The #1 Reason Smart People Waste Decades

Dear Legend,

Today I’m going to shake up your world. Not in the mean, bullying way, in the tough love sort of way.

One of the most important decisions we get to make is the direction of our lives. But how often do we actually change directions because what we have now is not working for us?

The truth is most of us wait too long to change.

We wait for a breakdown.
A diagnosis.
A layoff.
A betrayal.

Or in my most recent guest, Ron Tite’s case… a fire. Not a metaphorical one, a real one. One that almost cost him his life.

(Ron Tite is an award-winning advertising executive, stand-up comedian, bestselling author, and globally recognized keynote speaker. He’s the founder of Church+State, a creative agency that works with powerhouse brands like Walmart, Manulife, and Netflix. A former executive creative director and lifelong performer, Ron has built a reputation for blending sharp business insights with engaging storytelling. His latest book, The Purpose of Purpose, challenges how companies and individuals define meaning in a distracted world and what it really takes to live and lead with alignment.)

The story you NEED to hear…

It was the last night of Ron’s one-man comedy show at the Edmonton Fringe Festival, the biggest fringe festival in North America.

Sold-out crowds. Standing ovations.
The kind of week you remember for the rest of your life.

But comedy wasn’t his day job.

By day, Ron was the account director for the Intel business at Havas Canada. Big name, big role, big clients.

By night, he was on stage… living out the version of himself that felt real. This was the version of himself he loved.

And on the final night, after a week of packed performances, he went to sleep in his hotel suite. Alone, tired, satisfied.

And woke up choking on smoke. He was 3 minutes away from death. (See a photo of Ron being rescued.)

He was rescued. Physically, at least.

But something else inside him died that morning. He felt like something HAD to change in his life...specifically his work life.

That was it.

He moved into the creative department. Eventually started his own creative agency. He changed his trajectory and built a life that merged creativity, purpose, and storytelling.

All from that one moment.

❤️ Heartset: Don’t just tolerate life, make decisions that make you come alive.

Deep down you know. You knows that what you’re doing isn’t wrong… but it isn’t right either.

You’re not falling apart. But you’re not fired up.

And that’s more dangerous.

Because slowly… you’re starting to tolerate and stick to a version of success that you’ve poured time into, it probably even makes other people proud, but it leaves you numb.

This is due to one of the most insidious forms of bias: the Sunk Cost Fallacy. It’s a cognitive bias where we continue an endeavor, investment, or behavior solely because of the time or resources already spent, even when the current and future cost outweighs the benefit (more on that at the end.)

So what should you do? First shift your perspective.

🧠 Mindset: From “Don’t fix what ain’t broke” to “Fix what ain’t fire”

You do not need a crisis to course correct.

You do not need a brush with death to choose life.

And you are not crazy for wanting to change something that’s technically “working.”

The old mindset: If it’s not broken, don’t fix it

The new mindset: If you’re not burning with passion, change something”

And it starts with asking yourself some pretty hard questions (and answering them honestly)

🧰 Skillset: The Fire-Test Framework

If you want better answers, ask better questions.

Three steps:

1/ Ask: If it all ended today, what would make the cut?
Imagine your death today. What would you want people to say about you? Your title? Your corner office? Or your work that changed people’s lives? Or how it made people feel?

What REALLY matters at the end? How does what you do today align to that? Or not?

2/ Ask: What am I doing out of habit, fear, or identity protection?
What are you doing today simply because you’ve done it for a long time? Are there changes you wish to make but you fear what people will say? Is there an identity you feel you MUST protect, but really, it’s not serving you anymore?

If you started fresh but knowing what you know now, would you do the same thing over again?

3/ Ask: What will I regret not doing, even if it fails?
When you are faced with death, what will you regret? You are a miracle. Everyone of us is a miracle, having consciousness with a finite life in an infinite universe. When this miracle is over, what would you wish you would have done? Tried?

What will you do different to avoid the possibility of regret?

This framework is designed to jolt you out of your cruise control. Influence yourself to take a critical view on your life. I’m not suggesting you quit that job or take up skydiving. I’m simply here to remind you that we don’t have to wait until something drastic happens in our lives to change directions. It simply requires a committed decision.

Why is it so difficult? 👇🏽

The Sunk Cost Fallacy

Here’s what really keeps you stuck: “I’ve already put so much into this…”

The money. The time. The effort. The identity. So you stay, even when you know you shouldn’t. That’s the Sunk Cost Fallacy in action.

It’s a cognitive bias where we continue an endeavor, investment, or behavior solely because of the time or resources already spent, even when the current and future cost outweighs the benefit.

Research shows:

• A 1996 study by Arkes & Ayton found that people were significantly more likely to continue an ineffective course of action if they had already invested time or money even when the logical decision was to cut losses.

• In a Harvard Business Review article, researchers found that managers often continue failing projects for significantly longer than they should, because walking away would feel like admitting failure, even if continuing leads to greater loss.

• In a study published in Judgment and Decision Making, participants persisted 35–40% longer in a meaningless task when they had already invested 15 minutes, compared to those who started fresh.

We are biologically wired to "not waste." But in doing so, we waste something far more valuable: our future.

This bias hits alpha folks the hardest. Because we are great at finishing. Great at sticking with things. Great at pushing through.

But here’s the truth:

You’re not here to protect your past.
You’re here to design your future.

Make your mark, live your legend 🤘🏽

See you next Sunday!

Howie Chan

Creator of Legend Letters

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