Regrets of Retiring Too Late

Of the retirees here that could have retired sooner than they did (~55 or younger), do you wish you pulled the plug earlier??

What did you learn after you retired that would have impacted your decision to leave the workforce earlier, if you knew it?

How much earlier would you have left?

The short answer:
Yes.
Nothing; answer based on a full BS bucket.
<5yrs

The background:
Although DW & I have always LBYM (though not radically), I didn't start thinking seriously about retirement until I was in my early 40s. I read YMOYL and TMND, and a switch went on in my head, after which the pursuit of FI was an overarching goal. At that time, I began to educate myself financially and set a goal of retiring before turning 60 which, as time progressed, morphed into somewhere btwn age 55-60. This is not super early (and much later than many on this forum) but, it was somewhat specific and gave me a tangible goal (I do better with tangible goals).

As time passed, things were going well financially, I still enjoyed my career very much, and projections forecasted that we'd be FI in the early part of that 55-60yo window; then 2008/9 happened. So, we redoubled (ney...tripled) our savings efforts; banking bonuses, saving as much as possible elsewhere, were fortunate to benefit from the post-2009 runup, and were FI by 2012/13. During the last few years, my BS bucket quickly got full, and the time seemed right to FIRE. So, in Summer 2014, we did just that, at age 58 (technically Semi-FIRE since I'm doing a small bit of consulting).

Having been Semi-FIRED (and relocated to what we hope is our long term RE location) for only ~1yr, I can't say that I've learned anything in that one year that would have affected our RE timing decision significantly. What I have learned is that we're loving our new lifestyle. And, I think we could have loved it just as much, with no regrets, several years earlier; as early as age 55 or maybe a year or two earlier. However, any earlier and I feel like I'd have missed out on some of the most satisfying work of my career. So, that's why I say <5yrs earlier than 58.

Of course, that's just our story; everyone is different.

PS: I do want to say that this forum, and the people in it, were a tremendous help to me and very reassuring during trying times. The experience, wisdom, willingness to freely share (both like & contrary views), has been of great benefit to me, and I appreciate it very much. Thank you.
 
PS: I do want to say that this forum, and the people in it, were a tremendous help to me and very reassuring during trying times. The experience, wisdom, willingness to freely share (both like & contrary views), has been of great benefit to me, and I appreciate it very much. Thank you.

+1000
:flowers:
 
I have been doing a lot of research on retirement lately. I could probably write an entire encyclopedia by now...

I have read that one of the biggest regrets of retirement, is retiring too late. They wished they retired earlier. I understand that regret if someone works longer because they do not have the financial ability to retire, and wished they could have retired earlier.

I also understand the mentality of people that work until 67+ and wished they left the workforce earlier, after all, the time remaining is greatly diminished.

There is always the OMY syndrome, which I am in now (303 days left...). I do think it puts a final cap on me ever having to worry about any finances. And it will provide a much better lifestyle than I live now. I am sure others see their OMY that way too. I am already wishing I retired earlier, and I am not yet retired…

Of the retirees here that could have retired sooner than they did (~55 or younger), do you wish you pulled the plug earlier??

What did you learn after you retired that would have impacted your decision to leave the workforce earlier, if you knew it?

How much earlier would you have left?

I enjoy 7 weeks of vacation each year that I can take all at once if I want.

So this definitely will make retiring sooner than later a more difficult choice.

I have older coworkers in their 60s who can retire now but with 7 weeks of vacation and all major holidays and weekends off they are just not that motivated to call it quits.

I definitely would retire sooner than later with no or little vacation time.
 
Dash,
I am in this predicament right now. I'm 55 and really hate my job. to the point where it is making me miserable. For some reason I'm afraid to pull the plug even though I've gone over the numbers every which way to sunday and they say I'd be ok. my main fear is healthcare. My work atmosphere is horrible.
I would like to do something and that's what I'm investigating right now. I think I won't be so fearful if I fell like I have a plan in place.

Thanks for your story though,

Exactly the same as you, my job is getting harder and harder and it is getting me down in a big way. I'm 53 in January and as I sit here now I'm telling myself to pull the plug the day after my birthday. Like you I don't know why I can't pull the plug!! Finances work and I dream of freedom for the rest of my days. I've written the resignation letter but haven't handed it over. I guess I should be bold one morning and bloody well do it!!
 
My company overreacted to the financial blowup of 2008, and they retired everyone over 55 with 25 years' service. It was the best thing that ever happened to me. I'm just glad to have a defined pension, generous 401K program and Cadillac healthcare that included a retiree health savings account that paid my health insurance until 64 years old.

I've seen too many people at our RV campground work until "real" retirement age, only to find their health go south. Their dreams have not come to fruition.

