Whoa bro...that's a lot.

mrsconn23

Dear Prudence,

In the past eight years, I’ve been divorced, lost $1 million on lawyers, and survived a brain tumor, spinal repair, a heart attack, a stroke, and three other major medical events. My three teenage daughters won’t talk to me—and I just won custody because their mom is very troubled. Once a CEO, I’m now on a race to the bottom in my career, losing job after job due to my health and cognitive losses that make me less than CEO-ish. So, with a handful of cash left to my name, responsible for raising and supporting my girls and caring for a loyal dog, I want to start my own company. I know exactly what I want to do; I know the risks; I know the upside. However, my confidence is shaky, and if I bet half the hobby farm that remains, it could be disastrous. But I see no other options. I’m doing freelance consulting for hand-to-mouth money. My mental and physical being are stable, and who knows if I’ll ever have this window again: enough money to be dangerous and strong enough to take a few more blows. I turn 53 soon. You’d think I’m old enough to make my own decisions and to know better when not to. But I don’t.

—My Life’s a Mess. Time to Start My Own Business?

flantastic

mrsconn23 said:

Dear Prudence,

In the past eight years, I’ve been divorced, lost $1 million on lawyers, and survived a brain tumor, spinal repair, a heart attack, a stroke, and three other major medical events. My three teenage daughters won’t talk to me—and I just won custody because their mom is very troubled. Once a CEO, I’m now on a race to the bottom in my career, losing job after job due to my health and cognitive losses that make me less than CEO-ish. So, with a handful of cash left to my name, responsible for raising and supporting my girls and caring for a loyal dog, I want to start my own company. I know exactly what I want to do; I know the risks; I know the upside. However, my confidence is shaky, and if I bet half the hobby farm that remains, it could be disastrous. But I see no other options. I’m doing freelance consulting for hand-to-mouth money. My mental and physical being are stable, and who knows if I’ll ever have this window again: enough money to be dangerous and strong enough to take a few more blows. I turn 53 soon. You’d think I’m old enough to make my own decisions and to know better when not to. But I don’t.

—My Life’s a Mess. Time to Start My Own Business?

Prudie cannot answer this for you.

I get that you don't want to pay for financial/business advice, but that is what you are asking for. This is not a Prudie question.

ShesSoCold

Wow. That's all I got.

Except he has custody of his three daughters and they don't speak to him, but his big problem is whether or not to start a business? Sounds like part of the problem right there!

VarunaTT

Wow.  And IDK; also I feel like his personal life is still a disaster, so maybe not the time to start up a business.  I think he definitely needs an actual timeline written out to make sure he stays on track.

thisismynickname2

You know... Prudie said not to do it and instead to work on his relationships, get more doctor advice, and file for disability. 

The guy was a CEO. He knows what business takes. I wonder WHAT business he wants to start. I'm sitting over here kind of like... YOLO. 

Maybe see if he qualifies for disability first and then try the business idea. 

banana468

Yikes.   This sounds incredibly sad but I think LW needs to seek...NOT PRUDIE.

charlotte989875

I say do it. Get a good financial planner, but if other work isn’t cutting it and the business plannlines up, I say go for it. 

short+sassy

On the one hand, he says he is mentally and physically prepared.  But, on the other hand, he says he can't hold down CEO-type jobs because of his health and cognitive losses.  So what makes him think that being the CEO of his own company is going to be anything but disastrous?  I'm not being snarky and implying it's impossible.  But he needs to think about how opening his own business would be different from the jobs he has lost.  Because if they're similar scenarios...eeehhh...maybe now isn't the time.  And maybe it never will be, if he isn't able to physically, including cognitive abilities, regain what was lost.

With that said, this letter has fairly scant information and there is so much not clear to me about his situation.  I would assume that a former, successful CEO would have a financial advisor.  Probably friends/contacts who are also business-savvy.  He should be having a discussions like this, with them.

Another important consideration is his relationship with his daughters.  Apparently it is already a very contentious one.  And, if he starts his own business, he might have even less time/attention for them and make things worse.

I'd also like to know more about his financial situation.  Because it doesn't have to be CEO vs. business owner vs. nothing.  Is he still trying to live the same lifestyle on less money?  Maybe he is still capable of doing similar management work, but at a lower level.  As in, could he get a job more like the average person, even if it comes with a lower salary?  Sell the McMansion.  Sell the BMW(s).  Learn to live within that income bracket.  Heck, lowering his expenses (if he hasn't already) is one of the best things he can do right now, no matter which avenue he takes. 

Final note.  He's a gambler, at-heart.  Which has previously been a great strategy for him and also why he is heavily leaning toward opening his own business.  But, with all the turmoil he has had in recent years and now about to take full custody of his daughters, my gut says what he really needs is a period of stability with a job that is fully within the capabilities that he has now.  I think his daughters need that too.   

ShesSoCold

After thinking about this more, I'm wondering if he should have the stress of opening his own business. I can't imagine how stressful that would be (and especially when the situation is that you're fucked if you fail)  to have your own business and this guys is fairly young with a laundry list of health problems. I wonder if his doctors would recommend piling more stress on his heart's plate.

MesmrEwe

A cognitive loss would be opening his own business instead of just expanding his consulting work into more of a lucrative enterprise and ramp that up.  

There is more rehab for this guy to do before he is ready to start his own business.  Let the money that's left start working for him to gain equity and principle and start simple and build one's market.  Like - any other business owner would do!  Being the CEO vs. the owner are two ENTIRELY different positions to be in.  He's not ready for CEO, he's not ready for ownership level where you get to choose the 86 hours a week you work!