55 and Ready to Cash in the Chips

Thx. Believe me, I don't feel the least bit bad for leaving nor do I feel indispensable. I've only been at this place a year so I can be replaced very easily. Its more the psychology of walking away from the year end numbers. Even though logically I recognize it is a very small percentage of my current savings and long term would most likely be immaterial.
Many of us (me included) have suffered from the OMY syndrome. (One More Year) I stayed on 2 years longer than I really should have. Sure wish I had that time back now. But of course, only you can make that decision.
 
You can always make more money, you can not make more time.
Go now, enjoy your summer and start living the retirement life you dreamed and worked for!
 
You can always make more money, you can not make more time.
Not sure that I agree. Ask a somewhat ossified middle-manager who recently got downsized, how goes the prospect of being able to make more money. Sure, if he has a large portfolio, we can gamely call a layoff a forced segue into early retirement. That's a nice position in which to be. Many of us aim for it. But it's not the same as being able to make more money. Sometimes our money-making prowess is fragile. One oops, one bad quarter, and we're done... with no second chance.

What about making more time? Here too, it's situational. Why delay that vacation until retirement? Take leave without pay, if necessary. Prioritize family instead of work. Quiet-quit. There's plenty of time, if one chooses to make it. Just like there's plenty of cash to be saved, if one chooses to prioritize savings.

From my current vantage point, I'd much rather have more money, than more time. Money, I know how to save (which in my book, is putting it to good use). Time, I generally waste.
 
Based on the details you’ve provided, you’re financially able to retire. But the decision to retire is more than just a financial decision.

There’s something I’ve noticed after following retirement based content for years now. This idea of working one more year is common. It’s also easy to repeat the cycle. One more year can easily become 2-5 more years.

There could be multiple reasons for this but my guess is that it comes down to a couple of factors. The financial incentives that make working one more year tempting will still be available for the next year.

There’s a fear involved in shutting off the consistent paycheck. And there’s a natural fear of the unknown and for anyone who’s worked their whole life, retirement is a big unknown.

I’m in a similar situation but with lower numbers. I can retire today but will probably work until the end of this year or the spring of next year. My wife and I are mainly worried about travel expenses being more than we expected so we’re willing to work a little longer.

It’s a trade off that you must accept: working longer provides more of a financial benefit at the expense of having less time to spend that money and enjoy your retirement. Just know that you aren’t trading an average year of retirement for this additional income, you are trading an early retirement year where you are healthier and more likely to be able to do more activities.

The common feedback that you will see from people who have been retired for years can be summed up in two points:

- “I wish I had retired sooner.”

And

- “I worried too much about the money before retiring.”

That was a very telling trend for me to recognize. It will also keep me from working past the 1st quarter of 2027 no matter how much money I will be leaving on the table.

My advice to you is don’t just look at the cost of leaving work. Factor in the costs involved with the decision to continue to work. Those are real costs that shouldn’t be ignored.
 
You're obviously undecided and struggling with the decision at this time, so why not "test drive" retirement by taking FMLA for several weeks due to the family issues you mentioned? Then decide.
 
Thx. Believe me, I don't feel the least bit bad for leaving nor do I feel indispensable. I've only been at this place a year so I can be replaced very easily. Its more the psychology of walking away from the year end numbers. Even though logically I recognize it is a very small percentage of my current savings and long term would most likely be immaterial.
Given the way that your employer's golden handcuffs are structured and the timing of awards is there ever a point of time that you wouldn't be leaving money on the table? IME, one is always leaving money on the table.

Our year end was June 30 and IIRC bonuses were paid out in October so if you put in your notice the day after bonuses were paid and gave a month's notice you would still be leaving 5-1/2 months on the table. While I guess in theory one would be eligible for a bonus as long as you were on payroll on June 30, even though the firm was always fair to me I thought that if I left after July 1 that they might not pay the bonus that I had "earned" so I waited until the bonus had been paid before giving notice.

When combined with other things going on in my life, I gave notice in November, worked through late December and was on vacation from then until March 1 as I recall so I left about 1/2 year on the table. C'est la vie!
 
