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figuring out who should buy your business

The Irish Goodbye

I was recently chatting with my sister about the company her husband founded, a clothing start-up I thought the world didn’t particularly need. Fumbling about, I asked her should it not launch as well as planned if he might schedule an appointment to take it behind the shed and shoot it, which went over about as well as you might expect. Had a hard time sleeping that night knowing even with my heart in the right place this “healthy challenge” came off rude and unsupportive. Alas, if only I’d first read Quit by Annie Duke. Subtitled “The Power of Knowing When to Walk Away,” the book instructs on embedding rationality into our lives. One key takeaway is called kill criteria through which we commit, “If I am (or am not) in a particular state at a particular date or at a particular time, then I have to quit.” Bingo. I’m with Cher in wanting to turn back time because with a redo I might’ve said, “Sis, have y’all heard of states & dates?” and then nurtured a conversation on the topic. D’oh!

Duke’s career path is twisty and fascinating. A serious ailment redirected her from tenure-track opportunities in academia into a lucrative run as – of all things – a professional poker player. Over 18 years, she perfected the art of quitting, something amateurs struggle to understand. Pros know they’re playing one long game, “so in the grand scheme of things whether or not they lose one single hand of poker matters very little,” she writes (and don’t get her started on the boneheaded notion of quitting while you’re ahead because it should be the exact opposite). One must master expected value scenarios, which simply put are like forks in the road, left/right decisions we make in determining the (more) positive track. Duke peppers her book with inspirational tales of those who had the guts to eject as well as cautionary ones about those for whom quitting wasn’t an option. She makes it plain for the reader: “If you figure out that another path carries a higher expected value, then walking away from the path you’re currently on and switching to the new one will get you to where you’re going faster.” If that sounds easier said than done it’s because it is given human nature: our tendency toward irrationality and worrying about being deemed a loser.

The book’s only weakness is its overreach into goofy examples like exiting stalled romantic relationships or crappy movies. Regardless, managers should take note of the advice herein on goal setting. Duke outlines three ways this seemingly no-brainer exercise can be fraught with danger: grit is not always virtuous; the pass/fail model is broken; and default stick-to-it-tiveness is often unwise. “Escalation of commitment” is no doubt a term Elon Musk would adore, something his idiotic cot-dwelling minions demonstrate when pulling “hardcore” all-nighters. But here we learn of the downside of such single-mindedness, that rules will be bent and values sacrificed when employees feel they must “get across the finish line at all costs.” A hedge is what the author calls “unlesses”: in an ever-changing world, we should be flexible, nimble, and responsive to the evolving landscape. To wit: We will accomplish [state] by [date] unless some unforeseeable curveball screws everything up, at which point we may need to (sing it with me, ‘cuz you know it’s coming) pivot. Pass this nugget along to my brother-in-law, mmm’kay? Operators are standing by – he’s running a BOGO sale on EVERYBODY HATES CHRIS shirts.

If you have anything to say about this, kindly post it below (rather than emailing me) to spark conversation. Thank you!

4 comments for “The Irish Goodbye

  1. Oh man, nothing that in-laws like more than unsolicited business advice about when to throw in the towel on a bad idea… Who’d have thunk, Bondo?

    I do love this concept though. I think more entrepreneurs need to drop the “stick with it at all costs” mentality. It’s just foolish. I remember when you and I first met, I was committed to stick with it. I should have dropped that biz a long time before… will definitely give this a read.

    • You’ll like it for sure, Marc. And while short-term memory is getting spotty, the long one is in fine shape. Never shall I forget the day we met, brother. Thank you for the thoughtful commentary and being one of the good guys. 🙂

  2. Why is Kenny Rogers in my head now, Chris? Thanks for the summary. I will be passing this along to several people I care about, including your brother in law. Take care.

    • Bob! You always know just the right thing to say and do. Much obliged. Tell him hello and – because this is now required – “I hope all is well.” Haha.

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