Guest Post: Planning for Retirement — But Not How You Think

Planning for Retirement | CorporetteRetirement — and retirement hobbies — are likely a long way off in your mind. But I like to be prepared, so I asked Lisa from Privilege what those of us who are still working should know. Can one prepare to pursue hobbies? Were there things she thought she’d love but hasn’t -— or hobbies that, once she got deeper into them, she realized she could have made the time for, earlier? Lisa has guest posted* with us before, pondering the things you might miss about a corporate job once you’re out, and — in one of our top posts — advice from the VP/hiring manager level. Welcome back, Lisa!  -Kat

Many of us dream of retiring and finally having time for Anything But Work. I’ve taken a couple of stabs at retirement myself already, at 57. And, as it turns out, unsurprisingly for you smart folks, there’s more to it than romping around not working.

This is not to say that hobbies, travel, and sofa-intensive afternoons aren’t out there. They are. And they are good. The thing is, they’re even better when you’ve done a little advance research. And, it’s also true that many of us who’ve had jobs with responsibility and authority, despite the associated stress, don’t want to toss it all aside. We’d rather replicate what we love, add new pursuits, and get some autonomy over when we do what. (Pictured: Angela’s Garden Fabric-Back Leather Palm Garden Glove, $18.99 at Amazon.)

It’s worth planning to make that all happen.

What I dreamed of while working:

  • Writing
  • Cooking
  • Gardening
  • House Furnishing & Hanging Pictures
  • Giving Back
  • Traveling
  • Lying on The Sofa
  • Watching So Much Television

What I didn’t realize I’d miss:

  • Multi-Variable, Big Impact, Problem-Solving
  • Collaboration
  • Mentoring and Coaching
  • Authority
  • Clear Goals and Performance Metrics

So, as you sit at your desk, or wait outside the courthouse, imagine, what do you want to do when you’re done? Do you see palm trees? A golf course? Your crochet basket? Wait, do you feel like you’re wasting time? You’re not. The first step to retiring well is to start dreaming now. Not only is it a good stress reduction strategy, it’s good planning. If you retire from a high pressure job without anything you like to do but work, you and your near and dear will suffer.

So gaze off, now and then, into the horizon. Don’t worry, horizons know how to wait.

Now, what else to do in preparation? Well, what parts of your job do you love? (If it’s tough just now, just imagine the bully in the other office is long gone. Imagine your assistant is blazing through your To Do list. Better?)


You love adrenaline? Build up your thrill skills. I hear downhill skiing and bicycling are good for that, so you might want to arrive at retirement with good quadriceps. Coaching? Many public service organizations offer mentor opportunities, and you can start now. What about clear performance metrics? Once you retire, nobody sets goals but you. Sounds good, but what if you’re a classic Type A? You’ll might want to learn to back away from the list now, or in retirement you’ll catch yourself checking off activities that were supposed to be fun.

Planning for Retirement | CorporetteAnd how about hobbies and creative pursuits? Myself, so far I’m relying on skills already in place. It’s easy and meditative to relax into processes you learned a long time ago. I know we’re supposed to learn new stuff to keep the brain agile, but I find plenty of new in the long-known.

Take cooking. Invest in Le Creuset and All-Clad today, and in 20 or 30 years they’ll be waiting for you, cost fully amortized and well-seasoned. Time to master Peruvian food. How about gardening? Plant the basics now, in pots or beds. Roses, like good cookware, are patient. Felco pruners anyone? (Pictured: Le Creuset Signature Enameled Cast-Iron Braiser, $249.95 at Amazon.)

Oh, by the way, I’ll leave the wood-working and knitting to those of you with small motor skills. I’ll take the gross motor work; avoid thorns and burns, revel in fragrances and tastes.

There is one new skill I’m learning. My house needs so much attention. When I was working, as long as the stove, fridge, and TV functioned and there were enough places for everyone to sit, I didn’t much care about anything else. Interior design is complex, guys. If I disappear off the face of the earth, send the rescue dogs to Pottery Barn please. I’ll probably be under a coffee table.

