10 Truths About Retirement

I’ve been retired for over seven years now. The newness and shininess of retirement has worn off, and I’m now well-settled into this chapter of my life. Work has receded into a distant memory.

Has retirement turned out the way I thought it would?


Has retirement turned out well anyway?


Over the past seven years, I’ve cashed quite a few reality checks. Some of these are pretty universal, some are more unique to my situation. You probably have similar situations in your life, so hopefully my findings will be useful to you too. As they say, your mileage may vary.

Here are ten truths I’ve learned about being retired.

1. Retirement is not a permanent vacation.

While I was still working, I entertained some rather unrealistic fantasies about how idyllic retirement was going to be. I was a bit of a Pollyanna. I dreamed that each day would be a care-free, blissful nirvana in which my toughest decision would be whether to listen to music from my extensive jazz collection, go for a hike on a nearby mountain, or float in the pool sipping a mojito.

It didn’t take me long to learn that every day is not blissful leisure. There are still chores like household cleaning and maintenance. There are good days and bad days and plenty of average days. You’ll never be able to eliminate bad days from your life. Life is just not like that. You’ll have plenty of good days, but it’s unrealistic to expect that every day is going to be a good day.

The best you can do is try to raise the average. You still have some control of how good each day is.

2. You still need to have a purpose.

If you could construct a life of permanent vacation, where every day consisted of nothing but hedonistic pleasure, you would soon be miserable.

As humans, we have an innate desire to contribute something to the world. We need to have some reason for getting up in the morning. We need to matter in some way. It’s why most trust fund beneficiaries and lottery winners who could easily get by never working a day in their life still get jobs or find other ways to contribute something of non-monetary value to the world.

You need to have something to look forward to. When you’re an adolescent, you look forward to turning 18, then 21. When you’re a student, you look forward to graduating. When you’re in love, you look forward to getting married. When you are working, you look forward to your next promotion. Later in your career (or perhaps the day you start working), you look forward to retirement.

After you retire, what will you look forward to? Hopefully, it’s something other than just dying. Always have something ahead in your life that you can look forward to.

3. You will think about money a lot.

One of the biggest things that changes when you retire is your relationship with money. Even when you have sufficient financial resources, you will still be concerned about money.

While you worked, you knew that money would be reliably deposited into your bank account at the end of every pay period. You knew that even if you encountered a few unforeseen expenses or you made a few irresponsible impulse purchases, there would always be more money coming in.

After you retire, this changes. At some point you will receive Social Security payments, but that will represent only a portion of your income. You will start receiving regular payouts from your retirement savings, but that feels different because you know you are spending down money you have saved. It’s not new money that is coming in.

You become aware that the amount of money you are going to live on for the rest of your life is more finite.

That takes some mental adjustment. That also means that you will start evaluating purchases more wisely, which is a good thing. You’ll probably wish you had done that all along.

4. You can’t have it all.

When you dream of everything you want to do after you retire, some of those things will be contradictory.

For example, I enjoy playing my trombone and participating in several bands. I also want to travel a lot. If I travel a lot, I will miss a lot of band rehearsals and it will be difficult to practice regularly.

The best way to deal with this is to divide your retirement into chapters or phases. Set aside a year or two or ten for traveling, then settle down and engage in activities and groups that require regular participation.

Following on the previous point, many of your retirement options represent financial trade-offs. You might have to choose between taking a cruise, remodeling your kitchen, or buying that piano.

5. Entrepreneurial endeavors take much more effort and persistence than you ever imagined.

Many people start small businesses after they leave their careers. This may be anything from marketing your books, artwork, crafts, or music to setting up a consulting business.

One of my plans after I stopped working was to build a business of public speaking and presentation skills coaching. I did a little bit of prep work for that business before I retired, but after I retired I set about to find rental classrooms in which to present my workshops and launched a website offering weekly presentation skills tips. I joined a couple local networking groups and started pushing my services. I found a few guest speaking opportunities (not paying, of course). I joined an organization in which I could help coach presenters on a voluntary basis.

Shockingly, people didn’t beat a path to my door.

I learned that I was completely naïve about how long it takes to build a business, especially one that involves personal services such as training, consulting, or speaking. Several months into the endeavor, I quit. In hindsight, if I had stayed with it for a few years, I might have been successful. Or if I had started laying the groundwork for this business five years before I retired, that would have helped.

I have also learned that writing a book is harder and takes a lot longer than I imagined.

I have enjoyed a fair amount of success with Retire Fabulously!, but most of the rewards have been non-monetary. I’ve been at this for six years, yet there is still much farther to go and much more I could have done along the way.

