The most important part of my job is making sure nobody needs me to do it.

That sounds like a weird thing for a CEO to say. But I spend more time documenting, automating, and handing off responsibilities than I do on any single task at work. The goal is to make myself replaceable. And then — once I’ve done that — to find new ways to make myself necessary again. That cycle is the whole job. It’s also how progress works outside of work — we just don’t usually notice it.

Morgan Housel wrote about this from a historical perspective this week.

If you don’t know Housel, his book The Psychology of Money is the best personal finance book I’ve read. As a CPA who’s read well over a hundred books on finance and investing, that’s not a casual endorsement.

His latest piece is about why every generation looks spoiled to the one before it. He tells the story of Queen Anne of England, who had 18 children. Not one of them made it to adulthood. President Garfield died in 1881 partly because the best doctor in the country didn’t believe in germs. Two weeks before FDR died, his blood pressure was 260/150 and his doctors couldn’t do much about it because basic blood pressure medication didn’t exist yet.

Housel’s point: if you showed any of these people a modern pharmacy, they wouldn’t say “you’re amazing.” They’d say “you’re spoiled.”

And he’s right. We complain about the wait at CVS while standing ten feet from pills that would have looked like witchcraft 80 years ago.

My grandparents didn’t go to college. My parents didn’t graduate college. But they raised children, left legacies, built businesses and put me through college. My grandfather nearly lost his legs during World War II but a medical innovation prevented him from being a double amputee: Penicillin.

Every generation works hard so their kids don’t have to struggle the same way. Then when the kids don’t struggle, they look spoiled. The “spoiled” appearance isn’t a side effect of wealth. It is the intended outcome.

This is how I think about running a company.

At work I am constantly trying to eliminate myself from processes. If a process requires me specifically, it’s fragile. If I get sick, go on vacation, or just have a bad week, that process breaks.

So I document. I automate. I hand things off. I build the system so the next person can walk in and do the job without calling me. And then I go find the next problem that doesn’t have a system yet. In that way my job is constantly tackling the newest challenges. This excites me.

It’s a constant cycle: make yourself unnecessary, then find new ways to make yourself necessary. The first part is operations. The second part is leadership. Most people skip the first part entirely because it feels like giving away power. Ironically it’s how you make yourself valuable.

This is how you maintain your value in the age of AI. Not by hoping nobody builds an AI tool that does your job. Find or build the tool to automate what you’re doing and ask for more.

Five years ago, I was personally handling compliance paperwork. Now that’s systematized. So instead of worrying about whether the forms got filed, I get to worry about whether our marketing strategy actually works. Holding onto the compliance responsibility wouldn’t make me valuable because things would break without me in the loop. It would make me less valuable because I wouldn’t be moving up the ladder of higher-level challenges.

This week’s takeaway:

Pick one thing at work that only you know how to do. Not the glamorous stuff. The thing that would fall apart if you took two weeks off. Write down how to do it. Not a perfect SOP — just enough that someone else could stumble through it without calling you. Just one process, this week. The goal isn’t to hand it off immediately. The goal is to stop being the single point of failure. Your job is to give the next person better problems than the ones you inherited.

⚡ ONE MORE THING

The New York Times profiled a guy this week who built a $1.8 billion telehealth company with two employees and a stack of AI tools. Medvi did $401 million in its first year with 16% net margins. He automated and outsourced everything — code, marketing, customer service, fulfillment. It’s the extreme version of everything in this issue. This raises the bar across business, and particularly my own industry. The AI revolution isn’t coming, it’s here.

— Matt

P.S. That compliance example? Five years ago I did it myself. Then I handed it off. Now I’m working to automate it entirely. The person I handed it off to isn’t losing a job to automation — they’re getting a better one. That’s the whole cycle playing out.

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