Financially Independent but feeling trapped

sterlingmossy

Recycles dryer sheets
Joined
Jan 27, 2018
Messages
61
Location
Wilmette
Hi,

Life Situation: 52, male, happily married (26 years) two boys (one 24 working, one 21 a Junior at College), one dog (Lab) living in the suburbs of a major metropolitan city.

Have investable assets of around $5m plus house (@$1m). No debt. Last kid is a junior in college and should graduate 2019.

I started a company in 2003 and sold it in 2016. I got most of the money for the sale upfront. THe new owners are paying me a good salary until the end of 2019 with some extra incentive (around $400k) if the company performs well.

The trouble is that now I have sold the company my heart really is no longer in the work. I have transitioned day to day responsibility to a very competent CEO, the company is perfoming well and hitting all its targets and a feel a bit like an spare appendix (nice to have but not really needed).

So this is my question. Do I stick around until the end of 2019, fill the coffers some more, try to summon up enthusiam for the work or do I leave the money behind retire, rejunivate and find a new direction for my energy and efforts.

What would you do?
 
Welcome to the forum!

Everyone is different of course so "one size does NOT fit all" but if it was me I'd bail. I retired at age 52 from a public safety position where that age is fairly normal to retire. But I was also at the top of my game in the then-new field of computer forensics and in private industry they paid very well. But for me the cost would have been huge in terms of hours, travel (which I don't much care for) and horrible commuting times and conditions. We moved from near Washington, D.C. to West Virginia, about an hour and a half drive but worlds apart in terms of atmosphere and traffic conditions. In doing so we left a lot of money on the table and naturally we wondered if that was a wise decision.

Six months later we went to visit my younger sister, then living in Northern VA. The first thing she said was "I haven't seen you two look so relaxed in years".

We were then certain we'd made the right choice. YMMV.
 
If it's a binary choice, I would do the math on the net $$ for sticking around and determine the difference it would make in my life.

Perhaps there is a third option......

If you're feeling like a redundant spare part, the owners almost certainly feel it to. But, everyone wants to be honorable and hold up their side of the deal.

Perhaps there's a discussion about concluding your involvement early that gets you a few bucks and leaves everyone feeling good about how things were wrapped up?
 
If it's a binary choice, I would do the math on the net $$ for sticking around and determine the difference it would make in my life.

Perhaps there is a third option......

If you're feeling like a redundant spare part, the owners almost certainly feel it to. But, everyone wants to be honorable and hold up their side of the deal.

Perhaps there's a discussion about concluding your involvement early that gets you a few bucks and leaves everyone feeling good about how things were wrapped up?

I like your thinking. Great option. Thanks.
 
So this is my question. Do I stick around until the end of 2019, fill the coffers some more, try to summon up enthusiam for the work or do I leave the money behind retire, rejunivate and find a new direction for my energy and efforts.

I'd figure out what I wanted to do before I made any changes. You have a sense of what you DON'T want. Now figure out what you DO want first, then go for it.

Maybe you need a long vacation or a sabbatical to find the time to ponder your next move. Maybe not.

I left money on the table. But I never looked back.
 
I would not rush to a decision. Just work less. That's what I am doing. $6m is a lot but it's not endless depending on what your spending is or will be.
 
I'm pretty close to BTDT. My deal was a part-time "consulting" gig, IIRC maybe 15-20 hours a week. That worked well for me, as I could drift into the office around 9:30 or whatever time I felt like that day. I could also take days off easily.

I worked on various projects and coaching of staff, etc. No more trade shows or customer visits, etc. I could call and chitchat with business friends when I chose. I could also politely stick my nose it once in a while when the new owners needed some help or coaching as I, too, was getting future payments based on performance. It felt more like a hobby than work. Eventually I transitioned out, and that was good too as I became less and less necessary.

Maybe you could negotiate a deal like that?

EDIT: Oh, and for something new, look into volunteering with SCORE. It's great fun. www.score.org.
 
If it's a binary choice, I would do the math on the net $$ for sticking around and determine the difference it would make in my life.

Perhaps there is a third option......

If you're feeling like a redundant spare part, the owners almost certainly feel it to. But, everyone wants to be honorable and hold up their side of the deal.

Perhaps there's a discussion about concluding your involvement early that gets you a few bucks and leaves everyone feeling good about how things were wrapped up?


I was kinda leaning this way, but he added a different take...

Mine would be to see how many hours they really need from you for you to hit the $400K at the end of 2019...

But there is the other of just saying you have worked half and you would be willing to walk for $200K... and of course good luck....


For me, you say a good salary and $400K, so what is a good salary here? If it is $150K or so then you are talking $600K for 2 years... that is a pretty big chunk of change with the assets you have put down... I would finishing up if they did not do either of the other two....
 
I'd figure out what I wanted to do before I made any changes. You have a sense of what you DON'T want. Now figure out what you DO want first, then go for it.

I think there are many people on this forum who left their job when they felt they had enough to manage. It is likely they could have continued to work and accumulate cash.

I think joeea's suggestion was the most insightful so far. The money simply gives you the freedom to choose. If you feel you have enough, let the success you have experienced allow you to go in the direction you desire

If you still need to accumulate funds to get to FI, then balance your next step with the potential income. I am guessing many of us sucked it up to reach FI. However, I would suggest you make this choice knowing the financial end game.
 
