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Answer These 4 Questions to Plan Your Retirement Career

Some degree of compromise may be necessary for your next act

By Dorie Clark

(This article previously appeared on the Harvard Business Review website.)

Retiring to go play golf in Florida isn’t the draw it used to be.

In a 2014 Bank of America Merrill Lynch survey, 72 percent of employees over age 50 reported that they’d like to continue working in retirement. Partly that’s a response to the Great Recession and a need to compensate for diminished savings; a Conference Board study showed that in the past eight years, nearly two-thirds of 45- to 60-year-olds experienced a 20 percent or greater decline in their assets.

But much of the desire to stay employed is about personal and professional fulfillment. In fact, the Bank of America Merrill Lynch survey showed that the wealthiest people were the most likely to want to keep working, and 80 percent of retirees who work say they are doing so because they want to, rather than because they have to.

Wanted: An Atypical Work Schedule

The trick, however, is that most retirees don’t want a typical work schedule. Only 5 percent prefer a full-time arrangement, while 35 percent would like part-time work and 33 percent want to cycle between work and leisure. But as many professionals have already discovered, flexible work arrangements are in short supply.

Senior executives with extensive skills and an overflowing Rolodex may be able to write their own ticket. But for everyone else seeking something meaningful to do in retirement — which lasts, on average, for 18 years — planning, and some degree of compromise, may be necessary. As I discovered in the course of writing my book Reinventing You, here are four key questions to consider as you’re planning your next act:

1. How much money do you need to earn? If earning a certain amount of money is mandatory for your retirement plans, that criterion comes first, and will likely limit your options. Specifically, you’re more likely to need to continue working full-time (since those positions are usually more remunerative), and you may need to stick close to the field in which you spent the bulk of your career, because you’ll get paid more for the seniority and experience you’ve accrued.

If earning a robust salary isn’t mandatory, however, there are a number of other questions to consider.

2. How much location independence do you want? If you have visions of balancing a little bit of work with a lot of travel, or you’d like to winter in sunny climes, you’ll want to think carefully about how to cultivate a location-independent second act.


Perhaps you could choose a job that only operates for a portion of the year and allows flexibility the rest of the time (such as being a teacher or university instructor). Or you may want to focus on Internet-enabled jobs that can be done from anywhere, such as being a freelance journalist or a web designer or a business consultant.

As long as you have a deep enough base of contacts to land the work in the first place, it may not matter where you’re based when you’re actually performing it.

3. How radical of a change are you seeking? If you’re still interested in your current field, but would simply like to downshift a bit, you have some easy options.

One is to discuss the possibility with your current employer of transitioning from a full-time employee into a consultant role, perhaps working a few days a week, or focusing on a specific project. That can ease your transition into retirement with a guaranteed paycheck before you walk out the door.

Alternately, you may have other industry contacts that would like to hire you as a consultant, as well. If you’re looking for a bolder change and to leave your current field behind, you’ll need to start laying the groundwork because you’re likely to have fewer contacts in your new profession.

4. How can you start test-driving your future career now? In Reinventing You, I profiled a woman named Patricia Fripp, who started her career as a hairdresser but discovered that she loved public speaking. She honed her skills on the side initially, doing presentations at hair shows; eventually some of her hair-cutting clients who worked for corporations invited her to present on customer service and sales to their teams. But despite her passion for speaking, she knew it would be rash to quit her day job and try to make a living from it right away. Instead, she had a 10-year lease on her hair salon, and created a long-term plan to build up her book of speaking business so that when her lease expired, she could transition seamlessly into her new profession — and that’s what she did.

The further in advance you start planning, the more runway you have to experiment and try out new directions on the side, while you still have the security of your regular income.

The vast majority of today’s professionals want to keep working in retirement — ideally, taking on an interesting, personal growth opportunity. By asking yourself these questions, and starting to plan for your second act as soon as possible, you can create a runway that leads you directly into your next meaningful challenge.

Dorie Clark is a marketing strategist and professional speaker who teaches at Duke University's Fuqua School of Business. She is the author of Reinventing You and Stand Out.  You can receive her free Stand Out Self-Assessment Workbook. Visit her at and follow her on Twitter @dorieclark. Read More
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