What I Learned After 8 Years of Early Retirement

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Exploring Machu Picchu with our friends, Katie and Alan

Back in 2015, I struggled with the idea of early retirement. I thought after escaping my cubical prison I’d be gleefully cartwheeling out of my office, but things didn’t quite go according to plan.

The evening after I officially gave my notice, I started feeling this weird tightness in my chest and it was getting hard to breathe. I waited and tried to ignore it, thinking it would just go away but it didn’t. Before long, negative thoughts started ricocheting in my brain, and no matter how many times I looked at my spreadsheets (yes, they are my soothing security blanket and yes, I am fun at parties), they continued spawning, one after another. At some point I didn’t know where one bad thought began and another ended. The idea of quitting my job suddenly felt like jumping off a cliff. I was spiralling.

My biggest 3 worries, specifically, were (in order):

1) Running out of money

2) Losing my identity

3) Losing my work friends

I had spent a lot of time with spreadsheets coming up with backup plans A, B, C, D to mitigate Worry #1. But when it came to the psychological part of retirement, for the first time in my life, math (which is basically my religion) didn’t help.

As it turned out, facing the loss of those things wasn’t new or unique to my situation. This is the psychological struggle that regular retirees face all the time.

And recently, I came across a TedX talk from 73-year-old Riley E. Moynes, a retiree and author, who succinctly broken down the 4 stages of the mental journey that retirees go through when they are no longer defined by work:

Stage 1: Permanent Vacation

In this phase, it feels like you’ve just untied the tightest pair of dress shoes from your blistered feet, kicked them off, and flung them out the window. You will never need them again.

You go from always rushing, stressing, and obsessing, to relaxing, resting, and smelling the roses—and the delicious ramen you made (from scratch) with all the time in the world. You also end up driving your normal friends nuts by saying things like “what’s the rush?” and “why can’t you just take a day off?”

Most retirees spend more time with family, friends, and dust off their neglected hobbies for the first time. Some, like us, finally realize their dreams of travelling the world.

This phase usually lasts anywhere from 1 year to 5 years, and every day feels like a vacation.

Stage 2: Boredom and Depression

Some retirees never leave stage 1, but for those who do, they enter a phase that Moynes likes to call the “plunge into the abyss of insignificance”.

This phase kind of feels like the aftermath of a New Year’s Eve party, when all the guests have gone home, and your floor is a sticky mess of empty beer bottles, broken streamers, crumpled napkins, and smells like dried vomit and regret.

Moynes says the boredom and depression in this stage stems from the loss of five things:

Structure, identity, relationship, a sense of purpose, and for some, power.

This stage usually lasts 1-2 years. Sometimes when it lasts longer, the retiree decides retirement is not for them and goes back to work.  

Stage 3: Experimentation

This is the “trial and error” stage where the retiree picks themselves off the vomit-encrusted floor, hoses themselves off, and goes back to the drawing board to find new purpose and meaning.

They may volunteer, teach the next generation, give talks, write books, and/or create courses. All in the name of giving back, contributing, and leaving a legacy. Some prefer the flexible schedule of retirement and don’t want to go back to a full time job, or they simply don’t have the health and energy to go back, and prefer part-time jobs, freelance, or volunteer work to get the best of both worlds.

Stage 4: Re-invention

If one or more of the “experiments” work out, you enter the 4th and final stage where you are “re-born” with a new identity (or identities) and still retain your freedom.

For those who are able to find this balance, they become the happiest they’ve ever been.

Sometimes, stage 3 ends up not resulting in anything and the retiree might regress back to stage 2 or 1 where they go back to doing whatever they enjoy and indulging themselves. This is fine too. There are people out there who are perfectly happy just existing. Nothing wrong with that.

From Moynes’ research only 25% of retirees successfully move into stage 4.

But the ones who do are the happiest people he’s ever meet.

I agree with him for the most part on the stages, though it’s a bit different for early retirees since we are fortunate enough to still have health and energy on our side.

After 8 years in early retirement, here’s what I’ve learned:

Retirement Stages don’t have to happen in order

They can overlap. Sometimes you end up relapsing and sliding back into the previous stage. That’s ok and completely normal.

In our experience, we started stage 3 five whole years before we retired when we tried to write a children’s novel on the side while working full time jobs. It was exhausting and probably wasn’t great for my health, but the skills I learned during that period ended up being super useful later on.

