The Well-Designed Life

I struck up a conversation with a vibrant old man walking along the beach in Santa Barbara. He told me that when he graduated from college, all his friends moved to where they found the best job. But he didn’t jump on that train. He thought about where he wanted to spend his life. He projected that if he took a job somewhere he didn’t really want to be, the chances were he would meet a woman, get married, and his future wife might not want to move away from family. Bottom line, if he moved to a city because it offered the best short-term job opportunity, he might get stuck there.

Instead, he held out for a job near Santa Barbara, where he wanted to spend his life. He got the job, he got married to a local woman, and he got the life he wanted. He has lived in California for more than 60 years.

Well, we can’t go back in time and revisit all our decisions. But we can plan for the future. I think there is a good lesson to be learned from this man’s “life design.” How do we want to spend our time? Where do we want to spend the rest of our lives—or even a few months in the winter?

I have practically pleaded with some clients to rent a place in Florida for a month or two in the winter. Once I even went on (vacation rental by owner) to show them how it worked and what they could rent. The couple said it sounded great and it would be good for his health. But they cried they couldn’t afford it. Nonsense! They absolutely could have. You probably can too. You might have another reason you don’t want to do something like that, but if you are reading this column, you almost certainly can afford a VRBO for a month or two somewhere warm. The end of the story: The husband died. We don’t like thinking about it, but we must face the facts: we aren’t getting younger as time goes on.

I am trying to learn a lesson too. I am enjoying the working snowbird life. With the pandemic limiting face-to-face meetings, I have become a frequent “Zoomer.” I can work from anywhere. This past year and tentatively in the future, I plan to spend winters in Tucson and summers in Pittsburgh.

I’m concluding my winter cycling or in my case e-biking in the desert. I cycle about every day. Sometimes on the 110 miles of paved bicycle trails, sometimes up a gorgeous mountain called Mt. Lemmon, and recently on a beautiful 8-mile one-way loop in Saguaro National Park East. The sunrises and sunsets here are spectacular.

My snowbird life allows me to spend more time where I want to spend much of my time—outdoors. I have designed my life so I can comfortably spend a lot of time outdoors doing what I really love which is e-biking and hiking. My wife also loves hiking, and we go for a hike here in Tucson more days than we don’t.

But I can still work here effectively with Zoom. In fact, business is better than ever, and I have a lot of good things in process.

I start some days with a workout (three days a week with my Pittsburgh trainer on Zoom) and then spend the morning working. I then e-bike, and later meet my wife, Cindy, for a hike in the desert. I frequently work into the evening—an old habit.

An e-bike ride up Mt. Lemmon is an all-day affair. It is about a 6,000+ foot climb and is considered one of the 10 most beautiful cycling roads in the country. It is about 25 degrees colder near the top and is a great place to escape the April heat in the valley. I usually stop at most of the scenic view areas on the way up. I take a private shuttle down because I don’t want to be constantly braking or cycling kamikaze-like downhill—my devil-may-care days are done! Cindy also prefers I take a shuttle. Biking up and shuttling down makes for a much more relaxed and frankly much safer day.

Word-to-the-wise, you are much more likely to follow through on a plan if you pick some places and make reservations in advance. Take that under advisement. It can be like herding cats to get some of my friends to commit so sometimes it’s just Cindy and me and sometimes, just me.

During a recent client review, a proud new grandmother was sharing news of her new granddaughter. She was beaming, rightfully so. She and her husband are about to retire and frankly, they don’t have a “design.” I threw out the idea of renting a place near their new granddaughter (I like to start by renting first) where they could spend winters in a warm place near family. They are outdoorsy too so there will be a double benefit to spending winters in a warm place. It was an idea that they hadn’t considered. Assessing where and how you want to spend your time and thinking about what might energize you is a worthwhile endeavor.

Is there some type of “life design” change you could make? To learn more about making life-style changes to better serve your retirement, attend my upcoming July virtual event series. Register at