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What They Don’t Tell You About Retiring Early // Lessons From Jim Wang

As much as we love sharing our musings about our still-imaginary early retirement, we especially love sharing lessons from people who’ve done this crazy thing and retired early in actual, non-imaginary reality. Like our interview earlier this year with Robert and Robin Charlton, authors of our favorite early retirement book, How to Retire Early.

Today we’re thrilled to be sharing lessons from Jim Wang of WalletHacks.com. Jim retired at age 30 after selling his first massively successful first blog. But early retirement wasn’t what he expected. He’s clearly made a ton out of his years since then — including launching his current blog Wallet Hacks and other businesses — but the transition wasn’t easy or instant. He’s here today to share what they don’t tell you about retiring early.

OurNextLife.com // What They Don't Tell You About Early Retirement, Lessons from Jim Wang // Jim retired at age 30 after selling his massively successful blog. But what he learned immediately after that wasn't what he expected!

I met Jim at FinCon, and knowing his back story, expected him to be a bit aloof, a bit unapproachable. He got paid a whole bunch of money for a website he built all by himself, you guys! But that was just me projecting — Jim is an incredibly down-to-earth, humble guy. Oh, and he’s hilarious. So I’m honored to have him guest posting here today!

Here’s Jim! Jim Wang of WalletHacks.com

At the age of 30, I retired.

Six years later, I run three separate businesses and love every minute of it.

Financial independence is a popular phrase lately and with good reason. No one relishes the idea of working 40+ years until “retirement,” when you can finally have some fun.

If you break from the conventional thinking, there are two conclusions — you can go the route of Tim Ferriss and “mini-retirements” or you can go with early retirement by way of core FIRE principles.

My personal story is a little different. I inadvertently built a personal finance blog that would be valued in the millions of dollars and found myself, at the age of 30, with the ability to “retire early.”

Even if I didn’t formally retire, the decoupling of work and pay was a big enough psychological step that I felt like I retired.

What I describe below is the moment and then months immediately afterwards, which were surprisingly challenging, and this transition period is what a lot of people don’t talk about when they celebrate early retirement.

You can try to imagine what that transition is like. Ms. ONL pondered this question of how well do we really know our post-retirement selves just recently and I commented that it takes time to discover your post-retirement self.

It’s not something you can envisage ahead of time but you can plan the discovery process.

This is a look into my discovery process.

Early Retirement and Rediscovery

There are two days in my professional life that I vividly remember.

The day after I quit my full-time job to work on my personal finance blog and the day after I no longer controlled it.

The day I quit my full-time job was the last day I ever used an alarm clock to get up for work. I woke up the next day, and it was a Saturday, excited and ready to get to work on my baby. My head was swirling with ideas and I was itching to get them on digital paper and into the world.

I was ready to get to work and work is exactly what I did. In eight years, I wrote 4,400 posts and over two and a half million words.

And I loved every minute of it.

The day I no longer controlled my personal finance blog didn’t feel much different than any other. It was just the culmination of several months of conference calls, meetings, and the drudgery of due diligence.

I hopped on the Amtrak Acela to New York, signed some papers, ate a delicious lunch, and rode the Acela back home with a bottle of Dom, a gift from my benefactors.

The two-and-a-half hour ride back was surreal. I sat in my seat with this box wrapped in shiny purple wrapping paper with a purple bow. I had just been come into more money than I’d ever seen in my life but I felt a little empty. The thing that occupied my mind was no longer there.

That’s what few people talk about when it comes to retirement.

You’ve been going to a place for years, working on projects with co-workers, thinking about those projects, being stressed out about deadlines and the work, and despite all that, you were doing good work and accomplishing big things. Then, in an instant, you’re not.

The next morning, I remember staying in bed for an extra hour because I had no incentive to get up. I was no longer excited.

It’s not an easy transition.

It took me a few weeks to break out of the funk. When people talk about how depression isn’t sadness but emptiness, I now understand. I was a little depressed in those weeks and months afterwards because I no longer had a drive. No reason to get up in the morning!

How did I break out of my funk? I stumbled onto a TED Talk by Simon Sinek that resonated with me. It was recorded just a few months earlier and it pushed me to ask myself why I work.

For me, the answer was always money — and then I stopped thinking about it. When I kept pushing, I realized that there were other reasons.

When I look back to my time in the corporate world, there were things I enjoyed about working. As I pondered my why (beyond money), I believe I had two more — accomplishment and learning.

The #1 reason I worked was for the money — we all need to eat, a place to live, and toys — but there were others now that money was satisfied.

But when you retire, money gets taken off the table as a primary motivator but it’s rarely the only one. I would later realize that learning was a proxy for growth and progress, which is itself a stand-in for accomplishment.

I needed to feel like I was working towards a goal, overcoming challenges, constantly improving in something, and building something.

