Another career discussion: last laps before retirement

[Wannaretireearly]

I've been thinking a lot, which is dangerous
I'd like to hear from folks either in my situation, or have perhaps been thru my situation and can share their experiences.

Here goes:

I'm roughly 5 years away from my target retirement age. I don't see myself pushing that date out by much, perhaps just OMY.

How should i utilize my last 5 years of full time employment?

Current role: Very comfortable, great team, good visibility, limited upward mobility (i.e. limited financial opportunity).
I am close to FI. If push came to shove, i'm probably lean FI now.

1. I could keep going (inertia is the easiest option!).

2. I could look for new opportunities.
a. However, I am not interested in doing the same thing at a similar mega corp, even with a bigger title and more comp. I'd rather stay here than have to develop all those political friends and connections.

b. a smaller company seems enticing if it's in the right hot area (e.g. Gen AI/ML/Data Science) & i get an appropriate role with more comp obviously

Factors I'm considering:
- been in current company a long time. Not too long in my current role though.
- would like to leverage my leadership current role (Strat, Arch, Data Science).
- A kid in middle school and high school. Still involved being chauffeur, but kids need me a lot less.
- Agreement (reluctantly) with DW that this summer will be the last long vacation we'll take for a while. Kids college prep will take higher priority from next year (sigh) and we'll do shorter trips. This is important as i know I'll go from 5 weeks PTO here to nothing in a new job.

- This may be my last chance to move role. Could i take advantage of the new tech market and get a good leadership role? Take advantage of the $26bn in VC cash invested in the SF bay area, just in Q1?
- I've never been at a startup (not factoring the grad job i had at the end of the dot com days, that lasted like eight weeks). I could hate it, and leave. Perhaps this is a good time to take that kind of risk? If not now, when?
- I want to actively look at the market in the summer (after my big trip )

Has anyone successfully made a change like this towards the end of their career? Enjoyed it? Made super bank in their last few years and still hit their Target retirement age?

[jarjarM]

If you being in large corp for most of your career, you may really hate startups. Very fast pace and most wear multiple hats with limited resources. It won't be comfy and not really suited for end of career folks (unless you're aiming for the homerun). Also, the genAI craze may slow down significantly as folks realizing how much $$$ is involved in the backend support (those nvidia GPUs aren't cheap and you'll thousands of them for training). Most startups won't have the funding to run their own backend so they'll lean on Azure/AWS/Google Cloud and those cost will be going up. Current LLM has definitely deficiency since it's probability based and heavily dependent on training dataset. Curation of large dataset will be costly as well though many are exploring self rectifying capability (still sometime away from prod version). My bet is that 95% of the VC funded AI startups will fold within the next 5 years so it's definitely a high risk bet the one you join will be the future.

[Wannaretireearly]

If you being in large corp for most of your career, you may really hate startups. Very fast pace and most wear multiple hats with limited resources. It won't be comfy and not really suited for end of career folks (unless you're aiming for the homerun). Also, the genAI craze may slow down significantly as folks realizing how much $$$ is involved in the backend support (those nvidia GPUs aren't cheap and you'll thousands of them for training). Most startups won't have the funding to run their own backend so they'll lean on Azure/AWS/Google Cloud and those cost will be going up. Current LLM has definitely deficiency since it's probability based and heavily dependent on training dataset. Curation of large dataset will be costly as well though many are exploring self rectifying capability (still sometime away from prod version). My bet is that 95% of the VC funded AI startups will fold within the next 5 years so it's definitely a high risk bet the one you join will be the future.

Thank you, jarjarM. A very thoughtful response!

[Barsoom]

When I had five years to go after almost 35 years at MegaCorp, I was able to get a relocation to our sister office in the city of my eventual retirement.

I didn't have it in me to compete like a 25 year old anymore somewhere new.

-B

[Jack FFR1846]

So I'm exactly one month until retirement, so have gone through the time you're talking about quite recently. Having a job that is known, stable and not likely to make you work 120 hours a week to get that "important" project out the door. You can enjoy your kids. I had that job of carting them all over between karate, soccer, lacrosse, skateboarding and music lessons (2 boys). Be sure to be a part of what they're doing if you can. I would drive them to practice or away games with my cool car. I was an assistant soccer coach which meant nothing more than when the coach was unable to do practice, I would. I even learned to skateboard, dropping in on a vert half pipe for the first time at age 50. And when my younger son was ready to give up guitar lessons, I let him switch to bass and I picked up guitar again, taking the lesson at the same time as him. As for work? I tried to focus on things I liked doing. This actually worked out great as there's always plenty to do, so getting anything done is seen as a good thing.

Get your accounting together so you know exactly where you stand financially and perhaps start a "retirement spending budget" which is very different from a working budget.

Good Luck

[vrr106]

I am in the same place as you as far as kids and retirement target go, and although not qualified for the AI/ML space I have talked to a couple of founders about joining them. My current plan is to stay the course and run out the clock in my current role - reasons - I don't think I am ready for the pace of a startup, especially because of the work/life demands and my desire to maximize time spent with my high schooler before she leaves home.
Also, I should be in a position to be close to Fat-FIRE or at least afford a 15-20% spending increase over current levels if all goes to plan the next 5 years.
The only reason I would look at a new option if I were in your place is to try and get past a Lean-FIRE

[LeftCoastIV]

Another way to frame this question is, "At the end of your career, what will you regret having not tried or done?"

For a lot of people, I think the goal is to just make as much money as possible with a reasonable work-life balance, and interesting work, and that's great. But if you've had an itch to try something different, now would be the time to take a serious look at it. It's generally "free" to talk to people to learn more about potential new areas, get their feedback, etc. Your thoughts may evolve as you talk to, and learn from, a bunch of people on exploratory topics.

