IN HINDSIGHT, MY WIFE and I made a mistake by over-saving in tax-deferred accounts. It’s not that we saved too much overall. Rather, we ended up with retirement savings that aren’t diversified among different account types. In fairness, this was caused by the limitations of our work-sponsored retirement plans, coupled with the stock market’s handsome appreciation in recent years.
The classic approach is to build a three-legged stool for retirement—Social Security, a pension if available,

I’LL ACKNOWLEDGE THAT today’s topic isn’t the most upbeat. I want to talk about risk—and, specifically, some of the underappreciated risks related to retirement.

In thinking about risk, the hardest part—in my view—is that it defies a single definition. Because of that, there’s no uniform yardstick for measuring it and thus no single strategy for managing it. As Howard Marks states in his book The Most Important Thing, “Much of risk is subjective,

PREPARING FOR infirmity is one of the most important—and least popular—parts of financial planning. A neighbor’s recent stroke provides a stark example of this challenge. He’s in his mid-80s and has some underlying health problems.
Our neighbor lives in a second-story condominium, with external stairs as access. The stairs end at a narrow deck, with a right-hand turn into the home. An overhang blocks the screen door from opening fully.
When he had a stroke,

I LEARNED TO LIVE a lot more cheaply after I lost my job at age 58—and that’s allowed me to retire with a less-than-average income.
After getting laid off, I spent 18 months searching unsuccessfully for a position that reflected my experience and education. I ended up taking an administrative office job at 40% less pay.
Although I was already a thrifty and cautious person, my life became a lot leaner for the next four years,

AS THEY APPROACH retirement age, workers sometimes get to choose between a monthly pension and a lump-sum payout. It’s a choice I recently made—one I researched carefully. In the end, I made an unusual decision that took a few extra steps.
Let me start at the beginning. In 1984, I began working for American National Insurance Company as an investment analyst. I left the company in 1991, but still qualified for a small pension.

“HELP, I’VE FALLEN AND I can’t get up.”

It wasn’t too many years ago that I viewed that commercial as humorous. No more. A few days ago, my wife slipped on a curb and fell. No serious injury, just a cut on her lip and a scraped leg. But she couldn’t get up. Thankfully, my sons were there to help. I couldn’t do it on my own. My wife’s arthritis makes it difficult for her to walk long distances or climb stairs,

ONE OF MY FAVORITE movies is based on A Christmas Carol, the Charles Dickens classic. It’s about the mean and miserable Ebenezer Scrooge, a money lender who constantly bullies his poor clerk, Bob Cratchit, and rejects his nephew Fred’s wishes for a merry Christmas.
Scrooge lives only for money. He has no real friends or family, and cares only about his own well-being. As the story goes, on Christmas Eve, Scrooge is visited by three ghosts.

MY YEAR BEGAN WITH a fulltime job at an energy trading company. But I knew my days were numbered. I’d spent six years trading, working with clients and helping to manage risk, all while being surrounded by smart and fun people. But as side gigs, I’d also spent several years writing about finance and teaching as an adjunct professor. Writing became my passion—one that didn’t mesh well with my day job.
That’s how, in January,

DOES ANYONE DOUBT that planning for retirement is unique for each individual?

The way we manage money, how we handle debt, our desired lifestyle and our family status are all important variables to consider. From what I observe, however, many people ignore these differences and seek a one-size-fits-all answer.

I’m addicted to YouTube. In addition to history, archeology and general education videos, I watch many retirement planning shows. I also follow retirement groups on Facebook and bloggers who embrace the FIRE (financial independence-retire early) lifestyle.

I RECENTLY SPOKE with a colleague. I’d expected him to be retired by now. He told me that he’d planned to retire last spring, but his employer offered him a three-day-a-week part-time schedule with full benefits. He discussed it with his financial planner.
The planner told him that, if he retired, he had an 85% chance of meeting his retirement goals. By working part-time for two more years, his chances of meeting his goals went up to 95%.

I WAS RECENTLY talking with a younger acquaintance about my decision to leave the workforce early. I’d left a demanding career to pursue my personal passions, while I was still young and healthy enough to do so.
My acquaintance is in his early 30s. He’s single and makes a boatload of money working in IT for a pharma company. He’s also a big proponent of the FIRE (financial independence-retire early) movement. He takes part in Reddit boards and reads every investment article he can get his hands on.

AMERICANS THINK they need an average $1.9 million to retire, according to a survey of 401(k) plan participants by Charles Schwab. Years ago, a finding like that would have terrified me.
I worked really hard in my younger years and socked away money diligently. But between paying off the mortgage, saving for the kids’ education and being hit by an unexpected divorce, there’s no way I could ever have amassed $1.9 million.
Still, I’ve learned to live well in retirement.

AS WE GROW OLDER, maintaining the family home can become a burden. Eight years after I retired, my wife and I moved to a 2,000-square-foot condo. It’s about the same size as our old house. But it has no stairs, no basement—and no attic full of stuff. There’s also no exterior maintenance or landscaping work required of us.

I’ve been asking near-retirees how both downsizing and relocating figure into their retirement plans. Although there’s much talk about it,

I JUST TURNED 62. That’s the milestone age when so much of the magic—and the decision-making—of retirement begins to happen.
For the record, although I recently left the workforce early to pursue a long-simmering passion for writing, I won’t be starting Social Security payments early. Nor—unless something changes health-wise—do I intend to begin distributions from my IRAs any time soon. Before I go down those two routes, I plan to live off my taxable-account savings and minimal dividend income for as long as I can.

IN A RECENT TWITTER post, a man claimed that if all the Social Security taxes he and his employers pay were invested instead, he’d accumulate $1.9 million by age 67. That sum could then generate $95,000 in annual income, he added, which is more than his anticipated Social Security benefit. He concluded that Social Security was “theft.”

Claims like these bother me greatly because they’re often widely read and believed—and they’re nonsense.

Social Security is an insurance program,