Making a Life-Changing Decision

I was on a coaching call recently with a recreational poker player – let's call him Dan – who was wrestling with whether to leave what he called his "golden handcuffs" situation. He was in his mid-50s, successful in his career, and bringing in good money — but absolutely miserable at work. The kind of miserable where you can feel it weighing on you every Sunday night.

Dan talked about how he couldn’t wait to leave corporate America. He felt trapped in a system that was making him miserable, trading his happiness for a paycheck he didn't even need that much.

Life's too short to be miserable. When someone tells me they hate what they're doing, especially someone capable like Dan clearly was, my immediate thought is: We need to get you out of there. Let’s find a way – any way – to do something else.

And I believe that. When someone's doing something they hate and they're a capable person, there's absolutely a way to make a change. Why stay trapped in corporate America when you have options?

The Surface Story

Dan was making good money. He figured he could live on a fifth of his current income if he cut back on some non-essential expenses. He's a winning recreational poker player who, with more focus and study, could likely earn enough from poker to support a semi-retirement lifestyle.

The obvious conclusion seemed clear: reduce expenses, play more poker, maybe find some part-time consulting work to be safe, and escape corporate America for good. Get out of the rat race. Stop letting some corporation own your soul.

Everyone on the call was nodding along. It made perfect sense. Dan seemed ready and eager to move forward with this plan. It felt like he just needed permission and maybe a little bit of a push to take the plunge.

The math worked; he had the skills, and most importantly, he'd be free from the misery of corporate life.

Why wouldn't you take that opportunity?!

Then I Got Curious

But something made me want to understand his situation better. Instead of jumping straight to "quit your job," I started asking Dan more specific questions about what exactly he didn't like about his work. What part of corporate America was bothering him? What specifically made him feel trapped?

That's when the real story emerged – and it changed everything.

Dan used to love his job!

Years ago, when his company was smaller and scrappier, he was solving new problems constantly. The work was challenging and interesting, the kind of stuff that made him excited to dive in each morning. The culture was different, too. He felt connected to his team and the mission.

But as the company grew and matured, everything changed. Now he was doing the same tasks week after week, following processes that had been established years ago. There were no new interesting problems to work on – zero! – just repeating the execution of one that he had solved long ago. The culture had shifted immensely. He felt disconnected and not very useful.

The job hadn't just become boring – it had become the opposite of what made him love work in the first place.

Dan Has Needs

When I heard how his job had changed, things became a whole lot clearer for me.

I was immediately reminded of a framework that applies perfectly – Tony Robbins' concept of the Six Human Needs: certainty, variety, significance, love and connection, growth, and contribution.

The idea is simple: every behavior we choose is an attempt to meet one or more of these needs. The more needs an activity meets, the better it tends to feel. The fewer it meets, the more likely it is to feel draining, aimless, or, in Dan’s case, even soul-crushing.

It only takes meeting a few of these needs for something to be really enjoyable, or even addictive.

Looking at Dan's situation through this lens was like putting on the right prescription for the first time:

Certainty: His job still provided this. He had a steady income, and he knew what to expect.

But everything else? Gone.

Variety: Zero. Same tasks, same routine, week after week after week.

Significance: He used to solve interesting problems that felt meaningful for the company's success. He used to feel valued and important. Now, it felt like what he worked on didn’t matter – like he didn’t matter.

Love/Connection: The team culture and relationships that once energized him had disappeared as the company grew and changed.

Growth: No new challenges meant no reason to develop new skills or push himself intellectually. Show up, repeat the same tasks, go home.

Contribution: He used to make a meaningful impact on an organization he cared about. Now he was just going through the motions.

The Plot Twist

Dan's problem wasn't with jobs or corporate America in general – it was with this specific job at this specific company at this specific point in time.

If he could find a role that brought back variety, significance, connection, growth, and contribution – even just a couple of them – he'd likely be happy again. Maybe really happy, the way he used to be, if he found one that brought back most or all of them.

I could see this realization hit him in real time. "Oh yeah, wow. It's not just corporate America. It's this job. I've been so focused on this one experience that I assumed all corporate jobs in this field were the same. But I don’t have a good reason to believe that."

The Lesson

Think about what we almost did.

Dan was ready to abandon an entire career path because of one bad situation, and I was almost ready to advise him to. A few years ago, before discussing countless situations like this and before training to be a better coach, I would have. And I would’ve been confident it was the right choice.

We would have left a massive opportunity for success and happiness on the table simply by accepting his surface-level explanation and not digging into the why.

While there are several lessons we can take away from Dan’s story, this is the one I want to hammer home:

We don’t know what we don’t know. Get curious.

We are wired to find meaning – to find answers. Dan hated his job. He thought he knew why. He was pretty much sure he knew why!

And as someone giving advice, why even waste time questioning that?

We tend to diagnose ourselves (and others) quickly, and then we focus on solving the problem. We focus on the what and the how because we think the why is already sorted.

What should I do? How can I earn enough to support myself doing something I love? What’s the best strategy – should I save up for another miserable year or two before making the move? Should I cut my expenses? How do I decide what to cut?

I always considered myself a great problem solver. Give me the constraints, and I’ll figure something out. I’m sure Dan is a great problem solver – he’s thoughtful and very intelligent.

But the best problem solver in the world is useless if you’re trying to solve the wrong problem.

Accepting Your Limitations

I don’t care how thoughtful and smart you are. I don’t care how much you journal. (Actually, I kind of do care – that’s a useful way to get more insight.)

You can only see things through one set of eyes. You can only think with your own brain, and you can only reference your knowledge and experience.

When people say things like, “There’s no point in finding a therapist. There’s no reason to get a mindset coach. I know what’s wrong with me and what I should do,” I want to shake them.

No, you probably don’t know what’s “wrong” with you. Not all the way.

And even if you do, you probably don’t know how to solve it.

And even if you do, you haven’t done it yet. So why do you expect you’re suddenly going to?

You don’t need an expensive coach like me. You may not even need to hire anyone, depending how serious your challenges are. You just need someone, or someones, who will listen to you with their ears, see you with their eyes, and share with you what clicked in their brain.

And even if you don’t take my advice and seek help from others (you probably won’t), at the very least, try to dig a little bit deeper. Try not to accept as fact the first story that explains your situation.

This applies beyond career decisions, of course. Whether you're advising someone else or making decisions for yourself, it's worth pushing past the surface-level complaints to understand what's really missing. What specifically was good before? What specifically is wrong now?

Stay curious. The solution might be simple and powerful once you pinpoint the right problem.