Questions We Fail To Ask
What if we questioned things more? Our jobs, our choices, our assumptions?
I used to think that progress meant arriving at a point where everything finally clicked into place—where success begets ease. But the truth is, the higher you climb, the heavier the expectations become. And I’ve come to realize that performance is not a single act; it’s a continuum, a moving target that never stops shifting forward.
Like you, I’ve been striving—pushing through, trying to make significant progress in everything I do. I’ve had my share of successes, and I’ve also had projects that never made it past the Google Doc stage. At first, that used to bother me. Abandoned ideas felt like failures. But over time, I’ve learned to be okay with letting some things go. Not everything needs to be finished; some ideas serve their purpose simply by being explored. And that’s progress too, in its own way.
So, what is this piece about? It’s about performance. The relentless demand for more, for better, for the next level. If you were ever that kid in school who was pushed ahead of your peers, placed in advanced classes, or constantly compared to others—“Why can’t you be serious like Dennis?” or “Can’t you be more like him?”—then you know exactly what I’m talking about. That kind of differentiation isn’t something you choose; it’s placed upon you. And while I never thought it was fair, I also realized something else: people aren’t necessarily lacking intelligence or capability. Often, they just haven’t found their ‘why.’ They don’t see the point of unlocking their potential. And maybe, just maybe, the best way to help people rise isn’t by pushing them but by showing them enough love to believe they can.
Back to performance. The moment you achieve something—whether it’s good grades, a successful project, or a major career milestone—you set a new bar. And that bar only goes up. If you raised funds and delivered, next time, you’re expected to raise more and deliver bigger. If you crushed your targets last year, this year, you must outperform yourself. It’s common sense, isn’t it?
And yet, I wonder. Where does it stop? Or does it ever?
I sometimes think about celebrities and how much we demand from them. We consume their art, their work, their essence, and in return, we expect them to keep delivering—consistently, flawlessly. But have we ever stopped to wonder if they might just need a break? If we, too, might need one? If life isn’t meant to be an endless sprint but a journey with pauses, resets, and moments of grace?
Consistency. That word is thrown around like the holy grail of success. Show up every day, at the same level, with the same intensity. But should consistency mean perfection? What about the days when you simply can’t? What about grace? What about understanding?
Let’s take the workplace as an example. Say you had an outstanding performance in 2022. The expectation for 2023? Do even better. Because before your success, the bar was low. But after? It’s higher than ever. And if you deliver again in 2023, then guess what? In 2024, it rises again. It’s like playing a video game where the difficulty keeps increasing, except there’s no final level, no end credits—just the pressure to keep going. And for what?
We weren’t told that performance isn’t just a one-time thing—it’s a lifelong cycle. And if that’s the case, why is everyone in such a hurry to reach the top? If running a successful venture-backed business is about execution, consistency, and responsibility, why do so many people rush to be entrepreneurs without first learning how to manage? Why does our culture romanticize the end goal without valuing the apprenticeship—the process of truly mastering a craft before leading?
I’ve been thinking about this for months now. There’s something to be said for taking the time to learn. If you want to be a great manager, work under great managers. If you want to build a company, first learn how one operates. Work for a bad manager, even—see what not to do. Success isn’t about speed; it’s about foundation. And yet, the world around us seems obsessed with skipping steps, with rushing toward an undefined pinnacle.
Maybe I’m wrong. Maybe there’s a reason for the race. But historically, mastery has always been rooted in patience, practice, and persistence.
I don’t claim to know much about life yet. I’m still figuring things out. But the more I observe, the more I question this endless yearning for performance—this cycle where better is never enough. And I wonder: what happens when there’s nothing left in the tank? Is that what burnout is? Is that what work, corporate life, and retirement ultimately look like?
And most of all—Is outstanding performance a skill? Or is it a choice?