For years, it’d been my blog. That was gone.

What I discovered in my head needed to be tested. So I challenged myself to pursue something I knew would give me a sense of accomplishment and learning.

I started playing golf. Golf is a wonderfully frustrating game with a steep learning curve. My dad started playing many years ago and I would watch him practice in our backyard. He would hit golf balls into a net and do it over and over and over again. For hours. It looked hard and it was very hard.

I had friends who loved it and so I had plenty of people to play with. Within a year, I could hold my own and not be frustrated the entire time I was on the golf course. No other game is measured by how frustrated you get.

As I improved, I did feel a sense of accomplishment. I felt like I was progressing along a learning curve. It checked all those boxes… but it wasn’t enough. A test of “why I work” revealed it was more than accomplishment and learning. Golf is fun but it’s just a game. There are no stakes.

In the end, I went back to “work.” I realized that money was still a powerful force but not in the way I originally thought about it. I wasn’t motivated by the accumulation of money, it simply put that work in the proper context and more readily provided feedback on my performance.

I partnered with someone to build a meal plan subscription business (we send PDFs of recipes, not physical food) that is doing well. I started a new personal finance blog, since my interest in personal finance never waned, and it’s growing nicely too. I added to the list of “things I wish I knew about business before I started it” and loved the challenges.

While those projects make money, my interest in them is more about building something valuable, learning how to help those businesses succeed, and hitting milestones I set for them.

Generating a personal profit is not priority one but it’s still important as a gauge of progress. It gives the project a sense of tangible value and that is still important for me.

Nowadays, I wake up excited to work on my projects. I may have “retired” years ago but I haven’t stopped working.



How I Would Do It Differently

All in all, things turned out great.

As I look back on my process, and think about how I might have done it better, it may be valuable to think about “encore” careers. It’s the career after your first one(s), the one that you hope to retire from early. It’s one where personal meaning and impact matter more than income, though it should still bring in some income.

A prime example of this is Bill Gates and the Bill and Melinda Gates Foundation. Bill Gates made a fortune with Microsoft and his second career in philanthropy brings him personal joy and fulfillment, while having an impact in the world.

There’s an entire body of knowledge about encore careers. There are even companies who will help you find the perfect encore career! (Though I’m not entirely sure those are necessary.)

If I were to do it differently, I would’ve planned my encore earlier. In my specific case, as an entrepreneur, I would’ve started building the next project on the side to get the ball rolling. Businesses take time to ramp up and those early months and years can be very difficult. When you’re spending hours and not seeing much progress, it’s nice to have a day job where I can get still that feeling of accomplishment and growth. I can have wins in other areas to cover the drudgery of the start.

If you’re years away from retiring, it pays to start thinking about it now. You want to be ready to enjoy retirement, not seeking to fill an empty space, and now is the perfect time to do it. Think of it like planning for a vacation — except it’s a permanent vacation from your 9-to-5. :)

We all need to be working towards something, whether it’s our golf swing or a worthy cause, and it’s important to find that “something” as soon as possible. There are a lot of hours in the day and finding ways to fill it may be harder than you think!

Jim Wang writes about money and personal finance at his new blog Wallet Hacks. You should check it out because it’s amazing. Oh and sign up to the free email newsletter so you don’t miss a thing.

Chime in!

What do you think about Jim’s idea of getting an encore career moving before you leave your first one? We’re already doing that with this very blog you’re reading, as well as a few other projects behind the scenes — we totally buy into the idea of smoothing out the transition that way. And can you believe he wrote 2.5 million words on his first blog?! That’s almost ten times as much as I’ve written here… and I have a LOT to say. ;-)

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132 replies »

  1. Jim makes a lot of really poignant points here! I love the way he describes financial independence as “decoupling work and pay”. Too many people think of financial independence and early retirement as just quitting work, and worry about what happens when they get there.
    If you are one of the driven, motivated people who have what it takes to actually reach early retirement, chances are you are also the type of person who will really struggle to come with the sudden loss of your purpose and motivation, and slip into the funk that Jim describes. Planning your future after FIRE is just as important as the work to reach it, to ensure that the end lives up to the dream.

    • Thank you!

      Yes, I’d say all people who seek early retirement are driven and motivated. It’s hard to achieve it without those two characteristics and both are hard, if not impossible, to turn off just because you don’t have a 9-to-5.

    • Couldn’t agree more! I think the type of person who pursues FIRE is *exactly* the type who will struggle to adapt to not having something to focus energies on. I also think status is potentially part of that (I wrote an old post on that way back in the beginning!). But I love learning from Jim’s experience!

  2. Jim,
    Thank you for sharing! This is something we’ve been thinking about a lot and has shifted us away from the idea of traditional retirement. In it’s place, my wife is going to continue to work part-time while I explore the “encore” career experimenting with entrepreneurship. The key for us has shifted from not ever working, to having the freedom to work on the things and in the manner that we choose without money being the primary motivator. It is great to have this validation from someone who has already done/ is doing it though. Thanks!

