Why I'm Glad I Didn't Retire Even Earlier // Our Next Life // early retirement, financial independencewe retired early

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!

Why I'm Glad I Didn't Retire Even Earlier // Our Next Life // early retirement, financial independence

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!

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37 replies »

  1. You are an inspiration to not only me, but everyone looking to follow their dreams and actually achieve them. I love the fact that you’re sharing your story with us and letting us in on your life. I feel like you both have a lot of wisdom to share, but especially you Tanja. PS: I low-key wanna be you in 10 years hahaha. No, seriously, I think you just got yourself another fan!

  2. The arc of my career sounds very very similar to yours, except that I’ve been working for 7 years longer then what you did. One comment you made that really rang true to me was about being a senior manager or director and being in charge of the huge project with a lot of money feeling “both terrifying and thrilling”. That’s exactly how I felt once I started getting those projects! For me, I always had confidence deep down that I would succeed, but the sheer amount of money they gave me was terrifying. The monetary part of it was always a stress cloud hanging over me, and going to work every day with that stress cloud is something that after a few years, I just didn’t want to do anymore.

    So now in my semi-retirement I don’t have a budget to manage and execute, and I don’t have to manage people either. It really does make my 20 hours of work every week much more enjoyable.

  3. I’m targeting age 50 (2021) for FIRE which certainly isn’t extreme early or even just plain ole early by FIRE community standards. But it’s still early compared to the masses, and I’ll have about 26 years of post-graduate school work at that point. So I very much understood and appreciated the points you brought up. Another quality post Tanja!

  4. I really enjoyed this post and very much relate. As someone who’s always been very career driven, I’ve struggled with the idea of “getting out as soon as possible” and walking away from any dreams I had of working my way up to be a bigger influence in my company/industry. I appreciate not everyone wants those things, but I’m glad to hear I’m not the only nerd who does ;)
    I’m still super early stages in FI/FIRE planning and it’s a relief to be reminded I don’t have to race to the finish of it doesn’t support the rest of my life goals.

    PS sending this from Peru and if it’s not on your list, you should add it. I think youd really like it. The people here take zero waste to the next level, so resourceful and creative, and the culture is so rich with history. Fingers crossed my flight back lands on time Saturday and I’ll see you at Fat Cat!

  5. Happy Wednesday! A couple of times a year I go back to my undergraduate university to give a lecture/freshman seminar. The computer science department brings in graduates from industry to talk about different engineering careers – to “excite” people to stick with engineering. It is always great to get back to campus but even more fun to interact with students. Here are a few of the key messages I try to weave into my presentations. 1) when looking for employment look for a hot industry, look for a hot company and then look for a boss from whom you can learn a lot. 2) get the most from your current position before moving on as you will never go back. 3) There is a huge difference between “finger prints” and “impressions”.

    There are just more opportunities when your job is in a hot industry and the company is doing well. Pretty easy to understand. Also your first manager can play such an important role in developing you as an exceptional engineer (or any profession). It is possible to stay in a company or position too long (I probably did in the middle part of my career) but many young people seem to have “ants in their pants” and want to move from one project to another project or one company to another company before getting all that the current project or company has to offer. As an engineer it is very educational to see how your decisions and code (for a computer scientist) hold up after being in use for a period of time. Lastly, I have interviewed hundreds of prospective employees, from new grads to executive vice presidents, so many tell me about what they touched (fingerprints). I want to hear how the project was successful, or unsuccessful, because of their leadership or contribution (impressions). Many have probably heard of this but when you mention someone in industry people often say – “I know her”. What impresses me more is when I know that this person in industry knows the candidate – again because they left an impression.

    The FIRE movement can be a race for many – get out as fast as possible. I like your views on don’t miss the fun and the sense of real accomplishment by trying to hurry up and finish.

  6. I worked longer than I probably needed to but I left at the right time for me. My influence grew over the 17 years in my last job but I had a seat at the decision making table throughout. So it wasn’t that I was growing and operating at a completely different level but we had new clients and new challenges over time.