Tough decision for sure. I too am getting close to that point. The difference for me is that since 2021 my job went from being stressful to having little stress thanks to a new position. I would have retired by 2022 if not for that. You probably know you can easily retire now. But I would highly consider the stress you are under, stress only kills you early. The 9 or so months will go really fast but if the stress is bad enough, or even just uncomfortable, just let it go. Hope this helps
 
That $125,000 represents less than 2% of your net worth. After taxes and deductions probably closer to 1%. Is a 1% difference in your net worth enough of a difference to work longer?

You already know the answer.
 
I retired at age 68 in Oct 2026 from a job where I had peak earnings, a relatively enjoyable role and I left low 7-figures on the table (RSU, ESPP price lock, 4-year vest). While I was performing at a high level and not in danger of being aged out my wife convinced me to forget about the money and think about the limited time I have left to enjoy what we accumulated. I can tell you from my personal experience that leaving that money on the table has not been an issue at all after 9 months of retirement, never even thought about it. It is not life-changing money for us but it was a lot of money. We are very busy with a remodel so there is no shortage of things to stay occupied with.

But, one huge bonus for me personally is I started an options wheel strategy, mostly on a portion of my IRA and Roth (approximately 2.5M basis) so taxes are all deferred. I'm using +-.2 delta, 3-10 days out and averaging $38K/month in options premiums. I'm paying a loss (assigned stock runs or tanks vs buy&hold) of roughly 6% during these 9 months but that was expected. The bottom line is these options premiums are real cash, deposited into the account so there is no murkiness regarding the cashflow. I am indifferent to holding cash or owning the equity.
 
Not sure that I agree. Ask a somewhat ossified middle-manager who recently got downsized, how goes the prospect of being able to make more money. Sure, if he has a large portfolio, we can gamely call a layoff a forced segue into early retirement. That's a nice position in which to be. Many of us aim for it. But it's not the same as being able to make more money. Sometimes our money-making prowess is fragile. One oops, one bad quarter, and we're done... with no second chance.

What about making more time? Here too, it's situational. Why delay that vacation until retirement? Take leave without pay, if necessary. Prioritize family instead of work. Quiet-quit. There's plenty of time, if one chooses to make it. Just like there's plenty of cash to be saved, if one chooses to prioritize savings.

From my current vantage point, I'd much rather have more money, than more time. Money, I know how to save (which in my book, is putting it to good use). Time, I generally waste.
I tend to agree with your sentiment and statements, however, "Time, I generally waste" resonated very strongly with me when I was contemplating retirement before pulling the trigger last year. I was in a good role on the critical path and my efforts generated product revenue so it was materially contributing to the GNP, at least psychologically. I felt my time was not being wasted in a macroeconomic sense because I felt I was performing productive work for the overall economy. With that bolstering my ego it was difficult to conceive not being productive and switching to unemployment and retirement. I felt I was wasting time when I wasn't working and producing. I guess that is a defense mechanism to keep me gainfully employed in my adult life or something.

When I retired and walked away I never felt guilt or remorse about not working anymore. The adjustment happened the first Monday of retirement while not driving to the office. It was immediate and without friction. Kind of surprised me, to be honest. I thought I would have withdrawal or something but it didn't happen. I can't say it feels good or bad, it just is what it is and I'm satisfied that every day I wake up is like Saturday.

I still wake early and started going to the gym for 2 hours every morning. A1C is slowly coming down and I'm bench pressing 170lb now (I benched 300lb in high school). When I started I could barely bench 90lb and it was painful. I'm doing 5 machines (bench, tricep, curl, bar dip, abdominal lift) plus stair climbing for cardio. I've worked up to 90 reps in sets of 5 reps twice in progression for each machine so it is a little time consuming but relatively safe from injury this way. I bought a clicker/counter to keep track of my reps. My muscle definition is progressing but at a very slow rate given my age but friends have noticed the change.

So, at least 2 hours a day is not time I'm wasting and I never had this time when I was working and trying to tend to family obligations.
 
A few data points for you:
1) I retired the same day (at 55) that another guy at w*rk did (at 65). He made it less than 2.5 years before dying.
2) A good friend retired at 65 and I have been having a hard time reaching him lately. He called me today and told me about his surgery and the intense pain he has been in. This sometimes happens when you get old.
3) Neither of these people had anywhere close to $5.5M.
4) Leaving at 55 was one of the best things I have ever done. No regretting it in the least. I look back on it now and wish I would have left sooner. You will too...
 
