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Early Retirement and The Likelihood of Regret

likelihood of regret

When I discovered the FIRE movement in 2015, I had a pretty good idea I would be ready and able to retire early from medicine at some point.

Crunching numbers and considering some family dynamics, I came up with a roughly five-year plan to retire quite comfortably with a healthy margin of safety.

I enacted that “five-year plan” four years later in the summer of 2019. It seemed like the right time for a variety of reasons.

I didn’t want to retire as soon as I realized that I could; I would have regretted that. Conversely, if I had worked a decade longer than necessary, like this guy did, I’d regrettably still be working in a job that never felt like a true calling to me.

 

When is the best time to retire?

 

First, you must satisfy some pre-requisites:

Financial Independence achieved via saving at least 25x anticipated annual expenses or

• Passive plus active income will cover your expenses

• Career aspirations fulfilled (or willfully abandoned)

• A plan to retire To something.

 

If you can check those boxes, I would say you are ready to consider an early retirement. It’s time to do some soul searching and decide if and when you’ll be truly ready to retire. For me, it was all about minimizing the Likelihood of Regret.

 

Quito Cathedral
Is it time to retire?

 

What is the Likelihood of Regret?

 

There are two distinct likelihoods of regret that must be considered.

  1. The likelihood you’ll regret retiring too soon.
  2. The likelihood you’ll regret working too long.

 

Let’s consider each of these independently.

 

Why might you regret retiring too soon?

 

You could have earned more money.

More money would allow you to have a lower withdrawal rate, allowing you to sleep better at night. Sure, a 4% withdrawal rate works looking backward, but our lives are looking ahead to an uncertain future. A 3% withdrawal rate might make you more comfortable with an early retirement.

More money would allow you to undergo some lifestyle inflation. You may not enjoy the finer things in life right now, but people change. Even you. Even me. My desires are different than they were ten years ago, and I imagine they won’t be the same ten years from now. Or twenty. Or forty.

More money could be used to benefit others. Just imagine how much good could be done with the income from just one more year. How cool would it be to donate $200,000 to a favorite cause? You could use it to start your donor advised fund, if you haven’t already.

 

You may be wearing some golden handcuffs.

I wasn’t fully vested in my employer’s profit sharing and match money until the fall of 2018, which is one reason I worked beyond that date. If I had left sooner, I’d have left a five-figure sum on the table. Those were my golden handcuffs.

Golden handcuffs can come in many forms.

Pensions or pension increases. Provided healthcare when retiring after a certain age. Bonus payments tied to length-of-service or project completion. Golden handcuffs as financial incentives can be psychologically powerful, even for the financially independent.

 

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Life might not change that much anyway.

 

Circumstances may make retiring in the near term less enticing. For example, our boys were in a public gifted and talented “school within a school” that went through 4th grade. With our younger son accelerated one grade, they were only one grade apart.

If I had retired when they were in 1st and 2nd grade, we would have wanted them to continue the program, and we would have been married to that school schedule.

Early retirement for me is all about freedom. Many of the things I’ve got in mind for this early retirement are incompatible with the public school schedule, and we’re now better able to do them while worldschooling.

 

Why might you regret working too long?

 

There is a time opportunity cost.

Unless you absolutely love your job, and would do it for free, you are working in lieu of occupying your days and perhaps nights with something you’d rather be doing.

There is an obvious opportunity cost in terms of time when you’re working, unless there’s truly no place you’d rather be than at work.

 

You don’t want to experience full burnout.

I probably exhibited some mild burnout symptoms, but for the most part, I was reasonably content with my anesthesia job. But burnout is real and increasing, and I didn’t want to experience full-blown burnout personally.

That would have been bad for me, bad for my family, and bad for my patients. If you’ve got the means and are beginning to burn out, it’s best to retire sooner than later.

 

 

Life is short.

