Work & Money

Money: Handling the First Year of Retirement

The first year of retirement can be tougher than you think. For some, money is the least of your worries.

Retirement is supposed to be easy. But it can be tough. And being comfortable financially is just one part of a happy and successful retirement.


Multiple surveys, including a new one from the Alliance for Lifetime Income, show that most Americans worry that they will outlive their savings. But for those who didn’t plan how they would spend their time, retirement can be both stressful and boring. In fact, surveys have shown that retirees are prone to depression and loneliness. One study estimated that a third of retirees experience symptoms of depression in retirement.

“The first year is certainly an adjustment,” says Ross Hamilton, vice president, wealth management with The Minor Group of Raymond James in Bethesda, Maryland. “It’s a big change emotionally and psychologically. And trying to plan that out ahead of time is really, really important.”

“It can be overwhelming,” he says. “If you can get ahead of that, and kind of narrow down the list of things that are uncertain, you’ll have a lot more confidence as you enter that first year. And that will really allow you to focus on the non-financial things.”

Moving in Retirement

He says retirement can be especially jarring to those who buy new homes in retirement that is in new cities and states away from their friends and former colleagues.

“Shifting from work to retirement is a financial event. It is an emotional event. It’s a lifestyle event,” he says. “And you know if you can get the financial piece of it squared away ahead of time, it allows you to focus on the other things. The more work we can do ahead of time, the easier that transition, the more enjoyable that retirement will be.”

One Retiree’s Experience

Jeanne Thompson, former senior vice president at Fidelity Investments in Boston, can tell you how tough it was.

“The first year was tough,” says Jeanne Thompson, a former executive at Fidelity Investments. She took an early retirement buyout at 54 and says it took her a year to settle down and figure out what to do with her life. Her two children were in college and her husband was still working.

“I had a vision of the time to travel and be a free spirit,” she says. “And like you go on a trip for a week and then come home. And then then I realized how my identity was tied up in my job. I was raising kids; and my aging parents, and all that. It was all this family stuff and my job, and I didn’t have time for hobbies and interests.”

Shifting gears

She said for years she did nothing but take care of people and work a very demanding job. “And then my parents passed away,” she says. “My kids were gone, and I had an empty nest. And I’m walking around the house like, what’s next? I had an existential crisis.”

Making sure you are financially ready to retire is a huge part of retirement planning. But Thomson says she focused only on the financial part of retirement and neglected to plan for the other part. She had read the studies about people needed to plan for the social part of retirement, but she didn’t really buy into it. “I didn’t think it wouldn’t happen to me.”

She says part of the problem was she wasn’t quite ready to retire, but a buyout speeded up the process. “I ended up retiring probably three or four years before I wanted to,” she says. “Even though I was financially ready, I wasn’t actually ready. I was 54 at the time. I thought I wanted to retire early but at 58. And so it felt like I did I wasn’t mentally there.”

Thompson eventually figured it out, and now she’s busier than ever. She’s “corporatized” her life. She started writing and is about to publish her first book. She created a schedule, which allows her to know exactly what she would be doing the next day. She started doing TikTok videos (@jdawgretires) and has 11,000 followers, and she coaches people.

One thing is for sure. Her experiences have changed the way she will coach people about retirement. “The money matters. But it’s the rest of it that people struggle with.”


What was your experience of the first year of retirement like? Share your tips in the comments!


Rodney A. Brooks is the former deputy managing editor/Money at USA TODAY. His retirement columns appear in U.S. News & World Report and Senior He has written for National Geographic, The Washington Post and USA TODAY. The author of “Fixing the Racial Wealth Gap,” Brooks has testified before the U.S. Senate Special Committee on Aging. His website is


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11 responses to “Money: Handling the First Year of Retirement

  1. “What was your experience of the first year of retirement like?” ▪ My first year of retirement was a wondrous time of transition. I think the silenced alarm clock was the first delight. Midday shopping. Daily rail trail bicycling. Rediscovering photography, museums, leisure travel and reading. Much reading. And along the way realizing how much more I enjoyed weekdays than weekends for all activities. Yes, I now look forward to Mondays more than Saturdays. How’s that for a transition?

  2. I retired from teaching when my first grandchild was born. I babysat one day a week ( the other grandma had Mondays and daycare was the other 3) so I had a great time getting to know the newest members of our family. I continued through two more children, and kept going until all were in school full time. Now I have baseball, basketball and soccer games to see, as well as concerts and plays. My whole life has been filled with children and I couldn’t be happier!

  3. I have always wanted to be bilingual, but studying a foreign language while working wasn’t an option. So, I audited two classes at my local community college, but had to change course when Covid shut down many educational options. I signed up for online classes at Arizona State University and graduated this May with a BA in Spanish. It was a wonderful experience. I recommended language learning to many of my friends who are joining me in retirement.

  4. I couldn’t be happier over my early retirement 6 years ago. My retirement proceeds allowed our family to increase our savings for the big equity to get a mortgage for our first home. I look back now and realized that had I continued working despite my vision impairment, we wouldn’t have been able to find this best place and afford the cost which at current market prices have doubled up. Sometimes, an incapacity is actually a boon toward a happy early retirement as well as being debt-free.

  5. I had financially prepared by paying off all of my debts and had social security and a pension ready to go. My final day was in February, a month before my 66th birthday and right before COVID hit. I really enjoyed hiking and exploring places I hadn’t had time to see. I caught up on many projects around the house, chatted with neighbors on the streets, started writing letters to old friends, and tackled a big invasive plant project. Now I volunteer for some of the work I used to do at my job.

  6. I agree with Gigi Smiths’s experience post retirement. I retired early when the work just became drudgery. I couldn’t wait to create my own version of what retirement looks like. I’ve jumped into free educational opportunities on any topic unrelated to my former career. I continue to make use of those skills and new ones by working as a volunteer where I could bring some value to people in need. That in itself has been more rewarding than anything I’ve gotten a paycheck for doing.

    1. I’m the opposite. All tell me to retire and enjoy myself but working IS what I enjoy! I’ve been told I have the resources to retire but don’t know what I’d do with myself! I love what I do; am self-employed, can work as much or little as I want and can’t imagine NOT doing what I’m doing.
      I was cranking in my 50’s. Doing a lot! Traveling for work abd pleasure, studying yoga in India and Thai Massage in Montreal; attending workshops, teaching, doing trade shows, everything! I’ll be 69!

    2. Forced to retire by the pandemic, bec I could no longer work in families’ homes (children w language and speech delays in neighborhood of essential workers). Age also health consideration. Thought I’d have a 6 mo break but too many people refused vaccination and COVID persisted. I had lots of interests but financially forced to live on savings w growing medical expenses (check ups, referrals, follow ups…I didn’t know to expect this). Still have interests, but now have the financial worry

  7. Due to Covid, I was able to work from home for a year before I retired. Then I was able to work part time which helped me wind down my work career. My first full year of retirement, I gave myself permission to do nothing to recharge from the stresses of a c suite position. Now in my second year, I love the life I have. I have time to exercise regularly, do volunteer work at several organizations, take on line classes and visit more with family. I don’t miss the stress from work at all.

    1. Gigi,
      That is awesome! I left my position last year due to workplace environmental issues, although I had not planned to retire for another 3 – 4 yrs. I’ve completed an online certification and looking forward to another professional chapter, on my terms. I have enjoyed the freedom and flexibility to enhance relationships and travel at will :)

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