Growing up with my dad, we were always watching or listening to “the game.” Not The Game (i.e. Ohio State-Michigan rivalry), just the game, any game. Between Cleveland’s three major league sports teams, there was almost always “a game.” If we weren’t watching it, we were listening to it on the radio.

Baseball, particularly the Cleveland Guardians, is a special breed of games to listen to. There’s nothing else like it. Our radio announcer for baseball, Tom Hamilton AKA “Hammy,” is one of the best commentators of all time.

Hammy calling game-tying and game-winning home runs for the Cleveland Guardians gives me chills.

Watching game 7 of the Cleveland Cavaliers winning the NBA Finals to end a 52-year citywide championship drought—the last 3 minutes and 39 seconds—the block, the shot, and the stop, give me chills.

Cleveland sports give me chills. Even though most of the time, they disappoint. But just like a boomerang, we always come back to cheer. Why?

For the collective effervescence.

The tingling feeling of community. The bubbling burst of camaraderie. The sensation of belonging and navigating the ship towards the same North Star.

That feeling is unmistakable and irreplaceable. The yearning desire. It’s what makes us human. A tool of connection. The great unifier. (While also keeping us separated).

The Allegory of Struggle

The enduring disappointment and heartbreak of Cleveland sports are precisely what make it so special and unforgettable. It’s this shared struggle that fosters a sense of pride, even in the face of loss.

While watching the Guardians lose a championship series—like needing to win just one of their next three games but blowing a 3-1 lead to lose the World Series for example . . . you experience a magical journey of trying (and failing) the struggle gives context. It gives hope. It maintains that yearning desire. That thirst. That hunger.

When they lose, you feel a deep sense of disappointing brokenness. A somber sadness. While still existing a collective joy, an understanding. You expect them to lose, yet deep down you think this might be the time and really hope, fingers crossed, they win.

Just a few months before the Guardians’ demise, the Cavaliers broke the 52-year-long Cleveland Curse. That is special. I’ll always remember that moment in 2016. I’ll always remember that series, that game, where I was, everyone screaming and cheering. All of downtown, over a million, gathering together to celebrate. People who don’t watch or care about sports suddenly coming together, bonding and caring and watching.

Remembering, the years upon years of disappointment leading up to that magnificent moment. The heartbreak and betrayal of The Decision with LeBron leaving Cleveland—on my birthday, no less—hit me while celebrating with friends at our local roller skating rink, with the devastating news projected onto the big screen in the center of the rink.

The NBA Finals, and year, right before the Cavalier’s big win, competing against the same team, the Golden State Warriors, in the finals, and losing, coming short, again.

Setting the stage and providing context—making it that much more special.

To then come back the following year and win it all! It’s the quintessential “hero’s journey.”

Watching the Guardians in the playoffs is so special even when they lose because they haven’t won the World Series for 75 years (since 1948). The longest championship drought of any of the other 30 baseball teams in the league.

Watching their rise and fall time and time again.

“There’s always next year,” we say, holding onto the reigns of hope.

Versus experiencing the culture of an Ohio State football game. When Ohio State loses, there’s no hope, no pride. Just disappointment and a pool of misery. One game lost and all hope flies out the window. No specialness.

As one of the schools with the most wins in football ever, Ohio State is “supposed” to win. The same way the Yankees are expected to win after cementing their legacy with 27 World Series titles. Their ~300 million dollar salary budget stands in stark contrast to the Guardians’ ~100 million dollar budget. 

I recognize this might be trying to over-romanticize loss and losing, but that’s not my goal. My intention is to articulate the shared experience, the differences between two similar worlds, and why they exist.

Why is a nature of losing more impactful than a history of winning?

Why is the Cleveland Browns being one of only two teams in NFL history to finish a 16-game season without a single win more memorable than if they had won just one of them?

This phenomenon is encapsulated perfectly in the first Pirates of the Caribbean movie when Commodore Norrington exclaims to Captain Jack Sparrow, “You are without doubt the worst pirate I’ve ever heard of.”

To which Jack responds with, “But you have heard of me.”

Sometimes it’s better to be memorable than mediocre. In many ways, mediocre means being ordinary, apathetic, neglected. Memorable is extraordinary, regardless of why, it’s a story.