If it's a binary choice, I would do the math on the net $$ for sticking around and determine the difference it would make in my life.

Perhaps there is a third option......

If you're feeling like a redundant spare part, the owners almost certainly feel it to. But, everyone wants to be honorable and hold up their side of the deal.

Perhaps there's a discussion about concluding your involvement early that gets you a few bucks and leaves everyone feeling good about how things were wrapped up?

+1 Tell them... you got this and I'm a fifth wheel... congratulate each other on the deal working out much better than you both thought it would sooner that you both thought it would.... and renegotiate something that is mutually beneficial.
 
Perhaps there is a third option......

If you're feeling like a redundant spare part, the owners almost certainly feel it to. But, everyone wants to be honorable and hold up their side of the deal.

Perhaps there's a discussion about concluding your involvement early that gets you a few bucks and leaves everyone feeling good about how things were wrapped up?

Agree with above...

I also sold my company and got most of the payout upfront. I spent the minimum agreed upon time working for the acquiring company, and negotiated a small monthly retainer-like fee on the way out. However, I didn't have a kicker payment based on time/hurdles. That said, I actually think that puts you in a strong negotiating position (if you are willing to take less than the max kicker payout).
 
Couple of questions. Does your current nest egg support the lifestyle you want in retirement? Could you up this lifestyle if funds became available? To be safe you might want a cushion of say 20-25%. Are there other things you would rather do than go to work everyday? Sounds obvious to many around here, but maybe not for you? How bad is it actually showing up everyday? What does your wife think? Does she work?

The answer to these questions will help you decide. As others have stated, negotiating a compromise would probably be the way to go if you decide to leave. Amendments if this sort are quite common.
 
Life doesn't get any longer. With your assets I would move on. Good luck with your decision.

+1
 
Couple of questions. Does your current nest egg support the lifestyle you want in retirement?

Pretty much

Could you up this lifestyle if funds became available? To be safe you might want a cushion of say 20-25%.
Makes sense

Are there other things you would rather do than go to work everyday?
Yes, I have a long list

Sounds obvious to many around here, but maybe not for you? How bad is it actually showing up everyday?
Actually I don't even have to show up, I can work from home. Not really bad, just boring


What does your wife think?
She thinks I am crazy not to stay till the end.


Does she work?
No

The answer to these questions will help you decide. As others have stated, negotiating a compromise would probably be the way to go if you decide to leave. Amendments if this sort are quite common.

Thanks, Answers embedded
 
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At 52 healthcare may or may not be an issue. Inching towards 60 not mentioned in the previous suggestions and advice. Are your children on your healthcare policy? Just a thought to consider. No debt puts you in the drivers seat.
 
It depends on how much energy you REALLY need to expend to last to 2019 and get the additional money.

Sometimes, for those of us who tend to be "type A" in our work, it can be difficult to scale back our efforts and do "just enough". But if you can do that, maybe you just work at a more relaxed, slower pace until 2019 to gain that 400K.

For me, once I hit FI, it was tough scaling back my work efforts. I like a lot of my job, and things like being ready to travel to help on a project at a moment's notice, doing email on the weekends, and doing "extra" work on technologies to expand my skills nights and weekends was tough to cut back on. But being FI meant that raises and promotions were no longer needed, so why put in the extra effort to justify those things. I cut back so that while I am doing less work, I'll still meeting deadlines and not causing others to miss deadlines. A lot of projects that I would have lead in the past I am mentoring others on, which is a lot less work. And I have been working from home the last 2 years, which has been very relaxing.

So, in my view, if you could lessen up the work load, gain more time for yourself and start the transition to a retirement "mindset", I see no reason not to keep going to gain an additional 400K. But if you feel you cannot, then it would make sense to talk with them about bowing out as soon as possible.
 
At 52 healthcare may or may not be an issue. Inching towards 60 not mentioned in the previous suggestions and advice. Are your children on your healthcare policy? Just a thought to consider. No debt puts you in the drivers seat.

Good question. I am concerned about healthcare and really have no idea what things will look like post retirement. Yes both my kids are still on our healthcare.

I am toying with the idea of trying to negotiate part time work with my old company that allows me to keep some form of healthcare for a few more years.

Any suggested good links to read about healthcare options?
 
The answer is $350k per year.

Thanks for the thoughts.


Yep... that is pretty good...

So the real question is do you want to work for 2 more years for $1.1 mill...

That is almost a 20% increase from your current nest egg...


I do not have even half what you have, but I would work 2 years to get 20% of my current nest egg... IMO, the benefits would be huge...


Now, if your WD on what you have now is 2%, then you really do not need that extra cushion....
 
I think 10% bump per year to your nestegg is pretty significant. 2 years isn’t that long for this level of increase in my view. I stayed 3 years to get about 8-10% per year I think. Always better to have a little more.
 
Good question. I am concerned about healthcare and really have no idea what things will look like post retirement. Yes both my kids are still on our healthcare.

I am toying with the idea of trying to negotiate part time work with my old company that allows me to keep some form of healthcare for a few more years.

Any suggested good links to read about healthcare options?


What is the company policy on providing healthcare... FWIK, it cannot favor some and leave out others.... so if you are part time and get it then they are supposed to offer it to all part time employees if they reach the hours required....
 
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