I’ve helped many people transition into retirement over the years and when I ask a new retiree how things are going, the response is generally positive. That said, retirement is a huge transition and there are always unexpected feelings or emotions that crop up. That doesn’t necessarily mean that there’s something wrong with your retirement. It just means that you’re normal. So don’t be surprised if you feel one or more of the following:
The Problem: I feel guilty.
This is surprisingly common and I’ve seen it manifest itself in two ways. The first is guilt if you’re not doing much or making the most of your time. You finally have some free time and you struggle with how to use it. You feel guilty because watching T.V. or running errands doesn’t quite feel like sucking the marrow out of life.
The second is guilt if you’re doing fun stuff that your friends and family aren’t doing because they’re still working. I’ve actually had clients hesitate before responding to me when I ask “What did you do today?” The answer is “I went golfing” or “We saw a matinee and then went for a walk” but they are hesitant to say that because they know I spent my day behind a desk. When prodded, they say they don’t want to make others feel bad or come across as boastful.
The fix
For the first type of guilt, don’t worry! You’ll get better at it. You control a much bigger piece of your time in retirement and that takes some getting used to. Work hard to do things that leave you feeling happy and fulfilled, but keep in mind that not every minute of your day has to be spent bungee jumping or traveling. Sometimes the best way to spend a day is binge watching House of Cards on Netflix.
For the second type of guilt, just allow it to pass. Don’t become an insufferable braggart, but don’t feel guilty about enjoying your life either. You worked hard and made good decisions. Enjoy your time.
The problem: I’m second guessing my decision.
Buyer’s remorse is a real thing. Chances are you’ve felt it if you’ve ever bought a house or had to make some similar big decision and feared making the wrong choice. It can creep up after retirement as well and cause you to question whether you should have retired in the first place.
The fix
I have a client who has been dealing with this lately and she shared something that I thought was really insightful. She said, “Whenever I second guess my decision, I focus on why I retired in the first place.” Her choice would have been to work for five more years, but two things happened: Her mom was diagnosed with Alzheimer’s and her grandkids were all at an age when hanging out with grandma was just about the best the thing ever. If she had stuck to her timeline and worked for five more years, there’s a pretty good chance that her mom may no longer be around and her by then teenage grandkids will have priorities other than grandma. In other words, she gave something up, but got something far greater in return. There are pros and cons with most decisions in life. Retirement is no different. Keep that in mind.
The problem: I feel disappointed.
Most of us have an idealized view of retirement. Add years of anticipation to the mix or a personality that enjoys the structure and challenge of work and it’s not uncommon to feel a bit underwhelmed after entering retirement.
The fix
The best way to avoid disappointment is to retire TO something rather than FROM something. If all you do is subtract things—work, obligations, commitments—you simply create a void in your life. That void can open you to self-doubt, regret, lack of purpose and boredom. Nature abhors a vacuum. If you take something out, you need to replace it with something else (e.g. travel, school, a second career, hobby, etc.). The goal is not to do nothing. That just creates a void. The goal is to do what excites you.
And test those plans out before you retire. I most often see disappointment arise when a person has prepared for retirement using all lesson and no lab. In other words, all of their retirement plans are in their head or on a sheet of paper, and they haven’t spent any time actually testing and refining those plans. Reality can’t compete with 40 years of idealized assumptions.
The problem: I feel like a fish out of water.
No matter how prepared you think you are for retirement, you will probably still struggle. It’s a huge transition. The routine you’ve had for the last 40 years is out the window. That can be a bit disorienting for many people.
The fix
When talking with a client recently, she compared retirement to becoming a parent for the first time. “Before becoming parents we read books, painted the nursery, sought advice from other parents and bought all the cribs, carriers and countless other things that parents need. We thought we were totally prepared. And then we had our first child and all that went out the window. Retirement is similar. As prepared as you think you are, you really can’t grasp what it takes or what it will be like until you’re actually living it. Your experience will be totally different than the guy next door.” Great advice. Yes, there are tons of things that you can and should do to prepare, but the battle is always different than basic training. Don’t get discouraged. You’ll figure it out and get better at it with practice. Focus on living the life that you want to live. Imagine your ideal life and then work backwards from there to figure out the most direct path to where you want to be. Focus intently on the things that matter to you and throw yourself into them wholeheartedly. That kind of focus and tactical thinking will help you rapidly flatten your learning curve and smooth your transition into retirement.
Remember that retirement is not a date on the calendar, it’s a life stage that will last for years. Think back to when you first became an adult. Were you better at it at 28 than you were at 18? Of course. The same will be true with retirement. It might feel a little awkward at first, but you’ll get better at it over time.
~ Joe
Thank you. No one I’ve talked to understands the feelings of guilt.
You bet! That’s definitely one of those unexpected feelings that clients have shared with me over the years.
Thanks for your articles.
Thanks for your articles. I’m 54 and retired last month. I was miserable and my job and I feel so guilty for quitting. My husband continue working.
