Requesting Some Career Feedback

Hi folks,

I am currently in an odd phase of my career where I'm not sure what to do next given some recent turbulence in my career. I don't really have anyone I can turn to for advice so figured I'd reach out here for some general feedback (not a career anyone in my entire extended family knows anything about, and I'm a little shy to reach out to my former senior colleagues lol). Would sincerely appreciate any thoughts here as I try to figure out my path forward. Will provide as much information as I can without self-doxxing, hopefully. 

This has gotten really long now that I've typed it out - so TLDR: Career all over the place including 4+ years of PE at analyst and associate level, some corp dev, and most recent co-leading tech venture/growth strategy. Unfortunately no real deals closed in 3 years and current firm winding down. Frustrated with myself, trying to maximize comp, want to be close to family in state where no industry exists. Not getting many looks in recruiting. Should I stay in PE? Pursue IB instead? Is this a pivot thats feasible? B School? Appreciate y'alls time and thoughts!

• Background - Just turned 30 years old, single, moved to the US as a political refugee when I was a child.
• Education - Studied biology at a lower-tiered Ivy, pivoted from pre-med career aspirations to finance in my senior year [no academic issues, just need to support family asap, did not have 5-7 years flexibility]. Extended graduation 1 semester to get finance internship experience, took finance/corp. finance classes, took MBA level classes for intro to IB, modeling.
• Internship - NYC Healthcare bank working for an MD who specialized in PIPEs. Very learn teams so got to do a variety of things in preparing materials for various clients. During the semester I also did grunt work for some search funds.  
• 1st Job - PE Analyst to Associate (Generalist, 2.5 years total) at $100bn+ AUM. Great way to formally cut my teeth in the industry, really enjoyed working across industry verticals and asset classes (primarily direct buytouts and some real estate buyouts). Lean teams, learned basics of underwriting, technical skills, process management, etc. Got some large deals closed, got a good amount of screening reps that died in early stages of IC, got good amount of deals that went very far process-wise. In lieu of proper banking experience, felt very grateful for this experience. Some of my associates/sr. associates would give me a ton of their work (relative to my peers in our class) which I felt was very helpful for my development. The hours at this firm were very intense, but I sincerely enjoyed the work and culture - although the compensation was the lowest end of the market. Left this firm because of life curve-balls.
• 2nd Job - Non-M&A Corp Dev (2 years). COVID comes around and due to longstanding family issues I had to move closer to home to help sort things out (eldest of my siblings, no other option here) and put the PE career on pause. Did some strategy and ops work which was a new skillset to learn, but candidly the pace, intensity, and fullfilment just weren't there for me. Felt like my prior experience made me really efficient and I had a lot of time to work on side projects (tried launching 2 failed businesses, invested in many startups, started doing advisory work on the side). Left this firm to get back into PE once family issues were resolved.
• 3rd Job - PE associate (almost 2 years, generalist) at multi-strategy single family office. Can't give too much info on the family here, but the fund was run like a proper PE fund with a focus on structured growth equity. We evaluated buyouts, lead growth equity, 50/50 co-investments, minority co-investments, and regional fund investments. Essentially the same level of rigor, underwriting standards, and process management as my first fund. To the best of my understanding, some family offices are "lighter touch" in deal execution - sometimes relying on other parties' diligence and piggy-backing deals. My experience here did not reflect this, it felt purely additive to my prior fund, not a step back. I was the 3rd hire on this team (we grew from 2 team members prior to my joining, to 4 team members before I left). I took this gig because (a) was seriously impressed and wanted to work with the VP here and (b) felt like other firms weren't giving me a serious look given my 2 year break from PE. Great experience continuing to refine my underwriting skillset (diligence, process management, modeling, etc). I brought a few of my own deals to IC (one deal that I handled 100% end-to-end even got approved although it blew up in negotiations). Left this firm because of (a) comp and (b) desire to invest in tech deals (which is largely what I had brought to my firms IC but the firm expressed reticence in the vertical). Note, only deals closed here were small fund deals but we had a TON of opportunities explode for one reason or another at the 99-yard line (e.g., full IC approval but failed negotiations as we pushed for more value).
• 4th Job - Sr. Associate (1 year) at a tech investment firm (early stage, growth, and tech funds). I was the 2nd hire for the US office of a foreign entity. Again, can't say much more but the pitch I was sold was the firm had a large balance sheet and wanted to build the next big asset manager and I could be at the ground floor helping to establish its presence. This was awesome for the first 6+ months - I owned most of the investment strategy, as our Head of US essentially let me run with it as long as I also helped out on their deals. Got to meet some amazing founders and pitched some opportunities that would have been great investments. Unfortunately, we didn't have a committed capitial vehicle at the time, and thus our deployments were supposed to be carved out from other teams abroad. They had no incentive to help us and so every deal we worked on was stalled in IC before dying almost always from lack of feedback in a timely manner. Eventually, our mandate shifted twice before I found out in December, our firm has decided to shut down its US office and my team is being disbanded. Note, in this role I definitely grew a ton in my sourcing and process management. Although, the underwriting here was not as rigorous as my other 2 buy-side roles because our deals kept dying very early given the poor corporate governance internally. I took a chance on this opportunity and it blew up in my face.

