Biggest surprises in retirement? The experts weigh in

The Great Recession served up some nasty financial surprises to retirees – the housing crash, job loss and shrunken 401(k)s top the list of causes for the retirement insecurity that so many face.

But retirement can bring lifestyle surprises, too. It’s one of life’s biggest transitions, and a major leap into the unknown. Hoping to lessen the guesswork for people who aren’t there yet, I asked retirement experts who work with people transitioning to retirement – about the surprises they hear about most often from those who have already retired. My Reuters column this week explores their answers, but I received a great deal more feedback than I could fit into the column – so here are some additional thoughts from experts on a wide array of retirement surprises. If you’ve experienced a major retirement surprise yourself, please add a comment about it at the bottom of this post.

Michael Kitces

Michael Kitces

The need for purpose. “The biggest surprise I see early retirees discover as they transition into retirement is the importance of having meaning, purpose, and something to wake up to in the morning,” says Michael Kitces, partner and director of research for Maryland-based Pinnacle Advisory Group. “Having a ‘vacation for the rest of your life’ sounds like a great idea, until you’ve done it for six months and it starts to get boring. For many, this challenge then leads to encore careers they never considered, new businesses they had never conceived, or a new level of volunteer engagement!”

Time freedom. “Time freedom” is a big shock for many, says Richard Leider, an executive career coach and bestselling author (most recently, he co-authored Life Reimagined: Discovering Your New Life Possibilities, Berrett-Koehler Publishers 2013).

“Without the time structure of working, folks often go on autopilot, the default position of repeating old patterns,” he says. “However, there is no status in the status quo. So, at about the one year mark, they realize that “time” is their most precious currency. Often a wakeup call – health, relationships, money or caregiving – forces reflection and helps them to say ‘no’ to the less important things that simply clutter up a life and ‘yes’ to the more important things that define a purposeful life. They choose fulfilling time”

Kathleen Burns Kingsbury

Kathleen Burns Kingsbury

Wealth psychology expert Kathleen Burns Kingsbury also notices people struggling to structure their new lives. “One of the biggest surprises retirees face is the adjustment to not working full time,” says Kingsbury, author of How to Give Financial Advice to Couples (McGraw-Hill 2013). “While people typically fantasize about what life will be like without a job, the reality is sometimes it’s a bit of a shock to the system.

“Work provides structure, social connections and a sense of purpose. It is important for pre-retirees who are not going to work in retirement to consider how they will meet these needs outside of a work environment,” she adds.

The roles at home. People are often most surprised by the impact retirement has on their long-standing roles at home – everything from who does the dishes to whether or not you and your partner should eat lunch together every day,” says Nancy Collamer, author of Second-Act Careers: 50+ Ways to Profit From Your Passions During Semi-Retirement. “Most

couples have established patterns over time that both parties consider fair, desirable and equitable. But retirement often upsets the balance and can lead to serious resentments if expectations, responsibilities and duties are not discussed and renegotiated. ”

Chris Farrell

Chris Farrell

Busier than they expected. “What seems to surprise people most is how busy they are during their so-called retirement,” says Chris Farrell, a journalist specializing in economics and author of Unretirement: How Baby Boomers Are Changing the Way We Think About Work, Community and the Good Life. “The popular image is that retirement is for leisure, largely thanks to the advertising campaigns about the successful retirement by the finance and real estate industries. Golf. Long walks. Taking in a matinee. The reality is that days are full with part-time work, volunteer activities, bucket-list projects, family time and so on. Retirees express wonder at how pressed for time they find themselves.”

Heightened spirituality. The heightened search for meaning can lead to greater spirituality, according to Carol Orsborn, editor-in-chief of and author of 21 books about the baby boomer generation. “The heightened search for meaning in the face of mortality comes as no surprise. The bigger surprise is that as it turns out, many of the things we most fear—loss of identity, erosion of ego, increased marginalization—hold the potential to transform aging into a spiritual path.

“Many retirees report that they are achieving levels of fulfillment, peace and joy not despite the things that happen to them as they age, but because of them. This transcends individual experience, with sufficient mass to constitute what is being termed “the conscious aging movement.”

Helen Dennis

Helen Dennis

Money. Of course.  “The biggest surprise is about money,” reports Helen Dennis, a specialist in aging, employment and retirement. “This is true particularly among women who have earned a good income and find that eight or 10 years into retirement, they fear running short and need to change their lifestyle, all within an uncertain economy. Add to this their surprising initial discomfort in spending their retirement income without depositing a work-earned check.”

The need to move. Changing housing needs also can surprise – especially for single retirees. “For single retirees, recognizing that their current home or location no longer “works” is a common surprise,” says Jan Cullinane, author of The Single Woman’s Guide to Retirement (AARP/John Wiley, 2012). “Upon leaving a primary career, the daily social support built into a job is yanked away. Pairing that with becoming suddenly single through divorce or widowhood, the home that served them well may no longer be appropriate.

