The $95k Question from Your 95-Year-Old Self

What would your 95-year-old self pay you $95,000 to do next year?

What’s something you’re convincing yourself you don’t need to do, but which could pay major dividends in the long run? Better yet, something that’s not even on your radar.

Move to a new city? Quit your job and try something different? Hire a coach? Go back to school? Get a nose job?

That’s the question I’m going to work on for my year-end review. Because I’ve learned that year-long plans, goals, and resolutions never make it that far. So instead, I just want to start 2026 with a bang: something that shakes things up, challenges my self-perceived limits, and earns me new information.

Even if it doesn’t work out, I’ll learn something about myself. And that data helps me make better decisions going forward.

The Corporate Ladder of Your Life

To figure out what my 95-year-old self would bribe me to do, I’ll use data from my system. I log my life, review it weekly, monthly, quarterly, and yearly, and plan accordingly. It’s basically a corporate reporting structure where Daily Chris reports up to Weekly Chris, who reports to Monthly Chris, all the way up to 95-Year-Old Chris.

Why? Because my brain is a spin doctor. 

Last year, I fed all my logs into AI and asked it to analyze my patterns. One of the findings: “Stop wasting time writing blog posts and newsletters that get minimal engagement.”

It stings because it’s true. I’d been telling myself I was “building an audience” when really I was avoiding the scarier work of actually testing my frameworks with real people. My memory wanted to give me credit for effort. My logs showed I was hiding under a cozy cognitive security blanket.

Without the system, I’d still be congratulating myself for being “productive.” With it, I caught myself stalling and could actually fix it. 

That’s why my system is priceless to me. You couldn’t pay me to give it up.

Which made me wonder: 

I suspect many people’s 95-year-old selves would pay them $95,000 to install their own systems.

Coincidentally, Shaan Puri posted this in his latest newsletter on December 26th:

Shaan’s objectively successful. From what I can tell, he has similar priorities to me. He wants a system. He can’t make it stick.

Why? 

If someone smart, self-aware, and motivated like Shaan can’t implement something he intellectually agrees would help him, then something deeper is going on. I wish I knew what it is.

My 100% Failure 

One of the most unfortunate realities I’m going to have to face when reviewing 2025:

I had a 100% failure rate getting anyone else to implement their own system.

Early this year, I recruited five beta testers for my new ARC program. I promised to act as an agent on behalf of their 95-year-old selves to help them implement operating systems for their unique wiring so they’d stop scattering effort and start compounding it down deeply rewarding paths.

The “Innate Edge” mapping—where I help people identify their superpowers—resonated with everyone. They loved it. Success!

The systems part? 

It started well. Everyone logged their lives. Every week, we’d meet one-on-one to discuss: What’s going well? What could be better? What patterns are emerging? How can you act differently? 

Lots of insights. Combined with their Innate Edge clarity, everyone was ready to blast off.

Then things went sideways. Everyone loved discovering what made them unique. They hated the daily work of leveraging it.

Within a month or two, everyone’s systems were gathering dust (except one person who already had a system before we started). Their rationalizations:

• “I’m busy right now.”
• “I’ve been journaling from time to time.”
• “My life’s going so well, I don’t need it.”

Reactive, not proactive. Everyone reverted back to working in their lives, not on them. Back where they started.

My mission is to become world-class at helping people engineer extraordinary lives… but I can’t even get my own wife to stick with a system. Kim is super capable, has seen firsthand what this system does for me, and can’t ghost me and my check-ins. If it doesn’t work for her, that’s a data point I can’t rationalize away.

So what’s going on? What am I missing? 

The Three Trickiest Disconnects

I put my system into action to diagnose why my system fails for others.

I pulled my data: transcripts of client calls, their psychological profiles, personal reflections, detailed overview of my ARC frameworks. Then I asked my “AI Board of Directors” to help me spot patterns I couldn’t see. I also consulted BJ Fogg, James Clear, and Daniel Kahneman, by way of uploading their books to LLMs.

I—we?—unearthed 14 potential disconnects. Here are the three that seem to be the biggest culprits.

 (Full list here if you’re interested.)

1. Discovery vs. Discipline

When I spot a negative pattern in my logs—”Oh, I’m polishing my frameworks again instead of testing them in real life”—I get excited. It’s like finding a bug in code. Now I get to fix it.

Every blindspot I uncover makes my life more effective and energizing. More energy makes things easier. So to me, discipline is downstream of discovery. My system generates energy.

But when one client saw a similar pattern in his logs—another week of saying he’d work on his business but spending Saturday on other chores instead—he didn’t think, “interesting data.” He thought: I’m a fraud.

