Chicken Little and Small Regrets

“A ship in harbor is safe, but that’s not what ships are built for,” John Shedd wrote. I have been a fan of this saying since I first heard it in a business setting as inspiration to take risk.

What about the times, though, that we choose not to leave harbor, or worse, to leave, and then turn back? My 30-something niece and nephew did just that with my sister, 4 teenagers, and me on board recently, and I could not be more proud.

I had been looking forward to our annual scalloping trip. It’s a 2-hour drive to the marina. The agreed meet-up time is 7 a.m. Getting out early means less boat traffic and hunting the seagrass beds under more gentle sun.

We loaded in their pontoon boat on the Homosassa River. Winding down the 4-mile stretch to the Gulf, a rainbow stretched across a thundercloud ahead of us, while the sun rose in the blue sky behind. No one was worried – small scattered storms are normal in summer. You might get wet for 15 or 20 minutes, and then the sun comes out again. “It’ll go around,” we all agreed. The speedboats passing us by seemingly thought so, leaving us in their wakes.

With each passing mile and minute, though, the darkened sky grew closer. Cool downdrafts interrupted the humid stillness. They smelled like rain. Then lightning struck in the distance. “Hmm. We do know better than to be out on the water in lightning,” my sister said.

My niece, nephew, and sister began to discuss options – pulling over to wait, or heading south once we got to the Gulf. No one brought another up, so I did – turning around would be ok, too.

Earlier in my life, I would have been more fearful of turning around than forging ahead. After all, what if I panicked like Chicken Little, and then found out it was for nothing? I didn’t want to regret robbing myself and those in my party of fun, and feel like a panicky fool, because I was overly cautious.

As a result, I encountered 6-foot waves in a 16-foot boat, blizzards on ski lifts, and close-call landings in a small plane. None of those times were fun. Sometimes I wonder why I am still here to write about them. In the thick of those moments, life-size regret and embarrassment set in. Not the small-size kind you get from being Chicken Little.

As we rounded the final bend, many boats had stopped at the mouth and stared into a wall of advancing rain a mile away. The front line of gray now met the blue above our heads. It began to sprinkle.

My niece pointed out the other boats appeared to be waiting it out – maybe we should, too. My nephew, at the wheel, told her to drop the anchor. The teenagers were quiet, waiting to see what the adults would decide.

My nephew and I checked our phones’ radar. The storm appearing in red on our screens had ballooned like an atom bomb. A line of red, orange, and yellow along the Gulf coast was moving onshore. Turning south was not an option. Turning back was seeming wiser. It wasn’t going to “go around.”

Disappointment and disbelief took hold. We had anticipated the perfect scalloping day – loading, fueling, prepping the boat; getting the food, ice, drinks; the traveling; spending a few hours with family. Surely we didn’t do all that for nothing. We hesitated and looked around. No one else was turning back. But they weren’t any wiser  – they just didn’t want to be disappointed, or feel like Chicken Little, either. Everyone had planned the perfect day, starting on the Gulf at dawn. Now Mother Nature was saying, “Not today.”

My niece and nephew remembered a friend who lived on the water close by. Perhaps they could park the boat there for a while. She pulled up the anchor. Motoring back in light rain, rays of sunshine and blue sky would peek through the low gray clouds. Boats were heading out while we were heading in. Was there still a chance of a half-day on the water if we just waited?

It rained a little harder. Then a speedboat passed us heading back, too. Then another, and another, as if they had followed our lead. No more boats were going out. It felt like the right choice, although it didn’t make the regret and disappointment go away.

There are times we should take risks, leave harbor, set sail, and go forth. Then there are times when it’s clearly foolish to do so. It’s the gray areas, the in-betweens, that are more difficult to figure out. When it’s something clear and present, powerful, and unpredictable, I’ll take the safe choice over the adventure – now that I know the small-size regret hurts a lot less than the life-threatening kind.​

Holly Donaldson

Holly Donaldson, CFP® runs an hourly and fee-for-service financial planning practice virtually from her Tampa Bay, Florida office. She also works with clients throughout the U.S. (except Texas) interested in retirement and tax planning advice without product sales or investment management. Holly is the author of The Mindful Money Mentality: How to Find Balance in Your Financial Future (Porchview Publishing, 2013) and publisher of the award-winning monthly e-letter, "The View From the Porch."

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