6. Finding the right balance requires constant effort.

Since the early days of writing for this website, I have maintained that to have a happy retirement, you need to have a mix of activities that provide physical activity, mental stimulation, socialization, and fulfillment.

I still believe that this is true. Whenever I feel like my life isn’t quite the way I want it, I can just look at how I’m spending each day. That will always reveal that I’m shortchanging one or two of these four elements.

7. Old work behaviors die hard.

Throughout my career, most of my time was spent sitting in front of a computer screen. I checked email all day long. I wrote documents and presentations. I scheduled meetings. I researched information. I created and tracked budgets. I communicated with other people via computer.

I still do all of these things. I still spend many hours in front of a computer.  It’s weird, but I feel compulsively pulled towards it. After nearly 40 years of work, sitting in front of a computer has become ingrained into my existence and so far I have not been able to pull myself away from it.

Of course, part of that is due to the nature of the activities which now comprise my life. Writing books and content for Retire Fabulously! requires sitting at my computer. I am a wedding officiant, so corresponding with clients and working on their wedding scripts requires time at the computer. I spent two years as the president of the board of a non-profit arts organization, which required plenty of email correspondence, spreadsheets, documents, and scheduling. Between these various entrepreneurial endeavors and organizations, I maintain seven websites. So, more time at the computer.

I feel strangely at home in front of a computer. I frequently remind myself that I need to spend more of my life away from it. It also keeps me too sedentary.

8. You still need time management after you retire.

It’s easy to waste time. You will often say that you are even busier than when you worked – but you are probably not. The things in your life expand to fit the time allotted.

Of course, you don’t always have to be productive. That’s one of the greatest things about being retired. You can allocate a lot more time for fun and recreation than you could while you were working. But you do have to make plans for when you are going to get out and enjoy that fun and recreation. It doesn’t just happen by itself.

It’s easy to assume the attitude that you can do whatever you want today, including nothing. If you don’t feel like doing something, you don’t have to do it.

This is okay up to a point, but if you spend most of your time this way, you’ll get bored. Days and weeks will pass more and more quickly, and you’ll be unable to remember what, if anything, you did. Your life will become empty, which is the opposite of the fun and fulfilling retirement you envisioned.

It’s extremely difficult to achieve a good balance of activities in your life if you aren’t planning and scheduling them.

9. Now’s the time to start changing “someday” to “today.”

Someday, you’re going to run out of “somedays.”

You probably have a lot of things you want to do “someday” – places you want to go, classes you want to take, books you want to write, rooms you want to redecorate, and so on.

It’s easy to get into a daily routine of chores, TV watching, internet surfing and Facebooking, and regular meetings of groups you belong to. You can easily spend the rest of your days buried in your routine and never get around to anything you always wanted to do “someday,” unless you make a conscious effort to break out of your routine and make time for them.

Now’s the time to just pick one and do it.

Pick the trip you want to take next, schedule it, and start planning for it.

One of my friends recently bemoaned the fact that she will probably never work down her TBR list (To Be Read). You probably have a stack of books you haven’t read, videos you haven’t watched, or music you haven’t listened to yet.

So set aside some time each day and start on one of them. You’ll probably enjoy it more than watching the TV or surfing the internet.

I have found it useful to create an Adventure List. That’s a list of things to see and do in your local area, within a couple hours’ drive, that you have never done but want to try someday. There are probably a lot of places you don’t even know about.

After I launched this idea, Jeff and I created our Adventure List and set aside one day each week to go see one place on the list. It has been wonderful! Most of the time, we come away feeling enriched. Some places were more impactful than others, but we always enjoy the experience as well as the time together and the time out of the house.

10. Things don’t always turn out the way you planned – and that’s often a good thing.

I’m not teaching presentation skills and I’ve gotten very few speaking gigs. But that’s okay, other great things came along that I’m enjoying just as much or more. I’m having a much richer musical experience, for example.

Retirement didn’t turn out to be a permanent vacation, but that’s okay. If it was, it would become the new norm and I wouldn’t enjoy it as much. That’s not really fulfilling and, like most humans, I value fulfillment.

At this point, there are two reasons I’ll put the time and energy into doing something: 1) I’m getting paid, or 2) I love doing it. If it’s both, great. If it’s neither, forget about it. - Mark McNease

Despite all of the adjustments and the things that didn’t turn out as ideally as I had hoped, I enjoy being retired. It beats work hands-down.

Although I am now relieved of the fantasy that retirement is going to be a nirvana of endless carefree bliss, I still believe that retirement can be the best period of my life. It’s within my power to make it that way (or not).