-Some Frustrations-

I am at a stage now where I don't really know what to do next. I feel like I've hopped around a few different strategies and geographies. I worked pretty hard in the roles I've had and, although I'm extremely grateful for the breadth of experiences, I'm kind of on an island with nothing to show for it. 

I really enjoy the concept of private markets investing. I was a relatively successful debater in school and investing seems analogous to building a thesis, defending it with rigorous analysis that evaluates all sides of a position, and being rewarded for having skin in the game. I enjoy working with teams and have an immense respect for all my former colleagues who've helped train me. 

But I have some frustrations with the job, too. I'm sure we all have "I told you so's" and I am also keenly aware that there's some selection bias at play, but I feel like my anti-portfolio (deals I brought or advocated for that weren't done) is pretty solid. In my last two gigs, although it was for different reasons, it felt like my hands were tied behind my back with good opportunities being passed for reasons unrelated to the strength of the investment itself. I understand deals dying is par for the course in this game and have never historically had a problem with it, nor am I beholden to the idea of "my" deal being the one that needs to succeed. I think I've always been a team player. It's just frustrating when sometimes you don't get a fair shake. When deals aren't getting done, it begs the question what you're spending your life doing. Not to say we should do deals for the sake of doing deals. But it really becomes unfulfilling when you're in a constant cycle of doing work that leads nowhere for reasons that are unrelated to the quality of an investment. 

My other main frustration is compensation. Historically Ive been at firms where compensation has been on the lower end of the market. My first firm I made $130k a year by the time I left. I was working 80-100 hours most of my tenure, which I didn't mind given the quality of the experience. At my 2nd PE gig I was working similar hours for $250k all in and got offered $500k in carry after my final review. I felt this was still on the lower end for the amount of work I was doing. My most recent firm had really attractive base compensation but we aren't getting bonuses since we're winding down. I've become somewhat disillusioned with the idea of carry as well, given what I've read and heard about peoples' experiences with delays in seeing liquidity. Seems like the promise of long-term incentives is illusory at some firms, and might not be worth it relative to other options that compensate you earlier. 

At 30 years old, with a variety of experiences but seemingly no clear narrative, I realize that my next move matters a ton. I'd like to be at my next firm for 5-7 years and really build some upside for myself and contribute meaningfully to a mission. I want to plant my flag and stop moving around so much. I think when firms see my resume, they see too sporadic of a track record. I think folks with a more traditional path (IB to PE, fewer places worked, etc) are more likely to get looks for premier positions. 

