A drive with Leon

Interesting Uber ride in Boston this week as I was headed to New York to attend the Bloomberg Investor conference . Usually at the end of the week, I tune out in these rides.  But this was first thing in the morning and I was just starting my trip, so I was bright eyed and bushy tailed!

I was in the mood to engage!

My driver, Leon, was 49, and I quickly learned he had served in the Navy. That caught my interest. I asked him what he did now.

He told me he split his time between driving a tractor-trailer in the summer—transporting military officials between bases—and picking up Uber fares in the off-season. The trucking work, he explained, was both rewarding and lucrative. “Plus,” he added, “I can maintain my own rig, an American Eagle tractor trailer, so I don’t have to worry about layoffs.”

I could tell Leon was someone who planned ahead. So I asked him—what’s next?

He said he wanted to “retire” at 52, but he didn’t mean stopping altogether. He had a Navy pension, but there was still a long stretch before Social Security. He wanted to do something in between.

So, he went to HVAC school.

Bay State College. One-year certificate in appliance repair. The school had since closed, but Leon had learned what he needed. And now, he had a plan.

“I want to start a laundromat,” he said. “Now I know how to fix those machines myself.”  And it is a cash flow business.  And it is recession proof. “People need to wash their clothes.”

Unlike male teenagers, I queried… we both laughed.

We started talking about retirement in general—what makes for the best post-career vacations. Visiting family. Traveling. Maybe even river cruises. He was looking for a place to invest, somewhere he could settle into this next chapter.

Then, as we were driving, Leon asked a question—almost to himself.

“My life expectancy is 75, right?”

I told him that statistic included infant mortality. If he made it to 65, the odds were that he’d reach 85, not 75.

Long silence.

We pulled up to the airport. As I gathered my bag, Leon turned to me.

“You’ve added 10 more years to my planning.”

I shook his hand and wished him all the best.

Perhaps his next decade had just opened up.