[123]

Spend your final laps on the track you're familiar with.

Chances of blasting ahead on a new track and leading the pack are a long shot, everyone knows you won't be around for long.

There are a lot of fresh young horses joining the race every year.

[Wannaretireearly]

Thanks y'all. Some great responses above!

[Wannaretireearly]

Another way to frame this question is, "At the end of your career, what will you regret having not tried or done?"

For a lot of people, I think the goal is to just make as much money as possible with a reasonable work-life balance, and interesting work, and that's great. But if you've had an itch to try something different, now would be the time to take a serious look at it. It's generally "free" to talk to people to learn more about potential new areas, get their feedback, etc. Your thoughts may evolve as you talk to, and learn from, a bunch of people on exploratory topics.

Yep, this summarizes my thoughts very well. Perhaps i can 'scratch that itch' without completely changing roles. Yep, free to talk, interview, get feedback etc.

[Wannaretireearly]

I am in the same place as you as far as kids and retirement target go, and although not qualified for the AI/ML space I have talked to a couple of founders about joining them. My current plan is to stay the course and run out the clock in my current role - reasons - I don't think I am ready for the pace of a startup, especially because of the work/life demands and my desire to maximize time spent with my high schooler before she leaves home.
Also, I should be in a position to be close to Fat-FIRE or at least afford a 15-20% spending increase over current levels if all goes to plan the next 5 years.
The only reason I would look at a new option if I were in your place is to try and get past a Lean-FIRE

I think being lean FIRE now (and not fire FIRE ) is keeping me somewhat interested in looking outwards.

[Wannaretireearly]

So I'm exactly one month until retirement, so have gone through the time you're talking about quite recently. Having a job that is known, stable and not likely to make you work 120 hours a week to get that "important" project out the door. You can enjoy your kids. I had that job of carting them all over between karate, soccer, lacrosse, skateboarding and music lessons (2 boys). Be sure to be a part of what they're doing if you can. I would drive them to practice or away games with my cool car. I was an assistant soccer coach which meant nothing more than when the coach was unable to do practice, I would. I even learned to skateboard, dropping in on a vert half pipe for the first time at age 50. And when my younger son was ready to give up guitar lessons, I let him switch to bass and I picked up guitar again, taking the lesson at the same time as him. As for work? I tried to focus on things I liked doing. This actually worked out great as there's always plenty to do, so getting anything done is seen as a good thing.

Get your accounting together so you know exactly where you stand financially and perhaps start a "retirement spending budget" which is very different from a working budget.

Good Luck

Thanks Jack. A retirement spending budget would be a good next step. Right now, the college prep budget is out of control

[MJS]

.... I'd rather stay here than have to develop all those political friends and connections.
...
- A kid in middle school and high school.

"Move role" ... might this involve physically moving? Uprooting kids means they will "have to develop all those political friends and connections." If you've been changing houses, neighborhoods & schools every few years, then your kids already know how to find new friends, determine & adhere to local customs, and how to gain status in cliques. But jr & sr high are hard times to be thrown into new environments.

[Wannaretireearly]

.... I'd rather stay here than have to develop all those political friends and connections.
...
- A kid in middle school and high school.

"Move role" ... might this involve physically moving? Uprooting kids means they will "have to develop all those political friends and connections." If you've been changing houses, neighborhoods & schools every few years, then your kids already know how to find new friends, determine & adhere to local customs, and how to gain status in cliques. But jr & sr high are hard times to be thrown into new environments.

Nope, I meant I’d have to make new networks and connections at any new job really. But especially at megacorps where corp politics plays a part, especially in leadership roles.

I’d consider moving temporarily to a different location for the fun factor. But, not while the kids are at school for the reasons you’ve described above.

[AnnetteLouisan]

I relate to this a lot - top of ones game, comfortable, not ready to stop and kind of wanting to go out with a flourish of a good kind. How to land the plane, in a way. I asked a similar question on a thread back in August and the consensus was to stay put given the effort needed to build up connections and reputation at a new employer. I took that advice and was glad I did while also trying some new things for the challenge.

Fortunately there is still time to ponder this. I am going the way of zen and Jack Bogle - just standing there, watching and waiting for now as the landscape changes. I personally think all of the flux will create opportunities but flux is a great time to stand still.

[Wannaretireearly]

I relate to this a lot - top of ones game, comfortable, not ready to stop and kind of wanting to go out with a flourish of a good kind. How to land the plane, in a way. I asked a similar question on a thread back in August and the consensus was to stay put given the effort needed to build up connections and reputation at a new employer. I took that advice and was glad I did while also trying some new things for the challenge.

Fortunately there is still time to ponder this. I am going the way of zen and Jack Bogle - just standing there, watching and waiting for now as the landscape changes. I personally think all of the flux will create opportunities but flux is a great time to stand still.

Thanks Annette! I know for me this feeling won’t last forever. I’m the opposite of type A, lol. It will take a lot for me to be on any zoom call at 7am once I’m not already up for kids school runs

Working from home is another key factor ‘for’ staying put. I only go in once a week.

I think I’ll still explore this summer, just to try and get interview ready. Which I’m not right now!

[Watty]

- Agreement (reluctantly) with DW that this summer will be the last long vacation we'll take for a while. Kids college prep will take higher priority from next year (sigh) and we'll do shorter trips. This is important as i know I'll go from 5 weeks PTO here to nothing in a new job.

