Author Topic: Is OMY Worth It?  (Read 9423 times)

dougules

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Is OMY Worth It?
« on: March 26, 2021, 04:10:07 PM »
So as I'm getting closer to FI, I definitely think I may be prone to OMY syndrome.  Yes, it's mostly just about the fear from staring at all the financial risks in FIRE, but at the same time if I way overshoot out of too much caution, I would eventually end up with a lot of resources that could make a big difference in somebody else's life.  I really really want the luxury of not having to drag myself out of bed on Monday mornings, but I have a little twinge of guilt about that when I think about how much me sacrificing a few more Mondays could help people who have been way less fortunate than me.  Am I just over-rationalizing my fears, or is it worth it if indulging my possibly excessive need for security might help somebody who needs it way more than I need my Monday morning sleep?

dcheesi

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Re: Is OMY Worth It?
« Reply #1 on: March 26, 2021, 04:25:50 PM »
I'm probably the same way; as long as I'm still enjoying my job, it's going to be hard to justify leaving it.

When you talk about others, are you thinking in terms of loved ones, or just general charity?

One thing to ponder, would you leaving your position open up a slot for someone younger to come behind you? One of the frequent complaints among millenials is that "boomers" aren't retiring, and thus are hogging the senior positions that would normally go to the next generation(s). Maybe by moving out of the way, you make things better for a younger person (or several, depending on how high up in the pecking order you are?).

Malcat

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Re: Is OMY Worth It?
« Reply #2 on: March 26, 2021, 04:30:46 PM »
When there's a fear of change, it's not a great idea to give much weight to your rationalizations not to change.

Just decide what you want to do, and do that.

FIRE 20/20

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Re: Is OMY Worth It?
« Reply #3 on: March 26, 2021, 05:11:39 PM »
What does OMY mean to you?  Are you at a 3% withdrawal rate with plenty to cut and lots of money making skills that won't get too stale in a few years?  If so, then OMY is probably not worth it.  If you're going to be lean-FIRE with a 4% WDR and won't be able to easily re-enter the workforce then it's probably a good idea to OMY.  I'd like to hear more about your situation to provide any input.  Regardless of your situation, I have written on these boards innumerable times about how great going part-time was for both my partner and me.  If you're able to FIRE then even if your employer would have to bend over backwards to make your position work with a part-time employee they might do that if the option is losing you permanently.   

In no particular order, some of the things I would consider are:

Do you have dependents who rely on your income? 
Do you have a cushy, high paying job, or a terrible and low-paying job?
What are your back-up plans?  If you have lots of fat to cut in the FIRE budget, lots of skills that could generate FIRE income, a pension or Social Security that you aren't counting in your FIRE numbers, a spouse who will still be working, an ability to move to a lower cost of living location, or other back-up plans then quitting might not be as much of a cliff-dive as it feels like it is. 
If the motivation to OMY is based on charitable giving, could you do as much or more good volunteering your time?  Volunteering may help you as much as the people you're helping (I found that to be true). 
What withdrawal rate are you targeting?  If it's high then OMY might be a better idea than someone targeting a super low WDR. 
Do you get a lot of enjoyment and satisfaction from your work?
Can you re-enter your career a few years after quitting, or will you be locked out?

In my situation, I did OMY for a few reasons.  The primary reason for me was that my career required regular certifications that, once expired, are nearly impossible to get.  Now that I'm FIREd I'm basically locked out of my former career unless I luck into a very rare opening that lets me re-certify.  I also had a pretty cushy, high paying job.  They let me essentially go part-time, and the hours were very flexible.  I only have skills that can earn substantial compensation in a relatively narrow field, so my earnings potential now are much lower than before I FIREd.  We also support a number of family members who are unable to effectively provide for their own needs.  It was a priority for both of us to help those family members out long-term.  We also wanted to fund a Donor Advised Fund to continue to support other non-family charities that are important to us.  Finally, I'm just somewhat conservative when it comes to taking the kind of risk that goes along with a (hopefully) ~50 year retirement. 

Good luck with your decision!  OMY is a stressful decision to make, but it's absolutely amazing to be in a position to have that choice to make. 

Mmm_Donuts

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Re: Is OMY Worth It?
« Reply #4 on: March 28, 2021, 06:17:18 AM »
Iím going through the OMY questioning period as well. For me itís part fear (SORR and prolonged periods of inflation / downturns early in retirement), part the possibility of wanting to spend more, either in charitable giving or travel. Our expenses for FIRE are based on current spend. But I donít really know what Iíll get up to in FIRE. More travel? Expensive hobbies? I donít really know or want to feel limited.