In closing, as you make your way up the over-achieving ladder, you might take a weekend to assess whether you’ve planted all the right seeds to harvest in the autumn of your days. See? Retirement also gives you lots of time for completely asinine metaphors. I told you it was good.

Readers, have you thought much about what you’ll do in your retirement? What do you think you’ll miss about work? 


* As always, this guest poster has been invited by Kat to post on a subject of interest to the community. We value having different and diverse voices here, and indeed part of the benefit of guest bloggers is broadening the dialog beyond Kat’s own views. To that end, please note that opinions expressed by guest bloggers, like opinions expressed in comments, do not necessarily reflect the opinions of Kat, Katfry LLC, or any of our sponsors or other contributors.

N.B. PLEASE KEEP YOUR COMMENTS ON TOPIC; threadjacks will be deleted at our sole discretion and convenience. These substantive posts are intended to be a source of community comment on a particular topic, which readers can browse through without having to sift out a lot of unrelated comments. And so, although of course I highly value all comments by my readers, I’m going ask you to please respect some boundaries on substantive posts like this one. Thank you for your understanding!



  1. My retired parents are heading off on a Baltic Cruise today and I am SO jealous. I can’t wait to have the time to take long trips.

  2. Anonattorneytoo :

    I just wanted to comment about how much I enjoyed reading this. Sometimes I feel so guilty how much I think about NOT working having worked so hard to have my amazing job. Thank you for this!

    • You are welcome. I suspected this crew might need permission to daydream:).

    • hoola hoopa :

      This was a fun read. I admit I almost skipped it because I assumed it would be another (useful) post on saving money that would only make me feel guilty and behind. So glad I didn’t!

  3. Anne Shirley :

    Love this. My parents are heading into a retirement full of friends and travel. This reminds me if I want to do that in 30 years I need to do the work of keeping up with old friends and saving my pennies now.

  4. Senior Attorney :

    This is great advice and a lot of it applies to me even though I’m still working. My son is up and out, my marriage is over, my job isn’t the grind it once was, so I have a good amount of time on my hands to pursue outside interests.

    One thing Lisa didn’t mention that I think is key is this: Develop friendships with people who are younger than you and it will keep you young. I read this somewhere some years ago and thought it was very profound advice and I have made it a point to develop and nurture friendships with people of all ages. One of my best friends is young enough to be my daughter, but we have a great time going out for dinner or the ballet or to car shows. Plus it keeps me from getting too “get-off-my-lawn-y.” (And of course I value my friendships with people older than I, as well, who are great role models as I start thinking about retirement.)

    • I like your advice to develop and nurture friendships with people who are younger. I just realized most of my friends are in the same age group as me, so how does one set themselves up for more interactions with those of a younger age group? Suggestions?

      • As a young person, most of my friendships with older people have developed through long hours spent in careful research and evaluation of the various microbreweries near my home…

        • Middle Coast :

          We moved into a neighbor of primarily older neighbors and struck up friendships with them. I’m trying to do the same as new families move in.

      • One way is to participate in community organizations. I joined Toastmasters a few years ago, and we have a very friendly club that often goes out for drinks after our weekly meetings. I have made new friends in all age groups, from retirees to college students, all of them local.

        • This is so true! I have developed a real friendship with a group of young women I chat with on Twitter. Sure, it’s in the ether, but it’s real and very cherished.

      • I’m 26, and met most of my older friends through my running group. I love having people who have experience with all sorts of things that my peer group doesn’t (pregnancy and babies, buying houses, fancy restaurants that are nice for anniversaries, etc).

      • Senior Attorney :

        I was in a graduate program for a while and that was a gold mine of young women in their 20s, many of whom remain friends several years later!