    • If you’re thinking early retirement, you’ve already shifted away! :)

      Encore career was a term I only discovered after I started writing this guest post and I love it. I’m not technically in an encore career, in the way they define it (social/charitable work), but it’s an encore to my first career. :)

  3. This is something I’ve been thinking a lot about lately. Once I’ve met my goals, and my kids are grown, then what? I may have been thinking about it a lot but that doesn’t mean I have any answers yet! I’ve always heard you should retire to something, not from something, and that’s what I want to do. This is a topic I need to think more about.

    Thanks Jim and ONL for the thought provoking interview.

    • I’ve wondered if I would have to experience the same thing once our kids have grown and left the house. It’s very similar… years of worrying and caring for something, then poof… they’re gone.

      Granted, with kids, they’re never gone once they leave the house… but they’re certainly not the same level of concern and demand on time.

      I’m glad you enjoyed the post!

  4. Thanks for this awesome opportunity to share my story – I was caught off guard with how I felt and experienced and hopefully my experience can help others.

    BTW, if there was ever a word that, on first glance, meant the opposite of what you’d guess it to mean… it’s aloof. Aloof sounds like it should mean absentminded or something.

    • Thank YOU for sharing this. I think this is such a hugely important part of post-early retirement happiness, and not enough people are talking about it. I can say all day long that it’s important to think this through, but it’s easy to dismiss me because I haven’t actually done any of this yet. ;-) But you’ve actually been there and can speak from real experience — thank you for adding this important piece to the conversation.

      That’s funny re: aloof! I think you meant “a goof.” So I’ll rephrase: I expected you to be aloof, but now I know you’re a goof. ;-)

  5. Thanks for sharing, Jim! All your life you’ve had a clearly defined path: graduate high school, go to college, start your career and work your way up the ladder. Turning off that road onto a bumpy, twisty logging road has got to be difficult! It’s a great reminder FI isn’t the end- it’s just the beginning!

  6. Thanks for sharing your story Jim

    We are still years away from FI but a lot of what you say above still resonates with me – I get a lot of satisfaction out of building something myself (a lot more than I get at my day job that earns waaaaaaaaaay more money)

    Have never heard the term encore career – but I like the sound of it!

  7. Very insightful. Thanks for sharing your story.

    I like the idea of starting your encore career on the side. I like to always have some sort of project going on outside of work so that I have something to lean on when work gets slow or frustrating. I probably need to work on making these into longer term, sustainable projects rather than short-term things that I jump into and out of quickly. Definitely something I will be thinking about. Thanks!

    • Things always start off slow since you’re overcoming inertia (in a sense), so doing it on the side makes it so you don’t get frustrated. :)

  8. Thanks for sharing! This is something we have talked about – and what started thinking we wanted a ‘fully funded lifestyle change’ instead of early retirement. Since I quit my corporate job and started teaching, I have been so happy – if I could find the right teaching gig, I could probably do it for decades more. It was nice when we were able to make a career choice based on passion instead of paycheck.

  9. What a fantastic interview! I’m not really on the FIRE track (kinda sorta?), but I do know many teachers who express similar sentiments. The idea of going from 100 to 0 is hard, especially in any profession where you see it as part of your identity. I think that’s why so many of my soon-to-retire colleagues line up adjunct work, sponsor student teachers, or agree to sub throughout the year (when they’re not posting photos from their travels or of their grandkids!).

    • No one goes from 100 to 0 – that’s a freaking plane crash. :)

      I think of it like pedaling a bike. You pedal and pedal and pedal and then coast; you don’t stop suddenly (on purpose). Think about the coast. :)

    • I think you’re right! A lot of aspiring early retirees talk a big game about never working again (as I once did!), but I just don’t see most of us doing that! We’d get bored so fast!

  10. I’m sure it’s a shock to the system at first. I had that happen when I was laid off from my 8-year job in 2008. Then I went a little crazy with spending. whoops! I think with that experience I’d do things differently. I think I’d still want to “work,” but it would totally be on my own terms.

  11. Awesome topic, Jim. This article is definitely going in my Friday Feast this week because it’s an incredibly important issue that early retirees need to be focused on.

    In short: We aren’t retiring *FROM* something. Instead, we are retiring *TO* something.

    If our desire is to quit our jobs just so we can do nothing (Peter Gibbons style, from Office Space), then we probably won’t be happy in retirement. In fact, we will most likely find ourselves absolutely bored to tears, not knowing what to do with ourselves.

    Like you said, we need to feel productive. We need something to occupy our minds. Goals to achieve. Challenges to overcome. A reason to get ourselves out of bed in the morning. It’s not enough for most of us to simply “exist”. And quite frankly, that’s a good thing.