First, your numbers look really good. No doubt you can make that work. Certainly I get the guilty feeling; that's old habits dying hard, basically.

But I love what a couple have said above, about taking some time off and seeing how you feel at the end of it — eager to return to work or dreading it? In hindsight, that was a huge moment for me; I can even pinpoint the exact moment (on a vacation when its end felt waaaayyy too soon). You will know the real answer. It sounds like ... you know the real answer.
 
Hi All,
Currently evaluating if I should retire this July, or go through another 7 months to get the year-end bonus and stock vesting and then retire in Jan 2027. I would stay until Jan but I am feeling mentally checked-out and very tired from corporate stress/ commute etc., and I also have some family / personal matters that would benefit from more of my time this summer. My situation:

- 55yo married (wife 53) with about $5.5m in investable assets (half of this is in retirement accounts) and paid-off home worth about 950K
- Of the 5.5m about 1m in HY cash/cds to help mitigate sequence of return risk in the early years
- I can also access recent 401k (rule of 55) without penalty as needed (~600k)
- Annual expenses in retirement of $150k (includes healthcare for my wife and me)
- Two adult children - one just graduated college and has job/benefits, one finishing in couple years (paid off from fully-funded 529 plan).
- Corporate gig in financial services is stressful and I don't have mental stamina to continue much longer. The bonus and stock vesting at year end is about $125k after taxes. Plus the remaining 7 months of salary and benefits.
- Our plan is to sell our home in the northeast and move asap to more tax friendly and warmer state (FL, Tenn, SC) and begin Roth conversions in 2027. We would rent initially before buying property.
- Social security is close to max for me, wife works part time and spousal benefit would likely be higher for her.

I hate the idea of "leaving money on the table", but basically that will always be the case as there is always another bonus, another stock vesting with the job. While the math / models shows high confidence that my savings will support our expenses for 35+ years, I am feeling guilty to leave early in July and give up the nice paycheck and benefits. I also would feel badly to "quiet quit" or just coast to Jan as it would screw over my team. Hard to shake the accumulation mindset, but I also feel like trading these months in our relatively healthy years now to make an amount that is only a couple percent of our total is not a wise trade either. I'm thinking I will regret whichever decision I make on this. Any words of wisdom? Thx
I would retire. Life is too short. You have plenty of money.
 
When I retired and walked away I never felt guilt or remorse about not working anymore. The adjustment happened the first Monday of retirement while not driving to the office. It was immediate and without friction. ...
You retired at 68, correct? A lot of folks joining the Forum and contemplating retirement are 50-55, a full half-generation younger than you were, at point of retirement. They're going to have more soul-searching and more contemplative deliberation, even if they're fully prepared financially. You were ready. You knew that you were ready... so, you took action. You have no regrets.

Even the fellow who retires at 80, is leaving money on the table, compared to his colleague, who collapses in his executive-chair at 85. Whether it's a pro-athlete who retires at 28, or the lawyer who makes his final court appearance at 88, we all face opportunity cost. We all face the question of how to occupy our time post-retirement. We all face the what-ifs of career advancement left unpursued. And so on.

The older that we get, the smaller this opportunity cost. There is less questioning about whether we're right. We fit-in better with the modern white-collar-professional narrative (doctor/lawyer/scientist/engineer) that meaningful formal remunerative work needs to be pursued at long as possible, but the imperative ends at some canonical age... so, if we exceed that age, or at least closely approach it, we're good. And if not, not.
 
