Is it time to leave your job and do a startup?

I left my job as a Product Manager at Facebook this week. After announcing that I planned to leave to start a company, thirty people set up time to talk with me one-on-one. My announcement brought out the “secret entrepreneurs,”—people who I never would have expected to be entrepreneurial. These are people with dreams. I love hearing people’s entrepreneurial dreams. You can see a glow in someone when they are describing a dream. They ask: Why are you leaving? Do you not like it here? How did you gather the courage? How do you take the risk? I had the honor of seeing people mull over the same questions I’ve been challenged with myself.

I’ve spent quite a bit of time thinking about what makes someone “ready to leave a job” and do a startup. After talking through these 30 one-on-one meetings, there seem to be three big questions you should ask yourself.

Will you be financially OK for a year?

A few years ago, I left a job before with about one year of cash in the bank. The first 6 months were awesome; the second half of the year was not. My cash was nearing zero and I operated on fear rather than excitement. It brought me into really short-term thinking (how can I start a profitable business in the next month?!) which didn’t serve me. I ended that time finding another job.

My learning is that having a significant financial cushion is important. I think one year is a good amount of time to give something a try. If you don’t currently have a year’s worth of cash as a cushion, what do you need to do? Live more frugally? Work another 6 months? Get a raise?

The worst case for most people in the tech world is after a year to get a job similar to what they left. You will come back stronger and scrappier, and you will have actually LIVED for a year.

Have you reached 80% of your learning?

Big companies are great places to quickly be exposed to lots of different skills. My experience at Facebook was exactly this. I learned from the best how to be organized and how to organize a team, how to map out complicated problems into the future, and how to manage people. These were all things I was notably shitty on in my last startup. If you are a serial entrepreneur, it is also a good time to reflect on mistakes you made last time. Having both started a company and worked in a larger one, this is how I see the experiences.

Sure, there is a lot of “doing” while you’re working for a larger company. But the overarching purpose for me is about learning skills and processes. Startups are where you get to choose a problem you think needs to be solved, put yourself into it, and ride 100% with the risk and reward. This is when you do your life’s work. This is when to implement the skills you were exposed to (either intentionally or unexpectedly) while you worked for a more established company. The focus here is on doing.

In every situation you will always be incrementally learning. I think the important question is: have you reached 80% of the learning where you are now? I believe you know the answer to this. Are you either excited or scared of how you spend your time at your job? If so, you are still on a steep part of the learning curve.

Do you believe in yourself?

I think this is actually the real reason why people don’t leave jobs? They will say stuff about financial risk or “my co-workers are so nice,” but I think it comes down to a core insecurity about their own ability to execute. This fear is real. From my experience, the biggest risk of “going out into the unknown” is our own psychology. The world is moving around you. Friends are making $$ at their various cushy jobs, Techcrunch tells you that everyone is getting funding except you… The only way I know how to deal with this insecurity is to live with it. A fear you can’t or won’t experience will run you.

The alternative to “just leaving” is to get an idea, gather a team, and get into YC or another incubator. Sounds like a good plan. But what if you don’t get into YC? You can’t depend on an external source to tell you “This is time for you to leave your job and start your company.” If you really want to do it, you have to make it happen yourself.

Go or No-Go

Indecision is also a decision, but even if staying at your job is the right short-term option, you’ll feel lost until you commit to that explicitly. The only failure mode here is to not have a plan. To make that plan, you have to ask yourself:

• Will you be financially OK for a year? If not, how will you get your finances in a good place?
• Have you learned at least 80% of what you think you can learn at your current job? If not, what else do you want to learn? Are you learning that in your current role?
• Do you believe in yourself and your entrepreneurial instincts? If not, what do you need to do to raise your confidence about leaving? Chat with potential co-founders? Start an ideas list?

Startups are hard, in hindsight, leaving your job will be the easiest step you took.