I Spent 57 Years Chasing Certainty. Here’s What I Learned When I Stopped

I spent most of my life trying to figure “it” out. You know, the big question: how does life really work? I don’t mean life in the abstract. I mean the patterns. The sequences. The formulas. The right way to live, love, build, lead, and choose. The thing that, once I understood, would finally make me safe, lovable, and successful.

I remember hearing a story that I believed to be true (whether it’s actually true or not, I don’t know) that Albert Einstein once figured out the precise spot where you could strike a cue ball on the break, hitting the rack so perfectly that every ball would drop into a pocket with a single shot, if you hit it hard enough.

The idea always stuck with me. Not because of pool, but because of what it represented: the belief that if I could just figure it out, if I were smart enough, disciplined enough, willing to do the work others were not willing to do, I could be the one to figure it out.  Not where to hit the cue ball into the rack, but what levers I could pull, what patterns I could follow, what tactics I could employ, what words I could say, or what behaviors I could use, that would guarantee the outcomes I wanted with both confidence and certainty, in life, in business and in my relationships.

And once I had certainty, everything would settle. My anxiety would quiet. The fear of disappointment would go away. Not just the fear of being disappointed, but also the fear of being a disappointment to others. And that ever-present but subconscious fear of abandonment would finally loosen its grip. What I couldn’t see then was this:

Certainty wasn’t the prize. It was the chase.

Where the chase started

I grew up in a world where disappointment wasn’t allowed. In my childhood, excitement led to hope. And too often, hope led to disappointment. And that disappointment overwhelmed the people I depended on most. They couldn’t handle it.

The message was clear. Lower your expectations. Lower your excitement. Lower your desires. No one ever said to me, “Don’t want.” But everything in the environment communicated it. From their body language, to their verbal cues, from their disapproving looks, to their judgmental sighs.

The message was everywhere. Because disappointment wasn’t just painful. It was destabilizing. So I learned early that wanting was dangerous.

If I wanted less, I’d be disappointed less. If I expected less, I’d hurt fewer people. If I could predict outcomes, I could prevent emotional chaos.

That’s when I became a pattern-seeker. I learned to read rooms. Read people. Read systems. Read risk. Read opportunity. I learned to build businesses. Lead teams. Provide. Perform. Win. And all of it was driven by the same quiet question:

How do I make sure this turns out okay?

Certainty dressed up as intelligence

I told myself I was being smart. Wise. Brilliant. That I was willing to work harder and sacrifice more than others. That I had cracked the code on strategy, responsibility, and discipline. But underneath it all was a belief I never questioned:

If I can find certainty, I’ll finally be safe.

So I chased it everywhere. Business models. Leadership frameworks. Self-improvement. Healing. Spirituality. Manifestation. Insight. Belief systems. I told myself:

If I believe the right thing, the outcome will be guaranteed.
If I understand the system, I won’t be blindsided.
If I can explain it, I’ll be admired.
If I can prove it, I can control it.

When certainty didn’t come, I assumed I just hadn’t found the right belief yet.

The con we all participate in

Most people don’t know where the term “con man” comes from. A con is short for confidence. A confidence game works because the person selling the lie believes in it, or at least performs belief so convincingly that it feels like truth. Here’s the truth I finally had to face:

We sell certainty because we’re desperate for it ourselves.

That’s the real confidence game. Not always malicious. Not always intentional. But deeply human. We confidently tell others, “This is how I did it.” Or “Follow this because it worked for me.” Or “This is the right way.”

And we believe it. Because confidence calms anxiety. And calm in the face of anxiety feels like truth. So, certainty gets mistaken for wisdom. And so many people buy it because uncertainty is unbearable, especially when their identity, family, and future are on the line.

I’ve participated in that. Subtly. Well-meaningly. Without fully seeing it at the time. Until I finally asked myself an honest question:

What if the thing I’ve been chasing my entire life doesn’t exist?

What finally broke open

What landed wasn’t an idea. It was a bodily realization.

Certainty is the con.

Not because people are evil. But because confidence gets confused with truth. And once I saw that, this became unavoidable: There is no certainty. Not real certainty. Not the kind that guarantees outcomes. Not the kind that prevents pain. Not the kind that protects you from loss.

Yes, the sun rises. Until one day it won’t. Yes, patterns repeat. Until they don’t. Yes, systems work. Until life breaks them.

Certainty is not a feature of life. It’s a fantasy we use to tolerate fear. And the belief that certainty was possible? That was the false belief. Not which belief. Not how strong my belief was. But the belief that belief itself could produce certainty.

What I was really chasing

I wasn’t only chasing certainty for success. I was chasing it for safety too.

Safety from being wrong.
Safety from being disappointed.
Safety from being abandoned.
Safety from wanting something that might not work out.

I thought certainty would let me rest. Instead, it kept me braced. Hyper-vigilant. Always preparing. Always optimizing. Always waiting to finally live once I figured out how to get what I wanted 100% of the time.

