Retire at 58 w/ $4M or retire at 60 w/ $5M?

All that said, I am aware jobs like this take a toll. A co-worker who had a similar role retired last year says he loves every day of retirement but never understood how much stress he was under at work until he retired.

I said the same thing. I retired suddenly. The stress relief was instant. Sadly every day for a while they'd call with questions and that feeling came right back. I had absolutely no idea how incredibly awful it was until I retired. Then I blocked calls and emails. Finally, some real peace.

I knew it was stressful. I took it all in stride, performed as best I could under pressure. But the signs were there. Health took a very rough turn towards the end. They used me up and spit me out.
 
I said the same thing. I retired suddenly. The stress relief was instant. Sadly every day for a while they'd call with questions and that feeling came right back. I had absolutely no idea how incredibly awful it was until I retired. Then I blocked calls and emails. Finally, some real peace.

I knew it was stressful. I took it all in stride, performed as best I could under pressure. But the signs were there. Health took a very rough turn towards the end. They used me up and spit me out.
I would have been tempted to say "Every question I take is $100. Every answer is negotiable."
 
All that said, I am aware jobs like this take a toll. A co-worker who had a similar role retired last year says he loves every day of retirement but never understood how much stress he was under at work until he retired.
Many factors led me to pull the pin and get out. One of them was that I was curious who I would be if I wasn't under loads of work stress.

I really like being out of the stress.
I sleep better.
I exercise better.
I (think) I'm easier to live with.

And I don't miss the work environment at all.
 
Great responses on this post! I am 53 and FI. Have not pulled the trigger on the RE but you all have given me a lot to think about.

I never really considered RE until I hit 50 so must be something about this age.

I have had this same debate in my mind regarding if I put in another couple years, what is it going to mean. I have run the retirement calculators and talked with a financial advisor, and it all says that we are in really good shape. It is a really tough mental and emotional hurdle to get over.
 
I was in a similar position. Made the decision to retire at 58/59 rather than continue in the corporate world.

Our net worth increased substantially in the first 10 years post retirement. Equity investments more than doubled.

I was not ready to retire. Then, almost suddenly it seemed, I looked at my spouse and said I was ready. I was fed up with deadlines, travel, staff issues...you name it. Discussed and planned our retirement lifestyle changes over the next few months, then pulled the plug.

Four months later we were homeless and traveling internationally for nine months. It happened that fast. We had to pinch ourselves at our good fortune and for making an early retirement decision when we were ready for it. We never looked back.

I believe what made the lifestyle transition relatively easy for us is that we have both always believed in moving forward with our lives, embracing change. We both have always had 'why not' attitude to life.

I say do it if you are ready, if you have the resources, and if you have the desire. Will the increase in your equity make a difference when you are 85? And even if it does, so what?
 
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I have had this same debate in my mind regarding if I put in another couple years, what is it going to mean. I have run the retirement calculators and talked with a financial advisor, and it all says that we are in really good shape. It is a really tough mental and emotional hurdle to get over.
If you're already FI, then the additional contributions to savings, from OMY of working, won't noticeably affect the portfolio. Undulations in the market will have a much more significant effect.

But in our 50s, OMY does mean closing the gap between the present and eligibility for defined-benefit programs (workplace pension, SS, Medicare), and thus the psychological gap between "I'm tired of working, and want out" and "I've done canonically enough, and can now justify getting out".
 
OP - if you’re going to work another two years to add another $1m, make sure that million has a real, specific purpose and isn’t just moving forward on inertia because you’ve been so diligent all these years.

If I’d gone another 3 years, we’d have accumulated another $1m. That would have moved us from a beach house that is 600 feet from the beach to oceanfront.

I’m quite happy to spend these three years walking a bit to/from the beach rather than sitting in staff meetings earning money so that someday I didn’t have to walk at all to get on the beach.

A good friend’s sister just died of a stroke at age 51. She appeared healthy. Next day she was gone. DW almost died at 48 but thankfully recovered.

Life is not guaranteed.

If there isn’t something specific - nearly transaction - that keeps you working so you can get/do that thing … then punch out.

My $0.02.
“I’m quite happy to spend these three years walking a bit to/from the beach rather than sitting in staff meetings earning money so that someday I didn’t have to walk at all to get on the beach.”

Simple but powerful.
 
"Do I like my job?" It's a little complicated to answer. I am a regional director for a big box retailer. It's not an easy job - pressure, politics, metrics to make, on call 24/7, 13 direct reports spread across five states, etc. I think I am pretty good at it and seem to to be well thought of right now. They would probably let me do this for five more years if I wanted to. The work is interesting and challenging and I have a high performing, loyal team and my boss mostly leaves me alone.

All that said, I am aware jobs like this take a toll. A co-worker who had a similar role retired last year says he loves every day of retirement but never understood how much stress he was under at work until he retired.
My dad did a job like you - retail regional director. He got out around 63 and has spent the past 14 years being healthy, side hustles for fun, and gardening. He has already outlived his father by 8 years and functions really well.

My DW’s father retired in his early 60’s and just sits around drinking sweet tea and watching CSI. He is getting more and more immobile, which is sad.

Everyone’s perspective is different so make the decision that brings you happiness, fulfillment, and purpose. But stay active, no matter what.
 
“I’m quite happy to spend these three years walking a bit to/from the beach rather than sitting in staff meetings earning money so that someday I didn’t have to walk at all to get on the beach.”

