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

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

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.

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.

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:

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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