        The gym, for sure. My Rotary club has been a great source of friends of all ages, so a big “yes” to community groups. The above-mentioned friend started out as my tap dancing teacher and is now tap-teacher-and-close-friend. (And I’m also friends with the other people in the class.) The secret to developing friendships through groups like the gym and community organizations is to make sure you seek out and talk to people of all ages, and not just the people your age. It’s tempting to look for the people most similar to yourself and sit with/talk to them exclusively, and I make it a point to fight that temptation!

    • Rachelellen :

      I wish I was in the same city as Senior Attorney!

      • Senior Attorney :

        Awww! :)

      • As someone who is in the same city as Senior Attorney, and has had the chance to hang out with her several times, it is truly an honor and a pleasure to have her as a friend! I’m so grateful to her and other women who reach out across a generation. We all have so much to learn from each other.

  5. My father is still working at age 70, but is finally moving towards retirement. He’s CEO at a tech consulting company which had to be restructured from being privately held to becoming an employee-owned company so that the founders (dad included) could retire. Not sure how many readers are in a similar situation, but it’s something to think about for start-ups and entrepreneurs.

    • Coach Laura :

      I don’t ever see myself retiring so I’m always interested in people who have different retirement paths.

  6. Pretty Primadonna :

    I have been so focused on building a career (still haven’t “arrived” just yet) that I’ve never even considered what I wanted my life at retirement to look like. Thanks for the reminder to visualize the post-career future!

  7. My first thought is having income to do all those things on your list. I would like to write, do some travel, spend time with family and friends, and serve as a mentor to others–not sure in what capacity yet. Reading ie leisure reading comes to mind but I have to admit watching television doesn’t sound that exciting….

  8. I’ve got a good thirty years to go before retirement, but my parents are a few years away. For a number of reasons, my dad isn’t going to have the retirement he dreamed of (with my mom) so I’m trying to help him reformulate his plans. The one thing he has seemed excited about is a world cruise, so I’ve been researching which cruise lines are most hospitable to singles and have the educational activities that he would enjoy. It turns out that there’s a whole world of cruises out there that aren’t at all like the ones you see in commercials, and now my daydreams about retirement primarily involve spending three months seeing the world in between leisurely days of lounging around reading and evenings of eating delicious food and attending exciting lectures.

    • Anastasia :

      This is exactly my retirement dream. I volunteer as a zoo docent, and many of the other volunteers are at least twice my age, retired, and reasonably well-off. It seems like every month another one of them comes in with amazing photographs of their most recent adventure in the Amazon, Patagonia, cruising up the Nile, etc etc, and raving about the incredible scientists/lecturers who accompanied them. Once I knew to look, I found SO many companies that host learning/adventure vacations. I will attend the lectures and relay the highlights to my husband, and we’ll both admire the scenery and wildlife.

  9. Middle Coast :

    Thank you for this post; when you google retirement all the results seem to deal with financial planning, nothing on how to actually live the life. I became eligible for early retirement this year, I’ve been toying with the idea, writing up pro and con lists. I’ve thought of and discarded the notion of consulting. When I’m done working, I’m going to be completely done. I’m practicing – taking a week off here and there without any substantial plans to see what it would be like.

    After observing older relatives slowly congeal on the sofa watching tv while waiting to die, I’ve decided that a person needs to continue stay active, to set goals and work to achieve them. I want to revisit old hobbies which fell by the wayside and also to try out new things. I’ve been working on writing out a bucket list. I am looking into joining the Osher program at my local university (free auditing of classes and travel programs). So much to do, and who know how long I’ll have to do it!

    • Could not agree more regarding the need to stay active. The difference between my parents and my in-laws on this is astounding – although they are all close in age, my parents easily look (and act) ten years older because they are not all that active, socially and especially physically.

      On the flip side, my grandparents took community college classes for years after they both retired. For my grandfather especially, I think the classes added years to his life.