    Four things told me it was time to go. My staff knew what they needed to know to carry on without me. The conversations felt like they were on repeat–17 years of the same discussions with many of the same people is tiring. I didn’t have enough respect for the person who was elevated to review my work (I didn’t get the job because I was too open about my ER plans, oh and she’s since been demoted). And, what pushed me over the tipping point, I had a really difficult client who had already ruined too many of my hours and my days. I didn’t want him to have the ability to affect one more minute of my life.

    Big changes have happened at my company since I left. My former mentor and best friend was recently promoted to President/CEO (insert strong girl emoticon here!). The changes downstream from her promotion are interesting. I’m wondering how I would feel if I were still there and I’m thankful I’m not. The conversations with my former colleagues will be interesting when I get home to Colorado.

    I’m glad you feel your timing was right too! Have you kept in touch with your former colleagues? I enjoy chatting about my old company but not having to work there!

  7. I’ve been pondering this issue for a while now, so thanks for another timely post!

    I wonder how many people who are already FI and still working find that their work might be less exciting, less thrilling, and less rewarding than it used to be but planning on working for a while longer because…the work is still (a bit) exciting, thrilling, rewarding, and still making you feel like you are doing some good.

    In other words, if the work is not any more difficult than it used to be–and perhaps even easier because of your experience, and continuing to work helps pad the FI portion–do we simply fall into the “one more year” syndrome until some trigger (positive or negative) makes us want to leave?

    Just asking. ; )

  8. I write a lot about my fi and retirement date being disconnected. I will continue to work well past being able to retire because I enjoy work. But… it gives me that flexibility that if one day I start dreading work the next day I can leave. That actually makes work more enjoyable in my honest opinion.

  9. I am not retiring, but I am (probably) changing careers right now, and I’m glad I waited until I had my books (yes, plural) out and had spent a number of years teaching college. In fact, I’m about to teach my first graduate level class, and there’s a chance it’ll be my last class ever. (I actually think that’s unlikely and I will teach again, maybe as soon as September, but there’s a chance this is it.) You spend all that time in school — you want to *do the thing*. I think it wouldn’t have felt ok to me to move job spaces without what I thought of as rounding things off. This way, I can point to a lot of accomplishments, and I can also move on more or less my own terms. There are things to be sad and nostalgic about, but also a lot to feel good about, things I would have missed out on if I’d kept making the kind of every-two-years career changes I did in my early 20s.

  10. I like to think that I’d have been perfectly fine being born wealthy and never having to struggle for anything. But the accomplishments I’m most proud of were those that required hard work and usually lots of mistakes. I’d have never learned many important life lessons if I hadn’t worked a full career too.

  11. “Mark was a partner with his company, and I was a senior vice president with mine”

    You are hilarious Tanja. So many of your posts are simply “look at me,” “see how senior I was at work,” “wait for me big reveal,” etc.

    Why do you think you are so arrogant and conceited? Seriously.

    • How is stating your ending position arrogant and conceited? Should all people who make partner or the C-suites not be proud of their accomplishment or tell the world what they’ve done? Tanja does a great job of laying it all out there and being HONEST, which I greatly appreciate it. I don’t see her conceited or arrogant at all.

      I, for one, thoroughly enjoyed this post and Tanja’s look back on her journey to where she is today. Good for you, Tanja!

    • Tanja, thank you for your transparency around the positions that enabled your early retirements.

    • Hmmmmm. First time that I have seen a very negative statement in the FIRE community. Maybe I have just been lucky up until now :P

      There was a TV show called “The Guns of Will Sonnett”. I believe that it was only on for a few seasons in the mid 1960s. Walter Brennan was the star and he had a statement in the show that went something like “…no brag, just fact”.

      When we open up on the web, we open ourselves up to negative comments. It is hard, in written form, to convey emotions including humility. If you have read enough of ONL blogs, you should see as I have, no brag, just fact.

      The big reveal was a nice hook to this blog and I, for one, really enjoyed it and could appreciate the anonymity for career purposes.