    For me, I understand what I believe will be my next real venture – a traveling photographer / videographer. I’m not exactly sure what that is going to look like, yet. There are several avenues in which I can take it. But for me, producing entertaining and creative visual content will be my primary reason for getting up in the morning.

    And I’ve definitely already started. :)

    • That’s a good way to re-frame the process – you are most definitely retiring *to* something and you want to try to prepare for that as best you can.

      Everyone is different. Peter Gibbons was fine doing absolutely nothing… at least for a little bit. Eventually, most people will want to find something to do. :)

      You most definitely have already started and your love of it certainly shows.

  12. Great post Jim and Ms. ONL! This hit home really strong for me and while I thought I’d be just fine when I retired early about a year ago, Jim’s points are very true. You have to have something that gets you up in the morning and for me I also realized I needed additional relationships and personal contact that were now missing since I’m not in an office everyday. I’m certainly not regretting what I did, but I echo Jim’s advice to find meaningful pursuits that keep you engaged and allow you to achieve goals and have impact with people before you leave full-time work to help smooth your transition into your next chapter. I thought I knew what I wanted to do in my next chapter and it actually morphed some which meant a bit of a re-start after retirement, but I really think my new direction is even better, and I wouldn’t be surprised if my direction changes more times as well. I think it’s healthy to learn new things, meet new people, and try things I never could have done when I was in an office every day. I am really pumped that I can now spend more time helping people and have much more freedom to give my time to others and other pursuits that I want to support.

  13. I know this is going to sound bad, but think I’m just strongly against the concept of working in the first place, lol. “Driven” and “motivated” are never words that would come to mind when I want to describe myself. Feeling satisfied with the least amount of effort perfectly sums up my life goals.

    I think the big appeal of the frugality and FIRE movements to me are that I’m learning that I can manage my resources in a way that requires a whole lot less working over the course of a lifetime. Indeed a very privileged train of thought. But the main reason I’m willing to give the extra effort into reaching FIRE in the first place is because I know it’s temporary. To already be thinking about a future career seems counter-productive for me. If I wanted to keep working, why would I retire in the first place? Particularly when the status quo for most people is probably going to be the most financially lucrative?

    If I can use my time in a way that feels purposeful, but doesn’t feel like “work”, and it has the potential to bring in some cash, that would probably be my ideal. But that seems like finding the unicorn career.The challenge being that hobbies can very quickly feel like work once they become profitable and require more space in your head. I’ve often fought against the digital nomadic style of work for myself, because i feel like in that scenario I would be “on call” 24/7 rather than putting in my 8 hours per day and then going home for my me time.

    The “what would I do with my time?” is a legitimate fear for me, because I don’t perceive myself as an ambitious go-getter by any stretch, but at the same time, having a “go with the flow” personality means that I should be able to adapt to new circumstance and build a satisfying life for myself without too much ongoing stress.

    I’d also say that intentionally taking a year-long mini-retirement at age 31-32 will allow me to see if I even like the whole early retirement experience vs. powering hard to FIRE around age 40. If I love the mini-retired experience, maybe that lights a fire under me to reach FIRE that much sooner, but if I don’t love it, then I can just go back to work and plan to work for another 25-30 years and maybe loosen up my spending since the longer I work, the more of the baseline income stream from assets gets replaced by Social Security .

    • Then it’s not an issue of working vs non-working – take the terms out. It’s just about how you’re going to spend your time. You’re an ambitious go-getter at **something** – you have to discover it. For me, it was building something. For you, it could be something else… but we both now know it’s not where you ‘work’ today. :)

      The idea of a mini-retirement is great – like a trial test run to see what it’s like and what you’d probably replace working with.

      • Good food for thought. Thanks for the words of wisdom and also for further sharing your post-Bargaineering story in the subject post. :)

      • I agree wholeheartedly with Jim — I think you are passionate about something, you just haven’t found it yet. But I love that you’re going to take some time away from working to try to find it and answer those bigger questions for yourself. And if you still don’t find it through that journey, then you’ll go back to work until you do. :-)

  14. Thanks for sharing your experience here Jim, this was great. It is critical that anyone pursuing some form of lifestyle change through financial independence/early retirement (however you may define those terms) be prepared for the reality that it may not be an easy transition. We are about 4 months into a lifestyle transition based achieving some measure of financial independence, and it is not as intuitive as I presumed it would be. Whether we know it or not, all of us have some measure of our identity wrapped up in our day jobs, and transitioning to a new identity will be choppy. And after 16 years of working a day job—11 of those with children—the household develops a sense of the role that each member serves. A dramatic change in that landscape can be challenging, even if the new regime is much more family friendly (in terms of time at home, etc.). Getting a running start on an “encore career” as you have referred to it could really be helpful in smoothing the choppiness of this transition. But in any event I would say that it is critical to have a plan for the things you want to achieve during your newly discovered freedom period. Thanks!