For me, data strips the emotional noise of remembering and judging. For him, data creates it. A red X on my spreadsheet is a bug to fix. A red X on his spreadsheet is proof he’s defective.

For him, the system wasn’t a discovery tool. It was a discipline tool. A boss in his pocket—his past self giving his present self orders, with the looming pressure of his weekly self’s critical review. The whole process felt like work he had to do instead of a useful tool for making his life feel less like work. It sucked motivation instead of generating it. So he pulled the plug.

2. Credit vs. Critique

At the beginning of August, before I looked back on July 2025, my brain was complaining, “Rough month. Didn’t make enough progress on ARC. Got zero responses to outreach.”

But when I looked at the logs of what actually happened, the story was different: the Parksville trip, the FUKITS workouts I kickstarted, the processes I streamlined, the orcas I saw. So much that I actually wrote to myself, “Whoa, I can’t believe the 1st week of July was the same month.”

Without the system, I would have filed July away as a failure. With it, I realized it was one of the richest months of the year. 

Just as much as my system reveals hidden biases I need to correct, it gives me credit for things my memory is dismissing.

My clients experienced the opposite problem. Their brains already told them comforting lies—rationalizing scattered effort as “exploration,” endless research as “preparation.” But then the system exposed their brain’s ego-soothing BS.

Clients didn’t find pleasure in treating their logs as a treasure map in pursuit of suboptimally optimizing their lives. Their systems felt like a constant dissatisfaction generator. Always critiquing. Always needing more optimization. Never good enough.

3. Humility vs. Humiliation

When I look at my logs and see, “Yikes, I spent so much time cold emailing people about ARC and got zero responses,” my reaction is: Chris, you moron. Obviously your emails suck or they think what you’re doing isn’t worth their time. Stop wasting your time, too.

It’s amusing evidence of my naive optimism. I take the “insult” as personally as when my wife tells me my hair looks stupid. She’s objectively right. Why be upset about the truth?

My clients seem to be more sensitive.

One told me explicitly: “It was making me feel worse.” Another said seeing unchecked boxes “creates an even bigger heaviness.” Facing their “failures” strikes them as humiliation rather than humbling feedback.

The system is a mirror. If you don’t like what you’re seeing, the simplest solution is to stop looking.

A Solve-able Problem?

How do I fix these disconnects? Can I? Should I?

I don’t know.

Maybe some people genuinely can’t enjoy working on their lives. Maybe they need extrinsic scaffolding—coaches, peer pressure, stakes, rewards—that I’m not wired to provide. Maybe the curiosity-to-confidence path only works if you already have enough autonomy and patience to experiment.

Likely, I simply suck at installing systems for others.

But do systems simply suck for some people? I’ve tried as hard as I can to come up with a good reason why someone’s 95-year-old self would say, “I’m glad I never had any sort of system. I’m glad I just went with vibes and trusted my gut and hoped for the best.” I’ve yet to find a convincing argument.

I keep coming back to the same analogies. A business wouldn’t run without reporting. An astronaut wouldn’t fly without a dashboard. These comparisons hit home for me. But they clearly don’t convince others. Which means either I’m missing something fundamental about how other people work, or I’m right but explaining it wrong, or life is different from businesses and spaceships in ways I’m not seeing.

Maybe my system works because I’m already wired for it—high conscientiousness, low compassion and neuroticism (so I don’t flinch at bad news), analytical by nature. Maybe trying to export it to people with different wiring is like installing a submarine’s navigation system into a private jet. 

But I can’t shake the feeling that everyone’s 95-year-old self would want them to have some version of this. Not my version. Their version. I just don’t know how to help them build it yet.

Without a system, most people hand the steering wheel to their co-pilot I call “Landon”—the evolutionary wiring that wants you safe, comfortable, and conforming. Landon doesn’t care if your life’s extraordinary. Landon wants you to survive. The system is the only thing I’ve found that consistently beats Landon.

But I’ve failed to help others consistently beat their Landons. 

What Does Your 95-Year-Old Self Think? 

What would your 95-year-old self bribe you $95,000 to do next year?

Not what you already think you want to do. Not what would impress other people. What would the most fulfilled possible version of Future You, the one who’s already lived through all the consequences of your choices, bribe young(-er), naive, biased Present You to start right now?

Maybe it’s building a system. Maybe it’s something you can’t even see yet because you don’t have the data.

I still don’t know why systems work for me but not for most people. But I’m going to keep using mine to figure it out.

Thanks for reading.

Keep doing exciting things,

Chris