There’s no entitlement. Cleveland isn’t entitled to win. So there’s no anger during loss the way there is with Ohio State.

There’s frustration, sadness, and disappointment sure. But not anger.

“That’s kind of the way it is at our bar; it's a little broken and it's not that great but hell man, it's ours.” — Aaron Lee Tasjan, 12 Bar Blues

Expectations make misery. They’re the root of resentment. Melt away expectations, and be delighted by what’s left. Treat everything as an extraordinary miracle.

What gives me chills?

The bite of the underdog. The Sisyphean battle of bond. Masochistic? Maybe.

But isn’t that life?

To create meaning among the misery.

While I might not consider myself a sports fan. Cleveland gives me chills.

What gives you chills?

What’s next?

What do you want to be when you grow up?

Since shutting down the startup I co-founded, Helm, after 6 years of being relentlessly dedicated to building something out of nothing, I found myself at a loss of words.

Where the number of opportunities seems abundant, yet absent.

Some common themes did arise like a desire for:

Building connections.

Building community.

Building culture.

But figuring out what’s next is difficult after spending the past 6 years immersed in an identity of wearing ALL the hats. A different hat depending on the week, the day, and the hour. So which hat do you want to pursue?

And then a sense of imposter syndrome floods the system that you’re not actually equipped to wear any of the hats at all, so now what?

It feels like Sylvia Plath’s fig tree. Where you’re hungry, starving, eager to get your hands dirty and dive into the deep end. You have dozens of delicious figs dangling in front of you. But, you can’t decide which one to choose, to eat first. Because time is finite you ultimately can’t choose all of them. You must choose to kill and grieve the loss of most of them.

Yet the inability to choose any of the figs leaves you steeping in a poisonous, romantic cocktail of despair. As you watch each fig, each opportunity, rot right before your eyes and fall to the ground. One by one. Until the tree is bare, and there are no figs left.

So what do I want to be when I grow up?

I don’t know, but here’s what I’m doing now.

My friend Jessie was telling me a story about how she’s been pondering what’s next for her. She mentioned that someone gave her advice in the form of a question. A question I can’t stop thinking about. A question I’ve been using as a decision-making framework. A question I want to leave you with.

They asked her:

“What would BOLD Jessie do?”

So I continue to ask myself:

“What would BOLD Austin do?”

And now I want you to ask yourself:

What would BOLD you do?

So often we hear about the extremes and polarities in life. I’m an introvert or I’m an extrovert. I’m a liberal or I’m conservative. I’m assertive or I’m humble. Because identifying as both of something risks appearing inauthentic.

I think the reason people struggle with the idea of balance is because it’s simply not sexy. You don’t hear about it because the loudest voices are always on the ends of the spectrum, claiming their territory of identity. But that’s not the reality the majority of us experience.

The truth is we’re all human, there’s no one-size-fits-all solution or way of doing anything—regardless of how much we try to squeeze the square peg into a round hole.

Life is much more gray than advertised. An effort to make life black and white is a bit lazy. It’s a form of decision automation, trying to outsource the structure of our life design. Sure a rigid framework can be less fatiguing, but at what cost? We ought to interact in the world with relativity, not machines on autopilot.

“Do I contradict myself? Very well then I contradict myself. I am large, I contain multitudes.” — Walt Whitman

Some situations call for a leader to be more direct and decisive to keep people motivated. Other times a situation calls for a leader to take pause, listen, be more empathetic and understanding. It’s not one or the other, but rather both, relative to the context at the time.

It’s balance.

Try to visualize this with me.

Take a second and imagine you have to choose between inhaling or exhaling. You have to choose one, only one, for the rest of your life. Which do you choose?

The question’s absurd right?! You can’t have one without the other, it’s all relative. Both are necessary elements to sustain human life.

So then why do we try to fit ourselves into these absurd narratives, identities, and boxes in life?

Now take a deep inhale. Once you can’t sip any more air, exhale and release the breath—now you have a complete, balanced, system.

A question to ponder, journal, discuss:

What seemingly contradictory beliefs and identities make up your authentic self?

Balance beautifully

How do you balance the simply with the beautifully?

