How to Quit Your Job Without Second-Guessing

career, personal stories, quitting

An old boss’s office was stuffed with books. Wall to wall.

It left no doubt that his was a business built on NYT bestsellers, same as his predecessor before him, who repped authors like F. Scott Fitzgerald, Raymond Chandler, and Elmore Leonard.

Sitting in the chair across from his desk, I stared at the spines of all these books.

Man, he’s been in this business a long time.

I learned a lot. Was on all his calls. Listened to negotiations. Studied literary agreements and learned about reruns, spinoffs & subsequent productions, how to stipulate a sliding purchase price, and the importance of reversion language.

But today I wasn’t in his office for a lesson.

I looked up at him. I told him I was leaving the company to work for a writer.

He was upset and hurt. Understandably so.

“I think you’re making a big mistake.”

He focused on 2 leverage points to convince me to stay.


“What happens if a show doesn’t get picked up?”

“What happens if you lose your job after 12 weeks? I’ve seen it happen.”

And money:

“I hope you have a lot of money saved up.”

“The money is in representation, you know.”

It wasn’t a compelling argument. I’ve thought a lot about WHY it wasn’t compelling. This is what I realized.

The Upside

He thought he was showing me the upsides to staying: security and money.

He valued both. Someday, I will too. But at that point, they weren’t important. He didn’t understand that.

At that moment (and today) the three things that do matter to me:

  • Where do you work with the best?
  • Where will you learn the most?
  • Where will you have the most impact?

Some upsides he could have offered that would have been more compelling:

  • Hired another assistant so I could focus on higher-level tasks
  • Brought me into signing meetings
  • Incentivized bringing in new clients

The Downside

There’s a famous story told by Richard Branson about protecting his downside: in 1984 Branson decided to get into the aviation business. At the time, the core of his business was Virgin Records, a hot independent music label.

First he negotiated with Boeing:

“Once I had negotiated the price for a second-hand 747, I said to them that if Virgin Atlantic wasn’t successful, then I wanted to be able to hand the plane back at the end of the first year – therefore protecting the downside.”

Then Branson needed to convince his board of directors:

“I was able to say at the absolute worst we would lose six months’ worth of profits. But if it went well, we would then be able to buy a second and third plane, build another successful business and something we could be really proud of. Because I had the downside protected, they could see the logic of my decision. While they didn’t welcome it with open arms, they gave me their blessing.”

My old boss presented the downsides. He tried playing to fear.

But thinking it through, what was there to fear? What was the downside?

Even if the worse came to pass, there was a number of ways to protect against my downside beforehand:

  • Double-down on my networking efforts
  • Double-down on money I’m saving per month
  • Don’t burn bridges with the company

You protect the downside against forces outside your control.

Concurrently, focus on factors within your control:

  • Do amazing work
  • Anticipate needs before they arise
  • Work on your side project

Where Does the Greatest Risk Lie?

There are risks in change.

But there are risks in maintaining the status quo, too.

It’s easy to spot the former: new jobs, new industries, and new markets are by definition unproven.

It’s much harder to see the risk in staying the same. To measure it objectively, you have to ask: where is the upside? How great is it? And how can I protect my downside?

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