How I Accidentally Complicated My Life While Trying To Simplify It

Or... The Make It Easy Filter

My friend Kim Doyal told me recently that my “Make It Easy” philosophy deserves to be shared as a theory in itself. I laughed. It’s not unique, I said. Essentialism. Minimalism. The 80/20 principle. Marie Kondo asking if things spark joy. Tim Ferriss asking what this would look like if it were easy.

But then Kim pushed back: “It’s not the concept that’s unique. It’s how ruthlessly you actually use it.”

And she’s right. Though “ruthlessly” might be generous. “Obsessively” is probably more accurate. “To the point where I managed to turn ease into work” is closest to the truth.

The Filter That Changed Everything (Until It Didn’t)

Here’s the setup: I built and sold a seven-figure company. “Retired.” Got the financial freedom. Won the game.

And then kept playing anyway.

New business idea? Let me add seventeen features to make it impressive. New content strategy? Obviously this approach needs elaborate systems requiring daily management. New opportunity? Better say yes because it could be amazing, even though my entire nervous system is screaming no.

I had already won. But I kept acting like I was still trying to prove something.

The turning point came when I caught myself building a complex workflow to automate my “Make It Easy” decision-making process. I was literally creating systems to help me... not create systems.

That’s when I knew I’d gone too far.

The initial “Make it Easy” philosophy.

Four questions I’d ask before saying yes to anything:

• Does this energize me or drain me?

• Am I building a system or creating ongoing obligations?

• Will this stretch me in directions I want to grow?

• Does the money reflect the real value I’m creating?

If something drained me, created obligations, didn’t stretch me strategically, or paid poorly for high value, it became an automatic no. Even if it was objectively good. Even if other people thought I should do it.

And it worked. For a while.

But recently I discovered that I don’t actually consciously run through these four questions, and I never have. Mostly it’s not my brain, it’s my body that just knows. Some things make me lean in. Others make me want to close my laptop and stare at the ocean.

The four questions above were just my attempt to reverse-engineer an instinct so I could explain it to you. So I could turn it into content. So I could look like I had my shit figured out.

So here was my second discovery...I don’t actually want everything to be easy. Easy is boring. Easy makes me restless.

What I want is energizing.

Strategic complexity energizes me. Designing elegant systems that solve problems once? That’s play. That’s fun. That’s what I do for entertainment.

Operational complexity drains me. Managing those systems daily? Maintaining anything? Showing up consistently to perform the same tasks over and over? That’s my personal hell.

So when I said “Make It Easy,” what I really meant was “Make It Energizing.” But that doesn’t have the same ring to it. And it doesn’t fit on a coffee mug. And it’s harder to explain at dinner parties.

The problem is, the moment I started trying to teach this distinction, the moment I put together a first draft to support Kim’s conviction that this principle should be shared, it stopped being easy. It became work. Content strategy. A thing I had to maintain and explain and defend.

I’d like to hope that I’m the only one out there who could make ease complicated, but maybe not? Maybe your feeling the same?

I’m into the next stage.

Because here’s the uncomfortable part that I had to admit to myself after I’d written that first draft. The “Make it Easy” filter only works because I’ve achieved financial freedom.

The initial filter (the one without the energizing bit) should be used to address the common problem of, “what’s the minimum viable path to success?” But that wasn’t the problem that I had, so that wasn’t the question I should have been asking. The question I should have been asking is “now that I’ve won, what do I actually want?”

That’s a totally different question (and, let’s face it, a pretty insufferable question if you’re still in the building phase and grinding toward stability).

But, I still think the second version of the filter (the one with the energizing bit) is worth considering, even if you are still climbing. Asking yourself the question, “does this energize or drain me?” saves you from building the wrong thing. Trust me when I tell you that you can achieve the goal and still feel empty if the journey changed you into someone you are not.

I know this because I did the thing, yet, I’m still trying to figure out who I actually am underneath all the achievement.

I’m getting there. Figuring it out slowly from one realization to the next. I’m someone who gets bored easily. Who craves strategic complexity but hates operational maintenance. Who would rather write novels than build funnels. Who wants to host intimate salons, not scale a coaching empire.

