It was 2007 and Rails was only getting more popular. I had been working in the industry for a few years and was ready for a new job. Living in San Francisco and being young, I was enamored with startups. I spoke to a couple recruiters, found one I liked and let him do his thing.

I ended up interviewing with a startup I really liked - they were socially-minded, had an experienced CEO, and had a team that seemed to work well together. We did a few rounds of interviews, and then they sent me an offer letter: $250k/yr, 1% in stock options, full benefits.


I was 22 years old, a college dropout, and had just become “marketable” in the past couple years thanks to Rails. I was stunned by the offer. I had told the recruiter that that’s what I wanted, but I assumed that asking for that was as good as deleting his introduction letter. Guess not.

Still, I didn’t accept the offer right away. I called up a friend of mine and told him what was going on. He asked if I had any misgivings. I said, “Well, they want me to live within a mile of the office so I can get there quickly if they need me. And I was talking to one of the guys and he said the earliest people ever leave the office is 8:30 at night, and they’re usually there later.”

My friend replied: “Sounds like it’s two full-time jobs then, each paying $125k/yr. Most people with that salary don’t feel a need to work a second job. I guess you need to decide if you want one well-paying job and a life, or two well-paying jobs and no life.”

He really put things in context for me. I could have taken the job. Who knows what would have happened? Maybe I would have loved it, socked away some cash for a few years, and then cashed in on the stock options they offered me (I never followed the company so I don’t know what happened). There’s really no way for me to know. I bet my friend is right though, and I wouldn’t have had a life there at all. That would be a shame, given what a wonderful city San Francisco is. I probably would never have dated anyone. I probably would never have discovered my favorite restaurants and hangouts. I probably would not have gone swing dancing five nights a week. I probably wouldn’t have run naked through Golden Gate Park with tens of thousands of other people.

I still think back about that job from time to time. I’m glad I didn’t take it. I could have missed out, but I’m not sure I did. In the years since, I’ve learned a lot more about how some startup founders treat their employees. I’m pretty sure that that job wouldn’t have been “fun”, other than getting paid an absurd amount of money. Nobody pays a 22 year old dropout a quarter million a year without attaching some serious strings to it. How long would I have lasted, working 80+ hours a week? 3 months? 6 months? a year? Of course, it’s impossible to say what would have happened. Given what I know now, I don’t think I would have lasted very long. I think I would have burned out, and certainly would not have sustained a career as long as I have. I’ve done some pretty cool stuff since then that I would not trade for a few years of good salary.

As you work in the industry, you may come across jobs that seem “to good to be true.” Take a good, close look at how the companies operate. Do they they understand that the people who work there have lives, and that their work fits into their life in some way? Or do they dangle a high salary, stock options, and the promise of future riches in exchange for your “dedication” and “commitment” - and perhaps your happiness and sanity?