I recently quit my job to start my own business. I’ve gotten a lot of support and encouragement from my friends, family, and former employers, but I bump into a wall of skepticism whenever I share this decision with someone new. Inevitably, people want to know why I would do it this way instead of developing it in my free time while maintaining a source of income through a traditional job. Some people are pretty open minded and the conversation feels propelled by their genuine desire to understand. On the other hand, there are others who don’t even ask for my thoughts before telling me what I should be doing instead, like they know my situation better than I do, or like I haven’t thought things through. I don’t care much for the second group.
So why do it this way? Why not work nights and weekends until I’ve got something with a little bit of traction, and take it full time after it’s going well enough to pay my monthly expenses?
First, this approach adds urgency, and I badly need urgency. I’ve wasted hundreds of hours over the last two years starting projects but not finishing them. I was writing (am writing?) a book, blogging, learning to code, learning guitar, doing some design work, and for all that “busy-ness,” I have nothing to show for it. I remain terrible at all those things. The reason why is that each one of these projects has gotten crowded out in turn by its successor, creating a graveyard of once-exciting endeavors.
On one hand, I’ve genuinely enjoyed working on each of these things, and they’ve arguably made me a little more interesting to talk to, but I’m fed up with never getting anywhere. I can lie/rationalize to myself and say, “I’m building skills,” but I think it’s time to either put up or shut up. Either I really am better working for myself (like I think I am), or I have a lot to learn. And if the latter’s the case, I need to start learning, and fast!
Second, while it makes sense on paper to work two jobs and split your attention between a 9-5 and starting your own business, I feel this actually increases your risk of failure despite seeming like the safer option in the meantime. In addition to my bad habits of hobby-hopping and over-thinking (habits which I realize are not unique to me), there are plenty of other obstacles to starting a business. The main one is that starting a business is hard, and requires hard, focused work. Lots of it. You aren’t going to be able to put in enough hours of high quality sweat equity to make it pay when you’re spending 40 hours a week at another job. Jobs are pretty demanding, even if you’re half-assing them with the intent to dedicate your remaining hours to other purposes. Anything you spend 40 hours a week at (plus commuting, and all the stuff to get ready for work) is going to suck a lot of your energy, attention, and time. You’ll be serving two masters, and that most often leads to mediocrity, not success. The best results, to paraphrase the M.A.S.H. character Charles Winchester, come from “doing one thing, doing it very well, and then moving on.” If you absorb yourself so fully with something during the day that you are thinking about it in your sleep, you will gain an edge that no part-timer can replicate.
Third, consider the psychology of the situation. If you know you have a safe job to return to every week, and the start-up is providing nothing but a way to fill your weekends and evenings with extra work, it can be very easy to quit or slack off. There’s no cost to doing so; you would actually gain a lot of free time and a much nicer life. That’s a hard deal to turn down, and it eat away at your determination. By contrast, when you actually need results, it’s amazing how well you can force things to come together.
Fourth, it’s a competitive world. Who would you rather fight, the guy training 100 hours a week with obsessive desperation, or the guy who commits only weekends and evenings because he has something holding him back from going all in? You don’t become successful by half-doing many things. You need to win at one thing. On top of this, opportunities rarely last long, and winners can often use one early success to entrench themselves for years. Speed matters, and the part-time guy rarely wins that fight.
Fifth, reckless as what I’m proposing may sound, I believe the real risk inherent in this undertaking is moderate to low: I have a very cheap standard of living, theoretically allowing me to stretch my $24,000 in savings (plus a little bit in investments) to last up to 2 years. On top of that, if I can find a way to earn $1200 a month, I can extend this phase of the drawdown indefinitely (though, obviously, in the long term I will want more money so I can afford things like having kids, getting married, owning a home, and ceasing to feel like such a cheap bastard). Two years is a long time to figure out a better way to make $1200 (equivalent to $4/hr at 75 hours a week), so the bar to success pretty low.
Too, the price of failure is bearable. I mean, I don’t love the thought of re-entering employee-dom. The mere mention of it recalls memories of stale Sunday evenings at the end of yet-another-too-short weekend. But I won’t starve or be forced out on the streets. At worst, I work for a few more years, save up, and try again.
A risk to this is that I become obsolete in my job skills and fall behind in my traditional career such that getting a new job becomes more difficult. Another aspect of this is that I could remain stunted in my career development, and see many of my friends pass me by (which is already happening to some extent). This isn’t so bad in itself, but I know it will bother me to see friends making a lot more money than I am. On the other hand, and I don’t know for sure how this plays out over many years, I learn at a much higher pace on my own (making a podcast, creating my own financial analysis tools) than at work. And the skills and attitudes I’m acquiring are scarce among my peers. This knowledge could potentially give me unique opportunities down the road. So I could see this going either way.
In the big picture, I see the price of failure as fairly bearable. Too, the upside is tremendous, especially in a personal sense. While it’s possible that I might end up making an lot of money, the bigger prize is spending my life doing work I love. I could hardly ask for anything better.