Did I go off the Beaten Path too Early? Need Advice

I think you are doing quite well. Your logic resonates with me. Obviously, you cannot say life would be better or worse if you were at BlackRock or GS. Up to you to make this decision the right one!

Your decision, and the reasons for it, closely follows the way I generally think and I've made many similar decisions. A few quick examples:

1. Coming out of law school (a top 5 program that places most of the class at big NYC firms) I chose a mid-sized firm in a much smaller city because I knew I'd learn marketable skills there at a faster rate. Getting more exposure to the business logic of deals (which I wouldn't get at a bigger firm) helped me quickly realize I don't want to be a lawyer, and gave me the foundational knowledge to position myself well in the MBA admissions process and MBA recruiting.

2. Later on as an MBA student, I could only land a MM bank for my summer role because it was a tough market and I was late to commit to IB. I had a great summer at the MM and got a return offer; meanwhile the recruiting market also got better. So when fall FT recruiting started, all my friends told me to "trade up" to a BB or EB. But my thinking was that if I stick with my MM where I already have built good relationships and will have more say in who I work with, I have a higher probability of long term success there. Who knows what might've happened if I traded up, but I went to the MM and had a great 2 years; learned a ton that don't think I would've learned otherwise.

3. I recently left a VP role at top EB/BB for a buy side role at a family office. Its a mix of micro PE and HF type of work. Massive pay cut in terms of my comp in a normal or even good year. But if I hit a home run I could make about the same and if I hit a grand slam (lets define grand slam as once every 25 years if you rely on luck) I could do better than in IBD. If you put all those outcomes on a probability distribution, my expected pay is still lower in this job than the one I left behind. But the rub is, I have much more control over my work and I'm constantly learning what I think is the most useful thing. That changes the probability distribution. My % of a home run and/or a grand slam is higher because I have confidence that I will re-invest my knowledge in the right ways; I'm subject to my own distribution, not the luck-based bell curve that most would use. So my expected pay is actually higher in this role.

There's a small subset of people who think like you and I do, and there's everyone else. People like us will trade money for knowledge at many different points in life, because we have confidence that certain sets of knowledge actually have great value. Other people will only trade money for knowledge when there's a piece of paper (a certification/degree) attached to that knowledge. They've never really thought about the knowledge itself and what its worth, they can only process that a credential has some value because it provides near-term access to some job.

You made a good decision in my view. After a couple years there, you will be generally better positioned as a result of it. Maybe there will be some PE shops that don't give you a look because their process is more structured and they only look at bigger banks. But that's a maybe; you can probably wedge yourself in to most of those opportunities by impressing recruiters or contacts at the PE shops. Furthermore, there will no doubt be smaller PE shops where you have a leg up because of your bank's relationships with them. There's also the unknown opportunity . . areas like corp dev, startups etc might not be broadly attractive to you but there are needles in those haystacks that are attractive. On a broad level you're better positioned the more you know.