What We Got Right in Preparing for Retirement

The first couple of years in retirement are often the most difficult. But they also can set the stage for how you’ll fill the years ahead—both financially and psychologically. Stephen Kreider Yoder, 66, a longtime Wall Street Journal editor, joined his wife, Karen Kreider Yoder, 67, in retirement in late 2022. In this monthly Retirement Rookies column, they chronicle some of the issues they are dealing with early in retirement.

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Steve

The sun was setting over Success Lake last month as we discussed a recent reader email.

“What plans did you set in motion before retirement that you feel have yielded good returns,” the reader asked, “and what things do you wish you had done?”

For starters, Karen and I agreed, the fact that we were pitched on the edge of Success, in our tent, was thanks to just such a preretirement plan: to explore activities well beforehand that might continue to enrich our lives postcareer.

The Sierra Foothills lake was our last stop on a two-week bicycle tour down California’s Central Valley, from Shasta Lake to Bakersfield. We had rolled along mostly rural roads among nut groves, vineyards and ranches, often with distant snow-capped peaks to our left and the perfume of orange blossoms. The whole way, we felt blessed that we so loved this adventure together. 

We already knew we would. 

We began testing cycle touring several years before we quit work and concluded it was how we wanted to experience America when we were job-free. We spent a third of our first year of joint retirement on the road, and cycling is a defining feature on our 2024 and 2025 calendars. When anyone asks why, we respond: “There’s nothing like it.”

It’s one of the many things we got right. There’s plenty we didn’t, and we seem to be at a stage in retirement when we’re looking back and evaluating both.

One clear smart move: the good financial calls we made decades ago. We mostly lived below our means, saving toward retirement from our 20s, often through automatic contributions we could set and forget.

A more recent good call: We made sure we could keep our healthcare plan. Medicare, we found to our surprise, would let us continue practically the same coverage as before at our hospital system six blocks away at a reasonable cost. So far, that coverage has served us well.

We got it right on staying put. Work life was too busy for us to fully enjoy San Francisco, and we decided several years before retirement that remaining afterward might finally give us the time. We may eventually cash out and move to the Midwest. But we’re more sure, now that we’re in our second year of joint retirement, that this is where we belong.

Many close friends are here, so we have a community. We can walk or bike to anything we want—restaurants, grocery stores, museums, ballpark, church, ocean—and the weather is senior-friendly. A major airport is 14 miles away. 

The Lyft ride home from it last month gave us the same chill we got 35 years ago when our taxi rounded the curve on Highway 101 and we first saw the city lights spread out before us. As we neared home, Karen said: “We are so lucky to be retired here.”

Another good move was to go into retirement earmarking substantial travel funds, whether for biking or trips abroad with backpacks. Other travel-prone retirees we’ve met along the way have had the same idea, with travel modes such as cruising, RV-ing or Rick Steves tours.

So much for patting ourselves on the back; not surprisingly, we didn’t get everything right. One misstep: We waited too long to hire a financial planner, less than a year before I retired. We should have done so 10 years earlier, or 30. Our planner has mapped out reassuring scenarios for the rest of our lives. But with professional help earlier, we could have fine-tuned our savings, investments, charitable giving and tax strategies, allowing us to worry less about money leading up to retirement and avoiding what felt like a last-minute scramble.

We also probably got it wrong on staying in our house. We bought a Victorian in 1989 in what was a marginal neighborhood. It was, at first, a terrible decision. We could barely make the mortgage, and maintenance was a budget-killer, one of the few times we’ve lived beyond our means.

But then it turned out to be a great decision. Our neighborhood gained a vitality we never expected, and San Francisco property values, well, you know about those.

Now, sticking with it looks like a poor decision. The building is too big for us and tends toward entropy. It’s lovely living in a museum piece, but we should be in a bungalow or condo with lower costs, less maintenance, just enough extra room for our man and woman caves—a retirement essential—and less reason to feel silly leaving it behind for the months we’re gone.

Another big thing I got wrong: I didn’t adequately figure out before retiring what to do between monthslong trips. Our travels have been enriching and consuming, but I often find myself at loose ends at home.

Fortunately, that’s a wrong call I can override. One option may be to find some kind of part-time job or volunteer gig (aside from writing this column)—something meaningful or fun to fill the void. But that’s a subject for a future article.

Karen

The most important groundwork I laid for retirement was 45 years ago.

I picked the right partner. Steve agrees he did the same.

I didn’t know for sure at the time, but I had hints. The 19-year-old baritone I met in college choir was fascinating, handsome, bright and curious. I would soon find he was also adventuresome and frugal to a fault.

Those things came to matter very quickly as we began setting patterns for life together—including over money and how to spend it—in ways that are bearing fruit in retirement.

From the start, we saved first, spent later and little. Some colleagues were eating out, buying upscale clothes and new cars on credit. We weren’t happy unless our bank balance was growing, so we stuck with our ’71 VW and Friday nights at the movies. The one exception: spending on travel.

We lived largely on my $9,700 teacher’s salary the year we were married, yet saved several thousand dollars that we used to fly to Japan for the summer. Even there we were frugal, hitchhiking around the country and hostelling or camping at night.

By our late 20s, we had agreed that the spartan course could set us up for retirement. We couldn’t have done that if we didn’t happily concur on our home economics.

The other important groundwork for retirement was arranging my life to never be bored. Just before I retired, I asked myself, “Do I have enough going on to avoid boredom?”

I had rarely been bored in my life. There was always something to think about or wonder about, to make or create, to plan or organize. One of my most frequent utterances was “Wouldn’t it be great if we could…?” And then I set about to do that.

But retirement would be different, I figured. Without the structures of work for the first time, my wide-open schedule might be a challenge. 

I looked at what I was already doing: comforter tying, quilting, cycling. We had a pattern of travel to see family that we could continue—the train to Iowa, Thanksgiving in Kansas, trips abroad.

I concluded that my life had prepared me for retirement. In college, I decided I didn’t need to limit my interests to one field. Education, specifically teaching children, was the perfect way for me to continue learning about all areas of life. The classroom offered a home for scores of interests I could carry into my nonwork life: raising silkworms, reading historical fiction, propagating plants, quilting, interviewing community elders, mental math, singing, memorizing poetry. 

Retirement, I decided before I quit work, would offer even more flexibility to fill my days with whichever interests piqued my fancy. I now share those interests with friends and younger folk. We dye pysanky eggs. We discuss books. We clean out old houses. My women’s group gathers monthly to catch up.

Steve and I also concluded that the frugal ways of our early married years could sustain us in retirement. The impulse to use what I have, not buy another gadget or piece of clothing, helps us live within our means. 

So, back to the reader’s question—what did I set in motion before retirement that has yielded good results? I made sure I could maintain my lifetime of cultivating interests and staying curious to the world around me. 

And I determined to work with Steve just as we vowed at our wedding. “For richer or for poorer” we each pledged in 1979, “I promise to foster stability in our lives as well as adventure.”

The Yoders live in San Francisco. They can be reached at reports@wsj.com.