    • You’re welcome Joe — you’re experiencing what I did and it is not at all intuitive what you should do, what should be happening, and how you should feel.

  15. Jim, wonderful insight. I’ve learned in my transition that there are actually 5 things that “work” can provide and you need to really determine which of those things you need as you leave full-time employment. That understanding can help define your “encore career”. Financial Compensation is one. And this can be more than the money. It can be the other financial benefits (ex. health care) or what money means to you (ex. sign of great performance). The other 4 are: 1) affinity and connections 2) identity and status 3) time management and structure and 4) achievement and purpose. In my transition (OK, my early retirement was at 53 not 30… but still early in today’s society), I found that I really needed structure and connections, but could get involved in things other than work to do that. I also learned that work, in the short term, was needed for my identity, so I’m consulting in my field of expertise. But I’m also a “recovering workaholic” so I need to be careful not to let work take over life, which it did for many years.

    You started this big talking about personal discovery… that is so crucial to retirement transition. Know Thyself is said quite often…. and sometimes that is very hard to do. You think you work for the money…..and then need to figure out what work really means in your life – both the good and the bad. BTW – friends tell me “empty nest” does the exact same thing – understanding what needs being an active parent meet – the good and the bad. Good luck with that one… although from your picture, that’s years in the future. After your third or fourth encore career?

    • Thanks for the kind words and the confirmation that empty nest does the same thing (or at least the confirmation that you also heard it too!); I think anytime there is a big change physically, a big change psychologically is right behind it.

    • I love that you’re raising this stuff, Pat. People who write about FIRE tend to default to this way of talking about work as though it’s an overly simplified economic transaction only: “You hold me hostage and pay me money.” It’s important to acknowledge all the things you raised: work gives us an identity, it gives us people to socialize with who have something in common with us, it gives us purpose and meaning at least to some extent, it gives us validation. Those are HUGE things to lose that go way beyond the paycheck!

  16. We will be retiring in less than two years with two young kids (11, 9). So certainly not empty nesting and we are not super-early retirees either.

    Just being able to devote adequate time to being involved with the activities of two school-kids is going to take a healthy amount of fun time that those parents who pursue a dual career miss out on. When we look at a typical week and the amount of time we spend with our kids between Monday and Friday, the data is frightening. Often one hour with a parent pre-school and two hours with a parent after school. Time when both parents are together with kids – very, very small. Something not terribly right with that scenario…

    This will be an opportunity to do so many things that we can’t do right now. That is where we are starting from and that is just the tip of the iceberg.

    • Both my wife and I have flexible schedules now (our kids are younger, only one is in school) so we get a chance to spend time with our kids together. It’s not a huge jump up from one on one time in terms of enjoyment during those morning and afternoon periods (they’re so short, you’re really just doing little things) but it’s HUGE on days off during the week.

      Last week, on Yom Kippur when the public schools were out, we went to the DC Zoo. It was a lot of fun, avoided much of the crowds, and really enjoyed having that time to enjoy the weather and see (and smell) the animals. So in that respect, it’s great.

      The other fun thing is when you have flexibility, you start doing things you didn’t even know you could. I just got back from lunch with my son in their cafeteria… it’s amazing how the teachers keep the 100+ kids calm(ish), but that wasn’t something I even knew I could do.

  17. Retiring from your typical 9-5 work so you gain control of your life and time is so inspiring in. Love the story and great to know what FI feels like. I sure look forward to not having to wake up to alarms each morning.

  18. Great post, thought provoking. I’m < 2 years from FIRE, and am being intentional on "building bridges" (projects that last beyond retirement, like my blog!). It's an important, and often overlooked, element of retirement planning. Thanks for the reminder!

  19. Thanks for this great read. We have big plans for our “encore career” – but much of it will be focused on non-structured adventures with the family. We are still paying off debt, so full early retirement is not really an option. That’s why we’re aiming for semi-retirement, with just enough work to pay our living expenses (all debt paid off, investments left to grow). I’m pretty sure that we will be able to stay busy and maintain a sense of purpose, but it’s definitely something to think about ahead of time.

    • Semi-retirement is great because it let’s you “preview” what it would be like if you didn’t “work” in the traditional sense. Sometimes our situations push us in a certain direction and it’s a good thing, like in this case.

      You are pretty sure… but you’re not 100% certain (how can you be? you can’t see the future!), the semi-retirement thing kind of gives you a way to take that pretty sure into certainty without the leap.

  20. 4,400 posts and 2.5 million words? Goodness, you earned your millions!

    I look forward to a slower pace to life and some newfound autonomy, which is lacking in my current line of work. Blogging can be as time consuming as some full-time jobs, but I can choose to put as much or as little into it as I care, and I can say or do whatever the he** I want. That kind of autonomy is liberating.