The filter didn’t teach me that. Living did. The filter was just my attempt to systematize the living.

The Filter In Action (And Why It’s Also Ridiculous)

Let me show you how this plays out in real time.

Last week, I read this article that proposed a complex AI tool implementation that promised to revolutionize my workflow. Multiple agents running simultaneously. Automated research. Content generated in my voice while I sleep. The whole sci-fi dream.

It sounded amazing and other creators were raving about it.

I looked to my filter.

It certainly wouldn’t be easy, so it failed the first version, but might it be energizing, and dare I say...fun? I was confused and unsure (even though the little voice in my head was screaming at me - go on...prove you can do it. Prove your worth!), so I asked my AI advisor Sage (yes, I named my Claude project) to evaluate whether I should implement it.

Sage’s response was immediate: No. This fails every one of your filter questions.

The breakdown:

• Energize or drain? Drains. Requires learning terminal commands, maintaining GitHub repos, debugging technical issues.

• System or obligation? Ongoing obligations disguised as automation.

• Strategic growth? No. I want to grow as a writer, not a terminal jockey.

• Value match? Irrelevant. This would cost time without generating any actual value for my work.

Clear no. Five minutes. Done.

But here’s the ridiculous part: I didn’t need Sage to tell me that. I knew the moment I started reading about it. While my brain, and the little mean girl that lives inside of it, was screaming at me, my body pulled back. Running the question through the filter just gave me permission to trust what I already knew.

So why do I need the filter at all?

I think the real lesson isn’t about having a framework. It’s about trusting yourself enough to not need one.

The filter is training wheels. Eventually, you just... ride.

You notice what makes you lean in versus pull back. You do more of the first thing and less of the second thing. You stop needing to justify your choices with four-step processes. You just trust that your nervous system has better decision-making capabilities than your strategic brain. Which is a weird thing for a strategic brain to admit (and the mean girl is screaming bloody murder).

But here we are.

After 55 years of striving, the past few weeks have seen a massive discovery. You’re allowed to choose ease. Even if you’re capable of more. Even if others expect more from you (including the mean girl inside your brain). Even if the opportunity is objectively good.

You’re allowed to optimize for energy instead of output.

You’re allowed to say no to things that don’t stretch you in directions you actually want to grow.

You’re allowed to value your mornings, your creative energy, and your sense of play more than your productivity metrics.

But also? You’re allowed to stop systematizing your ease. You’re allowed to just be easy, without turning it into content or frameworks or things you teach other people.

What Happens Next

I’m officially retired (which doesn’t really mean anything, it’s just a word I’ve never given myself the grace to use). I’m stepping away from the active business building, anyway. Letting the Artist win over the Architect for once.

I’m writing novels now. I have a historical novel series about The Darien Scheme that has been nagging me to write it for years. I’m going to work on that in 2026.

The Salons will stay. They energize me, and they serve our community which is important. Even if the workload doesn’t justify the income, I can absorb that problem - sometimes the return on investment isn’t financial.

The Questbooks are still there if you want them. They are creative, physical objects you can hold and write in, which feels increasingly radical in our AI, digital everything world.

And I kept one thing: The Build. It’s this business architecture service I offer at a premium price, but only to people who find me organically. I design the entire foundation of their business in one intensive engagement, create them a custom AI advisor, and then exit. No ongoing coaching. No maintenance. Pure strategic complexity with zero operational obligation. It’s the only client work that still makes me lean in instead of pull back.

I might talk about it occasionally, because the work genuinely fascinates me. But mostly?

You’ll find me writing about our current visit to my brother and his family in the plains of Las Pampas. Followed by a trip down the Amazon in Peru. Followed by a week in freezing Brooklyn with my daughter for Christmas (yes, she will have to lend me a coat. There wasn’t a chance I was getting that, and clothes for three different seasons in our suitcase allowance).

That’s my life now. No frameworks. No filters. No complex systems.

Just me, doing the things that make me feel alive, and writing you letters about it (maybe teaching you something, maybe helping you realize something, maybe just sharing) when the mood strikes.

P.S. I’m going to release all of next year’s salon topics in a single document at the end of this month to help you plan your submissions. As always, I can’t wait to read them.