On the front lines, physicians see too many patients with devastating health problems that present far too soon. Raise your hand if you’ve lost a colleague, close friend, or family member well before full retirement age. We’ve got a room full of raised hands.

I plan on living a long, healthy life, but I certainly can’t guarantee it. The pandemic has emphasized this point in a way I never could have imagined.

 

Striking a Balance

 

In my analytical mind, I picture the Likelihoods of Regret as lines on a graph with a timeline along the X axis. The likelihood of regretting retiring too soon starts out high and decreases with time. The likelihood of regretting working too long starts low and increases with time.

LoRScale

 

At some point, those lines will intersect. That’s where the magic happens. That’s the best time to retire, at the nadir on the Likelihood of Regret scale.

Identifying the nadir is the tricky part. Clearly, many factors go into what those lines will look like for you, and those lines won’t be static. Family matters and career disturbances may cause sudden shifts in one or both lines.

My lines certainly shifted as I honed in on my final retirement date of August 2019, and my point of intersecting lines moved a bit to the left.

 

What changed?

  • A resident reached out, wanting to work in our small group starting in the summer of 2019.

 

 

Factors That Alter Your Ideal Retirement Date

 

The further out your hypothetical retirement date is, the more likely it is to jump around, and there are a number of factors that could move the dial in either direction.

 

Things that could move it to the right (retire later):

  • A prolonged market downturn
  • A big salary cut, making it more difficult to reach financial goals

 

Things that could move it to the left (retire sooner):

  • A terrible diagnosis with a poor prognosis (for yourself or a family member)
  • Excellent market returns
  • A sudden windfall (inheritance, lotto, 100-bagger investment)
  • New or increased work-related stress
  • A big salary cut, making work not worth the effort

 

Whether you’re looking at an early or standard retirement, I hope you’re able to minimize the likelihood of regretting working too long or of leaving too soon.

It helps to have this mental framework, and I recommend writing out a list of pros and cons of retiring either earlier or later than you currently anticipate.

 

 

What would your lines look like, and where would they intersect? What factors would cause a seismic shift? Are you more likely to regret retiring too soon or working too long?

 

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67 thoughts on “Early Retirement and The Likelihood of Regret”

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  20. Gosh this is a great post and I love the graph (very impressed with your artistic skills btw). Congratulations on your son skipping kindergarten- that’s a huge head start in his life- must be that early reading for him. I bought the book you recommended for our newborn lol, gotta get ready!

    For Australia/ New Zealand are there licensing criteria that you will need to fulfill to work there?

    Reply
  21. When I submitted a guest post to WCI last year about super-saving for an early retirement, I was majorly burned out and laser-focused on reaching my personal “finish line.” At the time, with all my conservative safety-factors built in, that date was 2023. Since then, partly because my practice was bought (sizable payout to the partners) and partly because I couldn’t take full-time work anymore on top of other responsibilities, I cut back to about 80% of my previous clinical schedule.

    That has made a tremendous impact on my mental state. I am so much happier, that I now enjoy my job more than before, and I think it’s possible that my retirement date could be pushed to 2026, when my daughter graduates high school (I know what you mean about having retirement plans that don’t jibe with the public school schedule).

    So going part-time has made me feel better about working longer. The other thing that makes me feel better about working is that I am now FI, and the knowledge that I could give notice tomorrow (if the powers-that-be make even more intrusive demands) is quite liberating. It makes a lot of the annoyances at work less annoying.

    Reply
    • Hello M. Say hi to Q for me!

      I read your post last year, linked here, and just revisited. Thank you for the update! I also finished residency when you & WCI did. You’re ahead of us by a solid million dollars or more, although we have only one income in the household.

      Glad to hear the FI has given you options, and made you feel better about the work that you do. I am glad knowing that I can be done whenever I want, and some days I can’t help but wonder why I subject myself to the stress. Most workdays are just fine, but not all.

      Do you have big plans for the oversized nest egg you could have in 10 years?