    Cheers to ONL & Jim Wang!

    • There the old chinese proverb that a dripping water and eat through a stone… I wrote and wrote and wrote, published most of it, and then after a few years I look back and it’s thousands of posts. I too was amazed by it but WordPress puts it on the dashboard in their At a Glance panel!

      Autonomy is amazing but can be daunting too, especially if you were previously in a role where someone told you exactly what to do. It’s easy to listen and execute. If you worked on the wrong thing, it was on your supervisor. When you have to hunt on your own, it’s a little harder. :)

      • What you say about autonomy makes sense. Fortunately, I do have some control over how I perform my duties, but zero control over when my services will be required, or how many places I’ll be expected to be at once.

        My best workdays are short workdays, and my best call shifts are the exceedingly uncommon nights with a silent pager. That’s how I know I’m ready to FIRE.

      • Yeah – so one of the big things in my life is reducing “real time work” – the stuff I MUST DO RIGHT NOW NOW NOW. Everything can be scheduled out, queued up, whatever — that’s the autonomy I was hoping for and so far it’s been achievable. It’s not always 100% zero real time work (more like bursts of real time work) but that distinction was a big moment for me.

  21. As I was reading this I was thinking about all the things I can’t wait to work on when I’m retired. I thought of your article, Mrs. ONL, on how creativity and pay don’t go together for you. Like you, I want to work on some bigger writing projects when I retire, but I would NEVER want to be a writer for a salary or any income that I was depending on, it would just kill it for me. I’m a little over half way through my first novel now and it’s the most rewarding work I’ve ever done. Even if I never get it published, it still will be, because it’s such a pure form of self-expression, without any external deadlines or pay or anyone else’s expectations influencing it. I think any of these things we do for the pure joy of it lead us back to who we really are at our cores. I can’t wait to find more projects like this one!

    • There’s something about the creative process and compensation that really mix badly. Being forced to be creative just doesn’t work and when there’s money (and pressure) involved, it can break that process. Just look at Dave Chapelle after he signed that huge deal with Comedy Central – it just didn’t work.

  22. Excellent points Jim. It all comes down to life purpose. Whether you have enough money to retire or not, figuring out the purpose you are on this blue planet for is a major pivotal moment in life. Then, in my experience, life shows you the way to fulfill that purpose. Congrats on your achievements!

    • Thank you!

      It does come down to the feeling of purpose but sometimes it’s hard to see that when you’re required to work for money. That’s why, when that need is removed, the transition can be so hard.

  23. Super helpful to get your thoughts on this, Jim (and thanks, ONL, for hosting a fantastic guest post!) Makes me think twice about some of my plans. I think my post on a hypothetical “first day of early retirement” comes off a bit too non-nonchalant, in retrospect. Will I enjoy taking care of rentals and being Mr. Mom? Or, will I miss the big drama and being the boss-man at the office? I have about 3 years to figure it out.

    • The fact that you’re thinking about it now means you’ll be far better prepared. You will miss the drama and the importance of your current role, but you can live without it if you find out what’s important to you and fill that void. You do have 3 years… don’t wait until 2 years and 300 days to start thinking about it though. :)

  24. The encore career sounds a great idea to me. That way, you retire into a new challenge, you do not retire, away from something. I like the positive edge that this gives.

  25. Such a great post. Thanks for sharing! We are taking a year off from work, and in some ways it feels like we are working more than ever. We always knew we enjoyed working, but didn’t have any idea how much till the jobs were gone. I think it is something best built slowly, and once you get to the point where you have no time left for your j-o-b, and can afford it, that is a good time to pull the plug.

  26. I saw my father and my father in law struggle with “what to do” once they retired, and it took almost a year in both cases before they found their groove and settled into retirement. I have lots of plans for my “early retirement” or as my wife mentioned earlier our “fully funded lifestyle change.”

    We’ve been able to get a sneak peek at that lifestyle due to all the free time that’s opened up with her teaching now and it has been awesome.

    I was on a work field trip this past week, and I had an idea for a side gig that could end up with huge rewards. It would take a lot of work to put together, but would combine geology, travel, and teaching. Beyond that, I just see myself as a staya t home dad with more time to get involved with the kids school and activities, play more music (banjo, resonator guitar), and even get tinto wood working now that there could be more time.

    So many possibilities, I’ll be excited to see what sticks and what goes by the wayside. :)

    • Seeing your father and FIL’s struggle is HUGE – it gives you a sneak peek at what’s ahead and helps you avoid it (as I hope this post is doing for some folks, even if they didn’t see me experience it in real time). It’s great you have your mind on a few things too because you’re right – some will stick, some will go by the wayside (and then maybe come back later!).

