The Transition to Retirement: Knowing Yourself and Getting to Know Yourself //, early retirement, work optional, financial independence, adventure, happiness, purpose, FIRE movementwe retired early

The Transition to Retirement: Knowing Yourself and Getting to Know Yourself (by Mark!)

Today is a special day here at Our Next Life, because it’s the second-ever post written by Mark (here’s the first), and — more importantly — it’s a really important topic that not enough people talk about publicly. Despite going through the transition to early retirement together, Mark and I had different experiences with it in some ways, simply because we are different people. If you’ve been reading here for a while, you’ve heard plenty about my view of the transition, but today I’m excited to share Mark’s experience and the insights he drew from that. (Spoiler: It’s really good. Which I’m allowed to say because I didn’t write it. But also because it’s true.)

Here’s Mark:

Today’s post is an excerpt from my talk at CampFI Mid-Atlantic over Memorial Day weekend (last week’s post was from Tanja’s talk at the same event), which was a really fun and inspiring event with lots of fun and inspiring people. Big thanks to Stephen for inviting me to speak along with Tanja, and to all the attendees for all the thought-provoking questions and engaged discussion.

Mark presenting at CampFI

Regular readers of this blog and/or Work Optional know that Tanja has made an effort to highlight some of the challenges that often accompany the transition to retirement – and those challenges exist whether you’re retiring early or at a more traditional age. At any age, retirement is a big event and a big change, and big changes are stressful to most humans. There are a few reasons why retiring early could be a little less jarring than retiring at a more traditional age: unlike two-thirds of traditional retirees, we get to retire when and how we want to, we should be in better health in our 30s, 40s, or 50s than later in life, we have plenty of money saved (right???), and we have the pride that comes with accomplishing a HUGE, really cool, and really rare goal!

But that doesn’t make early retirees immune to many of the issues that many people face when leaving full-time work, such as the potential loss of identity or purpose, or how to define or feel success without a job or career. Though admittedly anecdotal, my sense is that a lot of people in the FIRE community get seduced by the math of early retirement without an honest self-examination of what will truly bring happiness and fulfillment over the 40ish years some of us expect to be retired (that’s like 231,000 waking hours if you get a good night’s sleep). Despite all the time Tanja and I spent planning and talking about early retirement, and all the words she has written on the topic, I’ve still found several surprises and lessons in the 18 months since we retired. Some of those may be the topic of future posts. Today I want to talk specifically about the importance of both knowing yourself, and getting to know yourself to help with the transition to retirement.

The Transition to Retirement: Knowing Yourself and Getting to Know Yourself //, early retirement, work optional, financial independence, adventure, happiness, purpose, FIRE movement

41 Years In Two Bullet Points

Just a little background about me, not because my personal story is all that interesting, or because it is necessarily looks like yours. But it helps to have a little context so you know the values and priorities and personality traits (aka baggage) that have shaped how I’ve reacted to retirement thus far, and more importantly, the factors that might affect your happiness in retirement. Because what I’ve found is that being honest about who you are and what you want – or giving yourself time and space to discover who you are and what you want – is critical to shaping a retirement that you are happy with. So two things about me:

  • I’ve always had two competing instincts and values: a desire for freedom and work-life balance, but also a sense of obligation and guilt if I’m not doing what I’m “supposed” to do. As a kid I always dreamed of being a ski bum, but took the more responsible path of college and career instead.
  • I’ve always been someone who likes to do a good job at the things I commit to and is somewhat competitive, but was also kind of a good-not-great student, a good-not-great athlete, and never a true Type A achiever. Despite that I ended up in a high-stress job working long hours for 20 years. It was a bad fit for me personally (the non-Type A who wanted work-life balance), and honestly I sucked at it at first – I even got fired in my first year. But I didn’t want to fail, so I did what it took to succeed, even though it meant I was a square peg in a round hole.

Total Freedom: What We Crave and Sometimes Fear

Walking away from work was both thrilling and sad, but our first few weeks of retirement were really amazing. We celebrated with a trip to New Orleans. A few weeks later we traveled to Taiwan. Those were the first trips in years that Tanja and I didn’t have to do any work or even check email. We could truly unplug and explore and be together. After that we settled down back home to build our new life and new routines.

For most of us, the draw of financial independence is the total freedom to decide what you want our life to look like: that can be liberating, inspiring, and in some ways scary.

