What a Second Sailboat Taught Me About Money
- Jeannette Fennel
- Mar 17
- 3 min read
“I just don’t get it. Why would he keep spending like that when he’s so close to retirement?”
My friend was telling me about a guy she worked with. On paper, he was doing really well financially by earning well over $300,000 a year and getting close to retirement.
But she couldn’t figure something out.
The guy still owed a lot on his house.
He was still making payments on a sports car.
And he had just financed a second sailboat.
Yes… a second boat.
She kept saying, “I just don’t understand why he keeps spending like this.”
Instead of jumping to conclusions, I started asking a few questions.
“Is he married?”
“Not exactly,” she said. “His wife passed away last year from cancer.”
I paused for a second.
“When did he buy the new sailboat?”
“About three months ago.”
I paused again.
We looked at each other and then it all made sense.
This man wasn’t just buying a boat.He was trying to fill the hole in his heart after losing his wife.
When Emotions Show Up in Your Spending
Grief has a way of showing up in places we don’t expect including our spending.
The truth is, our emotions and our money are deeply connected whether we realize it or not.
Some of you have heard me talk about what happened after my dad passed away.
I spent a lot of money.
An embarrassing amount.
Clothes. Shoes. Trips to TJ Maxx, Target, and Nordstrom Rack like it was my part-time job.
At the time, I didn’t realize what I was doing. I just knew everything in my life felt like 💩 and buying something new gave me a tiny hit of relief. For a moment, I could feel good instead of sad.
Looking back, it’s obvious what was happening. I was trying to manage my emotions with my shopping habit.
It took me a while to figure out what was really going on.
But eventually I did. And I came out the other side with a lot more awareness about how emotions and money are deeply connected.
This is something I think about often when talking with people about their finances.
It’s easy to look at someone’s choices and think:
Why would they do that?
That makes no sense.
They’re being irresponsible.
But sometimes all it takes is a few honest questions to connect the dots.
When you understand the emotions behind the spending, things start to make a lot more sense.
In this scene from Season 1 of Ted Lasso, Ted is playing darts against Rupert at the pub. Rupert assumes Ted is just a clueless American who doesn’t know what he’s doing. As Ted lines up his final throw, he shares a quote his dad loved: “Be curious, not judgmental.”
Rupert had judged Ted without asking questions and it turns out Ted is actually very good at darts. With one final throw, Ted wins the game and proves his point.
Get Curious About Your Own Spending
So the next time you’re talking with someone about money (a friend, a partner, a client, or even yourself) remember the advice from Ted Lasso:
“Be curious, not judgmental.”
You might be surprised by what you learn.
And that curiosity can apply to your own spending, too.
If your spending feels a little out of control right now, try getting curious instead of judgmental.
Start by asking yourself a few honest questions:
When do I tend to make impulse purchases?
What do I usually buy?
How do I feel immediately afterward?
How do I feel a few days later?
Did a parent or caregiver model using money like this?
Do I feel pressure to keep up with friends, family, or coworkers?
Do I feel left out (hello, FOMO) if I can’t attend something?
Those questions aren’t meant to shame you.
They’re meant to help you understand yourself.
Because when you start asking curious questions instead of judging yourself, you often find the real reason behind the spending.
And once you understand the why, it becomes a lot easier to change the behavior.
Curiosity is often the first step toward healing your relationship with money.
➡️ When was the last time you paused and asked yourself “why” before making a purchase?
Hi! I’m Jeannette and I help professionals ditch debt without the overwhelm and build wealth without the stress.
📞 Contact me to schedule a FREE 15 minute phone call and start to make a plan with your money.
Friendly reminder: The information shared is for educational purposes only and isn’t a substitute for financial, legal, tax, or mental health advice. Please consult a qualified professional for guidance specific to your situation.
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