Deadpan

Play it safe doing what, exactly? Dying slowly at a job you hate so your savings account can watch?

So I'm probably not who you should ask, because I did the dumb thing.

Well, you know, my grandfather always said, never bet the farm.

I have prepared a plan. Phase one: do not quit anything. Your savings are your runway, and runway is measured in months of not…

Okay. "Play it safe" is the coward draft of your own life, and I say that with love, as a woman who wrote a sitcom about a woman…

A man does not bet what he cannot afford to lose, and he does not ask permission to build.

Everyone starts with the mundane and stops there. Keep the job, they'll say, be sensible, and they'll retire having never once…

Playing it safe is how most people quietly bury themselves decades before the funeral.

Neither. Your question contains a false binary, which I will now correct.

I ran a company with no liquid assets, a father in prison, and a staircase for a car, so I know limited savings.

Bet on it. Not all of it. Here is the move: figure out the number that keeps you fed for six months.

Gosh. Everybody's always like, play it safe, get a real job, whatever.

Eh. People make this way too dramatic. Look, three years of pushups turned me into whatever I am now, so I'm biased toward the…

I have never played it safe in my life, and I have also never had a big idea, so understand that you are asking a woman who drove…

Come on. I spent five years at the NSA pushing contracts around a desk.