    • Hey, Em. I’m sorry your life is lacking in some way to make you so very petty and jealous. I hope things look up for you. In the meantime, the rest of us are enjoying this blog.

  12. Interesting perspective. I wonder if you would feel the same way if you hadn’t gotten to that level of near-mastery and had just had unending years of doing the work without getting much credit or advancement? I think being able to enjoy your work probably has a lot to do with feeling that it was time well-spent.

  13. Interesting point on sticking around long enough to be the decision maker. You’re right that it is enlightening to see how many different pieces go into every business decision.

    I worked my way up as an associate at a law firm for many years. I knew it was time to get out when 1) I realized early retirement was likely in my future, and 2) many people don’t really “peak” in law practice until later in life, 50+ at a minimum. I mean, geez, look at the Supreme Court! It didn’t make sense to stick around in that career if I knew I was going to be out before I got to the really good stuff.

    So, instead, I went in-house, meaning that I’m a lot closer to driving the decisions that I would ever have been as a firm lawyer. Because I’m still firmly in the accumulating phase, it’s good to have work that’s satisfying.

  14. I think this links back to your post last week about surviving the middle years – once you get out, you look back and the journey didn’t seem that long at all even though it may feel like eternity when you’re working through it (you phrased it much better than me).

    What I mean is – maybe you can only say now you’re glad you didn’t retire earlier because you’re safely on the other side. I’m not sure you can really take off those rose tinted glasses.

    Then again, maybe I’m only saying that because I’m not safely on the other side, so I can only see the slog…

  15. This is really good to know. I find myself getting caught up in comparisons and what-ifs all the time. I like to remind myself that everyone is right where they’re meant to be. :)

  16. It took me a lot longer than you but I hit that mastery point the last few years of my career and felt really good about the work I was doing, the people I was managing, and the way I left. I was ambitious when I was younger but I don’t think I defined the end game and truth be told, I accomplished more than I ever envisioned and feel like I left at the right time – I had a little left in the tank and don’t think I could have ended on a higher note than I did. I also thought about my career an entirely different way after a few months away – I spent years playing a sport I loved and I had all sorts of ambitions and dreams related to that sport. And I accomplished relatively few of those dreams for a lot of reasons, some were within my control and some not. I felt in my career, I had control over a lot more of the outcome than I ever did in my sport and once I hit that point, I felt a sense of accomplishment and proficiency I had never felt before and it was a good way to end that chapter in my life and start a new and very open one! And funny, I spent 19 years in school and worked a “real job” for 20 years so I spent only a bit more time in my career than my education.

  17. The part about repaying the scholarship with your work struck me as odd. I think it’s inconsistent with this website and idea that you will do some form of work, significant volunteerism, significant charity, etc. So you can say that taxpayers made an investment in you, but even in your “retirement” you continue to pay back taxpayers.

    As for the rest of it, I think it depends on individual journeys. Even if you were financially independent, you could have still continued to work for fulfillment. Maybe it would have been easier to choose not to work when you are flying all over the place. I think it’s still better to have the choice.

  18. No regrets! Simple as that. When we start a career we want to acheive something. Getting to the C-suite or somewhere else is personal. How long you stay depends on whether you’ve achieved what you set out to do, or enough that you currently believe you can step away without regrets. Hard decision as what defines a regret. Hence brave decision when made. Hat’s off to you.

  19. i’m glad somebody squeezed some of the juice of satisfaction from a career. i haven’t had a career in 15 years, even with an education. i had a couple of satisfying things early on with smaller private chemical companies. the one tough choice was an offer into management at a place that made silver compounds. the v.p.’s there all started in my position so it held a lot of promise but the choice was take that or go with the future mrs. smidlap. i made the hard but right choice. once i got to big-soul-sucking-mega-corp time at work became just a good paying j.o.b. it’s ok once you recognize it for what it is.

  20. I really appreciated this part of your post: “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… And I know a lot of you guys are living that right now.”