  27. People always say that you need something to retire to, not from. I still have no idea what I’ll retire to, but that’s okay. My interests change with my age and I’m sure the things I’ll want to do with my time will as well. I just look forward to the freedom. With all the people that have become FI before me, I realize that I need to plan for when it happens and not just fall into it. Thanks for sharing!

    • There is definitely nothing wrong with keeping your options open! Just make sure you have *some* options in mind before you actually pull the ripcord! :-)

    • Just being aware and having that mindset (and believing it) is a big step — a lot of people are SO focused on the “end” (it’s not an end, it’s merely a transition) that they fail to plan for the post-credits. When you do that, you’ll poorly equipped to weather that transition.

  28. Nice post!
    I have an idea that my encore is going to involve writing in some shape or form, and I am so excited about it, but there is a niggling voice inside my head, one that just won’t shut up, that just worries and worries. I’m concerned that I am more defined by my job that I am ready to admit. I have had one career since I graduated college and I have defined how successful I am, how productive I am, how much I am contributing and why I am a useful member of society all in terms of my job. It is going to be jarring for that not to be true anymore. This article is an excellent reminder to face this head on, and plan for it, and not have it sneak up on you and bop you on the head at a time of your life (your early retirement) that is supposed to be happy.

    • I love how you put it: it’s best to face this head on. I think you’re right that many of us will have to cope with this loss of identity, but I definitely love having the blog identity here — that’s something I won’t lose when we quit, except that we can drop the goofy pseudonyms! :-)

    • Write more, embrace it, and make it so big that you identify with that more than your current job. Or learn that it’s not what your encore will be and find the next thing if that’s the case. :)

  29. Great read Jim, thanks! I have a side blog that’s generating some income but I couldn’t dream of selling it for a million dollars, it’s nowhere near that :)

  30. I started trying to learn a really hard language at the same time I began my business. The language learning did not last because I could not mentally afford to be incompetent at so many things at once. I needed some wins that were tangible.

    • That’s a great point — I feel the same way about needing wins. Sometimes when it feels like I’m failing at everything, it’s easy to go to a dark place. Good for you for recognizing that and reallocating your focus to get some wins in there!

  31. Thanks for sharing your story.

    “[T]he decoupling of work and pay was a big enough psychological step that I felt like I retired” I get that. When it happened to me, it made all the difference in the world. It helps make very clear the reason for working because we no longer have money/obligation/the regular pay check as the default reason.

    It’s a great gift to give ourselves and it’s not just about the money. It’s about self-determination. I feel I know myself better now than ever and I feel doubly thankful about having done it before 40.

    Note: I did have an encore career as a boutique gym trainer out of our home, or at least what I call “something to work with/do until I feel I should move on”. So far I’m quite enjoying it, along with writing/speaking, but I also think I’ll likely try my hand at a number of other “careers”, just because.

    • Decoupling was definitely a breakthrough for me, glad it resonates with you too. Very cool encore career and don’t be afraid to try several!

  32. I think it’s important to not have too many “irons in the fire” so to speak, but creating that bridge matters.

    You can’t just quit something that takes 30-80 hours a week and expect to be happy if you’ve got nothing to fill the void. That’s why so many people die soon after retiring (not to be morbid to you guys of course).

    Within the more “traditional” parts of Christian faith we speak about vocation. Vocation is a specific expression of the holiness that we believe God call us to. It is how we can serve and enjoy God, and how we can express God’s character through relationships. Vocations (specific callings) stay the same even when circumstances change.

    I think that this piece hits on something similar. Your major purpose in life won’t change when you retire. It will only look different. If your career was helping you achieve your major purpose and you let that go, what are you left with? You need to build something new.

    • We are all about purpose, and write about that a lot — we’ve just assumed that we’d exercise ours in a more volunteer or service-oriented capacity, instead of through paid work! But it’s interesting to reconsider that whole line of thinking and ponder that some of that purpose work could earn us some income as well.

  33. Amazing story, thanks for sharing.
    I wonder, since you retired twice, what are you doing with the 10x FU Money you probably have right now – since you demonstrated you’re awesome at building things and you’re still making money.

    Did you inflate your lifestyle? How much?

    • It’s not quite 10x FU money but it’s invested in a variety of things, mostly index funds. No lifestyle inflation that I’m aware of (I didn’t go out and buy a new car or anything like that) though inflation happens slowly right?

  34. I think retiring early and not choosing to do something you value is a bit of a waste. If you’re hard working and clever enough to have gotten to a position where you’re able to retire early, there is so much you can bring to the world. That could be in an entrepreneurial, creative or charitable way, but I think we need to continue to challenge ourselves to achieve fulfilment!

    • Could not agree more! And we’ve always planned to do work that would add value to the world — we just didn’t think about that work also earning money. ;-)

  35. Wow! 4400 posts in 8 years is not a joke. That was really a hard work. I’m really moved by this ‘encore career’ part. At least, my personal finance blog could be a starting phase even before I quit my job or retire.

