The Intentional Careerist - Have You Chosen the Right Race?

“The hare didn’t lose because he was arrogant. He lost because he chose the wrong race.”

We all know the fable — the overconfident hare, the steady tortoise, and the moral we grew up with: “Slow and steady wins the race.”

Comforting? Yes. Complete? Not quite.

Because the real lesson isn’t about speed or perseverance — it’s about purpose.

🏁 Beyond the Finish Line: The Question of Why

The story never tells us why the hare and the tortoise were racing in the first place. That missing “why” unlocks a deeper truth: intentionality.

It’s not the race that defines the outcome — it’s whether the race is worth running at all.

🐇 The Hare: Misaligned Effort

The hare didn’t lose because he lacked ability. He lost because the race didn’t matter to him.

Why would a creature built for speed waste its time racing a tortoise?

• No Challenge: The outcome was obvious.

• No Reward: Winning brought no growth or excitement.

• Everything to Lose: A win was expected, a loss humiliating.

  
  

Maybe his nap wasn’t arrogance. Maybe it was quiet rebellion — a subconscious protest against a goal that didn’t align with his strengths or values.

🐢 The Tortoise: The Pitfall of Blind Optimism

The tortoise, meanwhile, accepted a race he was certain to lose. Why?

• Optimism bias: We overestimate our odds.

• External validation: Maybe he wanted to prove something in a world that glorifies speed.

• Low-stakes gamble: “What’s the harm? I’ve got nothing to lose.”

  
  

His win? A happy accident — not a repeatable strategy.

🧍 The Human Parallel: When We Run the Wrong Races

In our careers, we’ve all been both — the hare and the tortoise.

We chase promotions we don’t care about, or grind away at goals that don’t fit us, simply because that’s what “success” looks like. And sometimes, we keep running long after the finish line has lost meaning.

🧩 Why We Fall Into These Races

Cultural conditioning: We’re taught that success means winning — grades, titles, paychecks — not alignment or joy.

Fear of judgment: Society rewards visible milestones, not quiet alignment. We chase applause instead of purpose.

Perfectionism: We finish things just to avoid the label of “quitter,” even when quitting would set us free.

Herd mentality: We follow familiar paths because they feel safe, not because they fit.

Sunk cost fallacy: We stay in misaligned roles just to justify past effort. But sunk time isn’t success — it’s tuition paid for wisdom.

🎯 The FIRST Framework: How to Choose the Right Race

Forget “slow and steady. ”Success belongs to the intentional careerist — the one who pauses to ask, “Is this my race?”

Before you start your next pursuit, run it through the FIRST checklist:

F – Feasibility: Do you have the strengths and resources to truly succeed here?

I – Impact: Does it align with your long-term purpose, or just look good on your résumé?

R – Relevance: Is it right for this season of your life and growth?

S – Specificity: Are your goals clear and measurable, or vague ambitions that drain energy?

T – Timeliness: Is now the right time — or are you racing out of habit or pressure?

🔥 The Bold Truth: Intentionality Over Inertia

Most career regrets don’t come from failure. They come from winning the wrong race.

We chase recognition that feels empty once achieved, or spend years perfecting a path we never truly chose. Success without alignment isn’t success — it’s just sophisticated inertia.

The wrong race can look like success — until it doesn’t.

🪞 Reflect and Reroute

Think of a race you’ve entered — in your career or life — that, in hindsight, wasn’t worth running. Why did you take it on? Ego? Pressure? Fear? Obligation?

The hare learned that speed means little in the wrong race.The tortoise learned that slow and steady only works when the race is yours to run.

The rest of us? We’re still learning to choose the races that truly matter.

If this idea of running your own race resonated, you might also enjoy The Anthopper Mindset — a lighthearted take on balancing the ant’s discipline with the grasshopper’s joy. It explores how to chase goals without losing your sense of play.