  10. I am 31. I want to stop working regular full time job by 50. If things go as planned, I will have enough financial security to retire by 50. After that I want to be very involved in volunteer work, mainly in girls’ education or even start a small non-profit organization to help poor girls. Other than that, I want to spend time with friends and family, learning Sanskrit (I am a Hindu) and reading and understanding scriptures, continue my music lessons which I stopped recently as I don’t have time to do justice to it, help take care of grandchildren if I have any, take care of my health so that I can be in good health and independent and travel a lot.

  11. Alot of good ideas here & worth making an effort before you retire . My own priorities were taking on voluntary work & getting two dogs . Both these give me the opportunity to turn strangers into acquaintances & acquaintances into friends – of all ages . Not sure about the Le Creuset though , you’ll need stronger wrists than me to heave those about in old age .

  12. Anon for this :

    Sorry to get all Debbie Downer but at 37, am I the only one who feels like planning fun stuff for retirement seems like tempting fate? DH brought up this topic recently and I was nearly in tears thinking about all the things that could go wrong that would prohibit us from enjoying retirement together. This is a little messed up right?

    Anyway Lisa, awesome post, love your writing! Horizons know how to wait – brilliant.

    • hoola hoopa :

      I have some of the same thoughts. My husband is more than a decade older than me, and since I’m the primary income and retirement fund our retirement won’t start until I’m typical retirement age. I worry that he’ll be too old by then for us to really enjoy retirement like we picture and we’ll end up moving straight from frantic working years to frantic health care years. It’s incredibly sad, so I pocket away more money and try to not think about it.

      It didn’t help when a family member’s spouse suffered a major stroke about a year before his planned retirement. She’s also significantly younger and is trying to balance her career and his medical needs. The immediate stress has been obviously enormously difficult for her, but so is the stress of losing their plans for the future.

    • Anonymous :

      Not to terrify you, but my family’s an example of why you don’t wait – my 40 year old spouse has an incurable degenerative disease that wiped out his ability to work mid-career and has paralyzed him. Don’t put off till tomorrow what you want to do today.

    • I often feel this way. I started my career late, and working in NPOs means I don’t make a ton of money. With school loans and small income, its hard to put much back. I have plenty of days I feel like I may never get the chance to truly retire.

      I work in a retirement community. And retirement is a very fluid word around here. Many of our residents still work part time, many because they have to for financial reasons. They’re proud of the fact they still earn an income, and proud of the fact they’re still active in their communities. I’ve learned there’s no shame in not having the “dream” retirement, and it can actually be enjoyable.

      So while it doesn’t help to forecast doom and gloom, it is okay to recognize that not having the type of retirement society tells us we should is okay.

    • This is a true point.

      My parents worked incredibly hard their whole lives and saved everything for retirement. Then my father became severely disabled after a car accident and cannot travel and has life threatening health care needs. And then my mother died suddenly soon after of cancer, leaving my father alone. They were both very healthy before, and never had any retirement.

      That’s why I now read Mr. Money Mustache, and have a very different philosophy about life and what is really important.

      It is not that difficult for many on this board to save aggressively and plan for an early retirement and do things that really matter to you, your family and your community. If you are fortunate enough to love your life as it is then this isn’t for you. But really, it is so easy to step back, simplify your life, and really enjoy it NOW…. and retire early. You can do it. I know you can.

      You never know what tomorrow will bring. So save like crazy, and make sure you are enjoying today and what’s really important in life.

  13. hoola hoopa :

    I’m most looking forward to spending time one-on-one with my husband. We started a family soon after meeting and marrying, so we’re excited to get some of that time together on the back end, after the kids have grown.

    I’ll most miss feeling important. I’m well respected in my career and fill a critical role in my projects, and I dread feeling like ‘just another elderly person’ who isn’t regarded as having any particular status or skills. My field of expertise doesn’t translate well to volunteerism, unfortunately. I’ve been watching my parents through their retirement (~15 year into it now) and while my dad in particular took to not working like a fish to water (huge surprise to everyone), this has been the hardest aspect for him.

