Early Retirement and The Likelihood of Regret

M.D. Financial Services

When this blog was first conceived sometime last year, I had a pretty good idea I would be ready and able to retire early at some point. Crunching numbers and considering some family dynamics, I came up with a five to six year plan to retire quite comfortably with a healthy margin of safety.

Seven months into this venture, I have done a lot, lot more number crunching, brainstorming, and talking with my wife about our future. The five or six year plan has essentially been cut in half. I’m thinking more in terms of a two and a half to three year plan, with perhaps an additional year working abroad.


When is the best time to retire?


First, you must satisfy some pre-requisites:
Financial Independence achieved 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’s 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 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’ll be fully vested in my employer’s profit sharing and match money in about two and a half years, which is one reason that is the minimum amount of time I intend to continue working. If I leave sooner, I’ll be leaving a high five-figure sum on the table. Those are 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.

Life might not change that much anyway.

Circumstances may make retiring in the near term less enticing. Our boys are in a public gifted and talented “school within a school” and can be for several more years.

If I were to retire now, we would want them to continue the program, and we will be married to that school schedule. Early retirement for me is all about freedom. My awesome early retirement ideas are incompatible with the public school schedule.


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’ve probably exhibited some mild burnout symptoms, but for the most part, I’m reasonably content with my job. But burnout is real and increasing, and I wouldn’t want to experience it personally. That would be 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, we 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.


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.



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 have certainly shifted over the course of the last year, and my nadir has moved to the left.

What changed?

  • I’ve begun to form some more definitive post-retirement plans.
  • My younger son is skipping kindergarten. Time warp!
  • We sold our oversized former home last fall, eliminating our last debt.
  • I’ve started to realize a small blog income, even after the charitable mission and expenses have been covered.
  • I discovered a love of writing, which could become a part time encore career.


Will my ideal retirement point change again?


It could.


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

  • A prolonged market downturn
  • Real or perceived need for higher future spending
  • Significant Lifestyle Inflation
  • A big salary cut, making it more difficult to reach my financial goals

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

  • A terrible diagnosis with a poor prognosis (for myself or a family member)
  • Excellent market returns
  • A sudden windfall (inheritance, lotto (which I don’t play))
  • New or increased work-related stress
  • A big salary cut, making work not worth the effort

If anything changes in our timeline, I’ll be sure to let you know. As of now, I’m targeting the summer of 2019 to leave my current full time job. New Zealand and / or Australia beckon, and I could see myself working there another year or more.

I guess I now have 2020 vision for my early retirement.

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?


I use Republic Wireless. I pay closer to $25 a month for 2 lines. Lots of new phones available!


  • 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!

  • 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!

    • 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.


  • 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!

    • 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]


  • 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.

  • The Green Swan

    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!

    • 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.


  • 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.

  • 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. 🙂

  • Matt @ Optimize Your Life

    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.

  • 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.

  • 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.

    • 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.


  • Mr Crazy Kicks

    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!

    • 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.


    • Anonymous

      A very good point.

  • 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!

    • 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.


  • ChooseBetterLife

    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.

  • 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!


    • 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.


  • Anonymous

    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.

  • 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.

  • 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.

    • 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.


  • Rob

    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.

    • Anonymous

      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.

    • 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.


  • 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.


    • 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.


  • neeraj Vij MDPLLC

    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?

    • 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.


  • Jon

    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”.

    • 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.


  • Michael @ Financially Alert

    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! 🙂

    • 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.


  • M

    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.

    • 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?


      • M

        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. 🙂

        • …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.


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