When I gave my notice and we quit our jobs in 2015 and after my mini panic attack, I pulled myself together, focusing on selling everything I owned, fit the rest into 2 backpacks and travelled the world. This was Stage 1. But even during this stage, we overlapped with Stage 3 again as we volunteered for a non-profit called WeNeedDiverseBooks, building an app for them while we enjoyed our freedom for the first time. And then when this blog took off, we got an offer from a Penguin editor to write a book, and things got pretty hectic. I would say 2019 was probably one of the busiest years of our lives. At one point, I had to cut my trip to Norway short in order to fly to London to read my audiobook for 4 days straight, then immediately rushed to the international premier of “Playing with FIRE” and did a 1 hour Q & A as one of the people featured in the documentary, then spent a whole week speaking at Chautauqua, then flew to New York to appear on Yahoo Finance, then flew to Ireland to do the same for the UK release of our book.

It was a crazy year. I think that was the year I asked myself “can I retire from retirement yet”?

Then 2020 came and it was the exact opposite. Our schedule was wiped clean and for the first time since retiring, I was forced to do absolutely nothing.

It was a struggle, at first. But I’m grateful for that year because I managed to work on my relationships, heal myself from childhood trauma, help my parents and my in-laws, create a group of “ride or die” friends, whom I refer to as my “chosen family” and forge some of the closest friendships I’ve ever had. 

I’m in full-on Stage 4 mode and I’m the happiest I’ve ever been.

Having gone through all that, I know the stages don’t have to happen in order and they can even overlap. Sometimes you regress and there’s nothing wrong with that. Everyone’s retirement journey will be different.

Don’t Be Afraid to Ask for Help

The skills that get you to FI isn’t necessarily helpful when you’re FIRE’d. In fact, they can even bite you in the ass.

As high achievers, we’re used to being independent so it’s difficult to ask for help. But just like you can’t solve an escape room all by yourself, you need diversity of thought from different brains to get past Stage 2.

Reaching out to those in the FIRE community and other people who’ve successfully gotten to Stage 4 can be immensely helpful. They can use their experience to help you get over your hurdles and give you direction on how to experiment in stage 3 so you get to stage 4.

One idea I found helpful is this diagram:

photo credit: Derived from works in the PUBLIC DOMAIN by Dennis Bodor (SVG) and Emmy van Deurzen (JPG), CC BY-SA 4.0 https://creativecommons.org/licenses/by-sa/4.0, via Wikimedia Commons

It’s not exactly Ikigai (it’s a westernize version of the Japanese concept), but it can be a starting point in figuring out how you can find your purpose.

Make a list of different passion projects and see if you can find ones that use a skill you’re good at, what you love to do, and is something that the world needs. If you simply love to do it and are good at it, it’s more of a hobby and it may not feel as rewarding. If it’s something the world needs, you will feel more fulfilled and connected to others.

Often, it’s difficult to get all 4 at once. Maybe what you do is needed by the world, you’re good at it, and you love it, but it doesn’t pay well (eg. volunteer or non-profit work) but if you’re retired and don’t need the money, you can choose to do it and feel fulfilled because you don’t need it to pay the bills.

Work Friends Are Just for Work (and that’s okay)

The first 3 years after retirement, we kept coming back to Toronto, catching up with ex-coworkers and other friends. But over time, we had less and less common with those with 9 to 5 jobs. You lose the camaraderie that comes with complaining about work deadlines, celebrating over promotions, and hating on bad bosses. As a result, those old “work friendships” have faded or disappeared altogether.

It also feels like we’re speaking a different language with family members who don’t travel and have no idea what we’re talking about when it comes to our experiences. We also have vastly different values from the people we used to hang out with.

In retirement, you will likely lose connections with your ex co-workers just because your values will diverge over time and you won’t have much in common anymore.

This is normal. Work friends may be just that—for work. You will need to find a whole new group of friends who share your new values and newfound freedom. Entrepreneurs, digital nomads, flight attendants, freelancers, other early retirees, these are the unconventional people who ended up having a similar schedule to ours. So those are the people we hang out with the most. And sometimes you end up having some of the deepest, thought-provoking conversations you’ve ever had with them. Other times, you even trauma bond and help each other with family and internal struggles that you’ve never told even your closest confident at work.

Because of Chautauqua, we’ve made more friends and forged the deepest friendships that we’ve ever had and it’s a huge blessing.

Don’t Let the Potential Downsides Scare You from Retiring

Being in Stage 4 has made me the happiest in my entire life. I know this because I used to be terrified of going near cemeteries. My mind would think “But I haven’t lived my life! There’s so much I haven’t done yet. I’d have so many regrets if I die!”

But now, I feel fulfilled and satisfied that I’ve lived life to its fullest, so if it’s my time to go, I have no regrets.

Don’t let the potential downsides in Stage 2 scare you into never retiring. If you don’t want to retire because you love your job, that’s one thing. But don’t subconsciously continue working at a job just because you are afraid of losing your identity or friends.

You can find a new identity (or identities) and/or friends who suit you better.

