Optionality Is How You Stay Free

At our live events, I used to guide people through a two-part exercise that consistently blew their minds.

First, I'd have them list all their non-financial assets: their experience, expertise, credibility, track record, relationships, social capital – everything they'd built over time that had real value but wasn't sitting in a bank account.

Then came the second part: mapping their financial assets. Cash, savings, home equity, available credit, what they could access if they liquidated everything. Not because I thought they should liquidate everything, but because it's useful to know what's actually available to you.

Without fail, the room would fill with a mixture of surprise and relief. People would look at their lists and realize something profound: they were far richer in assets – both financial and non-financial – than they felt on a daily basis.

Now, these were the same people who, just hours earlier, had described feeling trapped, stuck, out of options. They had built substantial expertise and networks and resources, and yet they felt like they had nothing to work with.

This disconnect isn't an accident. It's the predictable end result of what we explored in my previous essays:

First, that entrepreneurship demands that we choose to be the author, not the character, of our story (The Choice That Makes You). And second that stress collapses your field of vision and makes it nearly impossible to maintain that authorial stance (What Stress Is Really Trying to Tell You).

And there's a third piece to this puzzle. The piece that makes sovereignty – the ability to act as the author of your story – sustainable rather than just aspirational.

That piece is optionality.

To understand it, we first have to talk about where people go wrong.

The Hoarding Trap

Most entrepreneurs treat optionality like a retirement account – something precious to be saved for the worst-case scenario. They hoard their relationships, guard their expertise, and save their "good ideas" for when they really need them.

This is a catastrophic misunderstanding of how optionality actually works.

Unused optionality doesn't preserve value. It erodes it.

It's like keeping cash under your mattress – while you're "protecting" it from risk, inflation is quietly eating away at its purchasing power.

For example, your network grows stale if you don't engage with it. The person who could have opened doors for you five years ago has moved on to new priorities, new contacts, new problems to solve. When you finally reach out after years of silence, you're starting from scratch – or worse, you're an awkward interruption in their current reality.

Your reputation fades if you don't do anything worth remembering. The brilliant work you did three years ago has been eclipsed by someone else's brilliant work last month. The market has moved on. The conversation has shifted. What once made you remarkable now makes you irrelevant.

The sad part is that the people who feel most trapped aren't the ones who lack optionality. They're the ones who have it but refuse to use it, waiting for some perfect moment that never comes.

How Optionality Really Works

The problem is that most people think optionality goes away when they use it.

They imagine their network is like a bank account: every favor asked, every connection made, every piece of expertise shared is a withdrawal that leaves them with less.

But optionality isn't a bank account. It's more like a river than a pond – its power comes from movement, not storage.

When you help someone solve a problem using your expertise, you're not just "spending" your knowledge – you're demonstrating it. Your reputation grows. When you connect two people in your network, you're not depleting your social capital – you're strengthening your position as someone who creates value for others.

And optionality is a renewable resource. The more optionality flows, the more there is.

This is why the most successful entrepreneurs seem to effortlessly attract opportunities. They're not hoarding their assets; they're investing them. Every time they harvest optionality thoughtfully and generously, they create more of it.

The opposite of harvesting optionality isn't cultivating it. It's disengaging from it entirely. It's letting your assets sit unused while you wonder why nothing ever happens.

This changes how the cycle actually works in practice.

In theory, optionality follows a simple progression: you cultivate assets, then recognize opportunities, then harvest them strategically.

But that's not how it works in practice.

In the real world, you never start from zero. You already have relationships, knowledge, skills, and credibility from everything you've done before. The real cycle begins with recognition – suddenly seeing the resources you already possess.

Then comes the harvesting. And when you harvest thoughtfully and generously, you're not just using your optionality – you're cultivating more of it simultaneously.

Entrepreneurial Kryptonite: Why You Can't See What You Have

So why do smart, capable entrepreneurs consistently underestimate their optionality?

Because entrepreneurship demands a particular kind of vision – the ability to see what's missing, what's broken, what could be better. This forward-looking, gap-focused mindset is our superpower. It's what allows us to innovate, to create solutions that don't yet exist.

But it's also our kryptonite.