      Best,
      -PoF

      Reply
      • Good question. No, I don’t really have big plans for the oversized nest egg. My wife and I have been so frugal for so long, that the bit of purse-string loosening we’ve already done feels extravagant to us. To give an example of how our brains function: we recently took some family out for a swank dinner celebration and dropped a few hundred bucks; we probably won’t go out to an expensive dinner again for weeks, at least. Sure, we could afford to, but it just doesn’t feel right.

        Given my safety-factor upon safety-factor mindset when it comes to our finances, I think the best thing I can do for my sense of long-term financial security is not make big plans for the oversized nest egg. We will travel extensively, for sure, but you’ll probably find me in the back of the plane. 🙂

        Reply
        • …and we’ll be sitting next to you in coach. Just the other day, I canceled our hotel when I found out the “pet friendly” hotel had a $75 Non-refundable fee to have a dog overnight. I had camping gear in the car “just in case.” We skipped the $200 hotel and $75 pet fee, staying in tents in an $18 campsite instead. That’s $257 in my pocket.

          Cheers!
          -PoF

  22. PoF, I don’t have any regrets at all taking an early retirement 3+ years ago.

    Part of my decision process was speaking with older people and asking them if they had any regrets. Want to know the largest one? Not getting enough time spent with their kids while they were young.

    So, I’m really trying to exploit this unique opportunity to play house Dad for awhile at least. It’s an incredible blessing I will never take for granted. Even still the little ones are growing up so fast! 🙂

    Reply
    • Isn’t that the truth! Tomorrow, I’ll have two boys in elementary school. No more pre-school, multiple drop-offs and pickups, and no more paying for school! At least for the next ten years or so.

      I have yet to hear from someone who regretted retiring. I know they’re out there, though. Plenty of docs “fail retirement” because they have allowed themselves to be defined by their careers for so long.

      That has never been, and never will be me.

      Cheers!
      -PoF

      Reply
  23. You’re putting out some high quality content, POF. Well done. Where the career survival lines cross intersect with “first day of the rest of your life” perhaps? Tucked nearly in your back pocket ( when not wearing scrubs ) should be the
    knowledge that you can always take on locum work. Perhaps even to an outdoor nirvana such as Jackson Hole, WY and in the process be treated like “royalty” as oftentimes “temporary” workers…especially of a skilled trade/craft…are treated well and thanked profusely for “filling in”.

    Reply
    • I appreciate that, Jon.

      My scrubs do have a back pocket, actually. That’s where the wallet goes (for all you would be pickpocketers).

      My potential locums “dream job” is waiting for me in New Zealand or Australia. I imagine that’s where we’ll be in a few years. If we were empty nesters at that junction, I’d consider doing more short stints around the states, but with kids living with us for the next 12+ years, that likely won’t be a good option.

      Best,
      -PoF

      Reply
  24. hi I am a regular reader of pof and wci, IM hospitalist 52 years old, no yet at the magic 30x anticipated yearly expenses but am at 20x. I have now decided to work half time starting now and start to ease into cutting work and enjoying life more so that the regret of leaving early is not high (not leaving work cold turkey may be the ideal retirement is to work a little bit anyway) and the regret of not leaving early enough is also not high, what do you think?

    Reply
    • I think that’s great! Why wait to start enjoying life?

      As I mentioned above, I’ve given strong consideration to part time work and have written a couple posts about it (here and here). In my specific situation, it might not be the best choice, but I do understand the appeal.

      Best,
      -PoF

      Reply
  25. I’m more or less like Rob: I don’t necessarily want to retire early. However, having the option available to me to go 3/4 time or part-time is what I am really working toward. I think even if I was to “retire” from being a physician, I would still have other side projects that I would want to continue with (my blog for one), giving lectures to medical students, and probably some kind of other charitable endeavor or creation of a foundation.

