I've started training for a race I won't run for three or four years.

Everyone who knows me knows this: I hate running.

If I wrote a memoir, the title would be "Running's for Fugitives."

I've built an entire athletic identity around cycling specifically, because it's not running.

And yet here I am, choosing to intentionally train for a 50k trail run.

My friend Brett produces The Kilimanjaro Trail Run. I've never met him, but I love what he does, who he does it for, and why he does it. I need to support that. Plus, by the time I participate, I'll be nearing 60—which seems like a good time to try something different. (Assuming my hips and knees agree.)

Because I truly dislike—and even disparage—running, giving myself time and space to play the optimistic long game is important.

For this first year, my goal is simple: find a way to make running ... err, kinda tolerable.

I'm not optimistic that I'm going to love it. But I've trained for enough events to know that once I start showing up consistently, I can metabolize something I currently find intolerable into something sustainable.

This isn't positive thinking. It's not manifesting. This first phase is only training… it’s about making optimism about running an actual internal practice—one tiny, delicate step at a time.

That optimism is the critical, non-optional muscle for sustainably accomplishing anything.

Issue 8 of Shift Happens. Did someone forward this to you and you're questionably keen for more? Subscribe here.​

The Unvirtuous Cycle

For so many of the truly capable professionals I meet, there's a gap between where they are and the aspirations they hold. No matter how hard they move, that distance between them and their goal keeps moving—and never seems to shorten.

What's typically in that gap is an unvirtuous cycle of confusion, cognitive fatigue, and cynicism. In that cycle, our inner dialogue becomes:

• I don't have enough time. I need it happen now.
• It'll take money I don't have.
• My team can't handle it. I'll just do the work myself.
• I want to fire myself.
• What's the point of it?
• I'm all alone.

This is a paradoxical place to land—and a disempowering one.

We don’t get here because we’re incapable. Quite the opposite. It can be a case of over-performing that symptomatically feels like burnout or overwhelm.

Move those symptoms aside, though, and what I often see–and have even felt myself–is eroding self-trust, which makes it pretty damn hard to step with optimism.

What Optimism Isn't

"Think positive, man! You have to believe."

I'll just say this out loud. Barf.

If I were a Sesame Street character, I'd be Oscar the Grouch. I don't respond well to this kind of cheery agitprop—and I suspect many of you don't either.

Optimism isn't toxic positivity, manifesting without action, or blind cheerleading. It's not believing everything happens for the best.

Here's one more thing optimism is not. It's not necessarily inherited. Some studies suggest that 25% of us might have a genetic predisposition toward it.

The good news? Many of those same studies show that optimism is trainable—like a muscle.

Optimism Is Not a Mindset. It's a Muscle.

There are plenty of schools of thought on optimism, and you've heard many of the names: Leibnitz, Schopenhauer, Camus. I, however, prefer my optimism the same way I like my fitness: functional, purposeful, and particularly pragmatic.

For what it's worth, I think I've shaped my own imperfect optimism first by working with countless Holocaust survivor testimonies early in my career. And, second, by doing the hard work of sobriety—twice. In fact, I'm not confident my own sobriety could've happened without those first lessons.

If you've read Viktor Frankl's own survival story in Man's Search for Meaning—and if you haven't, it should be mandatory reading once a year—he shows that meaning doesn't come from denying our conditions. It comes from how we engage with them.

Here's how I define it for myself:

More practically, optimism is generative.

It creates. It clarifies. It mobilizes.

It carries within it a built-in sense of cooperation and conviction.

This becomes a game changer for the leaders and teams I help when they begin to realize—nay, actually embody—how their own efforts have their own weight, impact, and relevance. That can ignite the shift from "What's the point?" to "Heck yes, let's go!"

And that is the shift from resigned apathy to conviction.

Here's The Thing Most Of Us Get Backwards

We want the feeling--the inspiration, the confidence, the optimism, the clarity--to precede action. But our feelings follow action. We act first, and the feeling arrives.

We create optimism by acting as if. Acting as if something has meaning. Acting as if what we're doing is important. And then we act our way into a more optimistic stance.

This isn't just philosophical, it's strategic. Seth Godin puts it beautifully:

So, how does it look to consciously, actively, strategically embed optimism into your compass?

Not An Optimist? Or Just Allergic to Fantasy?

If all of this feels too sugary, I get it.

Someone I once had a business relationship with regularly gave me the ol' "Think positive, man! You have to believe" protest every time I tried to look critically at the habits we'd created that were keeping us from ever hitting our stride.

We had big aspirations for our business, but we lacked the clearheaded focus and compassionate discipline to discard outdated systems. You can imagine how that turned out.