Im currently on a sabbatical to pause and think it through. Iíve also been hating my job lately so if I do go back it would involve setting some very firm boundaries. Weíre at a 3.5% withdrawal rate based on current spend. DH is still working with no immediate plans to quit (he is naturally frugal but not completely sold on the 4% rule.)

Since OP mentions charitable giving - One way I started playing around with motivating myself is, what if I start donating a certain percentage of my earnings at every quarter end, and gradually up it till Iím giving 100% away? If I liked my job, Iíd do that indefinitely. I imagine it would feel great, and itíd be practice for not having a salary.

cool7hand

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Re: Is OMY Worth It?
« Reply #5 on: March 28, 2021, 07:26:27 AM »
So as I'm getting closer to FI, I definitely think I may be prone to OMY syndrome.  Yes, it's mostly just about the fear from staring at all the financial risks in FIRE, but at the same time if I way overshoot out of too much caution, I would eventually end up with a lot of resources that could make a big difference in somebody else's life.  I really really want the luxury of not having to drag myself out of bed on Monday mornings, but I have a little twinge of guilt about that when I think about how much me sacrificing a few more Mondays could help people who have been way less fortunate than me.  Am I just over-rationalizing my fears, or is it worth it if indulging my possibly excessive need for security might help somebody who needs it way more than I need my Monday morning sleep?

What is the precise nature of each fear (you probably have multiple contributing fears and perhaps conflicting fears)? How early can you trace the fear/fears back in childhood? The earlier, the better. You probably haven't found the origin if you haven't looked before five years of age. From which parent or guardian did you learn each fear? Where did that parent or guarding learn each fear, focusing on the same age range? How do you think each fear was designed to protect each parent or guarding from that age onward? How was each fear designed to protect you? Do you really require that protection? Is any fear preventing you from realizing your potential in any way? How did each fear limit each parent or guarding? Does it still? How will each fear continue to limit you?

dougules

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Re: Is OMY Worth It?
« Reply #6 on: March 28, 2021, 09:07:14 PM »
I'm probably the same way; as long as I'm still enjoying my job, it's going to be hard to justify leaving it.

When you talk about others, are you thinking in terms of loved ones, or just general charity?

One thing to ponder, would you leaving your position open up a slot for someone younger to come behind you? One of the frequent complaints among millenials is that "boomers" aren't retiring, and thus are hogging the senior positions that would normally go to the next generation(s). Maybe by moving out of the way, you make things better for a younger person (or several, depending on how high up in the pecking order you are?).

I'm not at all fond of my job.  I've been kind of burnt out for a long time to be honest.  A lot of it was my own issues that I would have probably taken to any job, though.  Getting help with my mental health has helped a lot.  I'm still just dragging myself through the day sometimes, though. 

I meant just general charity.  As we get closer to FIRE I'm starting to feel guilty that I'm being selfish when there are billions of people in the world that could use a little help.

I probably will free up a slot when I quit, but I'm not particularly worried about that.  My coworkers spend their money pretty frivolously. 


When there's a fear of change, it's not a great idea to give much weight to your rationalizations not to change.

Just decide what you want to do, and do that.

This is some zen shit.  Thanks.  I was kind of hoping you'd comment because you usually are good at cutting straight to the heart of the matter. 

dougules

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Re: Is OMY Worth It?
« Reply #7 on: March 28, 2021, 09:57:28 PM »
What does OMY mean to you?  Are you at a 3% withdrawal rate with plenty to cut and lots of money making skills that won't get too stale in a few years?  If so, then OMY is probably not worth it.  If you're going to be lean-FIRE with a 4% WDR and won't be able to easily re-enter the workforce then it's probably a good idea to OMY.  I'd like to hear more about your situation to provide any input.  Regardless of your situation, I have written on these boards innumerable times about how great going part-time was for both my partner and me.  If you're able to FIRE then even if your employer would have to bend over backwards to make your position work with a part-time employee they might do that if the option is losing you permanently.   