With kids in middle school and high school these are likely the last few years that you will be able to spend much time with them. I would be cautious about taking on a new job where you might need to travel a lot and work long hours and miss out on time left with your kid(s).

I would question the assumption that the kids college preparation will eat up the summer so that you cannot take longer vacations or vacations during their school breaks.

Where I am at summer break is around 10 weeks long so if they go on a three or four week trip that still leaves lots of time for college preparations.

.... as i know I'll go from 5 weeks PTO here to nothing in a new job.

That would be a non-starter for me.

Some other considerations;

1) Any 401k match might have a five year vesting schedule so you might lose part of the 401k match if you leave the job sooner than the vesting.

2) As a new hire you may be the first laid off if there are lay offs and you may get minimal severance.

3) In your current job you might get a large severance package if you are laid off. When I was a year or two out from wanting to retire I did everything I could to cross train people, all processes well documented, etc and make myself more expendable if there were layoff in the hope of getting good severance package right before I was ready to retire. I did not slack off but I did not get laid off even though the company could have gotten by fine without me by then.

I did retire at a good point in my career where my projects were in good shape and I felt good about my accomplishments. If you switch to a new job then you may be in the middle of projects that might be having issues when you retire and that might not feel as good.

[Wannaretireearly]

- Agreement (reluctantly) with DW that this summer will be the last long vacation we'll take for a while. Kids college prep will take higher priority from next year (sigh) and we'll do shorter trips. This is important as i know I'll go from 5 weeks PTO here to nothing in a new job.

With kids in middle school and high school these are likely the last few years that you will be able to spend much time with them. I would be cautious about taking on a new job where you might need to travel a lot and work long hours and miss out on time left with your kid(s).

I would question the assumption that the kids college preparation will eat up the summer so that you cannot take longer vacations or vacations during their school breaks.

Where I am at summer break is around 10 weeks long so if they go on a three or four week trip that still leaves lots of time for college preparations.

.... as i know I'll go from 5 weeks PTO here to nothing in a new job.

That would be a non-starter for me.

Some other considerations;

1) Any 401k match might have a five year vesting schedule so you might lose part of the 401k match if you leave the job sooner than the vesting.

2) As a new hire you may be the first laid off if there are lay offs and you may get minimal severance.

3) In your current job you might get a large severance package if you are laid off. When I was a year or two out from wanting to retire I did everything I could to cross train people, all processes well documented, etc and make myself more expendable if there were layoff in the hope of getting good severance package right before I was ready to retire. I did not slack off but I did not get laid off even though the company could have gotten by fine without me by then.

I did retire at a good point in my career where my projects were in good shape and I felt good about my accomplishments. If you switch to a new job then you may be in the middle of projects that might be having issues when you retire and that might not feel as good.

Great points Watty! Thank you much for the post.

I cannot disagree with any of these points. On the college prep, there is a program that is kinda continuous and demanding most summer which my freshman will likely be busy with next few summers. But, point taken on time off. It is like gold! I look back on the few years I was able to take 7-8 weeks off in a year. What great years!

[London]

I even learned to skateboard, dropping in on a vert half pipe for the first time at age 50.

I have nothing to add to this thread but I love this.

[wetware]

My bet is that 95% of the VC funded AI startups will fold within the next 5 years so it's definitely a high risk bet the one you join will be the future.

Most startups fail, regardless of field or timing, so this bet is not meaningful. But even if it's accurate, a 5% chance for a home run sure beats the lottery.

There are lots of reasons to be skeptic of LLMs and genAI, as the poster mentions, but there are also lots of reasons to be very bullish. Although the data is growing, developments in software, algorithms, and even hardware are at moment only accelerating, not slowing down, and the board could be tilted in favor of the small players (refer to the infamous leaked google memo: https://www.semianalysis.com/p/google-w ... nd-neither).

As for the OP's question: startup life is a serious commitment. Unless you're truly passionate about it (to the point where you're a cofounder, I'd say), then it's probably misaligned with your current life and career expectations). Hitting a home run could be nice, but not strictly necessary and far from certain, whereas investing (losing?) these years would be a certainty.

[jarjarM]

Most startups fail, regardless of field or timing, so this bet is not meaningful. But even if it's accurate, a 5% chance for a home run sure beats the lottery.

There are lots of reasons to be skeptic of LLMs and genAI, as the poster mentions, but there are also lots of reasons to be very bullish. Although the data is growing, developments in software, algorithms, and even hardware are at moment only accelerating, not slowing down, and the board could be tilted in favor of the small players (refer to the infamous leaked google memo: https://www.semianalysis.com/p/google-w ... nd-neither).

Very true, most startups do fail regardless. I guess my point is that the 95% genAIs startup now will not be here in 5yrs time, the rest 5% may get acquired by the bigger players as their exit strategy. The amount of computing resources to handle just the inference side of the model is already quite demanding and the model training is even more. It's hard for me to see how they'll be able to compete against the deep pockets of the big players (even openAI needed substantial injection of capitals from MSFT).

[MidwestSoutheast]

Thank you OP for asking this question, it captured a lot of what I’ve been mulling over. At 54 with many years at mega corp, I’m in a well paid, remote, and pretty low stress but boring position. I could take a pension next year and go for even more money elsewhere but that would come with the need to start over and prove my worth…something I don’t have to do now. My wife thinks I’m crazy for even thinking about it but I’m having a hard time checking out and wondering if I could do more. I’ll have enough $ to retire in 2 years but the idea of hanging it up is hard.

[quantAndHold]

Five years out from retirement, I left a cushy sinecure in government contracting to work for a FAANG. I made bank and retired a year earlier than I would have been able to otherwise, and it was interesting to see behind the curtain of a company like that, but it was super stressful to start over at a time when I really just wanted to coast, and even if I hadn’t reached FI when I did, I would have had to leave the job because of burnout.