Having a job and needing money give us excuses for NOT reaching our goals. Always thought about running a marathon? Don’t have time to train, too busy with work. Wanted to visit every continent? Not enough vacation time and can’t afford it. Whether those reasons are true or not, they’re still good excuses for ourselves and others. But financial independence means essentially total freedom and infinite free time. If we don’t accomplish our goals, we have no one to blame but ourselves. Ironically, that can feel like a lot of pressure.

What did that look like for me? I had/have a pretty clear list for my early retirement years, largely focused on outdoor things Tanja and I moved to Tahoe to do: skiing, mountain biking, hiking, climbing, and getting in (really good) shape.

Especially in year one of early retirement, I had friends who were working but still managed to get out and do all the sports I love to do more often, and on a higher level. I was excited to ski more often and get better, I still judged myself for only skiing 50 days instead of 100, or not pushing myself to jump bigger and bigger cliffs. Certainly there was some inertia at play – it took a while to really exhale and get work out of my system, and I was doing a little bit of part-time consulting. And when you feel like you have infinite time it’s easy to let a couple days slip by and be lazy.


They liked Mark’s talk so much at CampFI that they named a part of the camp after him.

Know Yourself (Retired You is Still You)

But I think it revealed something else that I knew intellectually but hadn’t really internalized: retired you is still you (credit: Maggie of Northern Expenditure). Retired me is still not a Type A hardcore charger, and that applies whether we’re talking about school or work or sports. If I wanted to be the guy who skied 100 days a season and jumped off 50-foot cliffs, I already had 40 years to do it. But I didn’t. The reality is I’m not going to be out there in terrible conditions so I can say I skied 100 days. And at 42, hucking 50-foot cliffs isn’t in the cards anymore. But it took me a while to realize that’s okay. Just because I have infinite time to spend on the sports I love, doesn’t mean I have to hit Red Bull levels of extreme for it to count.

Retired me is also someone who feels guilty if I go too long without accomplishing something I’m “supposed” to be doing. Between my nonprofit volunteer work and my little bit of consulting work, there has always been something I should (or at least could) be doing. And of course life doesn’t stop when you retire, there’s still home and car maintenance and bills and family and healthcare and on and on. It took about a year for me to feel comfortable saying “no,” or at least “not today,” to things, and really being okay with that, and that was truly liberating.

For those of you thinking about the transition to retirement, especially if you’re setting goals or creating ambitious life lists, start with an honest assessment of who you are, your values, how you operate, and what makes you happy. Avoid the temptation to compare with other people. It shouldn’t be based on someone else’s vision or goals or a fictitious version of yourself. If long trips stress you out, don’t decide you want to kick off your retirement with a 6-month round-the-world odyssey just because some people in the FIRE community travel constantly and have sick Instagram accounts. However you choose to fill those 20, 30, or 40+ years of retirement, it’s not a failure if you’re being true to yourself.


Get to Know Yourself

The flip-side to all of that is that early retirement is a unique opportunity to get to know yourself, or to relearn who you are. Retirement gives us time to sample new things and step out of our comfort zone. If you really DO want to run a marathon and work really was holding you back, by all means, hit the pavement! And you have LOTS of time for trial and error — to explore, be creative, try things you’ve never even considered before, whether it’s art, music, language, travel, reading, sports, mentoring, volunteering, etc.

But be deliberate and honest and nonjudgmental about it. If you go on a few long trips and it didn’t feel right, try shorter trips. Maybe you thought you wanted to paint, but you suck at it and that bums you out. That’s not a failure, maybe there’s another art medium like photography or ceramics that’s a better fit.

For me, this part of the process has been more about getting to know myself again. Twenty years of work in a tough environment did change some things about me. Some of those changes were good (a stronger work ethic and better organizational skills), but some were definitely for the worse (more baseline stress, guilt, and less patience). With time to exhale and re-center, the question is whether I can (or even want to) be more like the person I was at 22, or whether some of those changes were permanent?

Defining “Success” in Retirement

For most of us, happiness comes from a sense of contentment or achievement (or both). The challenge is that for most of our lives, those measures of success are external: grades in school, doing a good job or moving up at work. In retirement, those external markers of success go away, so we’re on our own to define what success looks like. And this is where honest self-reflection is really important. Setting too many or unrealistic goals for your retirement could leave you feeling disappointed in yourself (like it did for me initially). Conversely, failing to set meaningful goals would make it hard to fill 231,000 waking hours with a real sense of purpose.

