A young person's guide to quitting your day job

About 6 months ago I quit my hedge fund job to start buildingsomething with my friend Adrian. I figured I’d write a little about my experience, and hopefully offer some insight or advice to those of you considering doing the same.

I’m thinking about quitting. When’s the right time to go for it?

This is definitely the most personal, time-consuming and difficult question you need to ask yourself. For that reason, it’s also the question that most people give up on answering.

As an immigrant on a work visa, I knew there would never be a “perfect time” for me, but there were a few leading indicators that let me know I wouldn’t last much longer working for someone else. Do any of them apply to you?

1) I’m always working on side projects.

If you are working long hours at a day job, and still find the time to work on side projects chances are: you aren’t learning enough at your job, or it’s not that interesting. I’ve always built little side projects, or ran little businesses on the side. Eventually I realized that I could be doing that full time.

2) I’m not interested in being promoted, and not interested in working somewhere else.

So much success in the corporate world is driven by your title and where you’re at in the totem pole. Most companies won’t create new positions just for you. If you are wondering what your job will be in 5-7 years, your boss’ position is probably the closest thing to it. And in 7-15 years, it will likely be like your boss’ boss. By that time you’ll be 40. If that doesn’t interest you, you might try working somewhere “better” (For example, most people think going from Yahoo to Google would be a step up). But if you get to the top and you still don’t see a career path that doesn’t involve you being a founder or CEO, you should seriously consider doing something drastic.

3) Salaried money doesn’t drive me.

Salaries are strange creatures because they don’t go up and down based on your performance, and they only change once or twice a year. When you’re fresh out of school, you can get magnitudes better at what you do in a short time and see little to no change in compensation. If you own a large percentage of a company, your success is tied almost directly you and your partners actions (plus a little bit of luck).

4) I feel like I am slowly, but surely losing my edge.

Having a job is very different from being in university. If you’re smart and love learning, you can whip through university no problem, but working requires longevity. If you aren’t doing something you love, it will wear you down slowly but surely. This was definitely a tipping point for me. As an entrepreneur, it’s not always about how smart and hardworking you are – it’s about that edge/spark/drive you have deep down inside of you that makes you different from all your other co-workers. Don’t ever let it dull.

5) The opportunity cost of having a job keeps me up at night.

If haven’t quit yet, you will soon. At this point, you’ve probably realized that life isn’t a competition to see how upper middle class you can get. You’re ready to build something from nothing and try to be the best in the world.

I’ve decided to quit. What should I do before I leave my job?

1) Find a partner you can trust.

By far the most difficult thing you can come across. You may have a lot of old friends you can trust, but many of them may not share the same drive, passion, and outlook on life that you do. I wasfortunate enough to run into Adrian (there’s a whole story behind that, see more here).

2) Pick a simple idea to start with.

I think it’s important to have some idea or problem are you interested in solving. It’s hard to say what it should be, but I can tell you that Backspaces started out as a way to share walks I was taking around NYC, and organically evolved into something much more.

3) Pay off as much of your student debt as possible.

The nice thing about having a high paying job is that you can pay off your student debt very quickly. Just because you start making more money doesn’t mean you need to start spending more money. Don’t go out and spend hundreds of dollars at a club, and don’t go out and buy a house and a car. I paid all of my loans off in less than a year and after they were paid off, I felt a huge sense of relief because I had no financial obligations whatsoever.

4) Treat yourself and your family to something special

They’ve been supporting you your whole life. If you’re in the position to do something nice, show them you appreciate their support because there’s a good chance you’re not going to be able to do anything nice for them for a while.

I just quit. What do I do now?

Great! You’ve just taken the first step. You’ve got a blank slate, open road – but this time you’re the one in the driver’s seat. I can honestly say, that within the first 2 months of working on Backspaces, I had accomplished more than in 2 years working anywhere else. You’re at the start of something that could be very special, but at the same time very fragile.

In my next post, I will outline what Adrian, and I have done withBackspaces in the past six months, and what that process was like.

Highlights include: Going from idea to prototype in 3 days, getting beta testers within the first week, our magic “two week” iteration cycles, open sourcing Instagram over a weekend, our 3 month app store deadline, and more.

Thanks to @jcottr, @SandersAK, and @jacobfsamuel for reviewing this post.