Retirement Head Games


January 12, 2019…a big day for me. It’s the date I chose for my mandatory retirement. I can retire earlier, but no later than that date. It’s a long story, but ultimately, knowing specific retirement dates helps my employer with personnel planning and there are financial benefits for me.

After spending 30 years (or 35 years in 2019), working for the City of Denver, even thinking about retirement causes some concerns. Financially, I should be comfortable, but what about everything else?

I set the date knowing I have five years to work it all out. My niece, Shoshanna, hit the nail on the head when she suggested the limitless possibilities scare the shit out of me. I hadn’t thought about it until then, but she’s right.

Just think, I could:

  • Move to almost any place in the world, finances and laws permitting
  • Write a book or books
  • Volunteer for a vast number of organizations
  • Run for office (just kidding)
  • Explore the world
  • Be a full time couch potato (an option I’m not considering)
  • Change the world
  • Earn another degree
  • Start a new career

I know retirement will be here before I know it so I’m trying to make a road map.

There are plenty of resources about financially planning for retirement, but I haven’t seen many talking about how to transition into retirement. Here are the questions I hope to answer before then.

  • What do I love to do that I’d like to spend more time doing?
  • How can I make a positive contribution after I am no longer working full-time?
  • How do I challenge myself to continue to learn and grow?
  • How do I maintain my relationships and develop new ones?
  • How do I make sure my retirement is amazing?
  • What can I do now, and in the next few years, to make my transition easier?
  • How to I stay motivated to be active and healthy?

I don’t have the answers yet, but I’ve begun the journey. If you, or someone you know, has any suggestions, I’m all ears…

Carol Cassara

I’d suggest you do as little planning as possible, at least not firm planning. Spend a month or two getting used to…doing NOTHING! And out of that will probably emerge exactly what you want to do. Of course, if your pension requires a change in residence, then for sure make a plan. Retirement IS amazing — and too much planning might make it seem more like —work. Relax, read books, drink tea and let retirement happen!

Timothy Havenith

It sounds like you have some big decisions to make, but luckily to have time to make them. When my step dad took early retirement he began gardening for people and helping out at a charity once a week driving people to appointments. Both of which he really enjoys. I guess if you like your job you would always find a charity that needs the skills you currently use? I’ve also known people to retire and go on to study for a degree!
I guess you can start by trying out some options now? Then if you don’t like them you can cross them off your list?


I’m a type A personality, Carol. I’m not sure I can do it without planning. I love the idea of spending some time just getting used to it. Thank you for the fantastic advice. I think I’m afraid because my mother became a hermit and retirement was not what it should have been for her. I don’t want to follow in those footsteps, so I think I’m over planning it.


Great advice, Tim. Maybe I can try out volunteering at one of the many charities I admire and see how it goes. I do have a little extra time now since my son is grown. I’m glad your step dad had such a wonderful start to retirement.

Kelly @Try New Things

I agree with Carol. Just retire and then figure out what feels right. I retired a year and a half ago and I just relished the silence and the lack of demands on my time. I slept in. I worked out. I hung out with people without the intense scheduling that is needed when you are working. I read books. It was a fantastic time to restore and re-energize.

You can just wait for yourself to feel what is the right thing to do. At first it is alarming to have no long list of obligations….then it becomes delicious.

Now a year and a half in I am taking courses in a field that I love, I am travelling and doing yoga, I am working part time (not for the money but for the enjoyment of the work). Life flows now in a way it never did when I was working. And the peace and joy of life often overwhelms me.

So don’t plan of you can help it…just let it flow.


I’m so glad you stopped by, Kelly. Your experience and that of Tim and Carol, are helping me sort through things. With all the frigid weather, it’s been a struggle to go to work, knowing I could leave now. Finances would be a struggle, so I’m holding off. Yogo, tea, good books, sleeping in? They all sound wonderful. I’m glad retirement has been such a joy.

Kelly @Try New Things

Despite what life costs when you are working and bringing up a child, you will be shocked at how much less it costs once you leave work and the kids move on! I never believed I could live on less and it turns out to be quite simple.