    I also am in complete agreement with ChooseBetterLife:

    “Will I feel as though I wasted my education? Will my family and colleagues understand? Will I keep up my licences and board certification in case something happens and I need to re-enter the workforce? Re-entering a medical field is more difficult than many other fields, but the time and expense of renewing licenses, CME, and the alphabet soup certifications and board certifications are no joke either.”

    It would be very difficult to go back to practicing after retiring for even a few years. For that reason, although some may think that we are “saving too much” for early retirement (ie. $3 million in 2025 or $5 million 2035). I think that as a physician you really need to be sure you have enough money to retire on and that is why we’re so conservative with our numbers.

    I plan to write about Pensions in a future post. I think having a pension really helps one plan out their retirement late retirement. The ability to retire before 65 and start some Roth conversions before a pension kicks in at 65 is very helpful to be tax efficient I think.

    Great stuff as always PoF.

    -Sensei

    Reply
    • Thanks for your comments, Sensei!

      It is very true that anything beyond a few months away will require an explanation on every application you fill out, and more than a year away could make it difficult to land another job, particularly those which require hands-on skills.

      I’ll be covering all bases by having substantially more than Enough, some continued active and passive income, maintaining licensure, certifications, CME, etc… for at least a year or two.

      No pension here, but an annuity (SPIA) could be an option later in life. It can provide peace of mind and pretty much guaranteed passive income. By the time I am at an age where it might make sense, I doubt I’ll be cutting it close enough to need that peace of mind, though.

      Best,
      -PoF

      Reply
  26. Nice post.

    Personally, I don’t see FIRE as an all or nothing proposition. I am currently 3/4 time and plan to move to half time in the summer of 2018. I can stay on working like that for quite a while and if I feel like hanging up the stethoscope after a few yrs of that , then I believe that I will be able to. Being in that position gives me tremendous flexibility and makes it where I don’t have to put up with a lot of the annoying parts of my job. That , in my opinion, is power and the definition of FIRE.

    Reply
    • I agree.

      That’s what I’m moving towards. If I can pay most or all my bills with part time work then I plan to let my investments grow until I get really sick of working and putting up with the crap.

      Reply
    • I hear you, Rob. Trust me, I’ve given strong consideration to part time work and have written a couple posts about it (here and here).

      I agree that FI does not equal RE. They are two separate entities. Ideally, if you’re considering the latter, you’ve already achieved the former. It sounds like you’ve harnessed the power of FI to create an ideal job situation.

      Congrats!
      -PoF

      Reply
  27. Congratulations on being so close! That final countdown must be exciting. I’d be thrilled to be within 5 years of retirement. I’m probably 15-18 years away from retirement now, and it feels like a looooong time. I’m sure it will move pretty quickly though.

    Reply
    • Gracias! To be honest, I’m glad to have been blissfully unaware of the FIRE concept until quite recently. It might have been awfully difficult to be plugging away for that length of time if I knew I was saving aggressively with the goal of potentially walking away.

      Best,
      -PoF

      Reply
  28. Great post. Having a plan is indeed the key to a no-regret retirement. I don’t really have a regret about my early retirement @ age 51. I was somewhat golden handcuffed so I had a date to shoot for to take advantage of what was left of a pillaged and very diminished plan. Knowing what I know now in early retirement I just wish I hadn’t stressed so much about the future unknowns before pulling the trigger. Now 6+ years since leaving a long all-encompassing career I now know something I didn’t think about back them. All of the knowledge and skills used to get to FI will still be there to overcome uncertainties with the market, inflation, and other early retirement fears. I can’t say it is a regret because there is no way I could have known any different. I had to live it to know it. I did delay my retirement by a year because of these fears and the fact that it was 2008-2009 time-frame during the recession’s peak with no recovery in sight. But I see it as an unavoidable consequence of the crappy economy and my lack of first-hand FIRE experience. All you really KNOW before you actually retire is your career oriented lifestyle. It is only natural to have some fears of the unknown and total lifestyle change for even the best FI planners.