I'm all for belief powered by conviction, but not when it is fantasy. And, lemme tell ya, people get really mad when the fantasy is confronted by thoughtful skepticism or pierced by truth.

This is where optimism can become dangerous—when it crosses into optimism bias. That's when we start ignoring data, dismissing valid concerns, and labeling anyone who points out problems as "negative." Real optimism doesn't require ignoring reality. It requires engaging with it–deeply.

Skeptical of the premise? Consider trying this alternative approach: Make a list of everything that could go wrong. Be thorough. Be brutal. Then use that list not as evidence you shouldn't act, but as your preparation checklist.

For researchers who study optimism, this is a kind of defensive pessimism–it’s a pre-coping strategy for what might go sideways.

A defensive pessimist sees everything that could possibly go wrong—but that clarity can become mobilizing. They use it to prepare better, plan better, and act because they're worried, not despite it.

Jimmy Iovine, when he and Dr. Dre were building Beats Music, put it this way:

Defensive pessimists don't let fear stop them—they let it make them sharper.

My coaching career started with competitive and avid amateur cyclists. This was real-time, on-the-field work. I learned something (which is validated by many studies): we perform at higher levels when we’re feeling happy and confident.

In short, we’re instinctually better when we’re optimistic.

The Science (Not So Brief)

I asked my friend Dr. Scott Frey—a neuroscientist and performance coach—what optimism looks like in the brain. He didn't have a good answer. Optimism, he said, is too meta of an emotion. It's not a single brain state we can point to on a scan.

Scott's right that optimism itself is elusive. But researchers have found they can measure its effects. And the effects are remarkable.

Optimists live 11-15% longer than pessimists. They're one and a half times more likely to reach 85. They have 35% lower cardiovascular risk, lower rates of depression and anxiety, and better immune function under stress.

Here's what's fascinating: only 25% of that advantage comes from healthier behaviors like exercise or diet. The other 75%? It's something else entirely.

Optimists engage with stress differently. When faced with difficulty, they lean in rather than avoid. This creates more short-term stress—their cortisol actually spikes higher in the moment. But because they're acting on the problem rather than ruminating about it, the stress resolves faster. Their nervous systems return to baseline.

Pessimists who avoid problems feel better initially—no immediate cortisol spike. But the unresolved stress compounds. It becomes chronic. The body never gets the signal that the threat has been handled.

This is the mechanic under the hood: optimism isn't about feeling good. It's about engaging difficulty in a way that lets your body complete the stress cycle instead of staying stuck in it.

If I think about it in my body, optimism feels fluid or pliable, while cynicism feels defensive and brittle.

The enemy isn't pessimism. It's avoidance. It's circling the decision instead of making it.

One Book & One Talk I'm Into Right Now

A winemaker friend turned me on to Unreasonable Hospitality by Will Guidara. This isn't just about restaurants or service—it's about hospitality as a force for human transformation. It’s a way of seeing and engaging with the world. The extra gesture, the unreasonable care, creates conditions where people feel seen. To me, hospitality is optimism operationalised–an essential interpersonal skill for leaders–or all of us, really.

If I'm actively your consigliere right now, expect this in your mailbox this holiday season.

Shawn Achor's TED Talk "The Happy Secret to Better Work" explores how we've got the relationship between happiness and success backwards. Twelve minutes on happiness, optimism, and positive psychology that’s well worth your time.

A Leap of Faith

The phrase "leap of faith" tends to get it backwards—or at least our thinking about it does.

We think faith comes first—that we need it before we jump. But the jumping is acting as if. We take the step, and then the confidence builds from doing the work of what happens after we land.

My life is a whole series of leaps of faith. The confidence didn't come before. It came from having to figure it out on the other side.

I still hate running. But I'm showing up anyway, acting as if the training matters… 3 miles at a time, right now. That's the practice.

If you've been circling your next big move, waiting for clarity, waiting for confidence, waiting for certainty, waiting for that feeling of optimism—you've got it backwards.

Take the tiny, delicate step. Your muscle memory will build around it.

Done Circling?

If you've been circling a bold move you keep avoiding, I've got a few Strategic Reset conversations opening up in December. No pitch, no pressure—just 30 minutes to explore what's keeping you circling and what it might take to finally move.

Worth a conversation if you're done circling? Send me a quick email: 'Okay. I'm curious.'​

Remember to exhale.

Your partner in climb, Bryan

PS – Murray 🐈 has a conditional relationship to optimism. He feels it in the moment when his food hits the bowl and the pets start. In the absence of those things, he remains troublingly pessimistic.

PPS – Know someone who might benefit from this kind of thinking? Forward this their way. And if you ever want to make an introduction to someone you think I should meet, I'm always grateful for the connection.