Not Exactly Like Riding a Bike

Castaway Cay might be the greatest place on planet earth.

If you’re not familiar, Castaway Cay is a private island owned by Disney. The only way to visit the island is by hopping aboard a Disney cruise; all of their Caribbean itineraries stop for a day at Castaway. Somehow, and I don’t really understand how this works, it’s always between 74 and 82 degrees on the island, regardless of what time of year it is. A few dozen Disney employees live on the island, with nothing to do except keep it clean and prepare delicious food.

On our most recent trip to Castaway Cay (which was our fourth),  we decided to take part of the day and do something a little different from our usual routine of hanging out on the beach and gluttonously partaking in the buffet. Most of island is remote, with nothing but a bike path, so we rented bikes for a family ride around the island.

Lilly had her own bike (with training wheels), Molly had a regular bike, and I had a bike with a seat on the back for Amos to hang out in. Sure, I was wearing flip flops and hadn’t actually ridden a bike in probably 20 years, but riding a bike is literally the essence of something that you can’t forget how to do. How many times have you heard, “It’s just like riding a bike?”

Well, I quickly discovered that riding a bike, for the first time in a couple of decades, while wearing flip flops, with an almost-three-year-old in the back who kept drifting off to sleep and falling over to one side and throwing off the weight equilibrium…is actually not just like riding a bike.

You would have never been able to tell if you were just watching from afar, but at no point during our hour-long ride did I ever feel comfortable. The child seat on the back really makes it a lot harder to balance and accentuates your steering adjustments so that each slight shift of the handlebars created a giant steering overcorrection that had me constantly swerving back and forth. And right when I’d have a stretch where things were going somewhat smoothly, Amos would fall asleep again, lean over to one side, and nearly send me careening into the ditch. I never actually fell over, but I felt nervous and unstable the whole time.

So as I unsteadily wobbled my way back and forth across the island, it occurred to me…this is what retiring is like for a lot of people.

You’ve seen other people retire and it looks like a lot of fun. And as you start thinking about your own retirement, it really seems like a great idea. But then you actually start doing some of the things on your checklist—applying for Social Security and Medicare, nailing down a retirement date, helping train your replacement, making pension decisions, trying to be confident that you have enough money saved to last the rest of your life—and suddenly you feel unsteady and nervous and worried that you might have an embarrassing crash at any minute.

I’ve been guilty of lacking empathy for this feeling over the years, for a couple of reasons. First, I’ve never actually retired myself, so the whole planning process is just an objective, mathematical exercise for me. Second, once you’ve helped enough people through this process, you realize that, sure, there are landmines that you need to be aware of, but when the numbers in the plan work, they work. To me, it’s like riding a bike. What’s there to be nervous about?

So from now on, I’ll be more cognizant of the fact that when I’m helping you make the move from earning a paycheck to using your investments to create a paycheck, while it might seem simple to me, you’re probably going to feel nervous and unsteady, no matter how many reassuring things I say to you.