Anyway, the thing I found most satisfying at that point in my career was mentoring and teaching. If I were to do it again, I would rewrite my job description to create a role where I was helping the youngsters to develop their careers.

[Valuethinker]

Thank you OP for asking this question, it captured a lot of what I’ve been mulling over. At 54 with many years at mega corp, I’m in a well paid, remote, and pretty low stress but boring position. I could take a pension next year and go for even more money elsewhere but that would come with the need to start over and prove my worth…something I don’t have to do now. My wife thinks I’m crazy for even thinking about it but I’m having a hard time checking out and wondering if I could do more. I’ll have enough $ to retire in 2 years but the idea of hanging it up is hard.

There are lots of meaingful things in life than "working for the man".

Don't underestimate how hard it is, in your late 50s, to compete with people 20-30 years younger. Their brains work faster. They are hungrier.

If you are well paid and pretty low stress, then what you need to think about is what roles you might take on in retirement. Rather than jumping into some too hot to handle situation and losing your job, the knock to self esteem etc.

[cbox]

How should i utilize my last 5 years of full time employment?

Presuming you don't need to save aggressively because you've reached the point where you can put a date on retirement and feel good about it, here's the main suggestion I have from my recent experience in your situation:

Get stuff done pre-retirement: new car, fix the house (upgrades/renovations), etc., so that you can enter retirement w/o having to face a bunch of unexpected or put-off expenses. In short, give yourself license to live paycheck to paycheck for as long as it takes to get your life in order. Often when we're working, we focus a lot on savings, and we don't have time or energy to do anything much outside of work. Make time in your last working years, and spend your money on durable goods and upgrades that will last you well into the early years of retirement. Especially now w/ inflation running hot as it is, the dollars you spend now will go farther than those same dollars spent a few years down the road. Things ain't gonna get cheaper, in other words.

[rich126]

Once thing I would recommend people consider is setting up their skills for post-retirement in a way that you still have some kind of marketable skill in case you want to continue working either part time, as a consultant, etc. I often see people get to a certain level and then they just level off and have some skill the company kind of needs but really is of limited value to anyone else. That is kind of ok if you don't get laid off before retirement but if you want to work in some role post-retirement you need to figure out what value you can provide. I come from a tech background but I think it is relevant in most fields.

As someone who just started retirement this year but still is pondering whether to take another job, retirement is strange, at least the first year can be. Some people, even with tons of savings, just find it tough not to have a job. In my case I don't miss working but I miss the problem solving of engineering work and would like to find something 3-4 days a week to do but I talk to a bunch of companies who have openings and will offer me full time jobs but I have no interest in 40+ hrs of work, at any salary level but they don't want someone less than full time even in my case where I don't need any benefits.

[LiveSimple]

Read somewhere your job should make you enjoy and not lead you to depression…so stay put…

[8301]

Thank you OP for asking this question, it captured a lot of what I’ve been mulling over. At 54 with many years at mega corp, I’m in a well paid, remote, and pretty low stress but boring position. I could take a pension next year and go for even more money elsewhere but that would come with the need to start over and prove my worth…something I don’t have to do now. My wife thinks I’m crazy for even thinking about it but I’m having a hard time checking out and wondering if I could do more. I’ll have enough $ to retire in 2 years but the idea of hanging it up is hard.

If somebody thinks you are crazy, you may be on to something.

[simas]

- This may be my last chance to move role. Could i take advantage of the new tech market and get a good leadership role? Take advantage of the $26bn in VC cash invested in the SF bay area, just in Q1?

Just a data point - did some interview screening for people we are hiring (mid level IT) position last week, spoke with three different folks from different background, age groups ,etc. As part of interview, one of the usual questions is what attracts you about this position, opportunity, company ,etc. What really interests you and makes you move. The answer is the same from all of the people - we are seeing stability. people see that the storm is coming (recession ,etc) and the whole fantasies of I am a primadonna sitting pretty here and would decide who is good enough to even make their offer to me is getting old fast. If you are not buckled down and not in recession protected/proof industry, the AI/ML/next buzzword is going to be pretty irrelevant as it is for hundreds of thousands tech employees already let go in the last 6 months.
What people forget about this whole data science, we train model, AI solves everything thing is that ultimately for business it is all about transactions (sales, conversions, etc) and/or cost cutting. Cost cutting = your job. Sales - that is driven by consumer demand AND their ability to actually spent. If they do not have money it is totally irrelevant what you collect and how much you spy on that and how well you data mine. They will not buy because they can not spend what they do not have , especially if they are worried about lights on and basics. if people can not buy, sellers can not sell and all the ads in the world would not change it so all of the economy built on air of 'we own data, we own the world , because we can sell data to make more sales' is crashing pretty fast and hard.
My advice is stay put and think on how you will live through next few years and your cushy job is not there. Now is probably the worst time to abandon it because of greed. YMMV.

[Colorado14]

Here's another data point/sample of one: I made a last lap change in my late 40s (not to a start up) and gained a much higher salary than previously, learned new skills and generally enjoyed the role. However, I really disliked the limited vacation time and return to office (to spend the day on Zoom calls but very little time with other people.) So I would caution against giving up 5 weeks of PTO and a great team. These are very meaningful to me but you may have other aspirations. I retired at age 54 (in December 2022) somewhat as a result of limited PTO.

Starting over with 2 weeks of PTO was not ideal. I tried to negotiate for more, but was not successful (as was the case for other experienced recent hires. The PTO policy was not negotiable.) It seems as though you have a good gig so I would hang on to that.