Simple but powerful.
To the extent that we have the temerity to judge, we might say, that neither case is an enviable life. Both prior to retirement, and in retirement, we need some participatory animating function, something of archival value. That is neither just minutes-of-meeting files in the G: drive of our company's server, nor just our signatures on beachside café credit-card receipts. But it might be a poem scribbled on a napkin in said café or a poem in the margins of the notebook where the meeting-notes were taken.
 
To the extent that we have the temerity to judge, we might say, that neither case is an enviable life. Both prior to retirement, and in retirement, we need some participatory animating function, something of archival value. That is neither just minutes-of-meeting files in the G: drive of our company's server, nor just our signatures on beachside café credit-card receipts. But it might be a poem scribbled on a napkin in said café or a poem in the margins of the notebook where the meeting-notes were taken.
I'm not sure what point you're trying to make.

That one needs more than a single thing in life?
Right.

I'd rather have those other things exist near the beach than having them exist while I sit in staff meetings. Particularly if the purpose of sitting in those staff meetings is that so some day I can be a smidge closer to the beach.

If you don't think there is a difference between a bar napikin and the margin notes of a meeting, that's fine. For me? I'll take the beach.
 
I'm not sure what point you're trying to make.

That one needs more than a single thing in life?
Right.

I'd rather have those other things exist near the beach than having them exist while I sit in staff meetings. Particularly if the purpose of sitting in those staff meetings is that so some day I can be a smidge closer to the beach.

If you don't think there is a difference between a bar napikin and the margin notes of a meeting, that's fine. For me? I'll take the beach.
I mean that if we devoted our working-lives to a crummy and unrewarding career, then we'd slipped into a major blunder at age 19... should have thought better about our major in college etc.... or revised some years later, while still young. Retirement would only be band-aid fix.

It's a completely different story if our careers stagnate and wither in middle-age, so that by 50 or 55, the ideals of our youth are gone, vitiated and broken. Then we retire, if we can, to... something else.
 
I mean that if we devoted our working-lives to a crummy and unrewarding career, then we'd slipped into a major blunder at age 19... should have thought better about our major in college etc.... or revised some years later, while still young. Retirement would only be band-aid fix.

It's a completely different story if our careers stagnate and wither in middle-age, so that by 50 or 55, the ideals of our youth are gone, vitiated and broken. Then we retire, if we can, to... something else.
I for one had an "up and down" c@reer in terms of my enjoyment. It's true that one should probably not choose a c@reer (or at least not a w*rkplace) that is mind-numbing or soul-stealing. You need to "live" while you w*rk. Having said that, few people avoid the ups and downs that come with w*rking. My "best" years were my last years. The day they told me I had to change assignments, that was the day I gave my notice because I was already FI. YMMV
 
To the extent that we have the temerity to judge, we might say, that neither case is an enviable life. Both prior to retirement, and in retirement, we need some participatory animating function, something of archival value. That is neither just minutes-of-meeting files in the G: drive of our company's server, nor just our signatures on beachside café credit-card receipts. But it might be a poem scribbled on a napkin in said café or a poem in the margins of the notebook where the meeting-notes were taken.
I must say you have a unique and descriptive process with the ordinary scribblings most of us, including myself, partake in with regularity. Maybe you are some kind of writer? Just curious.

I think you are correct with pursuit of the creative wand that reaches beyond the mundane, at least in my mind, that provides relief from what could be a perfunctory reality. My take, anyway.
 
In money perspective, because you don't need to take care of your child, you have more than enough.

From a mental health perspective, you should retire ASAP. I am not an expert, but I have seen my father's life. Our minds are all getting more inflexible as we get older, and retirement is a huge huge change. I see my father struggle with that in a very hard, unnecessary way.
 
Morning All. Original poster here with an update.

My wife went ahead and retired a few weeks ago. She is very happy she walked and is so far not missing work at all. I have started the conversation with my boss about what retirement would look for me if I go this summer. Meaning, I am happy to stick around for a few more months depending on what severance compensation might look like. So, waiting on that answer before proceeding.

Thank you all for all the input so far. It has been really helpful.
 
We've been traveling heavily for the 3 years since I retired at 54. I wouldn't trade it for $1M.
Agree. I retired at 59, my dear wife was 62. We had 8 good years of travel (out of the 20-plus we imagined), then she was diagnosed with Parkinson's. While we still travel, it's much different for both of us and will likely only become more and more restricted.

My advice: don't trade money for time at this point in your life--treasure the present.
 
Morning All. Original poster here with an update.

My wife went ahead and retired a few weeks ago. She is very happy she walked and is so far not missing work at all. I have started the conversation with my boss about what retirement would look for me if I go this summer. Meaning, I am happy to stick around for a few more months depending on what severance compensation might look like. So, waiting on that answer before proceeding.

Thank you all for all the input so far. It has been really helpful.
Thanks for the update. Congratulations to your DW. I assume she is anxious for you to join her. I agree with Bryan B that time is worth more than money, assuming you are already close, financially. Best luck.
 
A million you can build up in a short enough time if you keep invested. I have averaged 1 million every three years in ER and that was after all expenses. New cars, bought land and many other projects that were costly.
Only you will know what is right for you, but I will say like everyone else, money won't be your problem.
Good Luck!!
 
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