At a crossroads

I spent the last ~4 years doing sell side research and my team got laid off about 6 weeks ago. Didn't take be my surprise per se given the bank I was at cares about one thing and one thing only and that is paying the executives and shareholders more each year and given deals have been down the last few years due to the 2020/2021 deal pull forward the only way to pay out more is to cut costs and research is the obvious place to do it. In any event I now find myself questioning where to go with my life both professionally and personally. My goal all along was buyside equities (have a masters and undergrad in finance) and I took the sell side job over a buyside offer when I was graduating because it was a smaller buyside firm in a city I didn’t want to live in and the pay was much higher with the sell side job. I regretted that decision about a year into the sell side job and started interviewing for buyside stuff and got to final rounds at a few different places and just didn’t make it over the finish line. All of this has caused me to take a step back and really question what I want in my life and to be thoughtful about the decision I make now because I don’t want to do something again that I regret later. I basically have 4 things that are a potential at the moment:

• A ~$2B AUM shop that specializes in small/micro cap stocks. They seem like good people, and I think small cap managers can still add value, and I think about stocks similarly to them. Downside is it’s in a city that I don’t like, there is only so much AUM you can manage in small caps and they don’t want to chase AUM (good in a way) but bad in that maybe the upside is they maybe get to $4B in 5-10 years and they’ve been pretty clear about how they aren’t going to be the type of place that has a lot of PMs. They have 2 PM’s, CIO (who is the founder) and CEO who is the cofounder, so I bet they will take almost all of the upside. I would be the analyst #5 on the team as well. I also just question what the career durability is as a stock picker particularly given, I just got fired from the sell side which is facing all of the same headwinds the buyside has for >20 years at this point and AI is only going to reduce the number of jobs out there.
• Alternative manager that does aviation leasing/lending. It’s an interesting asset class and I personally enjoy aviation plus it’s also basically impossible to replicate with a passive instrument. Downside is it’s also in a city I don’t like and this place is already built out so I will be a cog in the machine which means maybe I make 300-400k after a decade there (not a bad living at all and money isn’t everything but also not what I envisioned when I set my sights on finance).
• $1B wealth manager that does active SP500 stock picking and then manager selection for alternatives. What interests me in this one is they are talking about aggressive growth and equity being on the table within 3-5 years. But spending my time trying to grind out a few bps vs the S&P and then doing manager selection doesn’t sound very fun to me. A positive is it’s in a city that I wouldn’t say I love but also don’t hate.
• The last one is something very different than what I envisioned in my life but also what I think is a once in a lifetime chance. A family friend who took his manufacturing company from $1M revenues in 2001 to $65M this year offered to mentor me in entrepreneurial pursuits. He is an engineer by trade and went through the exact same thing I am right now, getting laid off in his late 20s and pondering what to do with life. Perhaps the more interesting part is he wants to exit in the next 5 years and does not want to sell to PE. He mentioned his vision is “to sell to a young hungry guy like me who will preserve his legacy, take care of his employees and take the company to the next level and if that means he has to provide seller financing that’s subordinated to bank debt for someone to buy it without putting money down then so be it”. That’s where the conversation ended so I am not sure if that was a serious comment meant to gauge my interest or him just more sharing it (this guy love to talk and tell stories). Assuming he was serious, my trepidation is I am not sure I want to move back to where I grew up (I know that’s a stupid reason to not pursue something like this), I never saw myself owning and running a business I’ve been 100% focused on being a stock picker for the better part of a decade and I feel like not doing that is quitting and also if I am going to be a business owner I think I prefer the idea of charting my own path in the city I want to live in vs stepping into someone else’s.  

Given all of that, what would you do in my shoes and/or how do you suggest I do the soul searching to find the answer that is right for me?