For folks on the FIRE journey, I’d encourage everyone to consider emotions and values that shape your life now, and what that might mean for the post-retirement life that will bring you the most joy. Who you are and where/how you find happiness very well may change over time, so this isn’t a one-and-done exercise—reassess periodically. As amazing as it is, early retirement is still a big change that comes with its own set of challenges. So also be patient and nonjudgmental with yourself – almost everything in life takes planning and practice to feel successful, and retirement is no different.

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19 replies »

  1. Wow, great article Mark! A lot of wisdom was packed in.

    As someone who is still dreaming (daily) of early retirement and making meaningful progress towards it, this is very helpful to hear/read.

    Thanks for writing again, already looking forward to your third post!


  2. I love that you realized that you’re still you even when you retire. You don’t magically change and do all of the things you’ve said you wanted to do for years, unless those are things you genuinely want to do. My partner said something on the weekend that made me think something along these lines. We were driving through a campground after a hike and he said he’d love to buy a trailer, even though he wishes he was ‘more of a Backcountry camping’ person. Acknowledging who you are (and more importantly, who you are not), can only serve to help direct your money and activities pre and post retirement.

  3. Mark

    It’s been awhile since I posted (been busy discovering what I wanted my retirement to be but now that it is 15 months old I believe I have it figured out) and like you I had to deal with the expectations of others as to what I “should” be doing. I do think the one thing that helped me, (that I know you two addressed frequently since I have been a long time reader but didn’t address In depth today) was making sure these are things you are thinking about in the year BEFORE you retire.

    When my last day of work occurred I was already “there” I mentally didn’t want a cold turkey exit and transition to retirement And I think this planning is every bit as important as the financial planning piece

    Also I am curious if now that you have spent more than a year in retirement and you have income you weren’t counting on if you have altered your asset utilization strategy at all.

    Thanks again for sharing and congratulations


  4. Not even close to FI yet, but enough space in our lives now that I get the feeling of MORE pressure to make the right choices. We are staying in our jobs and current lifestyle by choice now, which can confusingly make me feel even more “stuck” sometimes than if we actually were stuck due to finances.

  5. I relate to a lot of the things you discuss in this article, Mark! I, too didn’t like to work overly hard at things and lack a lot of those Type A instincts – like, I tended to shoot for an 80%/B average in all my classes and didn’t have a relentless drive to get better in my chosen sports. I worked really hard when I finally settled into a real job (at 25 – I spent 3 years messing around coaching college soccer) mostly because I enjoyed working super hard when I was allowed the freedom to work at my own pace and not forced to punch the clock for 12 hours when I only had 6 hours of work to do. I had a realization recently that I did hard core things when I was working to manage my stress and anxiety of work. 15-20 days skiing a season driving back and forth 400 miles in each direction, marathons, half-marathons, half-ironmans. Practicing yoga and meditation would have probably functioned in the same way but hindsight is 20/20 and been a whole lot healthier. Nearly 2 years into retirement and my desire to do anything hard core has pretty much gone away and I’m back to doing things at a slower and “good enough” pace. Thanks for sharing!

    • Hi Mark! We met at Tanja’s book event in DC and discovered a common connection to Rockville. Great post! I had a reality check a couple of years ago at work when I realized how much of what I did was driven by external factors. Even though I like my job, I had lost the part of me that took the job for my own reasons. I’ve been trying to re-learn how to be internally motivated to do a good job, even if it’s not recognized. Hopefully it will be good practice for when we reach FI (not close yet).

  6. Yeah great article Mark. Grade A stuff <– how's that for an external metric of success :P

    I think our personalities are similar and one thing I really enjoyed in early retirement was that while I was lazy and didn't accomplish something everyday. I felt like I didn't have to because I got to cut out all the bad parts of work that I didn't care for, so I really only had to 'replace' the parts that were consequential in the first place.

    I thought that was around 50% of my work time. Leaving lots of time for laziness.

  7. Great article. Since I read my first fire book, I have been somewhat consumed with the through of the free time post retirement. When I first tracked my living expenses, I was shocked to see for instance, how much work balancing I was doing with alcohol. In the odd year since i’ve started working on FIRE, I actually got Sober curious, and after a few bad evenings, joined aa. Now I have a great new group of people i’m connecting with on a whole new level and i’m opening myself to a whole new world of service. beyond that, the local orgs and charities i think could use my help more than the local businesses, so I look forward to just give it away wherever people need it. The prospect of not hiding behind job for an excuse does sober one up spiritually and seek new connections not before felt, at least for me.

