Why I’m Glad I Didn’t Retire Even Earlier

When I retired last year, I was 38 (still am), a not-super-impressively young age by early retirement blogger standards, but a freakishly young age by any normal, real-world retirement standards.

And though I once lamented feeling “late” to the party because it’s so easy to get sucked down the internet wormhole of endless comparison, and judge how you measure up against the most extreme outliers rather than the middle, I’ve come to feel glad that we didn’t create our early retirement plan sooner, and that we didn’t hit our magic number at younger ages.

Sound odd? Keep reading, and I’ll tell you why!

Psst! New York meetup folks – the location has changed because the prior venue booked a private party. Saturday’s meetup will now be at Fat Cat at 75 Christopher St., still 2-4 PM. See you there!

By the time we left our jobs, Mark was a partner with his company, and I was a senior vice president with mine. We didn’t have as much power as those titles might suggest, but we had plenty of responsibility and authority, and we got to weigh in on the decisions that mattered most to us.

Which was significant, because I’d spent so much of my career wishing that I could be a part of those decisions, and lamenting my lack of power and influence. “One day,” I told myself for years, “I’ll be the one making those decisions, and things will be better.”

I never became a sole decision-maker, but becoming a part of the decision-making team was hugely illuminating. When I wasn’t a part of decisions, I imagined that people who made ones I didn’t agree with were looking at the problem the wrong way – or were just wrong. But after having been in that role myself, I saw how truly complex corporate management is, and how many different needs and interests you’re having to weigh with every decision. You can never make a decision that will make everyone happy, so you always know you’re disappointing or even angering someone or some group, even when you’re doing your very best to do right by the most people possible. It’s exhausting. And while that exhaustion is a good reason not to want to have to do that work forever, I’m glad that I experienced it firsthand, because it will forever color my view of the world for the better.

We’re Not Left to Wonder

And that leads to the first big reason I’m glad I didn’t retire sooner. I’d spent my whole career wondering what it’s like to be in charge – my whole life, really – and if I’d retired much earlier than I did, I never would have had the answer. I would have been left to wonder.

We’d both have been left to wonder about a whole bunch of things, not just what it’s like to be a part of management. Like what it would be like to lead a team on a big client project. What it would be like to be the director – and therefore entirely responsible – for a high-stakes project (answer: both terrifying and thrilling). What it’s like to be the most senior person on a team who goes into a highly competitive pitch and wins the work. What it’s like to be known for your reputation.

But we don’t have to wonder, because we stuck around long enough to do all of those things. And looking back, I’m really glad about that. Some of the work I did in my last few years is the work I’m most proud of, and when I look back on my career, it’s what I’ll feel most nostalgic for.

We Left at a Time When We’re Sure We Want Out

Of course, our work was very particular in that it was largely politically aligned. Not all of it was strictly electoral, but there was enough politics in there to make us feel the full weight every day of how far U.S. elections have devolved in the last few decades, on both sides. But at the same time, this stuff is cyclical, and after one super negative election cycle, there’s always another that feels a bit better and gives you a bit more hope, and you manage to press on. If we’d left after an earlier election cycle, we might have been left to wonder, once again, if we could have made a difference if we’d stuck around. But 2016 was such a rough election cycle for everyone on all sides – including pretty much everyone in the country and many people around the world, not just those working on campaigns – and we knew for sure that we were okay being done with it all.

Our Careers Were Long Enough to Feel Like a Full Season of Life

I didn’t do everything in my career, but I did a whole lot. I worked as a journalist. I worked as a civil servant. I worked for the vast majority of my career as a communications consultant, but within that, I worked at nearly every possible level and worked on dozens of different causes and issues, becoming a near-expert in everything from traffic safety and education reform to climate change. As an assistant, age 24, I was quoted in the Wall Street Journal as a “well placed operative.” I shook hands with Ted Kennedy, Paul Newman, Nina Totenberg and dozens more incredible people. Through a client, I got to fly the real F/A-18 simulator at MCAS Miramar, the former Top Gun. (I sucked at it and crashed several times trying to land. But they were nice and didn’t laugh at me.) I chased Bruce Willis into a portapotty with an Access Hollywood crew, and then had to awkwardly stand around until he emerged, annoyed but gracious. In later years, I gave a few keynote speeches and got really into presenting. I got so good at moderating meetings that I felt proud. I wrote things that ended up in candidate speeches, in ads and in op-eds. I came to trust my ability to work with clients even in the most challenging circumstances and crises.

I’m proud of all of that. And of course those are just the sexy-sounding highlights. Most days were like nearly every job: work. Drowning in emails, spending nearly all my time in meetings so I couldn’t get my real work done and, in later years, flying more than 100 flights per year and racking up almost as many nights in hotels away from home.

But if I look back, I see a definite arc to my career. A period when I was young and eager to work hard but lacked experience, a middle period when I had built up a lot of skills and knowledge but still needed guidance, and the later years when I was operating in a state much closer to mastery. Which didn’t mean anything was easy, because they wouldn’t pay you if it wasn’t work, but it felt good. Not so good that I couldn’t imagine walking away from it, but good all the same.

I’m glad I stuck around long enough to know what that goodness feels like. What near-mastery feels like. To know what it’s like to be at the top of my game, something I wouldn’t have gotten to experience if I’d retired even earlier. And I’m glad I can look back at all the work years leading up to that, to see what got me there.

We Made Our Education Worth It

I wish I could recall where I read it, but I remember a few years a blogger wrote that you should work at least as long as you went to school. And while I wouldn’t dictate that rule to anyone else, I do like the harmony of knowing that my career lasted almost exactly as long as my education. I went to school for 16 years, and I worked after college for 16 1/2 years.

My college education was almost entirely paid for by the taxpayers of California thanks to an incredibly generous academic scholarship, and I’ve always believed that that privilege also came with a responsibility. It wouldn’t have felt right to me to retire before I’d more than paid back what the state paid for my education, and I love knowing that I’ve done so. But even if I’d had to pay my own way, I think I’d still want to feel like I’d paid myself back for the investment of all that time and hard work in school.

The Benefit of Hindsight

I remember well all those years in the slog, when I wanted so badly to be done with work, especially on the most stressful days. A year before we retired, I worried that I wouldn’t be able to make it to the finish line because the work was so taxing. And I know a lot of you guys are living that right now.

Which is why I’m sharing all of this. Of course it’s much easier in hindsight to put on the rose colored glasses and focus on the happy memories of work, but I’m trying my best not to do that. And in looking back at my career as objectively as possible, most of which was not the glamorous moments, and remembering the long hours, the stress, the frustrations and the bureaucratic annoyances, I’m still glad that I stayed in it long enough to consider it a full career and to have that full arc to look back on, as well as knowing the answers to all those things I might otherwise have wondered about.

Not everyone is the wondering sort, of course, but if you are, maybe this helps ease the journey a bit. Knowing that future you might be glad that it took you as long as you did to get to your financial goal. What feels like a slog now might one day be a set of memories you cherish deeply.

Share Your Thoughts!

What do you think? Could you imagine being glad you’d worked a little longer or sad you’d worked too short a career? Think I’m nuts? ;-) For folks who’ve already retired, how do you think about your career when you look back on it? Wish you’d retired sooner, later or happy with your timing? Let’s discuss in the comments!