Separation Anxiety in Early Retirement

Parting doesn’t have to be such sweet sorrow, does it?

“And ever has it been known that love knows not its own depth until the hour of separation.”
–Khalil Gibran

While I am fully aware of the possibility of jinxing myself by writing this article, our plan is to become PIRE within the next few years. Although I have the business model that I do because I think it’s the right one – offer a fully-contained, self-sufficient personal finance course so that you can create your own soup-to-nuts financial plan, and for the people who are not DIYers, offer hourly financial planning with the intent of teaching you everything you need to know for the rest of your days – it also enables a rapid transition into retirement. I don’t have to tell you to rebalance yearly or tell you how to value cost average and have check-ins with you like most financial planners set up their practices. This was all done with an exit plan in mind. If you’re starting your own business, you should start with the end in mind and work backwards.

I’ve also become quite aware that we’re going to be retired at a much younger age than most of our counterparts will be. Had I remained in the Army, I would have had a cohort of fellow retirees who could share in the retirement adventure. I didn’t, so we’re going to face a potentially different social dynamic for many years; all of our friends (at least, that I know of) will still have working careers and we won’t.

It’s a topic that my wife and I have begun to broach, although, admittedly, we don’t talk about it very often. We have a clear idea of what we’d like to try for the first few years – living part-time abroad and part-time back in the States once the dog is in the great treat factory in the sky. Beyond that, though, we haven’t really fleshed out many of the ideas beyond me reading great forums like and Expat Forum. We’ve sort of narrowed down the list of places we’d like to try and I know the visa requirements for most of them, as well as the costs (Numbeo is a fantastic resource to get ballpark estimates for costs of living in many places in the world). Beyond that, though, it’s still a blank slate.

The other blank slate is what we’ll do when we’re in the States. I’m not necessarily worried about answering the “what will you do all day” question (which Doug Nordman at The Military Guide has so adeptly answered), but I am concerned about how I’ll build up a social network of peers. Sure, we’ll continue to have the friends that we’ve always had, but I admit (now publicly) that I wonder how our status will change the relationship. I think most of our friends will be happy for us that we’ve reached the next phase in our lives, but who knows?

I even tried to look up the statistics for what percentage of Americans retire in their early 40s, just to see where I’d stand. The numbers don’t exist. All I got in results had to do with calculating how much you need to save for retirement and my article about how the media wants you to think that you can never retire (thanks, Google!). Tim Ferriss wrote about the phenomenon (if you can call it such) in The 4-Hour Workweek (#aff), usually telling the stories of people who had founded Silicon Valley companies and sold them at a young age, reaching financial independence, if not outright wealth, and then being somewhat alienated, as they’d reached levels that none of their peers had, and they wouldn’t reach those levels for decades yet.

Beyond answering the financial questions of early retirement, such as whether or not investment properties are a viable path or early retirement withdrawal strategies, there are the social and emotional questions that, I readily confess, remain unanswered, at least for me:

  • Will our status alienate our friends and family? We’ve told family and very close friends of our plans and relative timelines, and long-time readers of this website can infer some details, but it’s not something that we’re out and out talking about. Part of it is uncertainty. You don’t know how long it will take to get to the finish line until you’re really close, but we have a reasonable timeframe assuming that we stick to our plan. Once the scenario changes from possible/probable to actual, though, I don’t know how people will react.
  • If we embark upon the itinerant vagabonding lifestyle, how will we maintain connections? I’ve moved enough to know that you only keep a small percentage of the friends you once had after you move. Even with technology enabling everyone to be a Skype call or Facebook status post away, in-person bonds are the strongest. What will happen to those bonds when we’re only physically around for intermediate periods of time?
  • Can I, by force of will, help accelerate retirement for any of my friends? My parents used to joke about us “working stiffs” after they retired (both by way of state retirement systems, as my father was a state trooper and my mother was an elementary school teacher). They were teasing us gently but also reveling in their status of no longer having to get up to go to work every day. We’d love for our friends to join us on our adventures, but we also don’t want to be nags or, worse yet, have it appear that we’re boasting. Finding that balance is going to be important, but if I can find a way to move their retirement dates up so that they can join us, by goodness, I will!
  • Will I become detached from reality? If all goes according to plan, we’ll soon be living a life that others dream might happen once they reach retirement age. Yes, we’ll have earned that right (something I have to remind myself of occasionally), but it may still seem surreal that we’ll have achieved the goal that we’ve finally been working towards. I want to remain grounded and hope to be humble about it.

