Most people that I talk to who are nearing retirement struggle with the question “What will I do”. Even when they have the finances worked out, they’re concerned about how they’ll spend their days.
I get it. Within 3 weeks of retiring, I had a new part-time job. More about this in a minute, but I certainly had that feeling as well.
Working
I started a paper route before I was a teenager. I looked forward to my 16th birthday when I could trade the papers in for a better job. I live in New England. While delivering papers is a delight on a nice spring day, it’s a bit tedious when it’s snowing, or raining, or worse. Getting a job in the stockroom at Zayre’s department store was a huge upgrade.
During college, I left the stockroom to do roofing and construction with 2 friends who had started their own company. This is hard work when you’re 20. Kudos to the folks that do this for a career.
After college, I got a nice white collar job and stayed in the same industry for over 35 years.
To say work was a big part of my life is an understatement.
I worked a job outside of the house from when I was about 10 until I was 56. For those unskilled in math, that’s roughly 46 years of working.
And a huge part of our identity is work. When we meet someone at a cocktail party, we often introduce ourselves by telling others where we work and what we do. I’m a surgeon, I’m a roofer, I’m a paper boy.
Not Working
The idea of not working can be daunting.
Now I need to come up with things to do to fill 40 hours per week every week. That’s a lot.
And how do I introduce myself? I’m no longer a surgeon, a roofer or a paper boy. What am I?
The 2nd question is even more daunting than the first. Who am I? 2,000 hours every year is spent working. My work is important. What happens when it’s gone?
That’s scary.
Keeping Busy – My Story
For me, I’ve always loved cars and I decided to look for a part time job in something related to cars. Within a few weeks of retiring, I was a part-time used car salesman.
I worked a few weeks and then Covid hit and the dealership shut down for 2 months. Stuck at home.
In June, we were back to work and I worked a few months and then retired for a second time.
A couple of interesting things happened here.
Retirement was my decision. I decided to stop working. Covid was not my decision. I wanted to work, but the shut-down forced me to stay home.
I think that made it easier for me. After more than 40 years of working, it was hard for me to rationalize that I chose not to work any more.
And while Covid forced me to stay home, I started to learn how easy it was to fill my day.
Filling My Day
The first thing I learned is that I don’t need to fill 40 hours a week. This isn’t true for everyone, but it was for me.
What I really need is some social interaction, some exercise, some projects.
I’m almost 6 years into retirement now and I have what is a solid balance for me.
- I’m lucky to have 3 retired friends who golf. That makes a solid foursome and we play together once or twice a week. in the winter, we go to an indoor simulator.
- My wife started golf so we play once a week as well. We also have ball-hawking.
- I started this blog. I spent some time, while working, teaching personal finance classes. I tried some teaching after retirement, but I found I spent too much time marketing the class. I’d rather teach, so I started the blog.
- I started routines with some friends
- Coffee with Rich most Saturday mornings
- Lunch with Tony every couple of weeks
- Breakfast with Mike every couple of weeks
- BBQ with Tucker quarterly
- I joined a gym
- I take the dog and explore new places to hike. We average 2.5 miles per day year-round and I got myself a lifetime senior parking pass to all Massachusetts parks for $10 (thanks for the tip Mike).
My wife is always working on a project so I keep busy helping out.
Scheduling
I spend some time scheduling my activities. I just now got a text from Rich about golf next Tuesday. I look ahead and make sure I have a few things on the calendar. Spur of the moment is great and since I have a lot of retired friends, this can work, but having a couple of events planned in advance is important for me.
Wrap Up
Getting our minds to accept retirement is a big deal.
And often our friends and family make it even more difficult. “What are you going to do with yourself?” “I could never retire. I always need to be doing something”.
We probably all need some sort of transition plan. For me it was the car dealership and then Covid helped. My buddy Mike volunteers at the local food bank a couple of days a week.
As we transition, we’ll discover new things. I have more time now for the gym. I like hiking. I never had time before.
This week, my wife and I attended a retirement planning dinner put on by a local financial advisor – free dinner and met some nice people. Last week our credit card company put on an event at a museum in Boston. Great food, open bar and again, we met some nice people. This doesn’t happen every week, but I keep my eye out. In the past, I was too busy.
A couple of years ago, my wife, dog and I drove south and spent a little over a month in Air BNBs in Florida, Georgia and South Carolina. Not something we’ll do every year, but we couldn’t have done it while working.
Good luck. And please post any thoughts or ideas.