    Reply
    • Great insight, Tommy. The first ten years are crucial to the long-term plan working out. Based on market conditions, the first 6+ have been excellent for your portfolio.

      Cheers!
      -PoF

      Reply
  29. My biggest concern is a prolonged downturn in the market.

    My concern is we don’t know if that will happen. Studies show that if there is a major downturn within 4 to 5 years of retirement, the earning power will go down significantly.

    Reply
  30. LOVE the chart! Did you create it? It sums things up well. I have no regrets about leaving corporate America at 34. I had originally planned to stay until 40, but I found the greatest outlet of all: blogging! And, I discovered there was the ability to negotiate a severance.

    I didn’t want to lose 3 years of deferred cash and stock comp and this private investment that paid out in 1Q2017, so I had to figure out a way to keep it before leaving.

    If I didn’t negotiate a severance, I would have regretted leaving I think. Or maybe I would have been much more neutral. But to be able to collect a severance that has paid for 5 years of living expenses already feels like Christmas every single time I think of it! And then to be able to write a severance negotiation book and make some money off of that and help other people leave their soul sucking jobs… that’s a win!

    Sam

    Reply
    • Thank you, Sam! I had the Physician on FIRE graphic arts team put that one together. In other words, I opened Photoshop Elements, clicked on the brush, and went to town.

      I’d say you found the key to the golden handcuffs, freed yourself, and melted those handcuffs down to cash in on the precious metal. Keep living the dream and helping others achieve theirs.

      Cheers!
      -PoF

      Reply
  31. The numbers are very important, and there are other factors too. Will I feel as though I wasted my education? Will my family and colleagues understand? Will I keep up my licences and board certification in case something happens and I need to re-enter the workforce? Re-entering a medical field is more difficult than many other fields, but the time and expense of renewing licenses, CME, and the alphabet soup certifications and board certifications are no joke either.

    Reply
  32. As a finance/econ person I appreciate the cost/benefit analysis above. We seem to think alike! Our personal sweet spot is in early 2018, when those two lines get pretty close. We have a daughter who will start elementary school in 2020, so that gives us 2 years to cure our travel bug before we we’ll be pinned down by school schedules.
    As for golden handcuffs, tell me about it! In the finance sector they keep everybody excited and motivated by paying only a so-so salary and then a big bonus every start of the year. There is always the temptation to work for another year to cash in once more. It will take some strength to let go of that. Whether by greed or necessity after a market downturn, 2019 is still possible, even 2020.
    Good luck everybody!

    Reply
    • Congrats on being so close! It’ great that you can be flexible with the date, too.

      The school schedule can be limiting, for sure. We’ll have both boys in elementary school for the next few years. After that, we’re open to trying something different, such as schooling in a different country, or some form of travel / home schooling. I’ve never been a huge fan of the concept (my tax money built those public schools!) but it might work really well for our family, and we’ll have the time to devote to it when FIREd.

      Best,
      PoF

      Reply
  33. I lost two of my friends at work to cancer, both in their 40s. I would rather err on the side of retiring too early than leaving more prime years prisoner to a cubicle. So far I have no regrets. If I start making money on one of my hobbies that would be awesome. And if my future self has a sudden change of heart, he can always take his a** back to work. That’s the beauty of retiring early, doors are not yet shut on restarting a career or venture if you really need some lifestyle inflation, find a new passion, or want to take advantage of a down market. For now, doing exactly what I am doing suits me just fine. 2020 sounds like a great year to start a new chapter!

    Reply
    • Cancer sucks. A hometown friend lost his battle this week, and he’s a couple years younger than me.

      Glad to hear you are living the dream without regrets. I hope I’ll be able to say the same. In medicine, it’s a lot tougher to pick up where you left off after being away for more than a few months. A lot of work goes into maintaining licensure, board certification, skills, etc… I’ll probably hang onto them for a year or so, but beyond that, it might be tough to land a job without some remedial training or other headaches. Of course, there are non-clinical jobs, and jobs that have nothing to do with medicine.