What I’m choosing now - without guarantees

I want to be clear. I didn’t stop chasing certainty and arrive at peace. I didn’t unlock a new system. I don’t have proof this “works.” What I have is a decision. I am no longer organizing my life around the demand for certainty. Instead of asking, “Will this always work for me and for others?” I’m learning to ask, “Is this an honest expression of who I am?”

Instead of asking, “Can I be sure this won’t fail?” I’m practicing asking, “Am I willing to live inside the experience of choosing this?”

Instead of proving my value, I’m testing what it feels like to express it. Not to be right. Not to be validated. Not to be safe. But to be real. This isn’t a conclusion. It’s an experiment.

I don’t know how it ends. I don’t know what it costs. I don’t know who gets disappointed. And I don’t know who stays or who goes, in my business or my life.

What I do know is this: Chasing certainty cost me more than uncertainty ever did. Relationships. Opportunities. Bandwidth. Endless overthinking. Trying to convince everyone I knew that I had the way. And the fear of moving forward without knowing it would turn out exactly how I wanted.

What replaces certainty

As certainty starts to fall away, I am beginning to notice something important. I’m not being left with chaos and I’m not being left with nothing. And its not another belief system or a new promise. It’s capacity.

It’s practicing the capacity to stay present when outcomes aren’t guaranteed. It’s practicing the capacity to make decisions without knowing how everything is going to turn out.  And its practicing the capacity to respond, adjust, and recover instead of trying to control everyone and everything.

I’m beginning to see that what I was really looking for all along wasn’t certainty. It was confidence in my ability to handle what comes next. Not control. Not prediction. Just my Capacity.

What I mean by capacity

When I say capacity, I’m not talking about strength, toughness, or grit.

I’m talking about the internal ability to stay present and respond honestly when life doesn’t cooperate with the plan. Capacity is the difference between needing certainty and being able to live without it.

It’s the capacity to:

• remain grounded when outcomes are unclear

• make decisions without knowing how everything will turn out

• tolerate disappointment without collapsing or blaming

• adjust when things change instead of trying to control them

• repair when you’re wrong rather than defending your position

• stay in relationship when it would be easier to withdraw

• hold responsibility without shame

Capacity doesn’t guarantee success. It doesn’t prevent pain. It doesn’t make you immune to loss. What it does is give you room. Room to choose. Room to adapt. Room to recover. Room to keep going without needing certainty as permission.

For most of my life, I thought I was chasing certainty. What I see now is that I was really trying to build enough capacity to feel safe. I just went about it the wrong way.

The confidence I didn’t expect

Here’s the part I didn’t anticipate but in a short time I am already experiencing.  As I remember to stop chasing certainty, I find myself become less anxious and a little steadier. Not because I suddenly know how things will turn out, but because I can finally stop pretending that knowing is required.

I am finding that there is a quiet confidence that comes from acknowledging uncertainty and being okay with it. Not the confidence that says, “I’ve got this figured out.” But the confidence that says, “I believe I can handle whatever comes my way.” That confidence doesn’t come from prediction. It comes from self-trust.

From knowing I can:

         •        adjust when things change

         •        recover when I’m wrong

         •        repair when I disappoint

         •        stay present when outcomes aren’t guaranteed

That’s a very different kind of strength.

I spent years believing confidence came from certainty. What I’m learning now is that real confidence comes from capacity, the capacity to learn and grow, the capacity to be flexible and open minded, the capacity to take responsibility for doing whatever it takes, and the capacity to respond with self-assurance, not control. Uncertainty didn’t take my confidence away. It gave it back.

Taking responsibility for my past

I also have to own this. I’ve been a con man. I’ve spoken about my work, my coaching, my teaching with tremendous confidence. I even taught the confidence game to my servers and bartenders.  I tell them people aren’t just buying the food we sell, they are buying your confidence about what we sell.

And like I said earlier, most of us sell confidence because we want to believe it too. So yes- I’ve been complicit.

The only sentence I can honestly stand behind

I don’t promise certainty. I don’t offer a formula. I don’t claim this will work. All I’m saying is this:

I’m done waiting for certainty to give me permission to live.

Whatever comes next, I’ll meet it. That’s not belief. That’s not confidence. That’s not a system.

That’s capacity and that is existence.

Matt Charette is an executive and integration coach.

He works with founders, leaders, and business owners who are successful on paper but exhausted by the pressure to always be certain, always be right, and always have the answer.

He doesn’t offer guarantees.
He doesn’t sell formulas.
He doesn’t promise outcomes.

What he does offer is a place to think clearly, tell the truth, and learn how to lead, build, and live without abandoning yourself in the process.
In other words, the work together focuses on building the essential capacities to:

·       make decisions without needing certainty

·       tolerate uncertainty without collapsing or over-controlling

·       separate self-worth from outcomes and performance

·       respond rather than react when things don’t go as planned

·       repair relationships instead of managing perceptions

·       use discipline and structure in service of life, not fear

·       trust yourself to adapt, recover, and keep choosing

If this resonates, if you’re done chasing certainty and ready to take responsibility for choosing your life with integrity, you can learn more or reach out.  

No pressure.
No pitch.
Just an invitation.