The rule that worked too well.

Ever since I got my first taste of business success back in 2009, I had a very simple way of deciding what I wanted.

More.

I wanted to make more money, take on more (and bigger) responsibility, and find more customers and readers. If something worked well, my goal was to make it work better.

And candidly, for a long time, that was probably the right approach.

When I was 28, I had already been fired from a bunch of jobs, was deep in credit card debt, and struggling to survive in NYC. My life had been reduced to sleeping on a couch in my friend's living room in Brooklyn, next to a rusty old rolling rack that held all of my possessions.

That 28-year-old version of me didn’t need to sit around philosophizing about what “enough” meant. He needed to get his shit together and start making some money. More was incredibly important at that point in my life. It helped me get out of debt, get my own place, and eventually gave me and Jennifer better choices about where we lived and what we worked on.

And more continued to serve us for the next decade.

When I left my executive job in 2019 to start working for myself, I continued to need more. More attention, more content, more podcasts, more networking, more masterminds, and more of everything that would help me become a successful entrepreneur. I was trying to create as many opportunities as possible for someone to find me, pay me, and tell somebody else about me.

And it worked.

But there’s a problem with learning that more is always the solution.

If you think more is always the answer, there’s a good chance that you’ll adopt it as a permanent rule. And that’s exactly what I did. If my audience grew, I wanted it to grow even more. If something sold well, I thought about what else I could launch. If the business had a great year, I immediately started thinking about next year’s growth plan.

That’s normal entrepreneur behavior, of course. Growth in your business is good. Nobody writes a business book called How to Keep Everything About the Same. But this lesson can mess with your head if you start to believe that it will apply forever.

We’ve never had any employees or investors, a board, or anyone else demanding that this business grow like wildfire. There’s no payroll hanging over our heads. It’s just the two of us. So the pressure of bigger, better, faster, and more was coming directly from me. And I never stopped to ask a very obvious question:

Does more still improve our lives in a meaningful way?

Let’s say the business gets 30% bigger next year. Awesome. Does that make an ordinary weekday better? Do I get more enjoyment from my writing? Do Jennifer and I spend more time together, hang out with our friends more often, or wake up feeling any different?

Maybe. But probably not.

There comes a stage when the extra 30% mostly just gives you a 30% larger number on a spreadsheet and a chance to grow 30% bigger again the next year. That’s about it.

Sometimes I lie awake at night worrying that I could spend the next fifteen years crushing business goals while everything else slowly falls by the wayside. Then one day, I could look up and realize the best years Jennifer and I had together had slipped by in a haze of business, and it was too late to get them back.

We’re 45 and 47 years old, healthy, physically fit, and energetic. Right now, neither of us is caring for a parent. We can mostly do whatever we want with our time, but we have no idea how long this version of our life will last. Maybe five more years. Maybe fifteen. Maybe thirty if we’re lucky. But it won’t last forever, that’s for sure.

I worry that we might waste it. We could lock in on business growth, hit every goal we set, and everyone would probably cheer us on.

From the outside, we’d be succeeding.

At 28, money was scarce. When I started working for myself, attention and opportunity were scarce. Getting more solved both of those problems. But those aren’t the scarce things in our life anymore. The scarce thing now is the number of years we have this much freedom and the energy to use it.

And, up until a few years ago, I was still using a rule built for the problems I had in the past.

I came into entrepreneurship assuming that the hardest part of ambition was setting these big goals and having the discipline to get after them. A decade later, I think simply saying “more” is the easiest goal you can set. The harder part is knowing when more has stopped solving your problems.

You don’t need to learn anything about yourself to pursue more. If you earn $200,000, then $300,000 sounds even better. If 10,000 subscribers read your work, 50,000 sounds like a better goal. Wherever you finished this year, just make next year’s number larger and get to work.

Enough is a more difficult goal to set because nobody can tell you what your answer should be. It's up to you to figure out how you want to live, what work you actually enjoy doing, how much responsibility you want, and what money and success should make possible.

And that’s why more is such a difficult rule to break. If a strategy stops working, that's easy to question. But a strategy that keeps working can easily steal another decade from you before you ever ask if it still makes sense.

I certainly still have a lot of ambition. I like building stuff, making money, writing and publishing, and betting on fun ideas to see if they work. I’m just wired that way.

But I’ve also come to learn that not every successful thing needs to become a bigger successful thing. These days, I need more to have a real reason behind it. If it gives Jennifer and me something we actually want, then I’ll go for it. If a new project sounds fun, then I’ll absolutely take a swing at it. But “because it could be bigger or make more money” doesn’t feel like a reason to do almost anything anymore.

I spent a big part of my life getting better at maximizing everything. That 28-year-old version of me sleeping on a couch in Brooklyn definitely needed more, and I’m glad he chased it. The new entrepreneur in 2019 needed it too. But the goals that get you out of one stage of your life can follow you into the next without you even realizing it.

At some point, more will no longer improve your life.

But if you don’t stop and notice, it becomes the only goal you know how to set.