      Best,
      -PoF

      Reply
  34. I like your approach of crunching the numbers and having a plan, but maintaining flexibility and watching for key points that could move the target in either direction. Personally, I am far enough out that I am just saving and investing as much as possible and plan to do an analysis like yours once I am within sight of financial independence.

    Reply
  35. We landed on our summer 2018 date from a few different ways. First, like you, we started out around 2020 and after lots more number crunching realized 2017 would work, but then after her recent job switch, it’s back to 2018. Mrs. SSC always thought 2017 was a real stretch, but I was fine with aiming for it. Haha

    Also, I have golden handcuffs with this new company, so yeah that psychological draw of having multiple long term incentives rack up each year is really compelling and works how they intend it to. So hard to walk away from all of that false wealth. 🙂

    I would say my graph would look exactly like yours, that’s a great graph by the way. As far as the timing getting adjusted to the right, if in 2 more years this schedule and pace of life stay the same, it would be an easier decision to call it one more year and stick around until the 2019 LTI pays out. Extra padding in the account would be nice, and like you, if the schedule wouldn’t change much in FIRE/FFLC then why walk away at that point?

    Things that could move it to the left – Mrs. SSC landing a teaching gig outside of Houston. Talk about jumpstart FFLC! I’d be totally on board with it as long as I got to keep working thru Summer 2017 when the last of my 401k fully vests. Beyond that, I’m ready to jump in with both feet if she finds a good teaching gig somewhere with 4 seasons and topography. 🙂

    Reply
    • Like me, and all of the other commenters, you’ve certainly thought this through. Those golden handcuffs can be tough to unlock. Best of luck on your continued journey towards FFLC. And congrats on the Rockstar Finance feature, right alongside a post of mine yesterday. Pretty cool to see that!

      Cheers!
      -PoF

      Reply
  36. Ms. FP and I have a plan to be in a position to retire by the time we’re in our 40s, but it’s hard to know exactly what our timeline looks like since she’s still in her dental residency for another two years and we have no idea exactly what her income will look like or how starting a practice will impact us.

    We’re definitely looking to save at least 50% of our income however, which, assuming our income assumptions hold, should put us in a position to save six figures a year. At that amount, we should have a good chunk in the bank by the time we’re in our early to mid 40s.

    But all this is pretty general and vague at this point. We’re just not quite in the position to know our target point just yet.

    Reply
    • Good luck in the journey. Living on Half is a surefire way to achieve your goals relatively quickly. I’m guessing you’ll have some solid income from a specialized dentist. I’m the son of a dentist who was also the son of a dentist. That’s a great job.

      Best,
      -PoF

      Reply
      • Sigh-it can be a great job if you have the right personality for it–otherwise, not so much…..

        I went through a residency once I realized I probably would not last long as a general dentist. It allowed me to reach a certain level of net worth in my early 40’s and transitioned to part time for the last few years until kids out of college.

        Without kids and with a better health insurance environment, I would have fully transitioned to something else, something not as soul-sucking…

        Definitely stayed too long, but still stuck for a bit.

        Reply
  37. Thanks for sharing POF! I like your line chart and am unsure where my lines will cross. I’m farther out than you are and plan to have several “encore careers” (my new favorite term today). But I like the way you’ve framed the problem- retire at the point when it’ll cause the least regret which means it’s totally different for each person reading and number agnostic. As I continue to search for my “retirement” date, I’ll keep your chart in mind.

    Reply
  38. For us, the timing of summer 2018 has two factors in play.

    1. Our conservative approach. Two more years will allow us to build additional buffers into our plan. We will start at 3.3% WR in 2018 and four years later reduce that to 2% with a pension that I will get.
    2. Smoother transition for the kids. Eldest would be transitioning to a new school if we would remain in our current area and with our relocation to the mountains, he can start a new school there.