Even though I have to pay bills and do housework and yardwork, I still value the freedom I have to choose my activities and my schedule.

Even though not everything has gone the way I thought it would, I’m happy with how things have gone. I also understand that I have more control over my life than ever before, and if I’m not happy with something I can usually change it.

I still think retirement is fabulous!

Please feel welcome to comment below.

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© 2021 Dave Hughes. All rights reserved.

Photo credits:
Ray of sunlight in cave: Bimo Luki.
Beach (Cozumel, Mexico): The Travel Nook.
Money in wallet: 401(K) 2012. Some rights reserved.
Laptop: Rawpixel.com.
Man working at computer: louisehoffman83.
Appointment book: Steve Buissinne.

19 Responses

  1. Randy says:

    I’ve been retired an entire month. I’m still winding down I think. I do surf the internet and watch TV a bit. I spend a lot of time with my cats which I’ve really wanted to do. And I am just now starting to record music by myself and with others, which was always my desire to do. I’ve been able to Ride my bike during this COVID nightmare and I swam for a few weeks but I’m a little more Leary about it these days so I’ve paused the latter. I do feel like I don’t have a plan and that is something I want and need to do, but I really don’t know where to start. Other than volunteering for various things in the Band I’ve been in for years, I don’t have any other immediate ambitions. Travel perhaps … but I’m afraid that will have to wait; not for monetary reasons, but COVID restrictions. I’m sure it will work out fine. My primary concern is making sure I stay healthy and active in winter during a major pandemic. LOL.

    • Dave Hughes says:

      Hi Randy,

      Congratulations on your recent retirement! I’m glad you’re able to do some rewarding things such as recording music during these difficult times.

      Here’s a free resource that may help you with making plans for how you’ll spend your retirement. It’s the Retirement Visualization Guide, and you can download it here: http://retirefabulously.com/free-stuff/

      I hope that helps!


  2. Graham says:

    Dave, greetings from England! I appreciate your efforts and hope that you continue them. I retired a couple of years ago and managed to create a reasonably balanced lifestyle, although the coronavirus is making it much more difficult. I would suggest, as I am sure you have, that your readers plan each day and include exercise for the body, creative work or puzzles etc for the mind and meditation or prayer for the spirit. And don’t forget to try to help other people. Be happy, stay safe.

    • Dave Hughes says:

      Hi Graham,

      Thank you for your kind words.

      You’re right – the pandemic has reduced many of our options for exercise, socialization, and service. In particular, I’m not getting enough exercise. But there are still some things you can do! With so many limitations and distractions, it’s important to remain intentional.


  3. Ed says:

    Great article, Dave! I am 12-18 months from retirement, and I’m trying to do some proactive planning. I have to admit it’s scary from many angles. We will be relocating from Illinois to Cleveland to be closer to my husband’s family. It’s difficult to imagine adjusting to retirement and adjusting to a new city at the same time. Your article has helped me start the process of thinking through what I need in a new community and in retirement. Have you written any articles on relocating after retirement? Thanks!

  4. Carla Edge says:

    My husband retired at the end of February after 35 years and he’s 61. I have been planing on retiring this January after 31 years and I will be 57. After reading this article however, it leaves me feeling anxious and scared about making that decision. I worry what our days will be like together. I have dreams of traveling and a long bucket list of places I want to visit and things I want to experience, but I feel like my time is running out and I won’t have the money or time to do them. This really is a scary time for me. I want to take the plunge, but am afraid I might regret it and the worrying about the money really scares me. I’ve already started experiencing that since my husband retired. He made a good living and now that money is gone on a weekly basis. There are other factors driving my thoughts that I won’t go into, but yes I would like to see more about loving retirement and more positive aspects of it as a person facing it. I definetly do not want to work at my job any longer and want to get a part time job or do something else, but I’m afraid that may not work out either, as the other reader said. I’m young at heart and want to always be that way, so getting older, facing retirement and then what goes along with all of that has me all kinds of mixed up! Thanks for your insight though of your personal experiences.

    • Dave Hughes says:

      Hi Carla,

      I think many of us feel a bit of apprehension as our actual retirement date approaches or when we think about when to give notice. That’s normal.

      I think the fact that you are pondering all these things is good, because after you have worked through them you’ll be even more confident about your decision.

      Financially, you’ll always be better off working another year and postponing retirement. But at some point you just have to decide that you have enough money and it’s time to start really enjoying the rest of your life.

      And I think it’s better to have lots of things to do on your list (like places to travel) and not get to all of them, than to have nothing on your list and have nothing to live for. Just start doing them, one at a time, and get as far as you can.

