The tough trade-off between money and enjoyment of your work

When I graduated from college I was a complete idealist. I was 100% convinced that I could find a job that I liked and one that would pay me lots of money. I was unabashed about wanting both, which often surprised people. But looking back, what surprised people is the fact that I openly said that I wanted to make a lot of money, as if it were a bad thing. But that’s for another post.

I quickly got a series of jobs that made lots of money. I worked in the business world and in finance, industries that are flush with money and with people making millions in their late 20s. This wasn’t me, but by the age of 30 I was pulling in a nice fat salary, had a fancy title, and a job with lots of influence. (OK, some influence.) Except I didn’t love it. I liked parts of it, but I hated many others. So I decided to quit, give up the money, and try to do something for a living that I actually enjoy.

I can report that after six months of running Work It, Mom! I really enjoy what I do. I love digital media, I love online communities, content, interactive experiences. I knew almost nothing about these areas a year ago, before I started thinking up Work It, Mom!, but I was always drawn to them. The publishing company and the book were my attempts to try my hand at content; what I’ve learned is that I love online content and communities around it much more. I’ve found a job I love doing.

Except it comes without much money, at least for the near-term future. We’ve not raised venture capital for Work It, Mom! and don’t plan on doing it soon. (I do plan to write about our decision not to do it.) We’ve raised a bit of angel capital but we’re being extremely careful to invest it in critical things like technology and content. Which leaves me with a small monthly stipend, a tiny fraction of what I used to make in my last job. I need this money so we can pay our bills, otherwise I’d probably take even less.

And what I’ve discovered is that trading money for enjoyment of my work is really hard. I wish more people talked about this and I am being honest about it here because I want it to be OK to say things like this. There is this assumption out there–I’ve personally encountered it–that entrepreneurs who create their own companies are fine with not making money. They are passionate about what they are doing and financial profit can come second. But I don’t think this is correct, at least not in my case and in the cases of many fellow company founders I know. Working 18-hour days and constantly starting failure in the face is not easy, regardless of how passionate you are about what you’re doing. And doing this without making much money and without any guaranteed prospects of making good money makes it tougher.

Do I hope that one day Work It, Mom! is a huge financial success? Absolutely. But I know a little too much about the rarity of such success and the odds that are firmly stacked against start-up companies being successful. I love what I do and I know that I am lucky–many people never get to say this about their jobs. But my inner idealist has been tampered by this experience of trading money for enjoyment of my work. I wonder whether both are achievable at the same time and hope very much that I get to experience what feels like.

Because I bet it feels damn good.