In no particular order, some of the things I would consider are:

Do you have dependents who rely on your income? 
Do you have a cushy, high paying job, or a terrible and low-paying job?
What are your back-up plans?  If you have lots of fat to cut in the FIRE budget, lots of skills that could generate FIRE income, a pension or Social Security that you aren't counting in your FIRE numbers, a spouse who will still be working, an ability to move to a lower cost of living location, or other back-up plans then quitting might not be as much of a cliff-dive as it feels like it is. 
If the motivation to OMY is based on charitable giving, could you do as much or more good volunteering your time?  Volunteering may help you as much as the people you're helping (I found that to be true). 
What withdrawal rate are you targeting?  If it's high then OMY might be a better idea than someone targeting a super low WDR. 
Do you get a lot of enjoyment and satisfaction from your work?
Can you re-enter your career a few years after quitting, or will you be locked out?

In my situation, I did OMY for a few reasons.  The primary reason for me was that my career required regular certifications that, once expired, are nearly impossible to get.  Now that I'm FIREd I'm basically locked out of my former career unless I luck into a very rare opening that lets me re-certify.  I also had a pretty cushy, high paying job.  They let me essentially go part-time, and the hours were very flexible.  I only have skills that can earn substantial compensation in a relatively narrow field, so my earnings potential now are much lower than before I FIREd.  We also support a number of family members who are unable to effectively provide for their own needs.  It was a priority for both of us to help those family members out long-term.  We also wanted to fund a Donor Advised Fund to continue to support other non-family charities that are important to us.  Finally, I'm just somewhat conservative when it comes to taking the kind of risk that goes along with a (hopefully) ~50 year retirement. 

Right now we're at about 21x some spending numbers that aren't totally padded to worst case, but definitely lean in that direction.  A decent number of folks here would pull the plug tomorrow if they had the same numbers. 

Both me and DH would probably have a certain amount of difficulty getting back into our careers if needed.  More than that I don't want to have that hanging over my head as a fall-back.  Obviously there needs to be a certain amount of balance, but I'd rather work a tad longer to make sure the chances of needing to go back to setting an alarm clock are pretty low.  Honestly part-time seems like the worst of both worlds for me personally.  I'd like to get my working years out of the way and be done with it.

No dependents.  Only DH who earns more than me. 

I have a fairly well-paying professional job.  I wouldn't call it cushy, but it's not bad.  I am very prone to stressing over it, though. 

I don't have a lot of fall-back plans other than just being conservative with the numbers.  I'm also building in the ability to move to another city I really want to live in that's MCOL, so another fall-back may be to move back to our current LCOL location if worst comes to worst. 

I think in terms of charity I'll do a lot better with money than with labor. 

I'm fortunate that all of my family seems fairly self-sufficient.  SIL could probably use a little help here and there, but she's reasonably self-sufficient so more of a nicety to give my nephew a boost than a need. 

I feel you on being conservative.  My job entails a lot of "how could this go wrong?" so it's natural to turn that on FIRE planning.

Quote
Good luck with your decision!  OMY is a stressful decision to make, but it's absolutely amazing to be in a position to have that choice to make.

That's a good point.  Just having to make this decision means we're in a pretty good place.  We've made sacrifices to be where we are now, but we're also just incredibly fortunate.   I feel like I need to share that. 

FLBiker

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Re: Is OMY Worth It?
« Reply #8 on: March 29, 2021, 06:06:55 AM »
We're in a similar boat.  We're at the FI number we've had in mind, DW is working PT through May, and is open to PT after that as well.  I'm still FT.  We moved in July from the US to Canada, though, so my thinking is I want to get 18 months or so of expenses under our belt (because we had a lot of initial expenses that won't be annual) so I can see how much we really need.  Early indications are pretty good, though.

Plus, I think it's almost certain that both me and my wife will likely work part-time, probably forever (though probably not in the summer).  I've learned that swaths of totally unstructured time aren't good for me (despite that always having been my goal).  I tend to isolate, for one thing.  So I think having something that forces me to interact with folks for ~10-20 hours a week would be perfect.  And if we're both doing this, I definitely could quit my full-time job.

That said, my company just engaged a PEO so that they're able to hire me in Canada, so I want to give them a year.  Plus, I'm thinking that after that year, I might approach them about going to 50%, which would undoubtedly pay better than almost anything I could get locally.  We shall see.

tooqk4u22

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Re: Is OMY Worth It?
« Reply #9 on: March 29, 2021, 08:31:46 AM »
I did OMY and I don't regret it even if I didn't need it.  Partly for the following:

1.  After a short whole wouldn't be able to go back to the high paying gig (but aside from ego the reality is I would never need to make that much even if I had to go back to work)

2. Was so burned out that thought of having to return to work was worse than keep working g longer.

3.  Have 3 teens so expenses are high and growing probably near term.  Also DW spending ideals are more than mine (not eggregiously so) so it had to factored in.