Choosing Your Ego Comes at a Cost

Don’t get addicted to significance and ego. After travelling to Europe, I’ve learned that they have a very different mentally from our “live to work”, “climb the corporate ladder”, ultra-consumerist North American mindset. They work to live and don’t feel guilty for enjoying life. Nor do they constantly need to feed their egos with significance.

After all the family health emergencies, I’ve learned that there’s a cost to choosing your ego. Your addiction to significance and power will cost you in relationships and health (both mental and physical) and it might be too late by the time you realize it. Don’t give up the healthiest years of your life to a job just to appease your ego.

If you are happy with your job, healthy, and consciously choose to work that’s great. I’m happy for you. But don’t do it just for significance at the cost of your relationships and health.

Remember, no one ever said on their death bed “I wish I had worked more”. They say things like “I wish I had lived a life true to myself”, “I wish I hadn’t worked so hard”, and “I wish I’d kept in touch with my friends.”

Live the life you want with no regrets.

FIRE Doesn’t Fix Everything

FIRE is a tool that gives you time and space to think. But you still have to work on yourself. You can’t just rely on external validation.  For some this requires therapy, spending time in nature, getting out of your head and getting physically active. For others, it may require working on something with your hands, or practicing mindfulness/meditation. For me, the books on mindfulness written by Thích Nhất Hạnh, a Vietnamese monk and Nobel Peace prize nominee, got me through the pandemic. And as for friendships, you need to go out there and find other like-minded people. Living in a bubble doesn’t help you do that.

FIRE hasn’t solved all my problems. Even after retiring, I still have anxious thoughts from time to time. Over the years, however, I’ve learned how to calm them down. The trick isn’t to never worry. It’s to accept it, learn how to manage it, and design your life so that you have the time and space to do so. Just like you can’t heal a burn if you keep touching the stove, you can’t de-stress if you’re forced to work a stressful job and there’s no end in sight. By figuring out your finances and buying your freedom back, you give yourself the time and space to fix your problems.

There you have it. These are the lessons I learned after 8 years of early retirement. I now know that retirement is a journey and everyone’s path is different.

What do you think of these stages? Have you ever experienced any of them?

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27 thoughts on “What I Learned After 8 Years of Early Retirement”

  1. Just entering year three of retirement and very much still in Stage 1. I do feel a little guilty about not feeling guilty about doing nothing but enjoying life.

    Did you mean they “work to live” in this sentence: “ They live to work and don’t feel guilty for enjoying life.”

  2. This was quite thoughtful, especially the point about how the skills that get you to FI don’t necessarily help you ease into it once you bail on the 9 to 5. I tracked with many of the stages you mentioned below. We do have one difference. I don’t believe in ever retiring. I just believe in financial independence — and then doing whatever you feel like doing that contributes to your life, that of others, your community, etc. We are meant to contribute and that can take many forms.

  3. What a great read! We are still on our journey to retire early and will definitely keep this in mind when going through the stages..

  4. Excellent ! … I’m 1 year and 9 months into retirement. I’m still in the carefree stage, and I intend to stay there through summer 2023. I don’t want to think about the future just yet.

    The thing that really jumps out is that it’s actually working !! All the planning for all those years is actually working out. My net worth has increased since retiring, and I’m spending pretty much what I anticipated..nothing unexpected has happed. I’m guessing that as we get more years into retirement, all the latent worries about running out of money and having to return to work start to fade away.

  5. I stumbled upon “The 4 Stages of Retirement” a few months ago and I loved it – I’ve been wondering if/when a FIRE blogger would publish on it so thanks for that!

    I’m glad you brought up recycling phases, I think Moynes didn’t mention that very much and he should have since I think life for many goes in ~7 year “blocks” with a reinvention between them.

    I’ve been FI for about 6 years and have just finished the first experimentation phase – find a GF, global travel, RV travel, build a house. Now we just sold everything, moved across the country and are in an apt until we find a new home for our base camp and start the next amazing phase of this wonderful life.

    I’m not sure exactly what my purpose is but I plan on getting more serious about that once we are settled. As Alan and Katie would say “How do you know what your favorite flavor of ice cream is? You have to try all of them.”

    Lastly, in my experience High Achiever = Childhood Trauma. I’ve dabbled in unpacking and healing Lance’s Truckload of Crap but it’s probably time to hire some help and get serious about it. Thanks for being open about your own struggles, it inspires me to grab a shovel and get to work!

  6. Good or bad…
    Right or wrong…
    The majority of “successful” people will eventually become the victims of their own “successes” because of lost identities!

    You are comprised 2 of façades!

    Façade 1 is your instinct (Genes) and façade 2 is your mindfulness (Identity).

    As said “FIRE does not solve everything”…
    Do not chase after anything in life including “FIRE” if you have to compromise all of your identity along the journey!

    Good luck!