Good luck!

[theorist]

Just to add another data point:

I left a very stable and fairly lucrative job in early 50s (after realizing we are basically FI, I felt no risk aversion). I am now working for a much, much smaller employer (think going from 10,000 employees to 100). It is in a very different industry but emphasizes skills (statistics, computation, machine learning) that I have some facility with. The environment is faster paced, I feel like I am growing intellectually again, and the compensation is much higher (not by just a few percent, but by a factor of a few).

For me this has worked out well so far, but my situation is different (no kids to support at this point!).

After a few years, if I am no longer happy here, this will set me up well for focusing totally on more or less charitable endeavors. That is also nice.

Good luck!

[Wannaretireearly]

Thank you OP for asking this question, it captured a lot of what I’ve been mulling over. At 54 with many years at mega corp, I’m in a well paid, remote, and pretty low stress but boring position. I could take a pension next year and go for even more money elsewhere but that would come with the need to start over and prove my worth…something I don’t have to do now. My wife thinks I’m crazy for even thinking about it but I’m having a hard time checking out and wondering if I could do more. I’ll have enough $ to retire in 2 years but the idea of hanging it up is hard.

You’re very welcome

There is something psychological about this topic. What comes to my mind:

When I was a student or grad I wouldn’t think twice about taking a big risk (career, long vacations regardless of work etc). Now I’m in a financial position to take more risk (nearly FI) I tend to take less risk? Counter intuitive and I’m not doing a good job explaining this quick on my phone

Also, something about US work culture being so entwined in our lives is related to our generally similar thoughts. In contrast, work for most/many Europeans is transactional. Work to get paid, it’s all over otherwise. Plenty of non work things for ‘identity’. I’m European so I think of this more than I should

[Wannaretireearly]

How should i utilize my last 5 years of full time employment?

Presuming you don't need to save aggressively because you've reached the point where you can put a date on retirement and feel good about it, here's the main suggestion I have from my recent experience in your situation:

Get stuff done pre-retirement: new car, fix the house (upgrades/renovations), etc., so that you can enter retirement w/o having to face a bunch of unexpected or put-off expenses. In short, give yourself license to live paycheck to paycheck for as long as it takes to get your life in order. Often when we're working, we focus a lot on savings, and we don't have time or energy to do anything much outside of work. Make time in your last working years, and spend your money on durable goods and upgrades that will last you well into the early years of retirement. Especially now w/ inflation running hot as it is, the dollars you spend now will go farther than those same dollars spent a few years down the road. Things ain't gonna get cheaper, in other words.

I really like this. Thanks cbox!

[Wannaretireearly]

Once thing I would recommend people consider is setting up their skills for post-retirement in a way that you still have some kind of marketable skill in case you want to continue working either part time, as a consultant, etc. I often see people get to a certain level and then they just level off and have some skill the company kind of needs but really is of limited value to anyone else. That is kind of ok if you don't get laid off before retirement but if you want to work in some role post-retirement you need to figure out what value you can provide. I come from a tech background but I think it is relevant in most fields.

As someone who just started retirement this year but still is pondering whether to take another job, retirement is strange, at least the first year can be. Some people, even with tons of savings, just find it tough not to have a job. In my case I don't miss working but I miss the problem solving of engineering work and would like to find something 3-4 days a week to do but I talk to a bunch of companies who have openings and will offer me full time jobs but I have no interest in 40+ hrs of work, at any salary level but they don't want someone less than full time even in my case where I don't need any benefits.

Very interesting and insightful, thanks rich!

I would happily coach and mentor for money or even free. It’s the part of my job I love. I’ll have to think harder about how to formalize this skill set to be ready if needed. Perhaps take a formal course or cert that shows on my profile? That way if I wanted to pick up some part time/consulting gig I have some creds, beyond my desire to coach/mentor?

[Wannaretireearly]

- This may be my last chance to move role. Could i take advantage of the new tech market and get a good leadership role? Take advantage of the $26bn in VC cash invested in the SF bay area, just in Q1?

Just a data point - did some interview screening for people we are hiring (mid level IT) position last week, spoke with three different folks from different background, age groups ,etc. As part of interview, one of the usual questions is what attracts you about this position, opportunity, company ,etc. What really interests you and makes you move. The answer is the same from all of the people - we are seeing stability. people see that the storm is coming (recession ,etc) and the whole fantasies of I am a primadonna sitting pretty here and would decide who is good enough to even make their offer to me is getting old fast. If you are not buckled down and not in recession protected/proof industry, the AI/ML/next buzzword is going to be pretty irrelevant as it is for hundreds of thousands tech employees already let go in the last 6 months.
What people forget about this whole data science, we train model, AI solves everything thing is that ultimately for business it is all about transactions (sales, conversions, etc) and/or cost cutting. Cost cutting = your job. Sales - that is driven by consumer demand AND their ability to actually spent. If they do not have money it is totally irrelevant what you collect and how much you spy on that and how well you data mine. They will not buy because they can not spend what they do not have , especially if they are worried about lights on and basics. if people can not buy, sellers can not sell and all the ads in the world would not change it so all of the economy built on air of 'we own data, we own the world , because we can sell data to make more sales' is crashing pretty fast and hard.
My advice is stay put and think on how you will live through next few years and your cushy job is not there. Now is probably the worst time to abandon it because of greed. YMMV.

