(Continued from Part 1)

I told them that I'm interested in building a business that supports my lifestyle and gives me autonomy. In other words, I want to build a "lifestyle business" as opposed to a startup where growth is the primary objective. In college, I had aspirations to build a super hot billion dollar company, but over the years I realized that my primary motivation for that was fueled by my ego — I wanted to be successful in the eyes of others. I have nothing against building a large company, but if I ever go down that route, I'd want to make sure I'm doing it with eyes wide open about my motivations as well as the tradeoffs being made in pursuing such a goal.

The way that people usually think about work is as a means to a goal. This is especially common in startups, where people explicitly think about "sacrificing" several years of their life in the hopes of winning the startup lottery. Work intensely for some time and reap the rewards forever.

I'm trying to approach it differently, and it's reflected in the question at the bottom of every journal entry here: "Can I make a living building things I love?" I want my work to be a part of my ideal lifestyle, rather than just the means to it. In other words, if you were to ask me, "If money were not a concern, what would you spend your time doing?", I'd want to be able to answer "exactly what I'm doing right now".

So how true is that currently? If I had a billion dollars, would I be working on building a business right now?

Yes(ish) and no.

I'll start with the no: I'd love to go on another long meditation retreat and I'd be stoked to go sit at the Forest Refuge for several weeks to months right now. There are also a bunch of hobbies that I'd like to pursue more intensively, and dedicating myself full-time to learning things like dance, music, woodworking, and calisthenics would be amazing. I'd hire coaches for each skill and work on improving at them simply because it's just a lot of fun.

And now the yes(ish): I love creating things, and I'm sure I'll always come back to "working" in some capacity, even if I don't need to from a financial standpoint. At that point though, I'd probably just make stuff and give it away for free rather than trying to create businesses. So I'd be working, but not necessarily on a business.

For now, I'm quite enjoying the process of building a business from scratch. As a company of one, I feel a massive amount of autonomy and freedom in my work because I get to decide what I want to work on every day. Of course, there are tasks that I wish I didn't have to take care of and days where I just want to sit and do nothing rather than go through emails or fix some annoying bug, but overall, I'd say my work satisfaction feels quite high.

So I feel pretty settled with the direction of growing a business slowly and sustainably rather than going for rocket ship growth. But even within that, there's so much variety in what the business could look like, and these are things I'm actively asking myself and exploring:

• Do I want to keep this a solo venture or hire/bring others on at some point?
• Can I design the business in a way where I can step away for weeks or months at a time if desired? (e.g. B2C iPhone apps.) Can I do this alone or would I need to hire?
• Under what conditions would I be open to taking investments?
• Under what conditions would I be open to selling the business?

(Continued in Part 3)