-Some Reflections-

• If I could have my cake and eat it, too, I'd love to have a position where I can have decent compensation on annual basis, a clear path to meaningful upside, and flexibility to be near my family. Probably what we all want lol.
• I don't mind the hours of any gig per se (although as I'm getting older my endurance is waning lol). I have hobbies but I'm kind of married to the grind in that I spend a lot of my free time hustling (tinkering on side projects, sourcing new deals, reading about the space).
• I want to work in a field where I'm actually providing value. Buyside can create value over time, sell-side can provide value to clients immediately, being a founder can create value over time. I really want to avoid asking myself "what was the point of all that effort?" in my next role.
• Over the last few months I've been able to work remote. I have really enjoyed being closer to my extended family. For the first 5-6 years of my career I had been away and its been incredibly fulfilling to be able to see everyone again regularly. I would love to be able to visit family regularly if I'm not living in my home state (near the west coast). That means places like NYC are lower priority as opposed to SF, Seattle, Dallas, Austin. I realize I probably will have to move as my home state doesn't have any PE/IB presence, and industry is lacking. Remote gigs that compensate well are few and far between, if they exist at all.
• I'd like to be in a lower cost of living area to save more, as I don't mind not having the amenities of a big city, however I know the highest levels of compensation are generally in more expensive cities.
• When I evaluate my skillset, I think I have decent relationship management skills, pattern recognition for what makes good investments (at the risk of seeing things too rosy eyed at times), ability to thoroughly diligence and craft arguments/memos, and willingness to run through walls when the team needs it. I think my modeling is a little rusty but could be brought up to speed quickly, but at times I feel like I've forgotten everything about corporate finance/accounting. I'd like to think I don't have an ego and people enjoy working with me.
• I have very little savings for where I'm at in my career. Through a combination of lower compensated jobs, paying for family expenses (sibilings undergraduate education, parents sustainenance, etc), business endeavours that failed, and investing in way too many startups that saw great paper marks but not real liquidity, I feel like I don't have a real safety cushion.
• I think I want to prioritize short-medium term compensation over everything else for the next ~3 years to be able to build a safety cushion that can allow me reasonable optionality to take lower compensation gigs later on that allows me to (a) see my extended family and (b) support a future family of my own. 

-Conclusions-

So, the big question, what should I do and how should I go about executing on that path? If I could work at a high compensation firm even if I had to work 100 hours in my home city, I'd do it in a heartbeat regardless of strategy - but realistically that's not going to happen. In the last 3 years, although there were some very strong late stage deal reps, unfortunately I did not close anything meaningful besides some fund investments. Given some rust, I'm doubting my ability to stack up to the more pedigreed candidates at normal MF recruiting. I know I'm willing to roll up my sleeves and grind as hard as the next teammate when on the job, but feel like I am not getting many looks in applications (casting a wide net right now). If PE is getting concentrated and upside is becoming more illusory than tangibile, I am not sure I even want to dive back into the fire. But, what else could I be doing? Investing is fun and I have enjoyed the nature of the job, just had issues with renumeration in my experience. I am not sure I'd enjoy corp dev. I don't know if I have it in me to keep taking risks like an entrepeneur or that I have any creative ideas that would justify a startup at this stage. 

It seems like the two paths in front of me are (a) another investing gig or (b) sell-side work. In recent months I started doing some sell-side advisory work on the side with some very nascent boutique firms started by friends. I've found the process to be refreshing relative to investing as one can see immediate value provided to clients (even if its fleeting). However, I haven't been doing it long enough to know if I'd truly enjoy it in the long haul. 

I don't even know if I'd be good enough to break into a reputable sell-side firm. Or if a good buyside firm will even entertain me given my career trajectory. I really don't want to go to B school to reset my branding but that may be the only option to use time productively while I continue soul searching.

If I wanted to go to a bank, would I be able to break in at the Sr. Asc. level or above? Could I be a reasonable candidate for Sr. Asc/AVP at a PE firm? A major concern I have is joining a new firm at a more junior level - not because I care about titles but more so because I'd rather not take a step backwards in compensation. What should I do to make sure I'm optimizing my chances at recruiting? 

I know this is all over the place and its silly that I've even typed this up but would sincerely appreciate some crowd-sourced feedback. 

Thanks all!