Thank you for this! I know some of this directly. I had an employee leave my group for at least 50% increase in total comp. He is now out of work

[Wannaretireearly]

Here's another data point/sample of one: I made a last lap change in my late 40s (not to a start up) and gained a much higher salary than previously, learned new skills and generally enjoyed the role. However, I really disliked the limited vacation time and return to office (to spend the day on Zoom calls but very little time with other people.) So I would caution against giving up 5 weeks of PTO and a great team. These are very meaningful to me but you may have other aspirations. I retired at age 54 (in December 2022) somewhat as a result of limited PTO.

Starting over with 2 weeks of PTO was not ideal. I tried to negotiate for more, but was not successful (as was the case for other experienced recent hires. The PTO policy was not negotiable.) It seems as though you have a good gig so I would hang on to that.

Good luck!

Thank you my boglehead friends. I could see myself following your exact path, and being frustrated with the WLB/office work and PTO challenges. Thanks for sharing

[Wannaretireearly]

Just to add another data point:

I left a very stable and fairly lucrative job in early 50s (after realizing we are basically FI, I felt no risk aversion). I am now working for a much, much smaller employer (think going from 10,000 employees to 100). It is in a very different industry but emphasizes skills (statistics, computation, machine learning) that I have some facility with. The environment is faster paced, I feel like I am growing intellectually again, and the compensation is much higher (not by just a few percent, but by a factor of a few).

For me this has worked out well so far, but my situation is different (no kids to support at this point!).

After a few years, if I am no longer happy here, this will set me up well for focusing totally on more or less charitable endeavors. That is also nice.

Good luck!

Excellent, congrats theorist. Multiplying total comp by a factor of few can/will smooth out any of the other bumps. I think it would only be worth the ‘risk’ to change if there was massive upside as you’ve seen.

[simas]

Thank you for this! I know some of this directly. I had an employee leave my group for at least 50% increase in total comp. He is now out of work

Various companies have various corporate culture attitudes about it - generally we rehire..

[watchnerd]

When I had five years to go after almost 35 years at MegaCorp, I was able to get a relocation to our sister office in the city of my eventual retirement.

I didn't have it in me to compete like a 25 year old anymore somewhere new.

-B

This is interesting.

Because after 15 years in startups, and 6 years in megacorp, I miss the startup environment so will be going back to that world for my last gig before total retirement.

[cockersx3]

Not sure if these points were already addressed, but here are my thoughts:

Is becoming an independent consultant a practical option in your field? You mention being a leader in various topics, so perhaps someone is willing to pay you to consult on various problems. One risk of consulting is not having a steady income, but if you're already "lean FI" then it seems like you would be better prepared than others to take on that risk. If needed, perhaps you can build your "brand" by going to conferences, doing public speaking, etc near term to help pave the way for future consulting opportunities later. This may be a nice "middle ground" between the two options you seem to be looking at now - ie "grind it out for 5 more years in current role" or "joint super-fast startup."

Have any of your kids graduated high school yet? If not, be forewarned - that time will pass by very, very quickly. And once they "leave the nest" and head off to college, you may find yourself wishing you could have spent more quality time with them before they left the nest and truly became aduts - which may bias you pretty strongly against a startup role for which significant / unreasonable amounts of time at work would be expected.

This was one of my main drivers for leaving full-time work last year. I worked at a very demanding series of global roles and racked up a lot of "career points" over the years, which felt good at the time but cost me many missed opportunities to connect with my kids when they were younger. I very much remember my oldest heading off to college recently, and thinking to myself - is that it? If so all that time at work just wasn't worth the trade. I'm now a key volunteer in an extracurricular activity that my youngest is heavily involved in, and she really does appreciate it (in a weird teenager way of course!). I've noticed that my oldest is also more willing than ever to call me during the day just to chat - and also of course when she has issues or questions - which they would never have done back when I was working a million hours a week. Despite my regular insistence that I was fine with them calling, they didn't want to bother me at work. But having that better relationship with my girls - albeit at a late age - has a huge amount of value that I guess I just didn't appreciate before. Something for you to consider if you're serious about taking on a potentially demanding role with your kids being older.

Finally, how willing are you to take on responsibilities that are well outside of your normal skillset? My last job was at a very small company following a string of good MegaCorp jobs, and I found that there were countless things that I would have previously delegated to others, or things that I would have reached out to subject matter experts elsewhere in my MegaCorp before acting on, that I instead had to figure out myself and do in the smaller company where those SME's did not exist. I found it very unnerving, as they still expected me to be right all the time (and quickly!) despite the lack of knowledge of all these intricate details that I never had to deal with before. My feeling is that this is a common thing when MegaCorp people like me join smaller companies - which causes many of us to not last long in those environments. It's definitely something for you to consider if you go the startup route.

[simas]

Not sure if these points were already addressed, but here are my thoughts:

Is becoming an independent consultant a practical option in your field? You mention being a leader in various topics, so perhaps someone is willing to pay you to consult on various problems. One risk of consulting is not having a steady income, but if you're already "lean FI" then it seems like you would be better prepared than others to take on that risk. If needed, perhaps you can build your "brand" by going to conferences, doing public speaking, etc near term to help pave the way for future consulting opportunities later. This may be a nice "middle ground" between the two options you seem to be looking at now - ie "grind it out for 5 more years in current role" or "joint super-fast startup."

the thing about independent consulting is that you are constantly selling (even if you think you are solving some other problem) and if you are not, then you would be out of gigs pretty quickly. the other option is to partner with someone who handles sales/client search and takes a cut however that is much less 'independent' and a hard relationship to maintain. been there, done that. I dont advice independent consulting unless you have some unique situation where it is falling into your lap or you have character where sales is not an issue (or could even be a bonus).

