Playing the Long Game.

Trust, Risk, Hope, and the Art of Seeing Clearly

Feb 10, 2025

A little over a year ago, I asked myself a question that shifted everything:

“Is this a time to make money, or is it a time to learn?”

Of course, it’s never truly an either/or. But when I sat with it, I knew my answer.

I walked away from more than 50% of my income—not out of recklessness, not because I didn’t need money, but because I saw it as an investment. A calculated risk. A move made with long-term resilience in mind.

Because I’ve seen what happens when people find themselves in suboptimal situations—when their backs are against the wall, when they’re forced into reactive decisions, when their lack of preparation shrinks their options to near zero. They start grasping. They make short-sighted moves. They trade their long-term potential for short-term survival.

I don’t want to play that game.

I didn’t have to do it. I could do business as usual for years to come. But that would be a dead end. Eventually. I knew that what got me here won’t get me there, and that I was not done yet. There is way more I want to do. I felt like I needed to clear the decks and make room for it. It required my attention. That said, I am also famous for ignoring things that require my attention - if they’re too much outside of my comfort zone. This time, however, I felt that the stakes were much higher: my sanity was on the line.

But, being a very down to earth dreamer, I also believe in safety first—just not the kind of safety that keeps you small. Not the kind that makes you shrink and stall.

I believe in building a solid foundation so that when risk is necessary, it’s a choice, not a desperate reaction.

I ran my numbers. I mapped my runway.* I played out different scenarios. I asked myself, over and over:

“Does this feel like the right thing to do?”

And every time I felt that visceral yes, it gave me a fresh dose of energy. That kind of alignment is a superpower. It makes you resilient. It sharpens your cognitive and emotional agility—and in times like these, you need that. You need to be able to think clearly while everything around you feels like shifting sand.

This is Not Easy—But That’s Okay

Let’s be honest: this isn’t easy.

It’s a hero’s journey. A quest. Navigating uncharted territory. Mostly fun. But also—not fun at all. And that’s okay.

A lot of the time, I am beyond frustrated with what I do.

My days often feel like a Carrie Mathison-esque mania episode:

Relentlessly gathering snippets of information.
Weaving stories in my head. Then testing them in the real world - when I’m brave enough, that is.
Filtering out noise.
Watching for patterns to emerge.
Constantly - but inconspicuously - mumbling under my breath: What am I missing? What am I not seeing? What are my blind spots?

It’s unnerving. It’s frustrating. It’s hard to explain to anyone else (so I mostly don’t bother).

Because when logic fails and when data isn’t enough, you have to navigate differently.

You have to tune into:

Hunches.
Intuition.
Interoception. (Your ability to sense what’s happening inside your own body.)
Gut feelings. Because your head alone won’t be enough.

And that requires something most people struggle with: trust (and hope - but that’s for another post).

Trusting yourself when the path isn’t clear. Trusting yourself when you can’t justify your choices with a neat, logical explanation. Trusting yourself even when you feel like an idiot because you can’t fully articulate why something feels right or wrong—only that it does.
And trust is hard.

Because it’s easy to dismiss intuition.
It’s easy to cling to what we already know.
It’s easy to self-deceive just to sustain the status quo.

And I get it. I know how easy it is to see only what we want to see. To filter the world in a way that confirms what we already believe to be true.

That’s why radical honesty is non-negotiable. Because self-bullshitting is a slow poison.

It’s one thing to lie to others. It’s another thing entirely to lie to yourself.

So if you’re in this moment—standing at the edge of a decision, unsure of what’s next—tune in.

Ask yourself:

Am I looking at the full picture, or just the part I want to see?
Am I making decisions from a place of clarity, or from fear and scarcity?
Am I playing the long game—or just scrambling for the next move?

No one is coming to save you. And that’s a good thing.*

Because it means your future is in your hands.

So, what’s your next move?

*But be smart, get allies! Get guides! Don’t let your ego get in the way. As
Nicolas Cole
put it: “If you could have on your own, you would have already.” Nicolas is a smart guy.

*I mapped my runway. How long do I have/give myself? In my case: however long it takes. But your runway may vary. It’s about striking a balance between an invigorating sense of urgency and panic. Adequate sense of urgency is a great filter.

What you want is enough urgency AND a solid Margin of Safety

“Margin of safety is a secret weapon. It’s the buffer, the extra capacity, the redundancy that you build into a system to handle unexpected stress. It’s the difference between a bridge that can barely handle the expected load, and one that can hold ten times that load without breaking a sweat.

You can apply a margin of safety to any area of life with risk. The key is always asking yourself: What if I’m wrong? What if things don’t go as planned?

Margin of safety is the unsung hero of long-term success. It’s not flashy. It’s not exciting, but it’s the foundation on which everything else is built. Master it, and you’ll be well on your way to navigating the uncertainties of life with confidence and stability.”

— Source: The Great Mental Models v3: Systems and Mathematics

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