Why Hitting Your Numbers Won't Let You Leave

If the spreadsheet could set you free, you'd already be gone.

Listen here.

“Hey you, wake up! Why do you exist? Life is not meant to simply work, wait for the weekend and pay rent!” — Prince EA

This is the first in a five-part series on the blockages that keep us parked in the “safe” jobs. Last month, I asked 52 high achievers who had retired or were in that age range one question: when you think about retiring or leaving your job to do something you want to do, what’s actually stopping you?

Before I show you what they said, I want to be clear about what this series is not. It’s not about retirement accounts or beach chairs. It’s about the belief at the center of The Authentic Path: you were born to do something GREAT with your life, and playing it safe is how that greatness ends up on the shelf.

So as you read these next five issues, I want you to get curious about the question underneath all the others: what were you put on this earth to do?

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One of the leaders told me his financial advisor ran the projections and gave him the news: you have a 98-percent-plus chance of dying with more money than you started with.

Not “you’ll probably be OK.” Ninety-eight percent. Nearly certain to finish life richer than he is today.

He still checks the market on his phone every morning. He finally moved the app off his home screen just to slow himself down.

When the math says yes and your stomach says no, the problem was never the math.

Before you think I’m singling out my friend, let me back up. Forty-one of the fifty-two surveyed named money as their number-one barrier. Almost 80 percent.

The surprise was how they talked about it. Almost nobody described a math problem. They described a feeling. “Will it last?” “What is enough?” One retired executive wrote that he still wonders whether he was in a good enough position to leave, “no matter how many times I run the numbers.”

He’s retired. He made it. The plan worked. He’s still running the numbers.

Money was the most common answer in my survey. It was also the least interesting one.

Confession time. I started thinking about leaving corporate more than two years before I actually did, and for a long stretch of that time, I simply assumed the numbers wouldn’t work. I hadn’t tested that. I hadn’t proven it. I had decided it based on my overall aversion to risk.

The first real step I took was sitting down with my advisor, a man I’ve trusted for the last decade with our financial future. He ran the numbers several different ways. We met multiple times. And somewhere in those meetings, it sank in: we could actually do this. I could trade what I thought was certainty for what I now believe is my calling. The math took a few meetings. Untangling my fear from the math took a lot longer.

Here’s what I saw across those 52 responses, over and over, in three forms:

The flip from saving to spending. A leader who retired after a 41-year career put it plainly: “You have to shift your mentality from saving to spending, which is more difficult than you think.” You’ve spent three decades watching the number go up. Watching it go down on purpose feels like failure, even when it’s the plan.

The golden handcuffs. Base pay, bonuses, long-term incentives. Several people told me the hardest part isn’t having enough. It’s voluntarily walking away from more. That's not arithmetic. It's letting go.

The moving target. “What is enough” rarely stays still. Aging parents. Kids’ weddings. One leader told me his wife’s longevity projection runs past 100, and he wants his grandkids financially secure too. Every year you wait, “enough” keeps growing.

Notice what all three have in common: not one of them gets solved by running the numbers one more time.

One responder said perhaps the truest thing in the whole survey:

“The fastest return may not be in your portfolio. It may be in lowering the number you need to be free.”

That one stopped me. We spend years trying to raise the number we have. Almost nobody asks whether the number we need is negotiable.

So let me ask you what I had to ask myself: have you run the numbers with someone you trust or has your fear of “not enough” been running them on your behalf?

If your advisor says 80%+ and you still can’t relax, one more spreadsheet isn’t going to save you. Something else is holding the door shut. And every year that fear wins, whatever you were placed on this earth to do sits on the shelf, year after year after year.

Here’s your homework for this week. Call your financial advisor. If you don’t have one, get one. Get the real answer. Then be brave enough to believe it.

Money is just the first blockage. Over the next four Sundays, we’ll dig into the ones nobody warns you about. The first shows up about a month after you leave, when the phone goes quiet.

Let’s clear the way for you to live out your calling.

See you next Sunday.

→ I'm giving away three 1-hour coaching sessions as part of a new certification I earned. They’re free for the Authentic Path community. Just reply to this email to schedule a Zoom call.

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