[Wannaretireearly]

Thank you for this! I know some of this directly. I had an employee leave my group for at least 50% increase in total comp. He is now out of work

Various companies have various corporate culture attitudes about it - generally we rehire..

I would too. If we had an appropriate opening. I already hired the replacement.

[Wannaretireearly]

Not sure if these points were already addressed, but here are my thoughts:

Is becoming an independent consultant a practical option in your field? You mention being a leader in various topics, so perhaps someone is willing to pay you to consult on various problems. One risk of consulting is not having a steady income, but if you're already "lean FI" then it seems like you would be better prepared than others to take on that risk. If needed, perhaps you can build your "brand" by going to conferences, doing public speaking, etc near term to help pave the way for future consulting opportunities later. This may be a nice "middle ground" between the two options you seem to be looking at now - ie "grind it out for 5 more years in current role" or "joint super-fast startup."

Have any of your kids graduated high school yet? If not, be forewarned - that time will pass by very, very quickly. And once they "leave the nest" and head off to college, you may find yourself wishing you could have spent more quality time with them before they left the nest and truly became aduts - which may bias you pretty strongly against a startup role for which significant / unreasonable amounts of time at work would be expected.

This was one of my main drivers for leaving full-time work last year. I worked at a very demanding series of global roles and racked up a lot of "career points" over the years, which felt good at the time but cost me many missed opportunities to connect with my kids when they were younger. I very much remember my oldest heading off to college recently, and thinking to myself - is that it? If so all that time at work just wasn't worth the trade. I'm now a key volunteer in an extracurricular activity that my youngest is heavily involved in, and she really does appreciate it (in a weird teenager way of course!). I've noticed that my oldest is also more willing than ever to call me during the day just to chat - and also of course when she has issues or questions - which they would never have done back when I was working a million hours a week. Despite my regular insistence that I was fine with them calling, they didn't want to bother me at work. But having that better relationship with my girls - albeit at a late age - has a huge amount of value that I guess I just didn't appreciate before. Something for you to consider if you're serious about taking on a potentially demanding role with your kids being older.

Finally, how willing are you to take on responsibilities that are well outside of your normal skillset? My last job was at a very small company following a string of good MegaCorp jobs, and I found that there were countless things that I would have previously delegated to others, or things that I would have reached out to subject matter experts elsewhere in my MegaCorp before acting on, that I instead had to figure out myself and do in the smaller company where those SME's did not exist. I found it very unnerving, as they still expected me to be right all the time (and quickly!) despite the lack of knowledge of all these intricate details that I never had to deal with before. My feeling is that this is a common thing when MegaCorp people like me join smaller companies - which causes many of us to not last long in those environments. It's definitely something for you to consider if you go the startup route.

Thank you. I’d consider independent consultant and should fine tune my profile as you mention. It wouldn’t be something I’d jump to immediately. A good backup though.

Kids still in grade school, so that is a key consideration!

[Barsoom]

When I had five years to go after almost 35 years at MegaCorp, I was able to get a relocation to our sister office in the city of my eventual retirement.

I didn't have it in me to compete like a 25 year old anymore somewhere new.

-B

This is interesting.

Because after 15 years in startups, and 6 years in megacorp, I miss the startup environment so will be going back to that world for my last gig before total retirement.

Of course, you go with what you know. In my case, I knew my megacorp. I had many different roles over the years in my career. In the last years, I could see the company transitioning to a younger generation of worker and it was simply my time to go.

And honestly, after working nearly 40 years and hitting my FIRE number (I retired at age 60), I wanted to devote that time to myself and my wife, not to one more gig.

-B

[halfnine]

- Agreement (reluctantly) with DW that this summer will be the last long vacation we'll take for a while. Kids college prep will take higher priority from next year (sigh) and we'll do shorter trips. This is important as i know I'll go from 5 weeks PTO here to nothing in a new job.

With kids in middle school and high school these are likely the last few years that you will be able to spend much time with them. I would be cautious about taking on a new job where you might need to travel a lot and work long hours and miss out on time left with your kid(s).

I would question the assumption that the kids college preparation will eat up the summer so that you cannot take longer vacations or vacations during their school breaks.

Where I am at summer break is around 10 weeks long so if they go on a three or four week trip that still leaves lots of time for college preparations.

.... as i know I'll go from 5 weeks PTO here to nothing in a new job.

That would be a non-starter for me.

Some other considerations;

1) Any 401k match might have a five year vesting schedule so you might lose part of the 401k match if you leave the job sooner than the vesting.

2) As a new hire you may be the first laid off if there are lay offs and you may get minimal severance.

3) In your current job you might get a large severance package if you are laid off. When I was a year or two out from wanting to retire I did everything I could to cross train people, all processes well documented, etc and make myself more expendable if there were layoff in the hope of getting good severance package right before I was ready to retire. I did not slack off but I did not get laid off even though the company could have gotten by fine without me by then.

I did retire at a good point in my career where my projects were in good shape and I felt good about my accomplishments. If you switch to a new job then you may be in the middle of projects that might be having issues when you retire and that might not feel as good.

Great points Watty! Thank you much for the post.

I cannot disagree with any of these points. On the college prep, there is a program that is kinda continuous and demanding most summer which my freshman will likely be busy with next few summers. But, point taken on time off. It is like gold! I look back on the few years I was able to take 7-8 weeks off in a year. What great years!

Just wanted to add a +1 to what Watty wrote

[SunRainSnow]

Thank you OP for asking this question, it captured a lot of what I’ve been mulling over. At 54 with many years at mega corp, I’m in a well paid, remote, and pretty low stress but boring position. I could take a pension next year and go for even more money elsewhere but that would come with the need to start over and prove my worth…something I don’t have to do now. My wife thinks I’m crazy for even thinking about it but I’m having a hard time checking out and wondering if I could do more. I’ll have enough $ to retire in 2 years but the idea of hanging it up is hard.