    Sometimes – when all I see are people’s destinations and not the long roads they’ve traversed to get there – it’s easy to forget that it takes a lot of time, work, and consistency to reach one’s goals. Thank you for the reminder. Right now it DOES seem like a slog, but I also know that if we can keep putting one foot in front of the other and give it a few more years, we will be in a MUCH better financial situation.

  21. I enjoyed reading this. I’m only two years into my career and I’m not sure if it’s the career path I want to stay on. This is particularly because I feel like I’m not very good at what I do. But maybe I just haven’t reached my peak, yet.

  22. I’m in a sort of semi retirement at the moment, financially I could cut now, but just doing a kind of no-regrets wind down. I am contracting part time, at a more operative level than my previous management roles, and it has made realise I have reached mastery in my field. I am asked to peer review or offer solutions based on my experience every day. I am asked to contribute to projects just because they value my insight. I love this time of my career, being able to help those earlier in their career, and effortlessly provide worthwhile input to the company I am contracted to. I don’t Need the glory of fronting the projects or solutions, happy to support those that do from the background. And compared to my management roles, when I leave the office I take none of it with me. My husband is doing exactly the same thing and he’s being sent to troubleshoot for his previous company, using all the knowledge he’s gained but without the management responsibilities. There’s something to be said for slowing to savour the stage you’ve reached.

  23. I like the idea of working as long as I schooled and actually feeling like I mastered my business. Due to some political vagaries, it is very hard to feel that you fully know how to run my particular sort of business and I think I would feel sad if I never got close to that feeling. I’m going to try and remember this post on days when I’m extra frustrated.

  24. Hah this post makes me sad I’m so very NOT career-driven. I suspect I’ll never know what it’s like to lead a team or be responsible for a high-stress, important project because I have no idea what I want to do in the 40 hours I spend at work per week and I’m not sure I ever will. I have always envied people who a clear path out of college for what they wanted to do (or if not, at least figured it out within a few years). Not knowing what I want to do makes it very difficult to know where to begin when applying for jobs so yet again it’s taking me forever to leave an incredibly boring, unfulfilling position for something better. It’s why I want financial independence: I want the freedom to be able to explore my many, many interests and passions without the fear of needing to get it right/never failing at it because my ability to pay my rent depends on it.

  25. I just turned in my notice this last week and my last day won’t be for almost a year, but this article helped me clarify why it was time. Instinctively I new it was, my path took longer, but a similar route. 33 years at the same company to become a Director of my department overseeing multiple locations and large budgets, the peak for my skill path. It has only been a few months since a friend introduced me to the FI community, but it all just made sense. Now we are looking forward to the next chapter in our lives.

  26. I’m on the way to retiring by the time I’m 28 (much younger than most people in the FIRE community, I know) so I kind of see retirement as an opportunity to work MORE. Sounds weird, but I can put the effort that I’m giving to work right now and redirect it back to my life. I can learn more, accomplish my goals, and fail without much consequence. I think it’s a bit of a misconception that work will teach us valuable lessons that we couldn’t get anywhere else; I think there’s a broader scope pride and success that we can all find by ourselves if we try hard enough. And I guess if I really want to get a certain career later, I can go back and struggle for something I love because I’m young enough. For me, though, I don’t like my job that much… Your career sounded interesting though, it’s great to hear that work brought value to your life!

  27. Love the part about working as long as you went to school. Definitely an concept I think about, having spent a long time as a student. How much you “owe” yourself and those who supported you in your education?

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  29. This post resonated with me as someone who used to love their job and was planning on working until 65 and saving appropriately for that goal. Then the business sold to private equity and while it’s not horrible it’s just not the same and I no longer want to work here forever. Since my job satisfaction has diminished it has been great fuel to save like crazy to get out of the rat race and have the opportunity to retire much sooner. When I have a particularly bad day at work it’s easier to make a meal at home rather than eat out and to stay away from Zappos. I love your blog and I love your honesty. I had to laugh at the comment that was negative. I did not get an air of arrogance from this post. It was factual and you acknowledged that you were blessed for your hard work with success both financially and career wise.