Bouncing back from institutional sales disguised as PE advisory

Hey Monkeys,

I'm dealing with the repercussions of a difficult career decision I made and was hoping to harness the collective wisdom of the platform for ideas on how to get my life back together.

Background: I was the first person in my immediate family to go to University and wound up getting into a top Canadian school. Without knowing much about what I wanted to do with my life, I chose to do a B.Comm since I figured it would leave my options open. I wound up specializing in finance after an interesting summer abroad, and took a real estate private equity course with the extra credit I had to play with. The course ended up landing me a job in real estate PE in the summer of my junior year, and I had planned on going back FT upon graduating. It was a small deal x deal shop just getting off the ground though, and just before graduating I had the epiphany that I would probably be better off finding work at a larger firm.

I hadn't recruited for IB and opportunities at BBs had already been filled, so I had a little over a month to find something else before graduating. This is when I stumbled upon a firm providing advisory services to private equity managers worldwide, and they were hiring at the undergraduate level for the first time. The role had a heavy emphasis on sourcing deals which had been pitched to me as '"deal making", and being a naive kid I was delighted at the thought of getting into a client facing PE role immediately out of school. The group sounded sophisticated and portrayed itself as a major global player in a particular niche, so I jumped at the chance to join and started full time while wrapping up my final exams.

Fast forward a year into the job (2018) and I start to realize that the role is pretty much institutional sales dressed up as private equity advisory. Most of our diligence was at a very high level (i.e. ticking boxes), little to no modeling, and once you prove competent, you're thrown to the wolves to broker deals as a one-man team where management is breathing down your neck to crank out as many deals as possible with no regard for quality or reputation in the market.

I had worked really hard to get a couple 'complex' special situations deals done, earned myself a promotion to associate and deal lead, and had felt as if I had gained everything I could from the firm. There really wasn't any further career development from that point on and any promotion thereafter wouldn't change my level of responsibility. I spent 2019 extremely unhappy and started to feel like staying there any longer might pigeonhole me as a sales guy.

At the end of the year I had finally had enough and decided to quit. I didn't want to be tied to the firm any longer, and had secured a couple of interviews in NYC; one with the private equity arm of a BB (think GS, MS), and convinced the group head of an EB (think Evercore, PJT, etc.) to host me in their office to meet a few MDs. Sadly the BB role wound up being a poor fit/crummy super-day, however the EB had gone really well. I was supposed to check back in with them in the New Year for any open positions, but then they had some layoffs and weren't hiring for the group I had talked to.

I've since had a couple offers to rejoin the firm I left, but I had been beyond miserable and I politely declined with a sense of optimism that something would work out soon.

I've continued to network and have gotten my foot in the door at a number of good places, but the pandemic completely derailed most of them. I'm also Canadian and have been getting some push-back at places that had expressed interest but are unwilling to sponsor a TN visa.

I've done the WSO PE course, the full suite of BIWS modeling (intro, advanced, bonus), and have generally done a lot of prep (am currently reading 'Mastering Private Equity...' from that INSEAD prof). I'm confident I'd perform well in an interview, I just need someone to give me a chance to show them what I can do.

It's now been 6 months and I'm still getting leads here and there, but the stress of not finding something just hit me like a brick wall. I'm starting to become concerned firms will think I'm damaged goods for going after what I want, and it's in poor taste to say anything negative about your old firm so it's difficult to explain why I wouldn't just stay until I found something else.

Anyways, all this to say I've been down on my luck and am in need of some counsel; I'd really appreciate any advice the WSO community might have for me on how to go about my situation.

Thanks a lot!