4.  Wanted to pad the college accounts.

5.  Wanted to pad sinking fund accounts for travel, major house repairs, future care replacement, and health care OOP costs. This purely psychological for me and a drag on my overall returns.   

6.  Wanted to protect against SORR

7. Wanted a lower WR on pretty full budget so we can live how we want but have flex to cut when needed but not so much we can do anything all the time.


At the end of the day the one thing that influenced me more than anything would be how I would feel if markets went down a lot...six months before my planned FIRE markets went down 20% and it didn't phase me so I was ready...still stuck out the six months bc it was the plan but mostly bc of bonus, vesting rsu, etc that were meaningful.
 
When I fired I went to a more conservative aa and didn't care too much when markets tanked last year and just rebalanced when it did. 

So yeah, I don't regret it

dougules

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Re: Is OMY Worth It?
« Reply #10 on: March 29, 2021, 10:32:49 AM »
What is the precise nature of each fear (you probably have multiple contributing fears and perhaps conflicting fears)? How early can you trace the fear/fears back in childhood? The earlier, the better. You probably haven't found the origin if you haven't looked before five years of age. From which parent or guardian did you learn each fear? Where did that parent or guarding learn each fear, focusing on the same age range? How do you think each fear was designed to protect each parent or guarding from that age onward? How was each fear designed to protect you? Do you really require that protection? Is any fear preventing you from realizing your potential in any way? How did each fear limit each parent or guarding? Does it still? How will each fear continue to limit you?

It's totally fear from my dad pushing me as a kid.  He instilled a fear of failure that has been a real double edged sword in my life.  Learning how to fail is an important skill I haven't really picked up. 

2. Was so burned out that thought of having to return to work was worse than keep working g longer.

This!  I'm not sure how rational it is, but this is exactly where I'm at. 

nirodha

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Re: Is OMY Worth It?
« Reply #11 on: March 29, 2021, 10:34:18 AM »
Have you been able to take any sort of extended break in the past 5-10 years? If not, it's hard to compare OMY to an unknown.

I used FMLA to take 12 weeks last year. The next steps were obvious upon my return to work.

chasesfish

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Re: Is OMY Worth It?
« Reply #12 on: March 29, 2021, 11:46:53 AM »
I enjoy this question...I did One More Year and kind of regret it.

Do you enjoy your job?  That's the biggest driver.

In hindsight, where I think a lot of people get FIRE wrong is they only consider two phases of their life, the Hustle phase and the Financially Independent phase.

I think it should be in three phases, the hustle phase, the coast phase, and the financially independent phase.

I got incredibly burned out at my job, so much so it took at least 12 months for me not to twinge at the thought of work.  I should have dialed it back into a more comfortable employer/role before quitting.   When you get near the end, investment returns make up for a disproportionate amount of the returns.

I'm two years FIRE as of mid-April, my net worth has actually grown more than my old savings rate per year.   That likely won't continue, but I gave a couple of years worth of stress I didn't need to give.  Especially the last eight or nine months I grinded it out to get the next bonus / stock award.

To each their own, but I hope to convince more people to consider step 2.

Malcat

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Re: Is OMY Worth It?
« Reply #13 on: March 29, 2021, 01:02:05 PM »
What is the precise nature of each fear (you probably have multiple contributing fears and perhaps conflicting fears)? How early can you trace the fear/fears back in childhood? The earlier, the better. You probably haven't found the origin if you haven't looked before five years of age. From which parent or guardian did you learn each fear? Where did that parent or guarding learn each fear, focusing on the same age range? How do you think each fear was designed to protect each parent or guarding from that age onward? How was each fear designed to protect you? Do you really require that protection? Is any fear preventing you from realizing your potential in any way? How did each fear limit each parent or guarding? Does it still? How will each fear continue to limit you?

It's totally fear from my dad pushing me as a kid.  He instilled a fear of failure that has been a real double edged sword in my life.  Learning how to fail is an important skill I haven't really picked up. 

2. Was so burned out that thought of having to return to work was worse than keep working g longer.

This!  I'm not sure how rational it is, but this is exactly where I'm at.