My wife and I are perpetual travelers, and enjoy every minute of our travel lives. We just got in from Scandinavia and Russia last night--and saw so many travelers attempting to walk when their bodies said no.
 
Huston55,
What are the things you read?
I don't know what the acronyms mean....
Thanks....
 
Eileen I think the books are the millionaire next door and Your money or your life. Haven't read either one.
 
Oh, OK, thanks. I've seen both of those at bookstores but haven't read them either.
Have heard others talk about them/read about them online, too.
It's an interesting thread.
 
My company overreacted to the financial blowup of 2008, and they retired everyone over 55 with 25 years' service. It was the best thing that ever happened to me. I'm just glad to have a defined pension, generous 401K program and Cadillac healthcare that included a retiree health savings account that paid my health insurance until 64 years old.

I've seen too many people at our RV campground work until "real" retirement age, only to find their health go south. Their dreams have not come to fruition.

My wife and I are perpetual travelers, and enjoy every minute of our travel lives. We just got in from Scandinavia and Russia last night--and saw so many travelers attempting to walk when their bodies said no.


My thoughts entirely, I want to get out early to mid 50's whilst I still have good health and mind because I love travelling. Certainly don't want a pile of money at 70 years of age and not be able to travel around the world. That 55-70 years of age era is priceless as most people should still be in reasonable shape to still do things. I can't wait!
 
Dash,
I am in this predicament right now. I'm 55 and really hate my job. to the point where it is making me miserable. For some reason I'm afraid to pull the plug even though I've gone over the numbers every which way to sunday and they say I'd be ok. my main fear is healthcare. My work atmosphere is horrible.
I would like to do something and that's what I'm investigating right now. I think I won't be so fearful if I fell like I have a plan in place.

Thanks for your story though,

I retired at 58 (just crossed the 6 year mark this month) and wife joined me a year later at 57. I had jumped to a start up company that went under when the economy did back then. No regrets as I was getting tired of corporate life and this was quite challenging and I loved the problem solving aspect of it. I decided when they went under that my desire to retire early was passing me by (we had lived below our means and our savings was more than enough to pull it off - well before 58). The engineering side of that business picked up where the original company left off in bankruptcy, and I have been doing part-time consulting work for them +4 years now..

I had always told myself that my goals in life were to get out of debt by 35 and retire at 45. Lofty goals for someone in their 20's, but you have to have a plan or you'll just wander until it hits you. Was out of debt by 37, but retiring at 45 was questionable - even though I made my financial goal. The work a day world was very good to me and I always made a good living. Our savings are enough to live off of for the rest of our lives (no pensions or annuities).

It was difficult to retire as I had to fight the feeling back then that people who saw me out during the work week saw me as unemployed (a lot were back then). That went away quickly...

I also struggled with the healthcare coverage issue when deciding to retire early (back before the ACA was in place). It was actually cheaper back then, but wife and I both had permanent exclusions to our coverage. After I struggled with it six ways from Sunday - I came to the conclusion that it was impossible to get myself feeling comfortable with healthcare coverage. There were a lot of areas where it would be game over - and it would significantly hit our retirement savings. What made it possible for me to pull the plug was that this scenario was "fact" - whether we were retired or not. We do our best and hope that our health holds out for a long time. We have changed our eating habits and are much more active in retirement. I do wish we had retired sooner, but the 45 goal was not comfortable when I crossed that threshold - however 55 was very doable.

Over the years, I've watched more than a few people hit the game over scenario (retired and working), and told myself I wanted to retire early while I was still able to enjoy retirement. My parents died early (Mom at 39 cancer, and Dad at 59 heart attack). Wife's parents retired at normal retirement age and made it into their 70's, but both struggled with health issues all along the way (actually before retirement). Retirement traveling was severely hampered for them and eventually became impossible.

Our good friend and neighbor who lived across the street from us got sick right before he retired at 66 (was forced due to health issues) just under 2 years ago, and passed away this May. Had moved to Georgia to be near their kids, but he went quickly into bedridden and his retirement life was deteriorating in a hospice bed at home. Was not a pretty site when we stopped by to visit this March, on our way back from wintering in Florida this year. Financially, everything was not covered under Medicare.

Our neighborhood is a 12 year old gated retirement community of town homes and single family homes. We bought a SFH here 9 years ago when I was 55, and planned to stay for 5 years (economy has us still below original builder discounted purchase price - community completed just when economy tanked). There have been many changes on just our street (last street to be built out in subdivision) - people going into nursing homes and dying. The ambulance siren is a normal occurrence in a community like this one. Life is short - especially when you have more years behind you than in front of you. Enjoy it while you can (and as early as you can) - you never know.......
 