  36. Jim, thank-you for sharing the story of your experience.

    My husband, who retired early, is now 67. He likes to point out that as you age, you truly lose the energy level of your younger years. As a person just entering my 60’s, I am beginning to discover what he means.

    This is stating the obvious perhaps, but traditional retirement was developed for people 65 plus. At that stage of life, goals, desires, and capabilities may be very different than for those able to retire at 50, 40, or 30. It was also initiated at a time when people had shorter lifespans, and the typical number of years spent as a retiree was quite short. So I am not surprised that the traditional type of retirement may turn out to not be a good fit for many people who achieve FIRE. I enjoyed hearing how you moved into your encore careers.

    • Thanks Dr. Sock – perhaps in my 60s my energy level will dip to the point that I won’t need as much activity. The thought of sitting around all the time (just some of the time) isn’t that appealing right now, but that’s not to say I won’t love it more and more as time passes. :)

  37. My husband retired this past year at 50 and now he’s moved onto his encore career. We are not part of the new early retirees(30’s,40’s) and yet we have few friends who are retired and our age. He loves this phase of life but I’m struggling to find my new place. I’ve met my goals and I’m trying to figure out what is next.

    • I bet that’s tough! We’re wondering what that will be like, too — we don’t have kids, so won’t naturally meet parents. And most people our age work all day. Part of what we love about our mountain town is that a lot of people work non-traditional schedules, but we still expect the social interaction piece to be a formidable challenge!

  38. This is the reason I love blogs. Personal stories like Jim and yours ONL inspire me to do better. I never thought early retirement was possible for people like me until I started reading people’s stories who’ve done it. You don’t hear too many stories in real life about what to do after you retire. It’s nice to see that other side.

    I would love to get to be in both of your places soon! :)

    • That’s so awesome, Vic! How incredible to know that we’re helping inspire you on your journey. That’s the best compliment there is. :-) And you’ll be where we are sooner than you’d believe. ;-)

    • VIc – as always, great to “see” you on the internet. Early retirement is certainly possible and I hope my story sheds a little light on what might be on the other side of ER> :)

  39. FI just gives you choices. It doesn’t mean you have to stop, but you now have the choice…..
    I retired at 56 and haven’t looked back. I am a metal artist, interested in finance, just started a blog, love travel.
    My husband retired at the same time, but at the request from his office, chose to continue part-time in his own time. He goes to the office about once a month, the rest of the time works from home, doing his beloved maths. No admin, just the work he wants to do, along with a few wee foreign trips to see clients. He’s happy.
    It doesn’t stop us travelling. (Laptop, wifi, phone, he can work anywhere). This year so far, 6 weeks in Spain, 2 weeks in Ireland and about to have 4 weeks in New Zealand. (Given we don’t need the money, all his salary goes straight into a pension fund, benefitting from the 20% tax refund…)

    • Wow, you guys have it figured out! I’d be happy to keep working if it was minimal and took me abroad occasionally! :-) And your travel schedule sounds truly heavenly.

  40. Well said Jim. I love your perspective on needing to do something productive and meaningful in your “retirement” years, definitely need to plan for that. I actually have been hired by a publisher to write a book on how to retire early, so may be hitting you up for more of your insights ;)

  41. Thanks for sharing your perspective Jim. That feeling of emptiness is why I’m hesitant to ever sell. The big bucks is tempting, but I donno, I’ve felt like money stopped being a driving force a while ago… maybe since 911 happened. Too close to home, literally.

    It’s addicting and super fun to wake up to see what readers have to say about a latest post on FS. It feels like Christmas morning every time I press publish still after almost eight years. I’m determined to get to 10 years and see how things go then.

    The wave still feels like it’s going strong in the online media world. Perhaps it’s b/c I’m in SF so I’m biased or constantly exposed to new opportunities. We shall see!


    • It’s cool to hear that you still feel that excitement to check comments the morning after a post goes live — I feel that way, but we’re only two years in on this blog. Nice to know it’s possible to sustain that excitement long-term!

    • I think he wasn’t also working full-time at that point, and they weren’t LONG posts. But still! I agree it’s super impressive!

  42. Jim, I’m on the same page as you. The main benefit of financial independence is that it frees you up to do the work you really want to. When your work offers something to others, you’re contributing with a purpose. That’s what really matters.

  43. Wow, what a great post! I am in my late 20’s and this has given me some things to think about! I think our purpose is to continue growing and learning, so I can see the hard time he had just completely stopping the normal 9-5 job. My dad retired in his early 60’s and he still needed something to do, or some goals to set.

  44. I can totally relate to Jim’s story. I retired in my mid 30s and after a bumpy transition loved the first two years. I always felt like I should be doing more, until I became an “accidental blogger” and busier than ever. I describe retirement as a “career change”, and think the mental aspect of retiring is as important as the financial.