I am not ashamed to admit that I am an obsessive planner. In fact, if there is a remote possibility that advance preparation can be done to avoid a potential surprise, count me in. This obsession was especially helpful to me when I planned for my July retirement.

A full two years ago, I started listening to every podcast episode I could find that had the words “retirement” or “financial planning” in the title. I kept track monthly of our expenses and investments to assure myself, and more so my wife, that my retirement would not lead us down a road to future turmoil. I even wrote the date July 2026 in indelible marker on my office whiteboard in order to caution myself against procrastination as well as signal to my colleagues that I was serious about my intention, i.e. this time I’m actually leaving.

To belabor the point, I believe I entered retirement feeling that I had done everything in my power to prepare so that there would be no surprises. Three months in, and I am also not ashamed to admit, I was wrong.

At this point, I will share a warning that I am about to complain about an aspect of retirement. I completely understand any overworked, exhausted reader who chooses not to finish the rest of this column and wants to scream my name in anger (or send me a furious email). I will also inform you that you will need to get in line behind my wife, who still works herself.

In fact, she sees my retirement as a great opportunity for me to create a schedule of meal preparation, house cleaning, and laundry; and has even proposed some weekly rituals such as Marinating Monday, Toilet Cleaning Tuesday, and Fluff and Fold Friday.

The aspect of retirement that has me frustrated, and no one forewarned me about, is the massive amount of energy dedicated to daily planning. Let me explain.

Three months ago, and for the 35 years that preceded it, I was a nine-to-five office worker with a typical one-hour daily commute. This meant that for nine of the 16 hours of my workday waking life (subtracting eight hours for sleep, though I can only dream of getting eight hours with my sleep apnea), my schedule and whereabouts were set for me; no mental energy expended to plan the majority of the workweek hours.

Additionally, the remaining hours, including weekends, that were afforded me to do with as I pleased, weren’t so much discretionary planning as they were completion of errands; grocery shopping, lawn mowing, home maintenance, and child-related activities when they were young. There was also the obligatory rest and recovery. However, the circumstances have changed, not only with no longer working, but also living in a condominium as empty nesters.

While I do have considerable flexibility to plan my days as I choose, I am trying my hardest to fill my time with enjoyable and enriching experiences. In addition to writing my column, I am also a semi-regular participant on the pickleball courts, in the gym, and on the bike trails. I have also started a few per diem jobs (per diem being the Latin term for don’t call us, we’ll call you).

This collection of opportunities has been great and will perhaps even expand, but I have had to admit that it is not mathematically feasible to replace the nine-hour daily obligation that was my prior life.

It has also become clear that my obsessive planning behavior will not work successfully as in retirement as it did in my prior work and parenting life. Retirement is not going to change for me, but instead I am going to have to change for retirement. Obsessive will need to transform into adaptable, go with the flow or even devil-may-care. I think I can handle this transition since I have always lived by the motto that spontaneity does have its proper time and place.

Obviously, becoming an obsessive planner is not something that happened overnight, but instead developed over many years. Therefore, I will be giving myself some grace that retraining myself to be more flexible and comfortable with uncertainty will take time as well.

In the interim, I am still trying to find an activity for 1:30 to 2:30 p.m. one week from Wednesday.

The writer retired to Enfield in July 2026. He can frequently be seen at a sporting event, rallying on a pickleball court, biking the Northern Rail Trail, or kayaking on Lake Mascoma. He can be reached at vnewstalltales@gmail.com.