“When residences are too big or expensive, and the location doesn’t foster social contact, many singles unexpectedly find it’s time to pick up stakes and move.”

Dorian Mintzer

Dorian Mintzer

For married couples, the surprise might be a desire to get away from one another, rather than the house. “Many retirees end up bored with too much free time and often discover, if they’re in a relationship, that they get on each other’s nerves and want some space and time apart,” says Dorian Mintzer, a coach and co-author of The Couple’s Retirement Puzzle: 10 Must-Have Conversations for Creating an Amazing New Life Together (Sourcebooks, 2014.).

“They often haven’t thought about the role work played –providing structure, self-esteem, time together and time apart from a partner as well as connection engagement and purpose and meaning. Each partner may experience the transition differently and they may be ‘out of sync’ with each other. For example, one may want to travel and the other wants to start an encore career.”

Healthcare shocks. “Unquestionably the biggest surprise is the cost of healthcare,” says Art Koff, founder of, an information resources on retirement. “Out of pocket healthcare costs after Medicare eligibility are much greater than anticipated averaging $276,000 during a couple’s lifetime. In a 2013 survey conducted by, couples planning their retirement were asked for an estimate of the total cost they would pay for health care expenses (not including the possibility of needing either home health care or a nursing home. Fifty percent of those surveyed estimated a cost less than $25,000 once they were Medicare eligible.”


  1. Helen Gagel says:

    Several retirement surprises in this article match my experience. First, I am much busier than I’d expected to be, both with part-time work and community service. I have less leisure time than I’d like, but I realize it is important to fill my days with useful and satisfying activity. I like having more family time, e.g., being able to say yes when my granddaughter sends a text asking for a ride to dance class. Managing finances and health care is a drag–I have a tendency to procrastinate and avoid rather than confront and resolve. While experts on retirement planning would say I probably should have stayed in the full-time work world for a few more years, I Know I made the right decision for me.

  2. Linda Sears says:

    I was able to fully retire at age 52. I cannot overstate how much I love it. It took about two years for me to fully relax into my new freedom but I slowly noticed my personality changing into that of a much happier, calmer person. Now I am 64 and I STILL wake up every day so thankful that I don’t have to head into the daily grind to try to solve problem after problem and deal with the politics in a large state university. My job as business manager of a large department was horribly stressful. I can remember driving home in so much pain because I held the stress in my neck and shoulders. One of the things I noticed right away after I retired was the money I saved by not shopping for clothes and jewelry and not eating out every day. I also no longer had to spend money on chiropractors, therapists, and acupuncturists that I used to help me deal with the stress of job responsibility. Then I began to notice that I was no longer interested in buying “things” – constantly re-decorating the house, buying a new car. I eventually relocated to a very small town (a retirement dream of mine), and took a part-time job as a church secretary. It enabled me to meet tons of people in the community. After four years I stopped working due to problems with degenerative osteoarthritis and now I am very content to putter, work in the garden, be with friends and help out family. I am so thankful for my laid-back life away from the hustle and bustle of a big city and the terrible stress of a demanding job that caused me to wake up in the middle of the night to make lists of things I had to do. Even though I would have told you I loved my job and got much fulfillment from it, now I say thank God that’s over and I can enjoy life. Each day is a joy and I never take it for granted.

  3. Still very anecdotal. I’d love to see real studies to see how people are faring. We have millions (?) in “retirement” so we should have great data on what people are experiencing — the range of challenges they face, what they tried and what succeeded and what failed. We always seem to treat “retirement” as this special place we’ll all go to but we can only speculate and argue the best way to go there and provide some examples of what some people have reported back from this far away place.

    My own, I hate the word retirement, financial independence was achieved some years ago. I still work as a consultant on occasion but that is more for the fun of it then for any need (e.g., financial, self esteem, social, etc.). I tell people I’m a consultant and then confide to them that it is nothing more than a socially acceptable cover for doing whatever I want to do.

    My hobbies and interests became my primary activities. I spend more time with my kids, more time at the gym and running, more time reading journals, more time traveling (for fun), more time learning, more time writing, more on house repairs, more yardwork, etc.. I don’t lack for things to do, but I get to set the priorities and the pace.

    The nice surprise is I’m healthier than I was (e.g., lost weight, BMI 21, changed to a plant based diet, ran a marathon, etc.) because I shed the stress and crazy hours of the corporate world. I could have done these same things, I suppose, while staying in corporate life and accumulating more, but it is much easier now. I’m on no medications, never have been. I’m at my college weight. My arthritis, back, and knee pains have all disappeared. I tell my kids I plan to live to be 100 and to be a healthy active centurion.

    Now if we can just hold the world and country together life should continue to be rewarding, challenging and worth living.

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