Hi All,
Currently evaluating if I should retire this July, or go through another 7 months to get the year-end bonus and stock vesting and then retire in Jan 2027. I would stay until Jan but I am feeling mentally checked-out and very tired from corporate stress/ commute etc., and I also have some family / personal matters that would benefit from more of my time this summer. My situation:

- 55yo married (wife 53) with about $5.5m in investable assets (half of this is in retirement accounts) and paid-off home worth about 950K
4% of 5.5M is $220K. Way more than enough to cover your annual expenses even if you don't have a pension.
Leave it. Immediately. Do yourself and your loved ones a lot of good. They will be annoyed at having to replace you because it is an inconvenience, but beyond your immediate team and supervisor (maybe!) no one will care. And you will be quickly replaced at that salary.
FC
 
You retired at 68, correct? A lot of folks joining the Forum and contemplating retirement are 50-55, a full half-generation younger than you were, at point of retirement. They're going to have more soul-searching and more contemplative deliberation, even if they're fully prepared financially. You were ready. You knew that you were ready... so, you took action. You have no regrets.

Even the fellow who retires at 80, is leaving money on the table, compared to his colleague, who collapses in his executive-chair at 85. Whether it's a pro-athlete who retires at 28, or the lawyer who makes his final court appearance at 88, we all face opportunity cost. We all face the question of how to occupy our time post-retirement. We all face the what-ifs of career advancement left unpursued. And so on.

The older that we get, the smaller this opportunity cost. There is less questioning about whether we're right. We fit-in better with the modern white-collar-professional narrative (doctor/lawyer/scientist/engineer) that meaningful formal remunerative work needs to be pursued at long as possible, but the imperative ends at some canonical age... so, if we exceed that age, or at least closely approach it, we're good. And if not, not.
Well said. I was in a very enviable position at age 68. Peak earnings, satisfying role, minimal politics and BS, on the critical path and not just in an overhead role, high productivity reflected in reviews and metrics, voluntarily working 10+ hours/day by choice and most importantly, a good team around me with no troublemakers or noise. It was not a country club and the environment was very intense and pressure-packed, so don't get me wrong, but I found I functioned well in that environment. My wife convinced me to leave as I would never have left without her telling me it was time. Once I decided to leave a year prior things became incredibly enjoyable. I did not announce it to anyone until about 3 months prior and it was only because my manager was reviewing our roadmap and assigning me to various projects moving forward. At that point I felt it was my professional duty to let him know even though I really wanted to do it (resignation) 2 weeks prior to my target date. I spent those last 3 months working as hard as I ever worked in my life making sure everything was documented and turned over properly. My last day of work on a Friday had me in the office until 7PM attending one final meeting and this was on a Friday when my badge had already been disabled at 6PM. We all got a good laugh about that when I finally peeled myself away and said goodbye for the last time. I couldn't have scripted it any better than it turned out.

One amusing thing, like that pitcher who thinks he has one more strikeout in his arm or the receiver who feels he has one more game winning touchdown catch, I felt I still have a few more lines of code, another key troubleshooting victory or one more useful presentation to give when I walked away. The following Monday I no longer felt I had it and the thought of going back and fixing a problem or something was just so foreign to me when I woke up. I had successfully shutdown the mature, aging operating system gracefully, never to be booted up again.

I still write code and check it into my private repo but it is all for me now and deliverable to nobody or no organization. I think the imperative ended quite smoothly in my case.
 
Hi All,
Currently evaluating if I should retire this July, or go through another 7 months to get the year-end bonus and stock vesting and then retire in Jan 2027. I would stay until Jan but I am feeling mentally checked-out and very tired from corporate stress/ commute etc., and I also have some family / personal matters that would benefit from more of my time this summer. My situation:

- 55yo married (wife 53) with about $5.5m in investable assets (half of this is in retirement accounts) and paid-off home worth about 950K
- Of the 5.5m about 1m in HY cash/cds to help mitigate sequence of return risk in the early years
- I can also access recent 401k (rule of 55) without penalty as needed (~600k)
- Annual expenses in retirement of $150k (includes healthcare for my wife and me)
- Two adult children - one just graduated college and has job/benefits, one finishing in couple years (paid off from fully-funded 529 plan).
- Corporate gig in financial services is stressful and I don't have mental stamina to continue much longer. The bonus and stock vesting at year end is about $125k after taxes. Plus the remaining 7 months of salary and benefits.
- Our plan is to sell our home in the northeast and move asap to more tax friendly and warmer state (FL, Tenn, SC) and begin Roth conversions in 2027. We would rent initially before buying property.
- Social security is close to max for me, wife works part time and spousal benefit would likely be higher for her.