Some may say
The simple is beautiful

Some will challenge
Complex is best

Others will claim
Beauty is to be seen
Flourished and flashed

There must be a balance
Between the concise and complex

For if you add too much water there’ll be no taste around
Rather not any at all and you’ll blow out the sound

The whisper and blare
Running through the air
Trying to find its flair

The harmonious blend of each
Creating the most decadent treat

For more on this idea of balance, I recommend checking out my friend, Kai Mckinney’s blog, called, moving balance.

“a philosophy about navigating complexity, ambiguity, and totality through iteration and experimentation; an acknowledgement that nothing is static or cleanly defined—that the world and our way through it is continuous and fluid.”

Other recommendations to dive deeper into the rabbit hole of balance:

• Creator Science podcast with Derek Sivers: How to Find Balance and Stay Focused (I timestamped a specific section at 20 minutes in on balance, but the entire conversation is worth a listen!)

• Article on the Polarities Framework

Finally, after 12 months, it’s here!

I’ve been waiting for the perfect moment to launch this newsletter. When to start? What to write? Which platform to use? Feeling paralyzed by wanting to choose the best, most scalable solution. Falling into what I call the freedom trap or being a maximizer, as Barry Schwartz says in The Paradox of Choice. And it’s exhausting.

I’ve always struggled with perfectionism—the excuse of procrastination. Originally, I wrote this newsletter draft 1 year ago last January. But as I mentioned before, it wasn’t the right time. It wasn’t the right place. And other priorities took hold.

*insert excuses here*

As a kid, I was an extraordinaire of excuses. When I was in a youth bowling league, my mom even bought me a shirt like this.

Today isn’t the perfect moment either, because the perfect moment doesn’t exist. But it’s my attempt at taking imperfect action. Choosing progress over perfection. Practicing non-attachment. Relinquishing control.

Okay, time for the actual programming below.

On asking “Why?”

We ought to ask ourselves why more often. Growing up as kids and teenagers, our favorite question is undoubtedly, “Why?” Erupting a barrage of whys from the age of 2 as we start developing our sense of self.

Why do I have to stop playing with James?

Why do I have to take out the trash?

Why do I have to do my homework?

Why do I have to clean my room?

Why do I have to go to school?

But we don’t ask why? enough, as we age. Maybe it’s because of toxic workplaces that discourage and resent this question. That’s a deep dive for another day though. My point here is that we’d all benefit from asking ourselves, as adults, more of these same why questions.

Today I read an article alleging that remote work is contributing to Gen Z being the loneliest generation. It left me feeling frustrated, overwhelmed, and a deep-seated anxiety.

My initial reaction was to write a long-winded reply . . .

Which I followed through on and did. I nearly wrote an article in response to the article. Because of LinkedIn’s 1,250 character count limit, it took me 3 comments to fully respond.

Over an hour later, after eating leftover spaghetti bolognese for dinner, I was pacing around the kitchen snacking on walnuts asking myself, *hmmm* “Why do I feel this way?”

Why am I feeling anxious?

Why am I feeling frustrated?

Why am I feeling overwhelmed?

Finally, some clarity sprinkled to mind.

Well, the startup company I’m building, Helm, is directly advocating the opposite message of this article. We talk about the future of work being more flexible, remote, and asynchronous, with Gen Z strongly pushing for this. Feelings of loneliness and isolation are an epidemic through the roof, yes, and remote work is a scapegoat to the root causes.

We point to all of these ideas in the context that a better future of living is a world of work that is more flexible, with freedom of choice at the core.

So when the argument is made against this case why was I feeling frustrated? Anxious? And overwhelmed?

Because the point of the article indirectly challenged my identity as a founder of Helm. My identity as a thought leader for the future of work. It challenged the future I set out with intentions of Helm succeeding.

The article challenged Helm’s entire manifesto on the future of work.

Borrowing the lesson of “Yes and . . .” from improv.

This article can challenge my views, which is great for avoiding echo chambers to spark fruitful discussions. And I can feel frustrated with it. And it doesn’t discount me thinking the article’s argument is flawed.

Yes . . .

And it’s still important for me to be aware of why I felt these emotions so viscerally after reading the article.

As you have your next conversation, read the next piece of news, make your next judgment, ask yourself:

What if the opposite were also true?