with the fact (as stated above) that I now feel financially secure enough to have discretionary spending. So I’ll pickup food, products, try out online services, etc. just to see what they’re like. If I lose a few bucks, at least I tried. But I’ve already found several new products that I use every week because I’ve reignited my curiosity. And by saying yes to more social events, I’ve met people I never would have interacted with if I stayed in my comfort zone.

In v27, I’d like to try new projects outside of my comfort zone. But I want to frame them so that success is “explore this new path without any attachment to how it will benefit you long term” instead of “turn this into a million dollars.” And I’ll of course be careful to set them up so that I can swiftly cut them from my life if they aren’t bringing me happiness.

Be more present

I think I’m already pretty good at staying present in whatever I’m doing, but I’ve found presence to be one of the most powerful driving factors of my happiness, so I want to continue to devote resources to refining it.

Wrapping up

More than anything, I want to be happy and contribute to the happiness of the people in my life—family, friends, co-workers, etc. That’s my #1 and only goal. The items I’ve outlined above are things about myself that I think I can change to help me get there, but at the end of the day my only goal is to drive my life in the direction of happiness.

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