Comfortable Talk about Retiring Uncomfortably

Inkhaven content status: rife

I am uncomfortably retired. That was my intention, I achieved it, and I’m comfortable with it. But I am uncomfortable talking about it among my peers. I don’t like admitting retirement to friends and associates because, well they do that thing people do (“must be nice…”,“ um, I’m not even mad…”). I deny accusations that I’m retired. I still take on work because I deny it myself; and I do also like the work. It could be that I haven’t yet decided what to replace the work with. “A retired freelancer, not sure what to do next” instantly checks three boxes in Justis’ categories of Inkhaveners. At any rate, this title was too good to pass up and inkhaven is as comfortable an audience as I’ll find, so I share my story here.

I had been working toward a comfortable retirement, and I planned to leave work sometime in the early 2020’s. But work abruptly left me. Covid shut down my business - maybe permanently, maybe not. No one knew when my industry, live event production would return or in what form. Once I allowed the possibility it might not, the idea of shutting down took hold. By the time the prognosis improved, I had already packed my spiritual bags.

In retrospect, I hadn’t realized how much I wanted to get out of the business, even though I loved it. The anniversary just passed. I retired on April 24, 2020. I rarely attach dates to events, let alone remember them. But I remember in 2020 with my business in a medically induced coma, making the decision, and giving myself a seven day waiting period to reconsider. That was a formality; it was never in doubt. I counted down the week till that Friday, when I would call my clients, bid them good luck, and pull the plug. Opening up Calendar app, yes it’s still there.

4-24-20

Rick was my financial guy, with whom I had scheduled a meeting. Rick’s the guy who said, “This has gotta be the lowest net worth retirement I’ve seen, but yeah, it … works?”.

In 2020: I was definitely working

Of course 2020 wasn’t what anyone had planned. I owned a small “live event sound” company - the guys who shlep speakers and soundboards in and out of halls & hotels where there’s a speech, play, party, conference, wedding, execution, you know. Early spring 2020, pre-covid, not only did I not plan to retire, I was prepping a 40% increase in business. I had new clients coming on, and existing clients were growing. I was buying audio gear, texting techs, trying to cover the gig calendar, debating whether to buy or rent the 4th truck. I was full of the nervous, edge of my seat energy that had fed me on gigs for 20 years. It felt like crunch time and I’d never be ready for busy season, like it did every year.

But then, COVID. Once I was out of the maelstrom, I wanted to stay out, but didn’t know if I could, mathematically speaking. I ran spreadsheets with a thousand different scenarios, and I could’ve argued it either way - that I had hit “the number” or that I hadn’t. It was on the edge, and there were just so many damn variables. I wrestled until I got the insight that made everything clear.

Savor the Lightbulb Moments

We don’t get many moments when hard decisions suddenly become easy, when confusion snaps to clarity.

One day it clicked: I might not have enough saved to retire comfortably, but I certainly had enough to retire uncomfortably.

Oh, shit yes. I absolutely can afford an uncomfortable m-f’ing retirement. And an uncomfortable retirement beats every kind of work. If my numbers were too rosy and I didn’t have enough margin, would I be happy eating ramen, waking up every day knowing my time belonged to me? Are you fucking kidding me?

My advice: Retire Uncomfortably, If You Can. As Soon As You Can.

This is not financial advice. Don’t do what I did.

(But also - take my advice: Do what I did. It was the right move. Your time is precious.)


Post Script: I offer this shpiel on occasion to whoever listens. My GP & I are friendly & he once confided that he and his wife were on the fence with this decision, so I gave him my talk. The bastard was gone before my next checkup.