Will I Still Be Grinding When I Turn 68?

Will I Still Be Grinding When I Turn 68? | Reflections on Retirement and Planning For Your Happiness | Apollo Fields

As I was picking up some lunch before shooting a wedding, the woman at the register asked a regular customer how everything has been since he wasn’t in the restaurant for about a week or so. He replied with a generic, “oh good”, then paused, “okay, I guess. I mean, things could be better”.

She was an older woman and unabashedly asked him, “How old are you?”

He goes, “Sixty eight. I’m getting old”.

She sort of snickered, “Sixty eight isn’t old… These are the best days of your life. The hard work is over. You can be retired and enjoy your life now”.

The man looks back, “I am retired. But not the way I want to be. Things didn’t really work out the way I thought”. Some silence continues before he tries to turn it into a joke again, “The only people who think I am young now— no offense— are old women”.

They laughed. She handed over his change, and he left.

It was a short conversation between two almost-strangers, acquaintances at best. But so much was said between the melancholy sadness and authentic laughter. The surface level lesson here is perspective: the “older” woman is envious of the “younger” man, although he no longer views himself as young.

On the deeper level, you have a man who is experiencing some sort of disappointment in a life that he views is past his peak. Things didn’t really work out the way I thought.

Damn dude.

I was a silent observer in this interaction, but couldn’t help wonder what their lives must be like. Could this be me someday? I’ve been thinking about retirement a lot from a practical, financial perspective but have spent less time planning for my own happiness. I sort of wove it into my career path and tend to consider it a given; given that things work out.

But what if they don’t? Nobody plans on being a callous surly crank by 68, right, we all envision ourselves on an Adirondack chair on the front porch of their house watching the sun set, holding hands with their spouse, surrounded by dogs. Lots and lots of dogs… (Or is that just me?)

Here it goes: THINGS MIGHT NOT WORK OUT. Or at least, they might not look the way they we originally envisioned. There’s a good chance that at 68, I’ll be grinding just as hard as I am now, cleaning up horse shit after dark, behind on emails, and beating myself up for not being good enough at something. I might never shake some of my own demons, and that’s okay.

Our culture is moving away from the retirement lifestyle that many of our baby booming predecessors are currently enjoying. We’re not going straight into the work force from high school and college is no longer a luxury, but an expensive prerequisite to a minimum wage job. We’re not buying houses at 23 years old and we’re not having 2.5 kids by 30. It’s just not happening.

We are paying student loans and we are negotiating multiple careers. A lot of people—like myself—are saying ‘no’ to the 9-5 commuter life in search of something that feels more sustainable, and ideally, has more meaning to us. If this “works out” for me, it will hopefully ensure some sort of happiness and sustainability that will be more fulfilling than my IRA alone and maybe keep me from bitching about my old haunts to a cashier at my lunch joint. Fingers crossed.