Make a plan to quit

My wife and I have been contemplating a move to the Portland, OR area (where she is from) for a few years now, prompted by having out first kiddo.

I originally targeted early 2023, when the lease on our rental was up. But, in the fall of 2022 I knew we wouldn't be able to get our act together to move in that timeframe.

So we sat down and just decided that no matter what our circumstances were (the main consideration being have remote jobs or gigs), we'd move in spring 2024.

Basically, we made a committment to "quit" living here in a certain time frame. We knew if we didn't do so, we would just live here forever, always pushing off a big move that could kick off the next great stage in our lives.

Annie Duke, in her book Quit: The Power of Knowing When to Walk Away, describes the importance of planning to quit before you actually have to make the decision.

The second is that making a plan for when to quit should be done long before you are facing the quitting decision. It recognizes, as Daniel Kahneman has pointed out, that the worst time to make a decision is when you’re “in it.”

If you are a pilot or scuba diver, you make a plan on when to turn around or end your dive based on the amount of fuel or air you have left in our tanks. Making that decision on the fly (pun unintended) can get you killed.

The problem is, it's hard to do that with big life decisions.

When should you move to a new place? When should you quit your job? When should you retire?

These are hard questions, but if you don't ask them, you're at risk of making bad decisions, or the more likely case, making no decision at all.

Let's take the decision to go 1099. I've had people e-mail me asking about the book but then decide not to buy. That's totally okay. BUT, it appears to me that some times they're just procrastinating on taking action with their career.

I've followed up with a few of them on occasion a few months later and they tell me, "oh well I'm still considering a few things..." which implies they've done nothing.

And that's totally normal.

But if they were to think hard about what their "quit criteria" would be for their current professional situation, they'd probably be better off.

If they said, "if in six months I haven't received a raise or promtion, I'm going to committ to leaving my current job and apply for a new one," they could evaluate their situations at the appropriate time and take action.

So I want you think about where you'll be in six months with your career. If you're in the same job, would you consider that a failure? What should you stop doing and what should you begin doing?

If you have a minute, just reply to this e-mail and let me know your answers. I'd love to hear from you.

Get a free chapter of
Going 1099

Subscribe to receive Chapter 5: How to model and compare your 1099 income to your W2 compensation.

    We won't send you spam. Unsubscribe at any time.

    1 comment

    • $100 to buy the book now could pay off in tens of thousands and a whole new life. Just buy it already! If they read it and find out this is not for them, so much the better. They are then freer in their thoughts to move in and focus on other options. If they read it, and it is for them, they can start to plan. Win either way.


    Leave a comment

    Please note, comments must be approved before they are published