Sharon Greenthal

When we think about retiring (about 10 years from now) we consider moving somewhere tropical and exotic, but we just can’t imagine being that far from our friends and family. Who knows, we may change our minds!

You’ll know what to do when you get there, I think. Just like everything else in life, when the time comes you’ll be ready.


Good questions to ask, especially for those of us who are approaching retirement. I am hoping I will be able to live with one foot in 2 worlds, USA and Switzerland, but haven’t worked out the logistics.

Claudia Schmidt

I’m a big planner, so I can relate. I’m hoping that I can retire in about 5 years, also and am having fun musing about what I’d like to do in retirement but to be honest, I’ll probably wind up still working, just another type of work. And given the economy, my 2 kids will probably wind up living with us for another few years ’til they get on their feet so I have a feeling I have lots of time to figure it out. Enjoy the planning – it will all lead to the right choice in the end.

Tom Witowski

Take a few weeks to chill out. Things will start to bubble up that interest you. Do something totally unrelated to what you do now. I still make a daily “Things to Do” list…you know me! I goof off ’til 0900 and then get going…then goof off sometime in the afternoon and do fun stuff for me (walk, bike, geocache, “work” in the Man Room :-), coffee with the neighbor guys at Starbuck’s(3 hours!!), start dinner, plan my next trip, etc). I never watch TV, that’s a day waster fur sure! ps: I’m busier now than when I worked full time. Don’t lock yourself into any full time commitments. I’ve turned down job offers that require my presence 5 days a week…ummm, no thanks, I call the shots now. If you want more advice, we’ll have to go to lunch! Let me check my schedule. 🙂


I can’t imagine living any place but Colorado, Sharon. I have to admit, though, with this winter’s frigid weather, the tropics sound pretty good right now. I’m glad I have time to adjust.


Pat, Switzerland sounds like an amazing option. I hope you can make it work. I wouldn’t mind visiting other countries for a month at a time so I could really experience the culture and diverse environments.


Claudia- I’ll look forward to celebrating our retirements at the same time. I probably will work or volunteer as long as the schedule accommodates my travel. Thanks for your encouragement.


Thanks Rhonda. I tend to be pretty happy and optimistic, so after I get over a bit of this panic, I think I’ll be good. 🙂


I need to be on the Tom retirement plan. Three hours at Starbucks? That could get expensive. I’m not surprised you have a To Do list. We definitely need to meet for lunch again soon. Give me a call soon and we’ll get it on the calendar.


Mike- I hope things improve and that you have an amazing retirement. I’ve always been concerned about the finances, but things have worked out. May the same happen for you. 🙂


Very true, Wen. I think the definition of retirement has changed. I’ll be leaving my current job and moving into something else. Whether it’s volunteering or writing…I’m still not sure. Maybe we can do something together.


Is retirement coming soon, Diane? I guess I’m just a worry wart. It seem so permanent. I guess that’s a good thing.


I love the idea of retooling, Haralee. That’s a great word that opens up lots of options. Thanks for the suggestion.


Ahh you and I are real close on the same retirement timeline, Jennifer! It’s exciting at one point but frightening as heck on the other because will have worked at the County for 30 years but been around the specific department since I was a little boy. They are my family. That will be the biggest transition for me. I can’t buy years because it is not cost-effective to do so. I will definitely travel and hopefully be writing up a storm by then! Really good post here 🙂


Thanks, Mike. Congratulations! It will be hard to not see some of the same people everyday, but I’ll be glad to say goodbye to others. Traveling, writing and take pictures will be a big part of my future. I wish you the best and will be watching your journey.

Barbara Torris

Carol Cassara is absolutely right. Please don’t plan all the joy out of retirement! I have been retired for 17 years now and it has been a journey that brought many changes. If I had even guessed that I would be doing what I am doing now, it would have seemed impossible or even undesirable. My vision of retirement has changed over the years.

You can have fun or work or sleep or travel or all of the above. When something sounds like fun, do it.

b+ of Retire In Style Blog


Barbara, I learned so much through the comments from those of you who have retired. It has brought me a lot of peace. I’m so used to planning the intricate details of things that I can’t imagine letting life just happen and then taking advantage of the opportunities that develop. I’m glad your retirement has been so wonderful.

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