Early Retirement Is Harder Than It Looks

The Four Horsemen of the Early Retirement Apocalypse

Early retirement has its downsides. Just like AI image generators.

“What have we lost? Oh, nothing much, really—just our identity and meaning, just a structure for our lives.”

- What Happens When You Get What You Want? by Rick Eigenbrod

As I mentioned in my last post, I slipped into early retirement in February 2021—a transition that was rockier than I thought it was going to be. It’s common for people transitioning to early retirement to feel loss or depression, and I was no exception.

It probably didn’t help that I retired as COVID-19 was sweeping the planet. I remember reflecting on the uncertainty of life at that time—shops and restaurants shut because their staff were isolating, there were disrupted supply chains (were we going to have empty supermarket shelves?), every big event cancelled. It was a time where it was hard to look forward to anything.

There were lots of times I felt adrift over those first uncertain couple of years, unsure of what to do with myself. Here are some thoughts I jotted down at the time:

5 May 2021 - When the last time was that I was “light of heart”?

24 May 2021 - I am lonely

27 May 2021 - Lonely + Bored = Not good

17 June 2021 - Can structure defeat boredom?

19 June 2021 - I am lonely the minute the kids walk out the door

7 April 2022 - I am so bored…I lack a purpose

25 May 2022 - The only thing missing from my life is meaningful work

9 August 2022 - I’m looking for inspiration everywhere. Books on climate change. Macabre poems. Doomscrolling LinkedIn.

In particular, I feel like I lost four big things—what I now call the Four Horsemen of the Early Retirement Apocalypse:

1. Loss of Structure and Routine

When you’re working, your days have a rhythm. Your weeks, months, quarters, and years all have a structure. Retirement takes that away. Suddenly, time becomes fluid, and your calendar becomes amorphous. No deadlines. No Tuesday morning one-on-ones. You no longer have to remind yourself, “The meetings are the job.”

2. Loss of Connection

Work gives you a built-in social network. The banter over Slack, Friday night drinks, small talk before meetings, or catching up with the person the next desk over. Not to oversell it, many workplace friendships don’t persist beyond the job after all, but even talking with the bus driver or the barista is more social interaction than you get when you are at home alone with your cat. Even if he is a very handsome cat.

3. Loss of Identity

Your career provides a sense of identity and self-worth. So when you step away from that career, then what? Shedding the professional identity you’ve built over years can be unsettling. You are no longer part of a company, an industry, or a professional community. So, away from work, who are you? Even Michael Phelps, the most decorated Olympian of all time, has said, “I thought of myself as just a swimmer and not a human being.”

4. Loss of Meaning and Purpose

Worst of all is the loss of meaning and purpose. A “big” day might involve a mountain bike ride in the morning, a trip to the supermarket, sitting in the sun to read a book, and a meeting in the afternoon before the kids burst through the door. There is no motivating force, no dream to chase, and no BHAG over the horizon. As Markus Persson put it when he sold Minecraft to Microsoft for $2.5 billion, “The problem with getting everything is you run out of reasons to keep trying.”

Much of the advice that follows is all about countering these Four Horsemen—rebuilding the structure, routine, social connections, identity, and purpose that once came from your work life. But before diving into how to counter the Four Horsemen, it’s important to understand the emotional terrain ahead…which you’re going to hear all about next week :-)