I’d really like to retire in the next six months, but the guilt is getting to me. My supervisor will be at a loss, and budget constraints will make it very difficult to hire a replacement. My leaving will put a real burden on other coworkers who I really enjoy working with.
If you ended up costing the company an extra nickel per week, they would fire you without a second thought. Don’t place loyalty where it doesn’t belong.
This is really an awesome response.
Thank you ?
I have the same issue, but its mixed. My retiring will inconvenience the department I’m working for, but they don’t really appreciate many of the things I have done for them over the years which they take for granted , and they have advanced others at my level but not given me those same opportunities. I do feel rather guilty nevertheless, like I’m throwing away a well-paying job with benefits– but I’m simply exhausted. I’m 68 years old and I would like to relax and enjoy my life going forward for a change. I definitely , definitely can relate to your view and situation–
look I was in the same boat as you worked bloody hard as an Adult Social worker high case load, no consistent manager, 4 restructures putting in to keeping my job. Hot desking to the point I did not know what floor I was working on let alone who I may recognize! I retired early at 55 more out of concern with issues relating to my mother’s memory and health. I went with my gut and am glad I did as my mother’s health decline, and she died within 5 years. I’m so glad I did not have the worry of work and don’t regret my actions. Sure, I get bored at times and miss company, but I know my field of work has not improved and thank God I am solvent. I don t think my pipe dream of a job not for salary but for being appreciated exists in most people’s work life, but I envy those that have
I had the same feeling about leaving an unreasonable work load for others to pick up. There is a hiring freeze. However, I did not want to live through even one more month of the stress. It is damaging to health, and I have to take care of that or there is nothing.
Awkward explains it best. I have so many mixed emotions. It feels like i should be doing better with my time. My retirement date was May 31, 2019. I feel lost and alone.
Hi Pat. Don’t get discouraged. That awkward feeling is common. After all, you’re transitioning away from something that you’ve done for decades and that you were good at (your career) to something that is unfamiliar and challenging. The awkward feeling will start to go away as you begin to find your groove in retirement. Take another look at the fixes listed in the article. Also, there’s some good info in A Brief Guide to Retirement Bliss (available in our free retirement toolkit) and the Lifestyle Design Guide portion of The Ideal Retirement Design Guide (available in our store). Finally, make relationships a priority. They are a huge contributor to a happy retirement. Even one or two good relationships can go a long way to alleviating loneliness. Touch base if you have any questions or if I can ever help. – Joe
Hi Pat – I retired August 1, 2019 and feel similarly even though I’m still working on a temporary basis 15 hours per week at the same place. I think it will take time. Do things that make you feel good and make sure you get up and moving in the morning. Don’t worry about doing anything “better” with your time, just do what gives you pleasure, even if it isn’t remarkable by anyone else’s standards. Take care of you. This too shall pass.
I know this was posted several years ago, but I feel exactly as you feel…lost and alone. I’ve been retired since 2020 when COVID a was in full swing, and there was no “active” world to retire into; everything was shut down and virtual classes and communication were the new normal. As an adult with no children, I have few good friends and they’re scattered everywhere, my siblings, too. It was “ok” during COVID because everyone was in the same boat, but restrictions have been lifted, and I’m acutely aware that I’m on my own. I’m married and we love each other, but we have separate interests and that is more obvious now that we’re both home all day. Even where we decided to settle after retirement is a topic of debate. What I crave, he doesn’t care about, and what he desires is not on my Top 5 list of must-haves in terms of community. We have no plans to separate because we love each other and like each other, but we can’t find a common interest. Meeting new people when in your late-60s and 70s (unless a member of a church) is difficult. We’re spiritual but not religious, so to join a church for social reasons is unfair and hypocritical. I binge watch favorite shows, he plays online cribbage with strangers. If this is retirement, I’d rather work until the day I die.
I am contemplating retirement. I feel guilty for retiring and feel guilty keeping working. I never in my life thought I would feel this way.
Dear Annette:
I have the same issue, but its mixed. My retiring will inconvenience the department I’m working for, but they don’t really appreciate many of the things I have done for them over the years which they take for granted , and they have advanced others at my level but not given me those same opportunities. I do feel rather guilty nevertheless, like I’m throwing away a well-paying job with benefits– but I’m simply exhausted. I’m 68 years old and I would like to relax and enjoy my life going forward for a change. I definitely , definitely can relate to your view and situation–
Thank God! I thought there was something wrong with me! Retired in August. It’s been a struggle to find purpose each day. I don’t regret retiring in the slightest, though. I keep feeling like I should be doing something worthy of my time…because for soooo long there was a monetary value attached to my hourly life. It’s as if I should not waste my time on any hobbies or pursuits unless there is a equitable monetary gain. Weird. But I’m working on understanding that retirement is just like everything else in life. It’s a learning process. 🙂
The first 12 years of retirement came easy but now it’s hard. A feeling of not having any purpose is overwhelming. I am trying to find a volunteer position to give some meaning to my life. This overwhelming feeling has given rise to depression. I am taking anti-depressants and starting counseling tomorrow.
