I Tried Retirement For A Day And Here Is What I Learned…

I’m 57, much too young to retire, but curious to see what it’s like.  Monday morning, I texted my partners and said, “I am playing hooky today.”  Since opening our firm 14 years ago, I’ve probably worked more than I should, but I still felt guilty about my day off.

Being a checklist person, I developed a to-do list for my day:

  • Walk with the dogs
  • Eat healthy
  • Grudge Tennis Match with Cathy
  • Movie
  • Feed the fish
  • Clean the kitchen

As I was preparing to sleep in, Cathy paraded the dogs into the bedroom and asked if they wanted to go on a “WALK“. Predictably, all 3 retrievers were on the bed in a matter of seconds and “NO” was simply not an option.  I started the day strong with a long walk and a healthy breakfast.

Here is Lily on our walk, refusing to leave the river.

Cathy left for work, and unsupervised things deteriorated quickly.  I made not one, but two junk food journeys to the store.  Cold cereal and animal crackers are my weakness.  I devoured my snacks while counting our neighbor’s car trips (3 boys all with active sports schedules), and before I knew it, I was becoming the nosy neighbor.  Missing human interaction, I had to force myself not to greet the mailman when he swung through the cul-de-sac.

After my nap, I found the French Open at Roland Garros on TV, the exoticness of Paris in the spring mesmerized me.  By 1:30pm I was bored and started waiting for Cathy’s return and wondered why the office hadn’t called me (apparently, I’m not as essential as I thought).  Finally, at 3:00pm, Cathy returned and like the dogs, I was overly eager to greet her.

We headed right to the courts for our tennis match.  Being winless at mid-season with my men’s geriatric league, I was very eager for victory.  During warm-ups, the cold cereal started rising to the surface and after the first game, the Animal Crackers joined in on the journey!  I was in trouble and Cathy was playing well, and leading by a couple games.  After slamming a shot right at my head (despite her apologies, I know it wasn’t an accident) Cathy tweaked her wrist.  I convinced her she needed rest to prevent an injury (I tried to declare victory but was quickly denied).

I finished the day strong by taking Cathy to see Elton John’s Rocket Man.  I scored points for splurging on popcorn and earned bonus points for not falling asleep! You can find my review towards the end of this post.

To summarize my scorecard:

  • Walk with the dogs (yes)
  • Eat healthy (big no)
  • Tennis victory (no)
  • Movie (yes)
  • Feed the fish (yes)
  • Clean the kitchen (no)


I confirmed the retirement stereotype of men:

  • Over reliant on wife for companionship
  • Habits are key – without an established pattern of walking first thing in the morning, I would have bailed
  • Boredom contributed to my junk food cravings
  • TV – incredibly addicting and productivity sucking (if not the French open, I would have found something else to watch)
  • PURPOSE – as Ernie Zelinski says in How to Retire Happy, Wild and Free, you must have something to do in retirement.  Volunteering, hobbies, Osher Institute, paying it forward, grandchildren, etc.  Travel and golf are hobbies, not purpose.