Humans aren't rational creatures, they're rationalizing creatures.

The thing is, everything is failure, it just depends on how you frame it.

You are the only one defining for yourself what is failure and what isn't. Even if you base your concept of failure on your father's expectations, you are *choosing* to use his metrics to define success vs failure.

The other thing is, failure is defined as failing to live up to a set of expectations that were set in the past. Well, that's just stupid. Your past self is nowhere near as wise as your current self, so who cares what that asshat thought you should have accomplished by now. It's irrelevant.

What do you, in this present moment need to be happy and feel fulfilled?
Figure out what that is and do that.

Whatever expectations you are letting live in your head rent free are expectations a less mature, less experienced, and less insightful version of yourself glommed onto for, let's face it, probably pretty stupid and immature reasons.
Why? Because we're all stupid and immature in the past.

I wouldn't trust me from 10 years ago to pick a fucking outfit, much less decide what my life should look like right now.

Now back to the concept of failure. As I said, every single outcome can be measured as a failure, depending on how you look at it. There is no "correct" way to win at living life. There's just the question: would I change anything right now, or am I happy with the way things are at this moment?

If you are really satisfied and happy with your life exactly as it is, then for now, you are a major success. Things may change, and a future, even wiser version of yourself may want something different, but in the present, if you wouldn't change anything, then you have won.

If you aren't totally happy, then what the hell are you waiting for? Are you hung up on trying to live up to outdated expectations from your past? Your parents? Whatever??

Decide what success looks like for you RIGHT NOW, and unapologetically live that life.

FIRE 20/20

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Re: Is OMY Worth It?
« Reply #14 on: March 29, 2021, 01:34:27 PM »
Right now we're at about 21x some spending numbers that aren't totally padded to worst case, but definitely lean in that direction.  A decent number of folks here would pull the plug tomorrow if they had the same numbers. 
...
I have a fairly well-paying professional job.  I wouldn't call it cushy, but it's not bad.  I am very prone to stressing over it, though. 
...
I feel you on being conservative.  My job entails a lot of "how could this go wrong?" so it's natural to turn that on FIRE planning.

I cut and pasted the sections that resonated most with me.  I also had a job that entailed a lot of thinking about and planning for "how could this go wrong", so I can definitely relate to that!

I love @chasesfish 's idea of three phases, and really their entire post.  I've never though of it in exactly those terms before, but I have long advocated on this board for people to find a way to change their relationship with work as they move from about 10x to 20+x expenses.  Somewhere in that range you can choose do drop all the career development stuff, the striving for another promotion, the thinking of work outside of work hours, and let go of all the stress.  For me that meant actually changing jobs (within the same company) and using my hundreds of hours of PTO to DIY part-time.  That last 2 years or so when I coasted were by far the best of my career in large part because I knew I had won the game and I just needed to coast on in.  For others it might mean re-negotiating their current role, and for others it might mean changing companies or even changing careers altogether.  But the point is that once you're in that range the 'stache is doing the hard work and it will carry you across the finish line as long as you can pay the bills in the meantime.  Based on the quotes above, I'd suggest trying to figure out if there's some way you can make your remaining time bearable or even enjoyable.  Could you drop some responsibilities?  Could you find a way to let go of the stress if you can't change the job (therapy, meditation, a vacation, a change in mindset)?  There's really no reason to stress about work when you're as close to the end as you are, but stress doesn't listen to reason.  You've won - you don't have to stress any more, but your mind hasn't accepted that yet.  It actually doesn't sound like you have an OMY problem - it sounds like you might have some challenges related to burnout and stress.  If you can address those then my guess is that you'll be able to figure out when you're comfortable pulling the plug and being ok with doing so at the right time. 

dougules

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Re: Is OMY Worth It?
« Reply #15 on: March 31, 2021, 02:22:38 PM »
Humans aren't rational creatures, they're rationalizing creatures.

Very true.  It took me an almost embarrassing amount of time to understand that when I was younger.

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The thing is, everything is failure, it just depends on how you frame it.

That's a really good way of looking at it. 

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You are the only one defining for yourself what is failure and what isn't. Even if you base your concept of failure on your father's expectations, you are *choosing* to use his metrics to define success vs failure.

The other thing is, failure is defined as failing to live up to a set of expectations that were set in the past. Well, that's just stupid. Your past self is nowhere near as wise as your current self, so who cares what that asshat thought you should have accomplished by now. It's irrelevant.