    Agree with you on the prolonged market downturn. A nagging concern for sure, particularly for us in the conservative camp!!

    Some may say we are padding our portfolio but the ability to sleep easy and the psychology behind having a solid plan are worth those extra couple of years. Although I have to say that the date still seems a long way off. Many retirees speak to that phenomenon of the last year or two being the longest. It’s so true.

    Reply
    • Our plans are very similar. The timing for us also revolves around the end of grade school for our eldest, and several “one more years” to allow for a very safe withdrawal rate. Here’s hoping the next few years are good to us!

      Best,
      -PoF

      Reply
  39. I’m a bit further away from retirement than you, but I’ve felt my nadir moving to the left partly because of refinement of various cost and investment estimates. Similar to how you have a big drop in salary listed as both reasons for and against early retirement, I could see a big increase in salary be both a reason for and against. On the one hand it would allow me to boost my investments quicker, while on the other hand it would easy to stick around for one more year (and be a serial offender of it) due to the added luxury/cushion it would offer in retirement.

    That’s exciting to have a specific target in mind, congrats!

    Reply
    • I hear you, Green Swan. I think most of us who have spent a lot of time reading FIRE blogs, and exploring our own idea of retirement have likely seen a shift to the left. A few years ago, I would have guessed I’d be retiring in fifteen to twenty years or more.

      Cheers!
      -PoF

      Reply
  40. A great read as a sit on the inflection point and lean one way or another, depending on my mood, family needs, burnout score, level of inspiration in pursuing Career 2.0, etc.

    Reply
    • Indeed. You might be awfully close to the nadir on your Likelihood of Regret scale as well, VagabondMD. I have a feeling you’ll be working in some capacity for awhile, though.

      Best,
      -PoF

      Reply
  41. Great post and I think your approach is exactly right. I have a problem. I had a preview of early retirement about 18 months ago when I was briefly laid off and then re-hired at my same corporation for about three months. Why is this a problem? Because it was fantastic! I worked out every morning, dropped the kids off at the bus stop, hung out with my wife and looked for business to buy for a few hours in the daytime, practiced guitar for a little bit after lunch and then picked up the kids from the bus stop in the afternoon. The layoff moved my nadir significantly to the left, but I’m nowhere near FI yet.

    The realistic scenario and the one I am shooting for is in 9 years. I’ll be 55 and can get retirement healthcare from my employer. My youngest will have graduated college and the house will be paid off. All three life/insurance milestones converge at that time.

    Now, if I did get a windfall, and it would have to be relatively large, I’d be out much sooner. Maybe immediately with no regrets!

    Reply
    • Good point, Jon. A mini-retirement / sabbatical can give you a taste of what that feels like, leaving you yearning for more. Like a shark that has tasted man’s blood. [Cue Jaws theme… Daaaa dum… Daaaa dum]

      Cheers!
      -PoF

      Reply
  42. Good post POF. We don’t know what the future holds but our timelines seem to match up. Let’s circle back to this topic closer to 2020, at least to know whether we had 20/20 foresight in 2016!

    Reply
    • Cool. I’ll keep my fingers crossed that we don’t have another 2000 or 2008 in the meantime.

      Cheers!
      -PoF

      Reply
  43. Hi PoF. This is a great way to think about it!

    After being job free for nearly a year now, I do have a few thoughts on the ideal retirement point changing: I think it’s going to change all the time.

    I can already see it happening for myself. There’s always days when I regret things, and always days I rejoice at making the FIRE choice. I bounce around that continuum all the time.

    The best advice I have is to tie your life (and emotions) to your personal goals. When things get you down, having something in your life that isn’t about money is important!

    FYI – Congrats on your blog earning you some money!

    Reply
    • Thank you, Mr. Tako. It’s great to hear from someone who has made the leap. Based on what you’ve said, I believe you retired very near that ideal spot with a very low likelihood of regret either way.

      Best,
      -PoF

      Reply

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