  14. My husband and I have been toying seriously with the idea of becoming Park Rangers for the National Park Service after we retire from our current jobs. We love camping and seeing the country. Continuing to work in a lower stress environment where everyone around you is on vacation seems reasonable. Our youngest won’t be done with college for another 10 years (if all goes well), but we’ve been discussing this option since before she was born.

    • This is a great program. My family was recently in Yellowstone and talked to several elderly people who were spending the whole summer volunteering there. Not sure how it works financially/ if they get room and board. But it sure seemed like a great way to spend time.

    • Work camping is not necessarily a low stress job – you still have to deal with people, after all. Lake Powell has an absolute fleet of work campers, many of whom have administrative jobs, or other jobs that allow you to stay inside where the is air conditioning. They were paid positions. Much summer work camping is unpaid, but you get a full hookup site (power, water, sewer) for free. One of the many websites for jobs is

      There are many opportunities out there.

  15. I’m still in my early 30s, so retirement feels more like a vague dream than something I”ll ever achieve! But I’m a big hobbyist – I love to quilt, cook, bake, garden, read, perform (I’m a classical musician) and travel. My career is fundraising in nonprofits and the arts, which suits really well to serving on NPO boards, so I would love to do that, maybe even running a NPO consulting organization to help out small nonprofits.

    I would imagine I would miss having enforced structure to my day, but once I found a routine I would settle in.

  16. In the years since my oldest child was born, I’ve been SO consumed with the demands of my work and the kids that I’ve had almost no time for personal interests. I experimented with adult piano lessons a few years ago, but gave them up when I realized that I couldn’t fit in 20 minutes of practice per day. This month, for the first time, both kids are away at sleepaway camp, and I literally don’t know what to do with myself. It’s made me really think about how important it will be to make sure I have more going on in my own life (outside work) than I do now by the time the kids leave home, and of course by the time I retire. It’ll be a new season of life!

  17. I retired 2 years ago at 53, by choice (extremely thankful for a good job with benefits, a pension plan and a husband who shares my mindset of living below one’s means, saving aggressively for retirement and getting out of the corporate ratrace while we are still young and healthy). We spent years planning for it and while 99% of these 2 years has gone wonderfully as expected, there have been a couple surprises. Having been employed for 28 years straight (32 years in my husband’s case), there was no way to know what it would really be like to have such unencumbered time to ourselves. A 2 week vacation is not a true test. In spite of all the advance planning for the financial, emotional and psychological aspects of retirement, there are things that just can’t be foreseen or understood completely until one is in the midst of it. It is an evolving process and one must leave room for the unexpected. In my case, not having structure to my day anymore was more difficult to deal with than I thought it would be. 28 years spent as efficiency expert at the office makes it hard to look at leisure time without applying the same principles, still haven’t been able to shut that down.

  18. Super late to the party, but when I retire I want to end up as a professional (volunteer) Girl Scout. In part because the Scouts need to get back to knots and fires and camping and less sitting-around-in-a-circle-talking-about-ourselves. Love the program, love working with the girls, think I could help more (and help other plan better!) if I had more time.

  19. I dread retiring. I love my work, my team, the collaboration, the trust, the projects. I can imagine someday taking longer vacations, but I can’t imagine not working. I don’t want to lose the challenge and joy of getting things done and building product and going to work every day and coming home to spend time with my family in the evenings. I like that balance. I leave the door open for the possibility that I’ll feel differently in 10 or 20 years.

  20. Great tips, as always, Lisa!
    I’ve been preparing for retirment for a few years now. While I’m working full time at my day job, I’ve started an online business which is growing, participate in a local private university philanthropic group, teach part time in another university, have lunches with women I’ve met through each of the afore mentioned and participate in community fundraisers when I get the chance. I believe staying connected, continuing to build relationships and to keep learning will help us stay young. I look forward to a little more traveling and more volunteering when no longer at my day job. Using your skills as a volunteer is tremendously helpful – a retired executive assistant to a university vice chancellor is a once a week volunteer who assists me. She is amazing and a total blessing!

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