  7. Interesting article, thanks for sharing! I retired a year ago (at 56yo) and have gone through the first 3 stages already. 4 months of vacay, 4 months of 4 boredom, and 4 months of experimentation. Hope those speedy transitions mean I’ll get to some level of comfort and reinvention soon! 😁

  8. This was incredibly helpful, as I’m FIREing at the end of the month, and I’m experiencing exactly this same panic you describe feeling when you gave your notice. Thank you!!! I also really appreciate your honesty re your mental health struggles, because so many FIRE bloggers seem to only portray retirement as peak happiness 24/7. Kudos for all you’ve achieved already and feeling fulfilled!! I hope to meet you and the Wanderer IRL at the next Chautauqua 😊

  9. Thanks again for your helpful information and advice!

    I’m less than a year to FIRE although a bit later than you guys ~20 years later…lol
    We were on the professional treadmill in Canada 5 years back with the thought of retirement a dream so we moved to the Middle East East and put our heads down…we did not catch “Expatatitis” spending on anything but occasional travel and with no taxes we are almost at our goal!

    Although I had been researching FIRE for a few years reading Quit Like a Millionaire gave me the kick in the pants to move things forward. Fellow Canadian Andrew Hallam’s books were also super informative as we are non-residents for the time being.

    Thanks again Firecracker!

  10. A great TED Talk. I’ve forwarded it to my brother that is considering retiring early and I might write a post about these phases as I feel that in my 4.5 years of early retirement I had my own journey.

    That being said, as an European I am not worried about finding an amazing purpose. I feel that living in the present moment with the freedom to do whatever the hell I want is such a luxury. And when you add that to travel, you get always new things to discover.

    That being said, now that we start identifying our favorite place to travel to we might start having a bit of routine to it… or maybe not. I feel that I still need another 5 years to realized that.

    We just came back to Ubud and will be returning to Chiang Mai next week. So far our experience here in Bali experience has been completely different than the one we had in 2022. Let’s see if the same happened once we return to Thailand!

  11. Kristy, I think this may be your best blog post yet. So many people think hitting their FI number will bring happiness. But the real work of self-actualization comes with the freedom retirement brings.

  12. Remember, no one ever said on their death bed “I wish I had worked more”.


    This is false.

    I know for a fact that many individuals had wished that they had worked harder so that they could have provided more for their families.

  13. I put in my notice 2 weeks ago and had to take a Xanax right before,due to the anxiety that you described. I’ve also had the panic attacks of “what if I run out of money”, even though I have the multiple spreadsheets. This really helped me realize that the process I’m going through is completely normal. Thank you for sharing! I’m really looking forward to Stage 1!

  14. oh man, I’d be so happy FIREing but we decided to have kids so now I’ve extend my FIRE plans at least 18 yrs! I’m tired!! 2 baby to take care and I just want my time and life back!!! 😭😭😭😭😭😭😭😭😭😭😭😭 why did I listen to my wife instead of following my own path!

  15. Congrats! I remember you making amends with your mom, which is wonderful.

    Fascinating you had to fly to London to read. I had an audio coach on the phone and I just recorded my Buy This, Not That’s intro in my closet LOL. I also had to push to read my own book. Then we hired a pro for the meat of my book.

    Any more finance books in the future for you guys?

    I just finished my 10th year of fake retirement. Went by quick!

    Best, Sam

  16. It’s been about 7 years of financial independence for me and I have to say, it hasn’t been a cakewalk like I expected. While money has never been an issue since then, there are a lot of other obstacles to overcome.

  17. I am so glad you wrote this. I just finished listening to the audiobook “Four Thousand Weeks” by by Oliver Burkeman and he had a chapter about the loneliness of being a digital nomad and that hit me hard. I always thought I had done the right thing by starting my own business and being able to work from home. But I really miss people! I had been looking into co-housing, but not many of them that I can see are rent based and they cost a fortune to buy in. It would be nice if there were some way to find some like-minded people so that we can travel the world together. Like real old-fashioned nomads that took their families and communities with them whenever they moved.

  18. Still working toward FIRE, and in my early 50’s. Thanks for such a great comprehensive post about what my future could look like. My plan is to develop my ‘retirement identity’ before actually retiring, so that I can go straight pass stage 1 and 2 on day one of retirement. Safe travels!!

  19. It resonated with me when you stated “if it’s something the world needs, (and you like it and you’re good at it) you will feel more fulfilled and connected to others.”

    Any ideas on deciding on what the world needs? That’s tricky for me. Do random acts of kindness all day for the next 5 decades? Is that enough? What about helping to build more housing supply that’s affordable, but then am I hurting the environment and pissing off neighbours who don’t want development…is that enough?

    Help people one on one with life coaching? One on one isn’t a large reach so is that really what the world needs?

    Any ideas on finding this purpose and figuring out what the world needs appreciated;)

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