The main failure I'm afraid of on a conscious level is just simply being broke, cold, and hungry on the streets.  I have several layers of safety nets between me and that, though, and I know that's not what is actually bugging me on a deeper level.  Subconsciously it's a lot of stuff I'm still working through.

Quote
What do you, in this present moment need to be happy and feel fulfilled?
Figure out what that is and do that.

Better mental health and more self-confidence.  After that I don't know.  That's not an answer, but anything else I could say wouldn't be sincere.

Quote
Whatever expectations you are letting live in your head rent free are expectations a less mature, less experienced, and less insightful version of yourself glommed onto for, let's face it, probably pretty stupid and immature reasons.
Why? Because we're all stupid and immature in the past.

I wouldn't trust me from 10 years ago to pick a fucking outfit, much less decide what my life should look like right now.

Now back to the concept of failure. As I said, every single outcome can be measured as a failure, depending on how you look at it. There is no "correct" way to win at living life. There's just the question: would I change anything right now, or am I happy with the way things are at this moment?

If you are really satisfied and happy with your life exactly as it is, then for now, you are a major success. Things may change, and a future, even wiser version of yourself may want something different, but in the present, if you wouldn't change anything, then you have won.

If you aren't totally happy, then what the hell are you waiting for? Are you hung up on trying to live up to outdated expectations from your past? Your parents? Whatever??

Decide what success looks like for you RIGHT NOW, and unapologetically live that life.

No, I'm honestly fairly unhappy most days, but at least I will admit that now.  Not all that long ago I probably would have just said I was fine and moved on.  FWIW, I'm way less unhappy now than I was then.  I have days when I am totally happy, and in hindsight those were pretty rare a few years ago. 

What am I waiting for?  What does success look like to me?  Same as above, I'm honestly trying to give an answer, but I keep drawing a blank.  The younger me would have just thrown out something much better sounding that was trite and completely insincere to dodge the question. 

I love chasesfish's idea of three phases, and really their entire post.  I've never though of it in exactly those terms before, but I have long advocated on this board for people to find a way to change their relationship with work as they move from about 10x to 20+x expenses.  Somewhere in that range you can choose do drop all the career development stuff, the striving for another promotion, the thinking of work outside of work hours, and let go of all the stress.  For me that meant actually changing jobs (within the same company) and using my hundreds of hours of PTO to DIY part-time.  That last 2 years or so when I coasted were by far the best of my career in large part because I knew I had won the game and I just needed to coast on in.  For others it might mean re-negotiating their current role, and for others it might mean changing companies or even changing careers altogether.  But the point is that once you're in that range the 'stache is doing the hard work and it will carry you across the finish line as long as you can pay the bills in the meantime.  Based on the quotes above, I'd suggest trying to figure out if there's some way you can make your remaining time bearable or even enjoyable.  Could you drop some responsibilities?  Could you find a way to let go of the stress if you can't change the job (therapy, meditation, a vacation, a change in mindset)?  There's really no reason to stress about work when you're as close to the end as you are, but stress doesn't listen to reason.  You've won - you don't have to stress any more, but your mind hasn't accepted that yet.  It actually doesn't sound like you have an OMY problem - it sounds like you might have some challenges related to burnout and stress.  If you can address those then my guess is that you'll be able to figure out when you're comfortable pulling the plug and being ok with doing so at the right time.

Stress definitely does not listen to reason.  Therapy has helped a lot.  I think my tendency to stress is something intrinsic I would just carry right with me to any other job, although that is something of an open question. 

2sk22

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Re: Is OMY Worth It?
« Reply #16 on: April 01, 2021, 06:20:29 AM »
The main reason to do OMY is usually psychological, not financial. Purely on financial terms, I knew that I could FIRE at the beginning of 2019. However, it would absolutely not have been ok with my wife who has a generally higher level of anxiety about financial stability. So I did a few things:

Firstly I got my finances streamlined - money was scattered about in a dozen accounts. I consolidated everything in one place. Also got rid of some bad investments like whole life insurance.

Secondly, I quit my job at a big company and worked in a startup for a year - it was a sideways move financially but helped me a lot mentally: much less stress.

Thirdly, I steadily built up the early retirement case with my wife by assuaging her fears.

In the end, I was successfully able to retire in September 2020. It was a smooth transition and it worked out. I could not have done this any sooner.