When you're constantly focused on what's not working, you become blind to what is working. When your attention is always on the next challenge, you forget the challenges you've already solved.

And when you're fixated on the resources you lack, you can't see the resources you have.

This isn't just a psychological phenomenon either. It's physiological; when your brain perceives scarcity or threat, it floods your system with cortisol and adrenaline. Your heart rate accelerates, your muscles tense, and critically, your field of vision narrows. You literally cannot see as much.

This tunnel vision is an evolutionary marvel when you're being chased by a predator. But it's catastrophic when you're trying to solve complex business problems that require creativity, strategic thinking, and the ability to see multiple options simultaneously.

It’s especially damaging because most of the "risks" entrepreneurs face aren't actually risks at all – they're simply unknowns.

Tim Ferriss captures this beautifully in his redefinition of risk:

"Risk is the possibility of game-changing and irreversible negative outcomes.”

If it's either not game-changing or not irreversible, then it's just uncertainty, not risk.

But when you're operating in tunnel vision, uncertainty feels like mortal danger. Every decision feels like it could end everything. So you freeze, paralyzed by the illusion of having no good options.

The Gratitude Reset: Why Most Entrepreneurs Are Richer Than They Think

The paradox is that you can’t solve problems effectively from a clenched, panicked state. You need an open hand and a calm mind to spot the options that are actually available to you. It’s like that old proverb…

"You cannot receive anything with a closed fist."

When your fist is clenched, you can't pick anything up. You can’t accept anything from others. And when your mind is clenched – tight with fear, constricted by tunnel vision – you can't grasp the opportunities sitting right in front of you.

This is why every mastermind I run starts with the same exercise (and why it's not optional): I give people three minutes and ask them to list every win, success, and accomplishment from the past six months – big or small, personal or professional. Three minutes sounds short, but it feels eternal when you're trying to remember what's gone well. Most people write four or five things and think they're done. I tell them to keep going. Around the twelfth or thirteenth item, something shifts. The floodgates open. They start writing furiously. And inevitably, someone writes something down, looks at it, and realizes: "Wait, that was huge. That took me six months of work. How did I completely forget about it?"

This is more than a mindset exercise to make you feel good. It's a strategic tool designed to widen your field of vision so you can see the whole board before you start moving pieces. It shifts you from scarcity to abundance, from fear to gratitude, from tunnel vision to peripheral awareness.

It opens your hand and reminds you that you're richer than you think – not just financially, but in every dimension that matters.

The True Currency of Authorship

This brings us full circle to where we started this three-part series.

In the first essay, I argued that sovereignty begins with recognizing yourself as the author of your story rather than a character subject to circumstances.

In the second, we explored how stress – the perception of demand exceeding supply – creates tunnel vision that makes authorship nearly impossible to maintain.

Now we arrive at the infrastructure that makes sustained authorship possible: optionality that flows.

Your real wealth isn't just the cash in your bank account.

It's your relationships, your reputation, your expertise, your track record, your ability to create value for others. This is the currency of authorship, and like all currencies, it only maintains its value when it circulates.

Every expert who's built something sustainable has learned this truth: generosity is the highest-leverage form of investment. When you use your optionality to create value for others, you're not depleting your reserves – you're building a system that generates more options over time.

The Choice That Creates Freedom

Freedom isn't something you earn after you've succeeded. It's something you build by recognizing and thoughtfully deploying the optionality you already possess.

Most entrepreneurs spend years feeling trapped when they're actually sitting on a vault of assets they're too scared or too stressed to use. They're waiting for permission that will never come, or for perfect conditions that don't exist.

But optionality unused is optionality lost.

And the path back to authorship runs through a simple recognition: you're richer than you think. You have more options than you realize. You possess more influence than you're wielding.

The question isn't whether you have optionality. The question is whether you'll choose to see it, harvest it wisely, and trust that the river keeps flowing when you let it move.

The entrepreneurs who feel most free aren't the ones who've accumulated the most assets. They're the ones who've learned to recognize the assets they have and put them to work in service of something larger than themselves.

That's how you stay free. Not by holding tight to what you've got, but by trusting it enough to let it flow.