You’re very welcome

There is something psychological about this topic. What comes to my mind:

When I was a student or grad I wouldn’t think twice about taking a big risk (career, long vacations regardless of work etc). Now I’m in a financial position to take more risk (nearly FI) I tend to take less risk? Counter intuitive and I’m not doing a good job explaining this quick on my phone

Also, something about US work culture being so entwined in our lives is related to our generally similar thoughts. In contrast, work for most/many Europeans is transactional. Work to get paid, it’s all over otherwise. Plenty of non work things for ‘identity’. I’m European so I think of this more than I should

I relate to pretty much everything in your reply and just wanted to chime in on my experience. I 'retired' at 49, I'd reached a ceiling at my employer but the thought of going somewhere new didn't appeal to me at all. Build up new relationships, learn new systems/customers/industry etc., adapt (or try to influence) a new work culture........the list goes on. I was comfortable where I was, had put in the work and the finish line was in sight. I did not coast and always gave my all right until the last day but it was an environment I was familiar with and I didn't want the stress of changing that so close to the finish line. Unambitious? Maybe, but I came from humble beginnings and I can be proud of how it all turned out. In my 20's and 30's I'd have took more risk but mid 40's my appetite and life goals were different. No regrets.

[noco-hawkeye]

The points about a smaller startup are all valid, and can echo them. I've worked at megacorp(s), startup, and again at a megacorp. Returning to a megacorp I am amazed that it takes about 20 people to do what we would have a single person doing at a startup, or even that a megacorp would choose to spend it's time and resources in the way it does.

I knew this I would encounter this difference, and am ok with it. But I've seen plenty of people join that previous startup from a megacorp, and not thrive.

I think eventually I will go back to a startup, just because it is more challenging and thrilling - but megacorp sure is nice in that I can sleep well now. If you join a startup, just be prepared to invest yourself in a way you maybe have not done before.

[Hacksawdave]

I was in Systems and Data Processing (IT) for nearly 40 years, and at the same company. I was in your thinking shoes in the middle of 2016 and came up with a 5-year retirement transition plan. You didn’t mention if your career spent a long time in one place like me. I was typecast and knew going somewhere else would be awkward for both parties.

Hate to say it, but AI isn’t new, just like VM, Big Data, cloud, and other ‘new shiny things’ IT marketing vendors keep coming up with. I learned about what AI was back in 1986-1988.

As having no dependents, it made the decision easier to pick 2022 as the stopping point, only to then change it to 2020. The company decided to give many of us ‘unexpected early retirement’ at the end of 2019. Best promotion they ever gave me.

I ask about your tenure time with your current company as I tried outside consulting for 2 months in 2022 and found I absolutely did not want to do this anymore. Age, work ethics and corporate culture gaps mixed like oil and water. The grass was not greener.

If you still love what you do and the culture, stay the 5 more years. I would start a transition plan now that you are 5 years out in case things change as they did in my case. I was able to accomplish many leading (and a couple bleeding) edge tech things in my long tenure and left very satisfied, even though it was not on my terms at the end. You can always try the new gig after the fact you leave the current company and just permanently retire if you don’t like it like I did.

[Wannaretireearly]

I was in Systems and Data Processing (IT) for nearly 40 years, and at the same company. I was in your thinking shoes in the middle of 2016 and came up with a 5-year retirement transition plan. You didn’t mention if your career spent a long time in one place like me. I was typecast and knew going somewhere else would be awkward for both parties.

Hate to say it, but AI isn’t new, just like VM, Big Data, cloud, and other ‘new shiny things’ IT marketing vendors keep coming up with. I learned about what AI was back in 1986-1988.

As having no dependents, it made the decision easier to pick 2022 as the stopping point, only to then change it to 2020. The company decided to give many of us ‘unexpected early retirement’ at the end of 2019. Best promotion they ever gave me.

I ask about your tenure time with your current company as I tried outside consulting for 2 months in 2022 and found I absolutely did not want to do this anymore. Age, work ethics and corporate culture gaps mixed like oil and water. The grass was not greener.

If you still love what you do and the culture, stay the 5 more years. I would start a transition plan now that you are 5 years out in case things change as they did in my case. I was able to accomplish many leading (and a couple bleeding) edge tech things in my long tenure and left very satisfied, even though it was not on my terms at the end. You can always try the new gig after the fact you leave the current company and just permanently retire if you don’t like it like I did.

Fair points Dave. Thank you.
I have been at my current company most of my career! 3 different roles. Enjoy your retirement. Sounds wonderful

Agree on the culture and fit challenges.

[rustwood]

It is not unusual for someone to retire and then unretire a year or two later just because they are bored. About 7 years ago my plan was to retire last year and my current financial plan projections have me retiring in 3 years, but I don't really see myself quitting because I like my work situation. It is part time, flexible, and the people I work with appreciate my efforts. I was in a situation somewhat similar to yours 7 years ago and never would have expected things to have turned out like this.

My point is that perhaps you should think more about what you want to retire to and see if you can "land the plane" there. It might take you a couple of years to find the right fit for you, but once you do you might want to continue working part time for much longer - perhaps in a much easier role and at a significantly reduced salary. If so, another couple of years in your current position and some PT income might bring you very comfortably to FI. Of course I realize you may well have already considered this type of thing and are very much looking forward to pursuing leisure activities full-time, I just thought I'd throw it out there to round out the discussion.