I hate the idea of "leaving money on the table", but basically that will always be the case as there is always another bonus, another stock vesting with the job. While the math / models shows high confidence that my savings will support our expenses for 35+ years, I am feeling guilty to leave early in July and give up the nice paycheck and benefits. I also would feel badly to "quiet quit" or just coast to Jan as it would screw over my team. Hard to shake the accumulation mindset, but I also feel like trading these months in our relatively healthy years now to make an amount that is only a couple percent of our total is not a wise trade either. I'm thinking I will regret whichever decision I make on this. Any words of wisdom? Thx
The question is "What will you do for the six months remaining in 2026" if you pull the plug now?
Retirement is important if you have things you want to do besides work - not just to escape it.
 
Wow, nice! Either path you take is a win.

I’m in a similar boat, except my youngest still has one more lap to run in high school before launching into college, so I’m hanging on until bonus season. Fortunately, my job isn’t stressing me out, so I can afford to loiter a bit longer.

The universe is handing you an early exit wrapped in gold foil so hit the eject button and start sipping the sweet nectar of your own hard‑earned fruit.

Good luck!
 
What do envision retirement looking like? Do you have plans or are you okay with just sitting around? If you are moving to a new area, are you leaving friends and family? Are you comfortable making new friends? The money is not the issue, but it sounds like you are planning on changing your whole world at once. So the question is are you mentally and emotionally ready to retire?
 
Hi All,
Currently evaluating if I should retire this July, or go through another 7 months to get the year-end bonus and stock vesting and then retire in Jan 2027. I would stay until Jan but I am feeling mentally checked-out and very tired from corporate stress/ commute etc., and I also have some family / personal matters that would benefit from more of my time this summer. My situation:

- 55yo married (wife 53) with about $5.5m in investable assets (half of this is in retirement accounts) and paid-off home worth about 950K
- Of the 5.5m about 1m in HY cash/cds to help mitigate sequence of return risk in the early years
- I can also access recent 401k (rule of 55) without penalty as needed (~600k)
- Annual expenses in retirement of $150k (includes healthcare for my wife and me)
- Two adult children - one just graduated college and has job/benefits, one finishing in couple years (paid off from fully-funded 529 plan).
- Corporate gig in financial services is stressful and I don't have mental stamina to continue much longer. The bonus and stock vesting at year end is about $125k after taxes. Plus the remaining 7 months of salary and benefits.
- Our plan is to sell our home in the northeast and move asap to more tax friendly and warmer state (FL, Tenn, SC) and begin Roth conversions in 2027. We would rent initially before buying property.
- Social security is close to max for me, wife works part time and spousal benefit would likely be higher for her.

I hate the idea of "leaving money on the table", but basically that will always be the case as there is always another bonus, another stock vesting with the job. While the math / models shows high confidence that my savings will support our expenses for 35+ years, I am feeling guilty to leave early in July and give up the nice paycheck and benefits. I also would feel badly to "quiet quit" or just coast to Jan as it would screw over my team. Hard to shake the accumulation mindset, but I also feel like trading these months in our relatively healthy years now to make an amount that is only a couple percent of our total is not a wise trade either. I'm thinking I will regret whichever decision I make on this. Any words of wisdom? Thx
From a 54-year-old that pulled the plug last summer, I am glad I did it instead of giving away six months to my corporate role.

Financially, you are in a better position than I was when I walked away.

Not sure a couple of hundred thousand changes your life all that much but wish you luck with your decision.
 
Out of curiosity, when do you consider it "worth it" to stay? I’m in a similar situation to the author but younger and with less saved; mid-40s, $4.5M NW, $130k spend, no kids, and DW wants to keep working indefinitely making <$100k before tax.

I’m currently debating whether to work 3 more months to grab an extra $85k (after tax). The job is low-stress but unfulfilling, and staying means burning the whole summer. Obviously, everyone has a price where they’d stay, but where do you draw the line when you’re already financially set?

I almost resigned this week but chickened out, and now I’m caught in analysis paralysis...
 
Aston242,
If you retire now, I bet DW will be able to generate a long honey do list that will keep you tied up for years, with no pay. Is this what you want?
 
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