The Leap

The Courage Nobody Talks About

We are trained to manage risk. In finance, in operations, in leadership, an executive earns trust by seeing what could go wrong before anyone else in the room.

But that same skill, applied to your own career, can become the thing that holds you in place long after you should have moved.

I learned this the hard way, and I want to share it the way one professional might with another over a quiet conversation, years after the fact. I mentioned this decision briefly last month. What I did not describe was what it actually cost me to make that decision.

The Calculation That Does Not Fit a Spreadsheet

We had just bought our first home. Like many young families, we stretched to make it happen. When the closing was over, most of our savings were gone. Our first son had recently been born. Every month brought a mortgage payment, childcare expenses, and the ordinary costs that come with starting a life together.

Then an opportunity appeared.

The position offered more room to grow, but it also came with a lower salary and a six-month probation period. If it did not work out, I could lose the job and put everything we had just worked for at risk.

I remember lying awake some nights staring at the ceiling while the house was quiet. My wife and son were asleep, and I was running every scenario through my head.

What if I fail?

What if they made a mistake hiring me?

What if I lose the house?

What if I am risking my family's future for something that is not certain?

People often talk about taking chances as though courage feels exciting. It does not. Most of the time, courage feels like fear mixed with conviction. You are afraid that something could go wrong, but something inside you knows that staying where you are is no longer the right answer.

However, there was a variable that did not fit the model. The environment I was working in was costing me something that does not appear on any balance sheet: my peace of mind and my confidence. Both erode when you spend forty or fifty hours a week in a culture that does not value what you bring.

That cost is real, and it compounds.

I took the new role at a pay cut, with everything on the line. Looking back now, that decision changed my life. It led to opportunities I could never have predicted and eventually to a career at a large nonprofit healthcare organization that spanned more than three decades, including nearly twelve years as Corporate Controller.

What High Performers Forget to Apply to Themselves

Here is something I have observed in the leaders I have worked alongside over the decades: we bring great rigor to organizational decisions, yet we often fail to apply that same rigor to our own lives.

We pressure-test major decisions, challenge assumptions, and examine every variable before recommending a course of action. And then we stay in a role that stopped serving us years ago, because the familiar feels safer than the unknown.

We understand the sunk cost fallacy, and we know that past investment does not justify future commitment when the fundamentals have changed. We apply this thinking to organizations constantly, but we are slower to apply it to ourselves.

The Invisible Risk of Staying

There is a risk in remaining too long in the wrong place. It is slower and quieter than the risk of leaving, but it is not smaller.

It is the risk that a leader who is no longer challenged will slowly lose their edge. The risk of a talented professional who has been undervalued long enough that they have started to believe it.

These costs do not show up in any review. They accumulate quietly, in the quality of your thinking and in the standards you hold yourself to when no one is watching.

Many people avoid the leap because the cost of leaving is easy to see, while the cost of staying is not.

The Probation That Changed Everything

When I took that new role, I carried the weight of it privately. I arrived early every morning, produced more than was required, and used the probation to show what I was capable of.

The probation passed. That role became the foundation for everything that followed, including my years as Corporate Controller.

None of that would have happened if I had stayed where I was.

The same discipline that makes for strong senior leadership, the willingness to face an uncomfortable truth and act on it, applies just as much to your own career as it does to any organization you serve.

What the Leap Teaches You

Courage is a decision you make while the fear is still there. I did not feel ready when I made the move. I became ready by doing the work.

The culture you work inside shapes your judgment over time, in ways you do not notice while they are happening.

And the decision belongs to the person living the life. Outside judgment is almost always based on incomplete information. The people who questioned my move saw the pay cut and the risk. They did not see the months of quiet analysis, the internal certainty that a change was overdue.

A Question Worth Sitting With

What would you tell a talented colleague who came to you carrying the exact situation you are currently in? What would you say, honestly, about the cost of staying versus the cost of moving, the way you would if it were someone else's life?

You already know how to think through this. Now do it for yourself.

New editions of Reflections by Jimmy T. Singh, CPA publish the first Tuesday of every month. In October and November, I will share the financial mistakes I watched smart, capable people make over nearly forty years in corporate finance. If this was useful, subscribe here to get future editions delivered directly: LinkedIn.

All past editions, along with my books and other writing, now live at jimmytsingh.com.

The Wealth You Build: A Lifetime of Financial Wisdom is available beginning today in paperback and Kindle editions.

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The information in this article reflects my personal experiences and observations over nearly forty years in corporate finance and is intended for educational and informational purposes only. It should not be considered personalized financial, investment, tax, or legal advice. Every individual's circumstances are different, and readers should consult qualified professionals before making decisions based on their specific situation.

Jimmy T. Singh, CPA, is an independent financial consultant and author of A Life Well Lived: From a Small Village to a Life of Purpose, Success, and Love and The Wealth You Build: A Lifetime of Financial Wisdom. He served as Corporate Controller and writes about financial independence and purposeful living.

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