      If you’re really uncertain about whether you and your husband have enough money saved for retirement, it might be good to meet with a financial adviser.

      My observation is that the majority of people end up not regretting having retired when they did. You try your best to make the right decision – then you make the decision right.

      Good luck!

      • Carla says:

        Thank you Dave! I appreciate your feedback. I NEVER thought about retirement until I turned 50 and then it all came at me. Fortunately, we are both healthy, no bills to speak of and have always done ok for ourselves and family. Not rich by any stretch of the imagination, but we are proud of what we’ve accomplished and our 35 year marriage, 2 great kids, their spouses and our wonderful 2 grandsons. Life if pretty good! Now to pull the trigger and make a decision on when to retire. His was pretty easy, he got severance at the same time he was thinking about retiring, so it was sort of a win/win for him. I’m going to continue to follow your website and use your information to help us! Thanks again!

  5. Kevin Krull says:

    Good insight on retirement being full of surprises. For me, some new interests popped up and I gave up on some of my original plans. Toyed with the idea of a part time job, but nothing has materialized yet. Even Walmart doesn’t have greeters like they used to. I could out greet most of them that they had. Welcome to Walmart – I’d be great. Time management is still a problem, but hopefully I will get there. Enjoying this new phase of my life and just hope I can do it justice.

    • Dave Hughes says:

      Hi Kevin,

      I have a “time management problem” too. Just because I recognize the advantages of managing my time better doesn’t mean I do. The great thing about being retired is that nobody is going to give you a performance review (except maybe your spouse – LOL).

      The most important thing is that you are enjoying this new phase of your life.


  6. Marilyn says:

    So many truly USEFUL things on this list – thanks, Dave! For those of us freelancers who are actually enjoying steady income for the first time (SSA and pension payments), the paradigm is a little different, but most of what you say rings true re. economizing and prioritizing expenses, as well as staying engaged with activities and friends. Although much of the (music) business we pursued has disappeared, new insights come from looking back on past projects and outcomes – we’re really enjoying this time of life! Thanks for posting this! XO – M

    • Dave Hughes says:

      Hi Marilyn,

      Thanks for your comment! That’s an interesting and valuable perspective that, for people who were freelancers throughout their working years, the steady income from investments and Social Security is a change from how you receive income. You’re actually enjoying a higher level of income security than you did during your working years, or at least parts of those years. I hadn’t thought of that.

      In Phoenix, I’ve met a number of retired musicians (teachers, performers, and veterans of the military bands) who have moved here to retire and who are having varying levels of success finding their way into the music scene. Thanks to their retirement income, they can be less focused on whether or how much they are getting paid, which is a relief, but they still want to have gigs.

      This is another interesting observation: Professional musicians often don’t retire at all – not because they can’t afford to, but because they are already doing what they love. The retired music teachers and military band people still want to play music after they retire. Whereas for many of the rest of us, we look forward to being able to play more music (or other art forms) after we end our non-music careers.

  7. John says:

    Hi, Dave. I’m bored a lot. Also, I am anxious hoping that I get affordable 62+ housing sooner rather than later. It sucks having a low income and having to be on waiting lists for such housing.

    • Dave Hughes says:

      It’s certainly true that demand is far greater than supply where affordable (especially subsidized) housing is concerned.

      Relieving boredom is something you have a lot more control over.

  8. Jerry Buckley says:

    Great observations and wisdom, Dave. Thanks for sharing these important ideas and realities about retirement. I’m very happy being active as a consultant with two non-profits, serving on two boards of charitable organizations in San Diego, traveling often and running half marathons, thanks to a 72 year old body that still is healthy and fit.

    My only suggestion is share your thoughts about finding love in retirement. It’s been very hard for me as a gay man to find someone that shares a sense of excitement about life, is positive and well rounded like your article suggests. I’ll look forward to seeing if you can give your readers some guidance on this. Many thanks, again for your fabulous writings.

    • Dave Hughes says:

      Hi Jerry,

      I am happy to see that you are so healthy, energetic, and engaged. When I was much younger, I was a runner. I’d see 70+-year-old men running in those races and think, “Wow! I’m going to be just like them when I’m 70!” Well, I’m 62, and my running days are behind me. I’m still pretty healthy and active, but I need to do better. Thanks for the nudge!

      Your suggestion for an article about finding love after retirement is an excellent one. There are many single retired people, and half of the married ones will be single some day. Of course, not everyone will necessarily want another relationship, but many will.

      I’ll get to work on it. This would be a good topic to crowd-source, since I’m sure many readers will have experience and good advice to share that are beyond my experience and what I can think of.

      Thanks for your comment!

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