I retired the end of July. I was feeling so guilty about doing things I like to do every day! I didn’t realize that it was a common feeling. I am so glad I read this article. Now I will no longer feel badly when I wake up and smile that I can enjoy myself and if I feel guilty, I will just acknowledge it and move on!
This post and comments were very helpful in describing most of the emotions I’ve been experiencing in retirement. I’m 72, and worked as a clinical psychologist since 1970 (including graduate school). Stopped working “full time” about 5 years ago but still maintain a very small private practice. Constantly debating about doing this indefinitely vs. letting it all go. Financial need is irrelevant. I’ve turned to working on my musical side, playing guitar/singing and playing the assisted living circuit. Still, that nagging guilt about “working more” is there, the feeling that “I didn’t do enough” in the profession. I agree too that there’s a guilt about being very fortunate while others struggle at this stage. It’s difficult, from this vantage point, to feel that I really did work long and well and “deserve” to enjoy this period of life. It all seems to have gone by so fast! It’s as if retirement shouldn’t begin until you’re really old and exhausted. I never equated “retirement” with being active, healthy, and still growing. Maybe that’s the best way to view it.
Thank you, this article helped!
thank you for your article. I had tremendous feelings of guilt and like a fish out of water. Guilt from not just talking to people who are still working, but also of my co-workers who are struggling without me there to help. But I had to leave due to illness. My company was poorly managed and I didn’t feel like a valuable employee until I left. So, the void that was left is really on them. I also struggle with time management. I can see it now as an opportunity to learn to do it better. You also helped me understand the enormity of the transition from 25 year career to no routine at all. I was prepared and I had a plan. But like you said, training isn’t the same as experience. You don’t know what it’s like until you do it. My encouraging friends told me, “it’s the beginning of a new life!”
I’m newly retired now, aged 64. I had just resigned from my job that I had for 15 years. I had loved that job all along until the last few months. It had changed because the company lost a contract and many people were moving on. And there were lots of bickering and power struggles I had with the remaining workers. Also, around a year ago, many decided to work at home because of the pandemic, which hurt my job. My position required me to be at the site.
I feel alright about not being at my job, but I would have wanted to stay a little bit longer if the conditions were not so bad. So far I have been very busy with domestic stuff but I have some hours that I don’t do much. This has been an adjustment for me as I have felt depressed at times and feel more lonely.
I just retired after 42 years in education and 32 years in the classroom teaching. And in your article you say imagine your ideal life and work backwards. But my whole life has been around teaching and people in the teaching profession. And I’m not sure what my ideal life would look like. My husband retired about two years ago and he seems perfectly happy puttering around the house. I am not. He seems perfectly happy watching TV most of the day and waiting for the mail to come. I am not. Thank you for your article. It has given me things to think about.
So Thankful for the info you provided as I chose retirement at 62 after 35 years at a Large financial institute due to office move 85 km away as compared to 30 km and no option for work from home in future
Calculator states I would be paying double for transportation costs with no raise as well as loss of 3 hours daily driving
I enjoyed my job for majority of the 35 years but recently due to new management, outsourcing of positions and lack of Employees with skills I chose retirement with some guilt. As a previous commenter stated, leaving your friends aka work team with unresolved issues that my experience would have easily assisted in resolving left me unsettled
Thanks for the realization I AM OK
I find retirement unpleasant, because I have no direction or purpose to pursue each day.
I retired at 73, a reasonable age to retire. My husband recently died of Alzheimer’s, so I am alone and at sea.
I don’t feel guilt, I mostly feel sad when I see so many elderly people working after retirement, when they should be enjoying themselves, Shalom!
I wrote previously on here on June 17th of last year. I was brand new at retirement and it was unexpected. So now more than a year has passed. Things are still the same now as it was back then. But there is a different feeling. Some days I’m occupied and other days not so much. Believe it or not, at first, I did a lot of bike riding. But now I have cut back on it. I don’t know if it’s because of depression and getting sick of bike riding or is it because the places I ride at have become more dangerous.
And now I guess I can consider myself more like a “seasoned veteran” at retirement than over a year ago. I feel like I still have a lot of learning to do. I feel mixed about retirement. The financial strain gets to me the most followed by boredom. But the positive side of it is being able to do what I want and not have office politics to put up with. For some reason, everything I have moments of memories about in all of the jobs I had, they all are unpleasant.
I’m 75 and just retired 3 weeks ago and I find myself in a depression. I never was involved outside and now I don’t know what to do with myself. I literally have to force myself to go out somewhere. Some days it’s hard to go to the mailbox. I feel like I’ve loss my sense of usefullness. I thought it was only me but it has helped to read all these comments and know that This too shall pass.