It's funny how easy it is to forget why you're doing this whole entrepreneurship thing. A couple of things have happened recently that put things into perspective for me.
Money or Free Choice?
A few days ago, I was at a holiday party thrown by one of my friends from MIT, and a bunch of guys from my fraternity were there. All of us were about 10 years out of college, so it was interesting to reflect on what we had done with their lives thus far. It is actually kind of humbling to compare myself to my peers - most of them have done astoundingly well by various measures. I guess you could say that pretty much everyone had settled down, except for me. I was the only one who didn't work in finance, and I was also pretty much the only person who was single or who didn't own a condo in Manhattan.
So I was talking to one of my college classmates, and was telling him about what my startup is working on. He said something along the lines of "that's cool. It's nice that you get to do something where you call the shots." He told me that his job is interesting, not terribly difficult, and pays well (I'm pretty sure that this guy makes between five and ten times as much as I do). However, he had spent two years building some quantitative trading software, and then the hedge fund he worked for decided not to use it.
Another classmate kept saying he found it amazing that our investors pay me money to work on whatever I want. I reminded him that it is actually an investment, and that I also probably work longer hours (and have more stress) than he does. The tradeoff of working for someone else is that you have to work on their project, doing what they want you to do. And the more you get paid, the more expectations your bosses put on you. These guys have great jobs - I'm not going to tell you that they suck or that I would never want to have them (given other circumstances, I might). I will just say that I am grateful for having had the opportunity to found multiple ventures where I could dream crazy things up and then make them reality.
What Are You Looking To Get Out Of All This?
I had another realization when an old friend emailed me to check in. A while back, this guy quit a corporate job to found a startup that he was passionate about, and I think that's pretty incredible. In his email, he mentioned that he hadn't gotten into YCombinator. I started thinking about how to respond. The first thing I wrote was "the only thing that matters is success," but then I realized that this just isn't true. The truth is that you probably aren't going to get rich running a startup. A lot of people think that a startup is the road to riches, and I hope for their sake that they make piles of cash. But, realistically, the expected value of founding a startup is much lower the EV of working a job. Most people who found a successful startup could have made plenty of money working for someone else. A startup is a choice that you make when you think that you can make better use of your time than others can.
I've been doing this stuff for coming up on three years, and I have sort of released the outcome that I'm going to get rich. Mostly because it forces me to think about what the fuck I'm doing. Stop daydreaming about dollars, and ask yourself the important questions. If you never made any real money from your startup, would you feel like you had done something that was still rewarding to you? Would you have any regrets? Would you give up and go back to working for someone else? If not, is there something you can do to change that?
Another question this guy asked me in his email was "are you still meditating?" I can say fairly objectively that I am significantly happier when I do meditate regularly, but my answer was a weak "no." One of the nice things about being an entrepreneur is that you don't need to account for your time on an hourly basis. But you do need to be productive. And to do that, you need to be sure do the things that will make you the most productive, even if it seems like you don't have time for them right now. And if you don't, you will be the one who suffers, and the startup you've sacrificed so much for will fail. So be sure to eat right, get enough sleep, and pay attention to your mental health. And spend time with the people who matter to you - you never know what is going to happen.
Here's a story - shortly after I started my first company, I headed to Baltimore because my sister was getting married. For various reasons, it made sense to spend the week following the wedding at my parents' house rather than heading right back to California. It felt like a waste of time, because I was anxious to get to work on the startup. But I stayed around for the extra week, and spent plenty of time with my family. My father died suddenly a few months after the wedding, and that trip was the last time I ever saw him alive.
In the end, I wrote the following response to my friend:
Remember that the only thing that really matters is having control of your destiny and enjoying yourself more days than not. A lot of people judge their success by external factors (like whether they get into YC or whether they get onto some list of "people who matter"), but I try to remind myself regularly that the only important thing is whether I get to work on something interesting and personally meaningful.
The only one you really need to answer to is yourself.
The Choice is Ours
The truth is that we can control the direction of our lives (if we want to). Despite societal pressure to the contrary, we can actually do pretty much whatever we want on a day-to-day basis, although we may of course have to live with the consequences of our decisions. Sometimes we make decisions that limit our choices (like getting married or having kids), but strangely, many people manage to work around those limitations. I know a number of successful entrepreneurs who have have done it both with kids and without huge cash reserves.
It is important to periodically remind myself that I have the best job in the world, and it is my privilege and responsibility to make the most I possibly can from it.
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