Hello Forum

I stuck around on an off for 5 years before finally pulling the plug for good. Five years of OMY syndrome. Mainly due to fears of not being able to get or afford health insurance. Cobra can be expensive-you're paying your share and the company's share and it only lasts 18 months anyway. Start checking out your state's ACA exchange.

Everyone eventually sticks around for money and/or ego, unless they truly enjoy the work. Remember, time > money.


If Megacorp hadn't supplied me with retiree insurance, I would likely have stayed to 65. This was before ACA, so would have been dicey getting single (well double - DW and I) health insurance with the health conditions I had at retirement. I still give thanks for that Megacorp health insurance.
 
Well, I chickened out.

Today was the day I was going to formally announce the plan to retire in Feb 2024.

Here's how my day goes.

10am - annual exam with my Dr. BP is high and she asks why I'm so anxious, so I tell her. She's excited for me and reminds me to be "compassionate" with myself. I thought that was interesting.

11am - shareholder call with our ceo where I'm expecting him to lay out the plan for our IPO that he emphatically said would happen by Q1 2024. Long story short, ain't happening, and might not happen for 3 or 4 years. I understand the reasons, they make sense, but when you say one thing, and mentally prepare decisions, and that changes, well. Lots of cursing at my laptop this morning. I don't need to sell the shares but knowing the liquidity is there is a huge safety net.

1:30 - meet and greet with one of my fellow partners (also a shareholder) in his newly appointed role as head of growth. I was prepared to do it but the shareholder call had me on edge and I danced around emphatically telling him I was done. We discussed where I was at mentally, and every time the conversation went to me leaving, he redirected.

I like the guy, he's been nothing but nice, and asked me to do 1 thing. Well 2 things.
One was a measurable task and the second was to give him the chance to help me "re-engage."

So there you go. I just closed my laptop for the day and am going to pour a large tequila to get rid of this tension headache.
 
Well, I chickened out.

Today was the day I was going to formally announce the plan to retire in Feb 2024.

Here's how my day goes.

10am - annual exam with my Dr. BP is high and she asks why I'm so anxious, so I tell her. She's excited for me and reminds me to be "compassionate" with myself. I thought that was interesting.

11am - shareholder call with our ceo where I'm expecting him to lay out the plan for our IPO that he emphatically said would happen by Q1 2024. Long story short, ain't happening, and might not happen for 3 or 4 years. I understand the reasons, they make sense, but when you say one thing, and mentally prepare decisions, and that changes, well. Lots of cursing at my laptop this morning. I don't need to sell the shares but knowing the liquidity is there is a huge safety net.

1:30 - meet and greet with one of my fellow partners (also a shareholder) in his newly appointed role as head of growth. I was prepared to do it but the shareholder call had me on edge and I danced around emphatically telling him I was done. We discussed where I was at mentally, and every time the conversation went to me leaving, he redirected.

I like the guy, he's been nothing but nice, and asked me to do 1 thing. Well 2 things.
One was a measurable task and the second was to give him the chance to help me "re-engage."

So there you go. I just closed my laptop for the day and am going to pour a large tequila to get rid of this tension headache.

Nothing to say but fingers crossed for you and fill that glass.
 
I had a similar issue. One third of my retirement assets were held in an ESOP (employee stock ownership plan). Management planned to take the company public. I thought the share value could fall, but I couldn't sell shares until turning 62. The IPO started off okay, with a nearly immediate ~50% appreciation. Since then, it's gone up a bit more. Today, I still have to wait another 5 years to receive my ESOP shares. I'm somewhat nervous, but the company's doing well, and I FIRED two and a half years ago. If my ESOP shares fell to $0, I'd have to cut the lifestyle a bunch, and probably exchange the house for a condo. Still, you only live once, and you'll never be as young as you are now. Time >$. I made the right decision.

If the rest of your ducks are in a row, and a lack of an IPO won't kill your ER plans, then bite the bullet and go for it! If your successful ER hinges on an IPO and enhanced share value, you might have to gut it out...
 
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Well, I chickened out.

11am - shareholder call with our ceo where I'm expecting him to lay out the plan for our IPO that he emphatically said would happen by Q1 2024. Long story short, ain't happening, and might not happen for 3 or 4 years. I understand the reasons, they make sense, but when you say one thing, and mentally prepare decisions, and that changes, well. Lots of cursing at my laptop this morning. I don't need to sell the shares but knowing the liquidity is there is a huge safety net.


Are you fully vested? What do you leave on the table if you go now?

Does marking your company's equity to $0 change your retirement planning numbers substantially?
 
Thanks. I appreciate your perspective given the similarity.

I'm re-evaluating the financial position, literally, as I type this. The anger has subsided and looking at the situation again, nothing really changed, just shifting things around. There is talk of a liquidity event in q1 but no details yet. I've got a 200k accrued dividend that if paid would push me over the edge. Just need that little bit of extra liquidity to make me comfortable.

I won't lie, this whole thing is terrifying. :LOL: There is also a touch of mournfulness, considering I've been doing this since I was 18, right out of High School.

Anyway, it's fine..it'll be fine.
 
Are you fully vested? What do you leave on the table if you go now?

Does marking your company's equity to $0 change your retirement planning numbers substantially?
There is no vesting, as it were. I wouldn't leave anything on the table aside from the paycheck if I left. I would take a hair cut if I were to tender my shares, but that depends on what our internal marketplace is doing at the time.

