What 30 Years as a CPA Taught Me About Money — And What Leaving Finally Did
Seventeen years ago, Todd and I sat on a boat in the Bahamas trying to figure out how we could stay.
Seriously.
I was willing to cook. Clean. Cocktail waitress. Bartend. Even be crew on someone else's yacht.
I DID NOT care.
I had fallen in love.
In love with the life.
The water.
And the ability for me to just chill (not a trait by nature).
Todd had skills. He could go back to being a first mate.
But he also—and I'm not joking—considered pumping fuel at one of the cool docks in the Bahamas.
We talked about all of it.
We were trying to figure out how to make enough money to stay in a place and live a life we had completely fallen in love with.
We'd spent four months living on our 33-foot Grady-White Express, including two months cruising the Bahamas.
That boat came to us in 2009. The 2008–09 recession had gutted boat sales that year, and the trickle-down reached Todd's position with Grady-White.
As a result, we got a great deal on the 33 — and instead of scrambling straight into whatever came next, we pointed it toward the Bahamas.
That trip was actually a test.
For me.
Todd already knew he loved life on the water. He'd lived on boats. Worked on yachts. This wasn't a new dream for him.
The question was whether I could actually do it.
And we said that out loud.
Because boat life is definitely not for everyone.
Back then, we didn't have Starlink. We weren't constantly connected to the internet.
Unlike our current Grady, that boat didn't have enclosed helm air. Around 7 p.m., when the bugs came out, we went down below.
It felt like a cave.
Even then, though, I loved every damn minute of that trip.
We anchored out for days at a time.
Every week or so, we'd pull into a marina, fill up with fuel and water, maybe catch an NFL game, and then head back out.
We slept on the boat every single night.
We had each other.
I had my sketch pad.
And every morning, I stepped out into the cockpit and looked at the most beautiful backyard I'd ever seen.
The Bahama-blue ocean.
We dreamed about how we could make this our life.
But then...
We went home.
Back to reality.
Back to work.
And somewhere along the way, the dream became a story we told about this incredible thing we'd done on a boat in 2009.
For more than 30 years, I've worked with money.
I became a CPA. I worked in corporate and public accounting. I've audited financial statements, reviewed budgets, analyzed numbers, and spent more hours in spreadsheets than I care to calculate.
I'm good with numbers.
I "get" money.
But I'm starting to understand something that has absolutely nothing to do with accounting.
Understanding money and knowing what you want it to make possible are two completely different things.
Todd and I talked about retirement.
We knew we wanted to travel.
We knew we wanted more time on the water.
But the life we'd fallen in love with seventeen years ago somehow kept living in the future.
Someday.
Then Todd retired.
A month later, I unexpectedly lost the job I'd had for roughly 13 years.
Seventeen years ago, a job ending gave us that trip.
This time, a job ending gave it back.
And suddenly, someday showed up.
But this time, being back in the Bahamas, I started thinking about those conversations Todd and I had seventeen years ago.
We already knew what we wanted.
We had known for years.
The question back then was:
How can we afford to stay?
Maybe the question now is:
What are we waiting for?
Today, I'm writing this from our boat in the Bahamas.
Yesterday, we went through Devil's Backbone, anchored at a beach for a few hours, and then ran the boat to Egg Island.
The water was so clear it barely looked real.
We snorkeled and saw so much new growth beneath us.
After hearing so much about the damage to the reefs, it was incredible to see them looking so healthy.
Some of the other Grady White owners were anchored around us.
And somewhere in the middle of all that Bahama-blue water, I thought about the two people sitting on a Grady seventeen years ago, willing to take almost any job if it meant they could stay.
We didn't stay.
We went home.
We worked.
We built careers.
We became grandparents.
Life happened.
But maybe the dream didn't disappear.
Maybe we were building our way back to it all along.
Seventeen years later, the boat is newer.
Thank God the helm has air conditioning.
We still cook.
Todd is still happiest on the water.
And I still step into the cockpit and can't believe the color of my backyard.
But I'm different.
At almost 60, I'm finally beginning to understand something my CPA brain could never put into a spreadsheet.
The goal was never just to have enough money.
The goal was to build a life we actually wanted to live.
And then trust ourselves enough to live it.
Maybe that's what this next chapter is really about.
Not starting over.
Not walking away from everything we built.
Finally understanding what we built it for.
Seventeen years ago, we weren't just dreaming.
We were drawing the Chart.
Maybe now, we're finally following it.
Where Are You In Your Next Chapter?
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