I WROTE MY FIRST column for HumbleDollar four years ago. In that article, I described how a midlife divorce had forced me to learn as much as I could about investing and personal finance. As part of that education process, I spent hours creating spreadsheets designed to predict my financial health over the next decade.
Planning didn’t seem difficult back then because my life was quite simple. I shared a one-bedroom apartment with my elderly dog.

AS SOON AS THE BALL dropped, ushering in the new year, I got my ball rolling, making contributions to three tax-favored accounts. Why did I do this in January? I like my investments to have all year to grow.
I go through the same routine every year, and it’s always a chore. I invariably forget what to do and, in any case, the steps involved often change.
The first account I contributed to was my Roth IRA.

THERE ARE TWO GREAT debates in retirement planning: whether the famous 4% rule is valid—and how much income folks need, relative to their final salary, to retire in comfort.
I find both subjects frustrating, in part because there’s so little consensus. I also find much of the advice way too complicated for the average American.
I participate in NewRetirement’s Facebook group and occasionally give my views on both topics. I recently expressed the opinion that the goal in retirement should be to replace 100% of the base income you earned immediately before retirement.

HOW DO WE GET FROM here to retirement? Amid the financial markets’ daily turmoil, it might seem like one big crapshoot.
But in truth, navigating this journey is pretty straightforward, because there are just five key variables—our time horizon, current nest egg, savings rate, target nest egg and investment return. With a few tweaks to these “dials,” we may discover it’s far easier to reach our retirement goal. Which dials are most effective? Much depends on how close we are to retirement age.

AS MY WIFE AND I approached our June 2014 retirement, I set out to consolidate and simplify our investments.
The first account I dealt with was my 403(b). Fidelity Investments was handling the 403(b) plan for the University of North Carolina System, which is where I worked. But while Fidelity was the administrator, the plan included several Vanguard Group funds, to which I’d been contributing. This was where I had the majority of my retirement money.

I’D LIKE TO DESCRIBE—and recommend to you—what I’ll call the John Cleese approach to financial planning. It is, in my view, the simplest and most effective way to think about saving for retirement or any other goal.
John Cleese, the English actor and comedian, is largely retired. But in an interview, he described his approach to getting work done. When he had a weekly TV show, Cleese said, he didn’t worry about being unproductive some days.

IF A SALESPERSON had tried to get me to sink my hard-earned money into an investment that’s illiquid or issued by an insurance company, I would have shut down in a New York minute—until now.
My spouse and I recently became owners of a deferred income annuity (DIA), with plans to put perhaps 15% of our savings into these products. Also known as longevity insurance, a DIA involves plunking down money today in return for regular monthly income starting at a future date.

I GREW UP IN INDIA, where I worked for a few years before venturing overseas and finally emigrating to the U.S. In our culture, most parents feel responsible for their children until their offspring are fully settled in their career and their life, which is often well into adulthood. In turn, the children feel dutybound to support their parents in old age, financially and otherwise.
This cultural tradition is mutually beneficial when both parents and children can fulfill their respective responsibilities.

IN SUMMER 2012, MY boss of 17 years announced he planned to retire the following year. I had enjoyed working for him and considered him both a mentor and a friend, and I had some trepidation about working for a new manager at this late stage in my career. While I enjoyed my job and was good at it, and I liked most of the people I worked with, it was a stressful, demanding position,

LIKE OTHERS, I TOOK my first part-time job as a teenager and, once working fulltime, stayed at it steadily for decades. Being an adult meant being a worker, affiliated with some firm or another, one industry or another.
My plans for ever exiting the labor force were vague: “Save for the future, so someday you will retire with honor and dignity to spend your waning days as you desire.” I saved steadily,

BY EARLY 2009, I HAD been investing for 22 years. My wife had invested for a bit longer, and our savings were starting to seem like a significant chunk of money. I was reasonably happy with our investments. Still, I knew that—for those 22 years—we had been paying too much in investment expenses, thanks to the high-fee funds in our employer-sponsored retirement accounts.
Another source of frustration was that our money was spread over seven financial accounts and 14 mutual funds.

I’VE BEEN EMPLOYED fulltime for nearly three decades—and retirement is now on the horizon. That means I’m spending more time trying to figure out how best to generate retirement income.
One obstacle: I keep getting bogged down by the seemingly endless choices. Despite knowing how critical these decisions are, I often find myself throwing up my hands in frustration and opting to do nothing. My experience isn’t uncommon. Welcome to the paradox of choice: When faced with a host of options,

AS I PLAN MY retirement, I have the advantage of a strong background in finance. I worked for 35 years in the investment field, primarily managing mutual funds. Early on, I obtained the Chartered Financial Analyst designation, which helped immensely.
Six years ago, when I was age 55, I embarked on a journey to comprehend the myriad rules and strategies surrounding retirement. I studied to become an RICP—a Retirement Income Certified Professional. While the CFA was useful for investment management,

THREE WEEKS AGO, I wrote about my plan for generating retirement income, including my intention to make a series of immediate fixed annuity purchases. Immediate annuities are a profoundly unpopular product, so I was surprised when the article generated a slew of questions from readers.
Perhaps that interest reflects today’s miserably low bond yields, which have left immediate annuities as one of the few ways to generate a safe and sizable income stream. Intrigued?

I’M PROBABLY A YEAR or two away from regularly tapping my portfolio for income. That prospect—coupled with this year’s market turmoil—has led me to tinker with my investment mix and ponder how I’ll generate cash once I’m retired. One surprising result: I have more in stocks today than I’ve had at any time in the past three years, and I’m thinking of increasing my allocation even further.
Since 2014, I’ve thought of myself as semi-retired.