Long term, if the stock doesn't come to fruition, yeah, it would be a problem.

The shares and accrued dividend represent approximately 16 years of expenses.
 
Well, I did it.

Was called into a meeting with the same gentlemen noted back in November, only this time to discuss historical performance and 2024 expectations.

Revisited the same operational challenges as well as my mental state. I could see he wasn't hearing me, until I told him, you're not hearing me.

I told him that I'd like to stay around as long (reasonably) as it takes to assign my clients and to assist in that process, and offered "a couple of months." No idea how long it will take and it's in their hands now.

Wow.
 
Right on!!
"you're not hearing me"
LOL. Tap tap, wake up man. Depart from the script for a minute.
 
Well Congratulations!
I would make a note of what you feel is a reasonable amount of time for transition and let them know. Otherwise, it might drag on.

My boss knew several months what my last day was, still didn't hire my replacement until after I was gone.
I went back on call to train, but had a few months off first!
 
In 2004 I bought an old kinda run down cape cod house with the vision to renovate it, add a full second story, essenitally build a new house around the existing.

I'll never forget, on May 2nd, 2005, I had just moved my young family into a rental (we lived in the new place for 6 months while plans were drawn) and I was about half way through demoing the deck when the panic set it. "I can fix this." "We can live with the house the way it is, it's not so bad" Felt like I was staring over a cliff. That fight or flight emotion kicked in, and after a few minutes it passed and I got back to work.

Kinda how I feel right now, but it will pass.
 
Well Congratulations!
I would make a note of what you feel is a reasonable amount of time for transition and let them know. Otherwise, it might drag on.

My boss knew several months what my last day was, still didn't hire my replacement until after I was gone.
I went back on call to train, but had a few months off first!
I told him "a couple of months" but will go back to quantify it. Thinking no later than 7/1, that puts a pin a 39 year career, almost to the day.
 
I told him "a couple of months" but will go back to quantify it. Thinking no later than 7/1, that puts a pin a 39 year career, almost to the day.

DO IT! I would remind him every 2 weeks or so. Then I would give written notice about 1 June. What they do with your position should be none of your concern. If God forbid the unthinkable happens (tonight), the company will be just fine tomorrow. We are all replaceable. Best of luck to you sir.
 
My feelings on easing out aren't driven by ego or anything similar. I've got relationships with these clients that is important to me and a significant amount of my wealth tied up in equity in the company, also very important to me. Everything I do to make a smooth transition is in my best interest, first, company second.

I appreciate the encouragement. Not gonna lie, it's daunting. lol
 
I get it and had similar feelings. When I resigned in November I initially left it open but clearly stated that I wanted to leave in a way that both I and the firm were happy about my exit. Boss said, ok that sounds good to me, work out a date with your colleagues and HR... and that is what I did. Ended up with a date in early Feb so I could get employer subsidized health insurance for the entire month. It worked out well. In fact, I was pretty much twiddling my fingers for the last few weeks since all my work had been reassigned and I wasn't taking on any new projects... just consultation calls here and there.
 
seems word is slowing making its way around, and I'm oddly at peace. I expected to be on edge.

at the same time, we had a shareholder call last week, and the plans we expected to materialize went sideways, my CEO is pissed, made the rally cry, and OMY (or a portion of it anyway) seems reasonable.

I don't feel like I'm going out on my terms, as if, "you aren't hearing me" isn't enough (laugh out loud) but I'd like to go out on a high note, and all the sudden our IPO is suddenly much closer and I'd rather be able to say I was there when they rang the bell rather than I bailed 3 years before they rang the bell.

I'm sure none of this is a unique experience to anyone here, except for this one. I saw my ceo's face, and he looked tired, and looked like he needed help. that among everything else resonated.

waiting to hear back.
 
Looks like its OMY.

I appreciate everyone's support and guidance. This feels like the right decision.
 
What do you expect to accomplish this next year that you haven't already done?

If the decision feels right for you, then "trust your gut", as my Mom always said.
 
Really, nothing. I'm not looking to advance, get a new designation, take over an office...nothing like that. I would like to be productive and contribute in the final push getting us to public. If that circumstance changes than so do my plans. 7/1/25 is my date, one way or the other. That puts a pin in a 40 year career and I'll be happy with that.

Men make plans and God chuckles...
 
Really, nothing. I'm not looking to advance, get a new designation, take over an office...nothing like that. I would like to be productive and contribute in the final push getting us to public. If that circumstance changes than so do my plans. 7/1/25 is my date, one way or the other. That puts a pin in a 40 year career and I'll be happy with that.

Men make plans and God chuckles...

So, true!!! I'm late to your party but I wish you the best. I know many that just cannot give up their identity with the work they do. That is who and what they are and the title etc. is their priority. I don't think that is wrong but there is also more to live than a title.
 
Really, nothing. I'm not looking to advance, get a new designation, take over an office...nothing like that. I would like to be productive and contribute in the final push getting us to public. If that circumstance changes than so do my plans. 7/1/25 is my date, one way or the other. That puts a pin in a 40 year career and I'll be happy with that.

Men make plans and God chuckles...


Best of luck that everything aligns by then. We look forward to having you on "this" side of FIRE. Keep us posted.
 
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