  8. Really appreciated reading this blog post, Mark. Actually, I just opened up on my own blog for the first time about being smack dab in the middle of the emotions of a confusing early retirement. When you are a high achiever and take the path of “letting the universe guide you ” following retirement, its a scary place to be. I’m finding you just can’t “make” the right thing to do land in your lap. And I thought I was prepared for retirement! Keep writing – its helpful !

  9. Great article, Mark. I read it at such a timely point in my week, and in fact had just opened up briefly on my own blog about admitting my sense of disorientation in my first year of early retirement. Its amazing to me how a seemingly successful, well organized individual can very quickly feel lost and unsure of him/herself (talking about myself here!) until they have their feet on a sure path again, setting and obtaining goals of any type. Maybe that’s just my A type personality showing! Keep writing!!

  10. Glad you’ve been able to find your sea-legs with this new phase, Mark! Despite my work-optional path being a few years off, this topic’s very much been on my mind as of late (no doubt, the quandary teed up by Tanja’s book!). Some of the themes you mention feel pretty familiar!

  11. Love this Mark. Totally agree that a retired you is still you. You and you alone have the power to define what you want to do in retirement, don’t let other people tell you what to do.

    BTW, how was Mt. Rainier? Saw some pics of you summiting a few weeks ago, gotta say, I was a bit jealous. :)

  12. Realizing this is what can make the path to FI so fun. For anyone able to do mostly what he or she would do after being FI, well, life just is that much sweeter.

  13. My experience with quiting was a little different. My career spanned 40 years, and was pretty type A. I pretty much ran 2 or 2.5 standard deviation above the mean. I could and did DO it, it didn’t burn me out, I found the work interesting and worthy of my time invested. I didn’t hate my life. I lived parsimoniously neither frugal or extravagant and I saved my cash and learned to invest and killed it. My life was like driving 100mph on I-95 heading North out of Miami to parts unknown. There was a destination but no plan, just drive-on daddy drive-on. When I decided to retire, I realized every day I went to work just bought me more risk, since I already had enough. In my biz we have a target on our backs for law suits so I pulled the plug. It was like getting off the off ramp and slowing down to 25 mph. I could look out the window and not worry about driving off the road. It wasn’t about DOING anything, I just did or didn’t do what I wanted and my engagement in doing became irrelevant. What became relevant was BEING. It was so relaxing to just be and engage in the past time of being. It’s a very Zen kind of experience and I found I love it. It’s an experience worthy of study. I got into the Stoic philosophers, had time to explore a spiritual life, worked out every day WITHOUT a goal of running a marathon. My goal came to experience my body in the state of exercise, the heart pounding, the heavy breathing, the sweating while I clomped on the treadmill or push and pulled weights in my gym. The need to do evaporated and was readily replaced with the need to be. My wife joined me in that pursuit. We of course do stuff together but we have no longer that as a need.

  14. Mark, thank you for taking the time to share your reflections. For me, your comment of “a lot of people in the FIRE community get seduced by the math of early retirement without an honest self-examination of what will truly bring happiness and fulfillment’ had the biggest impact. I think a lot of people think that retirement will bring this new found happiness, but if you are not happy today, retirement won’t be the answer. You need to find what makes you happy today and do it. Waiting to be happy is silly. If there are people that you want to spend time with or hobbies that you are passionate about, make the time today. I have found that philosophies such as stoicism really help prioritize what’s important in life.

  15. I can see how going from a Type A environment to retiring would be difficult. I went from corporate to entrepreneurship first and then once my business was running and our FIRE assets, I dialed it back till it suited me. So it was never on v. off. My husband went from a hectic office job to helping me with my business, giving him that same kind of runway. Perhaps the acronym should be FIRS for FI, Retire Slowly to remind people to give themselves some runway. Work takes up so much of your life when it’s full-time that stopping completely must feel like going from 60 mph to 0 right at the red light.

  16. Hi there, I rarely comment on blogs, but i just had to say that this post was really thoughtful and it resonates deeply with me. I am still in the accumulation phase of FIRE (probably 7 years out) and these are things i’ve started to think a lot on lately. Thank you for sharing your journey.

  17. Thanks for this awesome blog, loved reading it but Waiting to be happy is silly. If there are people that you want to spend time with or hobbies that you are passionate about, make the time today. I have found that philosophies such as stoicism really help prioritize what’s important in life.

  18. Retirement does not mean sleeping on your chair it can means travelling the world with no inhibition and strings attached and of course rediscovering yourself.