In this context, FI/RE—the promise of a career finish line you can sprint past, into the land of compounding returns and endless summer vacation—was an irresistible dangling carrot. 

It’s important to recall, of course, that most people who “retire” early end up doing some other job or filling their time with something productive (otherwise, as Jared put it, your “visions of going to the beach, traveling, or visiting the grandkids” turn into spending your days “in the living room with the brown carpet with Fox News turned up to 11”). 

The point is, life is long, and if you’re just going to get another job—or otherwise devote your time and effort to something productive—in retirement, the thinking goes, What’s the rush? Why not just make money doing something you like, so you don’t have to rely on the fickle mistress of the public markets for 40+ years?

I was reminded of a conversation I had with a friend a few years ago who was self-employed working part-time. She only worked in the afternoons, took random days off, and approached work at a leisurely pace. As I worked four jobs simultaneously to produce as much margin as possible, I couldn’t understand why she wasn’t more interested in maximizing her income. When she asked me why I was working so hard, I scoffed at how silly the question was: “So I can get to the point where I can work however I want,” I explained. Duh! 

She didn’t seem to understand. “Oh,” she replied, “Well…I already work however I want.” Mic = dropped.

I’ve spent the better part of the last four years on a six- or seven-days-per-week schedule, putting in between eight and 10 bonus hours every weekend for maximum output. It began during the pandemic when I started working from home, and my personal and professional lives blurred inextricably together. Seeing my desk from the couch felt like an ever-present invitation; a reproach against my Sunday morning lazing. 

While at first I enjoyed the edge working all weekend gave me, somewhere along the line, it stopped providing an edge and became a necessity: In order to keep up with the pace I had set for myself (and the expectations that created!), I had to work every day. FI/RE, I figured, was the reward.


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