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Jason Hull was the co-founder of Broadtree Partners, a firm that acquires $1-5MM EBITDA companies. He also was the co-founder of open source search consultancy OpenSource Connections, a premier Solr and ElasticSearch firm. He and his wife FIREd (financial independence retire early) at 46 and 45, respectively. He has a BS from the United States Military Academy at West Point and a MBA from the University of Virginia Darden Graduate School of Business. He held a CFP certification from 2015 - 2021. You can read more about him in the About Page. If you live in Johnson County, Texas or the surrounding areas, he and his wife are cash buyers of Johnson County, Texas houses.

12 thoughts on “Separation Anxiety in Early Retirement

  1. As soon as you figure out this one Jason, you’ve got to call me and fill me in! Kidding aside, the world’s shrinking each day and it’s easier to stay in touch with technology. Think you also have to redefine retirement. It’s not an absence of work, but a shift in priorities. One that moves experiences way up the list. Ironically some of those experiences may actually HELP with PIRE. Probably a good lesson in here about the results improving when you start focusing on the process and doing the right thing. As always, thanks for sharing!

    1. One of my favorite quotations is from a friend of mine: “I collect friends and experiences.” That’s how I live my life, so I imagine that retirement won’t be much different, except that I won’t be doing financial planning every day! Thanks for commenting, Curt!

  2. My wife and I retired at 41 and 45 respectively in March of this year – and moved to Costa Rica in June. We were fearful of separation anxiety from many different avenues;

    work – we had both developed successful careers and were used to being depended on, in my case, 24/7.

    Friends – not one of our friends our age could relate to our situation

    Country – culture shock in our new home of Costa Rica

    After 4 months here I can say, it is not that big of a deal. We have found new friends here, rather quickly, and have even found some our age and younger who operate location independent type businesses. One thing that helped us is that we had planned and prepared for our exit over the last 2 years and prepared ourselves for the very worst as far as feelings of separation goes, and it is not THAT bad.

    1. Hey, Greg- Thanks for commenting and sharing your experience! Congrats on early financial independence and retirement!

      We are planning on visiting Costa Rica next year, and it’s certainly on the shortlist of “half-off” places to live. Do you think being in Costa Rica helped you, since there are so many location independent entrepreneurs and retired/semi-retired expats there?

      BTW, I love your definition of retirement on your website. Costa Rican coffee and sunrises sounds ideal!

      1. The expat community here really did help out – before and after our move. There is a definite “pay-it-forward” vibe here and, we have found, almost everyone to be very welcoming. Give me a shout if have any questions about CR – visiting or living here – I am happy to help.

  3. Thanks for the hat tip, Jason!

    I agree that PIRE will help you tell the difference between your co-workers and your true friends. Your true friends will make time for you because you’re worth making time for. It’ll be just like your working days: lunches, evenings, & weekends. The “co-workers” and other working acquaintances will slowly start spacing out the intervals between lunches and just sort of drift on to new things.

    The good news is that you’ll make new friends, both in the community and online. I’ve made dozens of new friends at the beach just by bringing a longboard.

    It’s even possible that you’ll look forward to your expat trips to give your inner introvert a well-deserved break…

    1. I think we’ve already seen that with our moves. It’s the same with the military. You’re forced to change people and locations on a frequent basis, and there are a few people who are worth the effort. Facebook can serve as a proxy for friendship for only so long. But, yes, there will be a shakeup when we hit PIRE.

      You are right in that we meet new people all of the time. Dunbar’s number reigns, and we lose some of the old ties. I’d argue that there’s a smaller subset of Dunbar’s number – the number of meaningful relationships that you can have. I think my Dunbar2 is probably about 25.

  4. I just can’t handle the topic of retirement. Maybe it’s age 45….but although financially I’m close, I have zero desire to stop doing what I’m doing. My goal? Do what I do now from anywhere in the world.

    I just got home from watching Jeanne Robertson (comedian) getting people rolling in the aisles at age 70. I want that “job”…..not retirement.

    1. After all, retirement is the wrong goal for people to shoot for.

      Actually, if I could do anything after PIRE, it would be to work for the United States Soccer Federation. I’d be happy to be the lackey blogger writing up game summaries and scouting opposition. The good thing about PIRE is that I could volunteer. Just have to start networking so I can be the next Grant Wahl or Ian Darke. Oh, and I need to practice my English accent…

  5. We are not planning on retiring as early you Jason but it will still likely be years before our friends and family. I hadn’t thought of any of the items you brought up. Looks like I have some more things to ponder and discuss with my wife.

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