Work and a life well-lived

The below is an excerpt from my monthly newsletter

I’ve been thinking a lot about work lately. At this point in my life, I’m fortunate that I can dictate pretty much everything about my working life. I get to decide what to work on, who to work with, how to structure my day… pretty much everything 20-year-old Justin could have hoped for when he first started thinking about startups as a career path. 

Though I wouldn’t have it any other way, this work freedom comes with its own challenges. It can feel like being dropped in the middle of the ocean: sure you’re “free” to swim in any direction you’d like, but without constraints, how do you decide where to go? 

I’ve seen friends face similar challenges as they’ve gone through career transitions, sold a company, or made a lot of money “investing” in crypto. 

When your career choices are not constrained by the normal factors (How much will you make? Where will you live? How stable is this job?), it leads to a lot of questions. It’s the whole “what do I do with my life” mid-life crisis, just experienced at a younger age. I think. 

As I was talking with a brilliant friend a few weeks back, he said something that has stuck with me:

Ultimately, what you choose to do for work is a reflection of a deeper question – what does a well-lived life look like to you?

Not anyone’s life. Just yours: what does it mean to live a good life?  

If your goal is to find meaningful work – to answer the work component of the “what does a well-lived life look like?” question – you can approach this a few ways. 

The first of these is process-oriented. Rather than focus on the end goal (be a billionaire! Go to mars!), you focus on the process. Someone focused on the process portion of a life well-lived will focus less on headlines, and far more on the day-to-day, hour-by-hour of what one’s life looks like. Am I spending time with people I love and find amazing? Are my days structured in ways I enjoy? Am I able to travel, get sunlight, be healthy, and work the amount I want to? 

The Archetype of this approach might be a digital nomad. Someone more interested in life’s daily offerings and adventures than in achieving a big goal or solving a huge problem. For these people, life is a journey, not a destination. And that journey really, really matters.

Others have more of an outcome-oriented approach to work and a life well-lived. This orientation goes well beyond just financial (though includes a fair number of people), but also includes those driven to solve problems in the world. Elon Musk, Bill Gates, Nelson Mandela… these are people who (from the outside at least – they still won’t answer my phone calls) seem more motivated to achieve an outcome than they are by any day to day considerations. 

I’m sure that Bill Gates, Bezos, and Elon Musk would all have much happier personal lives had they been more process-focused. But boy did they also seem to knock their chosen outcomes out of the park. 

Archetype: a single-minded founder hell-bent on creating some outcome in the world or solving a specific problem. 

Last (in my likely incorrect, smooth-brained way of thinking) is the understanding-oriented crew. This group is motivated almost entirely by a desire to understand the universe. They are less focused on solving a problem or driving a specific outcome, and rarely consumed by how to craft each hour of their life. 

Instead, these folks are often consumed by a desire to understand more deeply what is going on in the world. Whether a scientist, independent researcher, philosopher, or whatever, there are a smattering of folks purely motivated by increasing their understanding of the world. 

Each of these 3 approaches has tradeoffs, and all have bits and pieces of one another. However, knowing which type you are can often be discovered by looking at where you make sacrifices. 

When push comes to shove, do you often skip friend hangs in order to progress towards an outcome? Do you prioritize travel, and daily routine over any and all other responsibilities (process-oriented)? Or do you eschew responsibilities and commitments, choosing instead to spend as much of your time as possible reading, learning and understanding more of the world around you? 

I’m still answering these questions for myself. But I’ve found this frame helpful in thinking through what I care about work-wise. Hopefully, it helps you as well. 

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