Last edited:
I semi-retired at 58 & that was perfect for me. I work at home about 10 hours/week doing something that I love. 3 years later I have no regrets. I started my career later in life then most people due to getting married & having kids young & then going to college & grad school, etc. I really enjoyed my career. I have seen bad things happen to people so I think it is important to not work too long but do what feels right to you.
 
Certainly don't want a pile of money at 70 years of age and not be able to travel around the world. That 55-70 years of age era is priceless as most people should still be in reasonable shape to still do things. I can't wait!

+1

That was it for me, except "traveling" is more local and very active (cycling, kayaking, skiing, birding, etc.). The fact that I hated my j*b the last few years awakened me to the reality that time is passing and I wanted to spend 15-20 years with DW actively living our passions. I didn't want to further increase the risk that time was running out...

Much of w*rk was good, but ER has been great! :dance:
 
+1

That was it for me, except "traveling" is more local and very active (cycling, kayaking, skiing, birding, etc.). The fact that I hated my j*b the last few years awakened me to the reality that time is passing and I wanted to spend 15-20 years with DW actively living our passions. I didn't want to further increase the risk that time was running out...

Much of w*rk was good, but ER has been great! :dance:

+1

Well said.
 
Related elsewhere, I was FI at 51 but waited until 58. I had w*rked my way to my "dream" j*b and still enjoyed it - until it changed. Then I was gone with 4 days notice (official one month notice, including accrued vacation so I could/would still be contacted with "issues.") At 51, my modest pension would have been considerably more modest and my stash would have been significantly more modest as well. Still we could have pulled it off.

Other issues included still having kids at home. Our goal was to move 5000 miles upon retirement. That was not practical until the last kid was well entrenched at University.

So, regrets, not really. I could take the occasional 6 week vacation while still w*rking. Most of the stuff we wanted to do in retirement (except move 5000 miles away) we could do while still w*rking. Time is a funny thing. It can be wasted or enjoyed, but, for me at least, I see no particular advantage of thinking what "might have been." Instead, I try to see what MORE we can now do with the time remaining because we do actually have a much better financial situation - beyond the FI we had at 51. As always, YMMV.
 
DW and I had the conversation with both of us age 43. Calculated we could retire at absolute soonest when she turned 50. Some have written of the "penalty" for opting out of a pension system before a certain age and "paying" x% forever after. We looked at getting out the first year possible as an Opportunity. Now fast forward a decade. I turned 60 this year and have immensely enjoyed 10 years of doing whatever the heck I want with DW each and everyday.

We certainly have chosen to live on less than some, but we have wanted for nothing. Planning ahead to have a paid for home, paid for cars, helps. However we hardly would consider ourselves LBYM's types. So we essentially have a comfortable relatively fixed income (with the bonus of SS as a future enhancement), therefore no regrets. Couldn't have got out any earlier, so glad we didn't wait till later.

You can't get those years back.

Seldom sure what day it is. Value? Priceless
 
DW and I had the conversation with both of us age 43. Calculated we could retire at absolute soonest when she turned 50. Some have written of the "penalty" for opting out of a pension system before a certain age and "paying" x% forever after. We looked at getting out the first year possible as an Opportunity. Now fast forward a decade. I turned 60 this year and have immensely enjoyed 10 years of doing whatever the heck I want with DW each and everyday.

We certainly have chosen to live on less than some, but we have wanted for nothing. Planning ahead to have a paid for home, paid for cars, helps. However we hardly would consider ourselves LBYM's types. So we essentially have a comfortable relatively fixed income (with the bonus of SS as a future enhancement), therefore no regrets. Couldn't have got out any earlier, so glad we didn't wait till later.

You can't get those years back.

Seldom sure what day it is. Value? Priceless

+1

Couldn't have said it any better JohnnyM! We FIRED ourselves just about 7 months ago and now life is great :dance:

Overall, we have always LBYM, but we have splurged in specific areas that follow our passions. Since we FIRED so early, we have a limited capacity to pay for expensive toys and fancy trips, at least compared to our days in the w*rkforce. However, our appetite of such stuff has greatly diminished since purchasing our freedom.

Our toys are now older but now serve us even better since we have time to enjoy them. Local fun and friends keep us busy, and we feel much less of a need to escape through expensive vacations.

Time and freedom are most precious to us. It's encouraging that you and DW also felt this way and still do after a decade of ER. You guys and others like you are my heroes! Couldn't find any such folks to admire in the w*rkforce...
 
Last edited:
I always wanted to retire at 18 like a couple of acquaintances. Inspired by them, I only had to work another 40 years.
 
Back
Top Bottom