[#46] So, You’ve Built a Business or Career You Don’t Want to Run Anymore. Now What?

The smartest, highest-performing people I know are terrible at one thing: thinking outside a binary.

Makes sense. We were trained this way and rewarded for it. You got the grades or you didn’t. You got into the school, landed the job, got the client, made the sale, exited the business… or didn’t.

Thinking in binaries is a big part of what makes us fast, decisive, and good at what we do. It also makes us spiral when those structures disappear.

Athletes get an offseason. Students get a graduation ceremony. Hard-charging, high-performing people get neither. No one gives us a hard break, so we never end our own seasons or know what to do when one has clearly ended.

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Last year at my friend Selena Soo’s live event in NYC, my public commitment to the group was to reduce my Zoom calls by 90%. People applauded. I also realize this can sound really pretentious to the average person:

"Oh, look at me – I work too much and have done well but I still overwork and that’s my hardest challenge, boohoo!"

Well, good thing average people don’t read this newsletter! Average people don’t read, haha. So, let us reason together, fellow Workaholics.

After coming home from my self-imposed summer vacation last month, I opened my calendar and saw that I accomplished my 90% Zoom reduction goal. None of this is me disowning what I built, of course. I’m incredibly grateful for clients and colleagues I’ve worked with over the years.

It took me a while to see it but the business I built did what it was supposed to do. It ran. It scaled. Like a house, I didn’t actually need to rebuild it or even repair it. I needed to renovate.

Are You Just So Good That You’re Bored?

It’s been said that boredom is a sign that you’ve achieved mastery: what you once spent so much effort to learn is now routine. True masters learn to fall in love with the ordinary grind.

I don’t know, sounds like torture to me. I don’t want to do the same thing –– I have to do something new. Blow up my business, burn it all down, start from square one!

There is the binary.

1. Stick with the thing you built and suffer boredom forever, or…
2. Nuke everything and start all over.

I’m convinced this is a false binary.

In every season, we carry the same skills, experiences, wisdom, and habits (good or bad) into whatever comes next. We never truly start over, we just transfer.

I read David Brooks’ The Second Mountain last year and really resonated with this line:

"A job is a way of making a living, but work is a particular way of being needed."

I’m going to hack this line in a way that makes more sense to me: "Work is a way of making a living, but a calling is a particular way of being needed."

Maybe that’s what happens. Somewhere along the way, work stops serving your calling, and the calling starts serving the work. After all, you’re great at what you do.

For me, I needed a renovation. I found a helpful blueprint from author and NYU Stern professor Suzy Welch, who coined the 10-10-10 concept: How will I feel about this decision in ten minutes, ten months, and ten years? (Brooks mentions it in his book, which is probably why it was on my mind.)

I run a modified version: ten days, ten months, ten years. (No life decision feels different in ten minutes, that’s just adrenaline.)

Let’s imagine a real decision: releasing a toxic client.

• Ten days: An awkward email, some guilt, a dip in revenue.
• Ten months: You don’t even think about this person. If you do, you may realize you dodged a bullet. Maybe as a result, you’ve spent nearly a year making that kind of healthy decision over and over again and your life (and revenue) is better.
• Ten years: You’re probably much healthier in drawing boundaries, your business serves you vs. the other way around, and you’ve got confidence in other areas of life because most business problems are personal problems in disguise anyways.

Try writing this 10-10-10 thing out on an upcoming decision. You may realize that you don’t have to burn anything down and just need to renovate.

Late last year I wrote in Issue #16 about how I plan my annual calendar on a big white board. I’ve been tempted more than once to erase all of the past months, but it’s been cool to see it take shape.

I can see the ebb and flow of my life. While in the hospital back in January, I chewed on this question:

"Can I live in a way that I look forward to looking back?"

Seeing this on my wall for the past almost ten months has clearly shown me where my attention has gone and if I have cultivated a life that germinates more days worth repeating.

These ten months are going to matter in ten years, probably way more than I realize right now.

Hit reply and tell me if you’re going to run a decision through 10-10-10. Would genuinely love to hear about it.

Happy 10-10-10-ing,

Mike Kim

All em-dashes in this issue were human-generated, by me. I refuse to let AI have my em-dashes.