More Comfortable Shackles

About a year ago, for the first time in 60 years, I truly had nowhere to go and all day to get there.

Corporate America and I had an amicable breakup.

One cardboard box and an elevator ride down, and I was once again a free man.

The problem was, my relationship with work wasn’t a passing affair. It was a fifty-some-odd-year commitment.

As Chicago likes to sing, that’s a hard habit to break.

Not that I wasn’t delighted. Retirement had eliminated the last obstacle to a life of writing. But the lack of structure was a bit unnerving.

My friend Scott, also recently retired, decided to spend a full year doing nothing while figuring out what he wanted to do long term.

Turns out, that was nothing.

I love self-awareness.

Scott’s my hero.

There are times when I’m more delusional than aware, so I jumped right to an expert in the field when it came to becoming a successful man—Matthew McConaughey.

Alright, alright, alright.

Buying his “The Successful Man” journals, I figured it would be the perfect way to create a framework for success, as he promised self-development, accountability, and progression.

Hell, it’s right on the journal cover.

After all, when has an actor ever lied to you?

That lasted about a week.

The journals provided lots of goal setting, positive nonsense, looking deeply inside yourself, daily updates, vision statements, goals, action plans, yada, yada, yada. If McConaughey really used all this to become successful, then he was experiencing something I wasn’t.

Then I remembered the man who brought us Dallas Buyers Club also brought us Surfer, Dude.

Next.

The Habits app was simple enough. Pick any number of things that you are setting out to do every day. That felt like a healthy amount of structure without being too intrusive. I started with 5 habits: responsible social media use, physical therapy, reading 30 minutes per day, writing 500 words per day, and meditating.

Easy peasy lemon squeezy.

Then the reminders started coming.

And the metrics.

And the failures.

You’d be surprised how a day fills up when you have nothing officially to do. I wasn’t even wasting my time lying around watching TV. Days just inexplicably fill up.

You’ll find out.

Staring at the monthly results didn’t do much for my sense of self-esteem. I couldn’t believe I was better at navigating the inane maze of corporate bullshit than figuring out what to do with complete freedom.

I didn’t even have HR to irritate me this time.

Next stop—calorie journaling.

Everything I ate and drank.

Every day.

Until I die.

And I thought parenthood was a big commitment.

There were more.

The magic algorithm of Reels recognized a lost and slightly insecure man.

It sensed blood in the water.

Recommendations ranged from the simple, MS To Do, to the incredibly complex, Notion (yeah, I said it).

I tried them all. Mostly on a free trial basis.

But that’s the thing about trials—you are judged.

My Apple Watch even told me that I could be hypertensive, probably because I wasn’t exercising enough.

You’re my watch, not my mother.

I even started rooting for those sad sacks in animated ads where they let themselves go so badly that they get passed over for promotion, get talked about behind their backs, eat too much cake, and inevitably lose their wives.

There’s nothing wrong with cake.

You be you, you magnificent sad sack.

As it turned out, the round-the-clock monitoring, measuring, and notifying that I was falling short of near-impossible standards wasn’t helping; it was nagging.

At least Mom loved me.

Then it dawned on me.

A year after freeing myself, I was just trying to wear more comfortable shackles.

At least they weren’t fuzzy and pink.

Progress.

When my former boss Jason retired at a relatively young age, he warned me that it would take six months to detox from corporate life.

Turns out I needed 11.

Free of Matthew McConaughey journals and self-help apps that were more self-flagellation than self-help, I bought a pad of long Post-it notes.

With limitless opportunity before me, I started each morning with my “First Five” list: five things I must accomplish today.

Make that “should,” not “must.”

Goddamn.

At least I resisted color-coding them.

Some days I even add “Next Five.”

And the beauty of my Post-it notes is that I can ball them up when finished, and they quietly fall off when their adhesive dries up.

There’s no app for that.

I should design one.

I’ll just add that to my “Never Five” list.