Left PE for an operating role and starting to regret it

Left a PE seat for an operating role ~6 months ago and I’m already thinking about leaving. Looking for perspectives from anyone who made a similar jump and struggled early.

Background is 2 yrs BB IB, then 18 months at a MM PE firm where I closed a platform and closed a bunch of add-ons for another portco. Left because I felt I had seen enough to know PE (at least buyouts) wasn’t for me long term, so I turned down the SA promote. Wasn’t planning to leave at 18 months, but an ops role at a startup fell in my lap and felt too good to pass up on at the time (sector I care about, top-tier VCs, the city I wanted, strong momentum, and we’ve since closed a Series B with another top-tier VC).

-6 months in and it’s been rough. I’m buried, the company is disorganized, the founders are young and making textbook first-time founder mistakes, and the talent bar around me isn’t what I expected. It feels like we’re always 1 bad week from blowing up, and the work itself is repetitive and mindless (even compared to banking). I don’t feel like I’m learning at the same pace I was while in PE and I certainly don’t think I’m being challenged intillectualy.

Two things I’d value input on.

1. How do you figure out what’s actually wrong? How did you separate what you genuinely dislike from the discomfort that comes with any early-stage company? And how do you tell a bad-company problem apart from just how startups feel?
I can’t tell if I picked wrong, if I just don’t like operating, or if this uncertainty is something I’ll just get used to with time. That changes whether I grind it out, try a better startup, or go corporate (FP&A or corp dev).

2. Is 6 months too soon to leave since I already left PE at 18 months instead of the standard two years? Leaving again this fast feels like it could do real damage. I know the answer depends on where I’m headed next, but the honest answer is I don’t know.

Anyone who’s been through a version of this, how did you think about it and what did you do?

13 Comments
 

Based on the most helpful WSO content, here’s how you can approach your situation:

1. Figuring Out What’s Actually Wrong

  • Startup Realities vs. Bad Fit: Startups are inherently chaotic, but there are signs of deeper issues. If the company is disorganized, founders are making repeated mistakes, and the talent bar is lower than expected, these could be structural problems rather than just "startup growing pains." Reflect on whether these issues are fixable or systemic.
  • Self-Reflection: Ask yourself if the discomfort stems from the nature of operating roles or this specific company. For example, do you dislike the repetitive work and lack of intellectual challenge because of the startup's environment, or is it because operating roles don’t align with your strengths and interests?
  • Perspective from Others: Speak with mentors or peers who’ve worked in startups or transitioned from PE to operating roles. They can help you distinguish between normal startup challenges and red flags.

2. Is 6 Months Too Soon to Leave?

  • Career Narrative: Leaving after 6 months could raise questions, especially since you left PE early. However, it’s not career-ending if you can craft a compelling narrative. For example, you could frame it as a calculated risk to gain operating experience, which provided clarity on your long-term goals.
  • Next Steps Matter: The key is where you go next. If you’re pivoting to a role that aligns with your skills and interests (e.g., corporate development, FP&A, or even a better startup), it can mitigate concerns about short stints. Recruiters and hiring managers are more forgiving if your next move demonstrates intentionality and progression.

Additional Insights:

  • Startup Outcomes and Re-Entry to PE: If the startup doesn’t succeed, it could reflect poorly on your judgment, as noted in WSO threads. However, if you can articulate the lessons learned and how the experience adds value to your next role, it can still be a net positive.
  • Time to Decide: While 6 months feels short, it’s enough time to assess whether the role aligns with your goals. If you decide to leave, ensure you have a clear plan and avoid jumping into another role without thorough due diligence.

Actionable Steps:

  1. Evaluate the Startup: Assess whether the company’s issues are fixable or systemic. If systemic, it might be time to move on.
  2. Clarify Your Goals: Reflect on what you want long-term—whether it’s staying in operating roles, returning to PE, or exploring corporate roles.
  3. Network Strategically: Reach out to former colleagues, mentors, or WSO connections to explore opportunities and gather advice.
  4. Craft Your Narrative: Prepare a story that explains your transitions as intentional and focused on growth.

Remember, careers are long, and a few short stints won’t define you if you learn from them and make thoughtful moves going forward.

Sources: From PE >> Startup >> Back to PE, Q&A: I grew up in Consulting and reinvented my brand 3 times, Corporate Development: My Experiences and Background, Joined New Firm; Complete Non-Cultural Fit > Let Go in 6 Months, Should I leave PE after a month and go back to my MBB?

I'm an AI bot trained on the most helpful WSO content across 17+ years.
 

You seem like you don’t have much of an entrepreneurial mindset. This is the job… you should try and bring the structure from banking and PE to the startup?

 
Most Helpful

I think you're overcomplicating it.

There are people who join startups to influence decisions, and there are people who join startups and end up doing analyst work in a worse environment.

The fact that the company is disorganized, founders make bad decisions, and everything is on fire isn't automatically a red flag that's half of startups lol

The real qn is whether you're increasingly in the room helping shape those decisions, or whether you're still just cleaning up after them.

If you're 6 months in and still basically functioning as a PE associate with worse processes and lower-quality talent around you, then I'd be looking at the company rather than questioning whether operating is for you.

 

Start ups are shitshow and big companies are better. The fascination with startups as PE exits is so confusing to me, you should all just go to the highest paying big company you can find. Get good quality branding, experience, and cash. 

If you want to go back to PE, start looking sooner rather than later. The longer you’re out, the harder it will be to get back in. 

 

Interested in your take that you should try to jump back into PE asap. Since OP jumped ship from old PE firm after 18 months, would leaving current startup after less than 1 year look odd and be a black mark? My read is that OP needs to duke it out for 2ish years and by then can pitch themselves as having operating experience when they want to re-enter PE

 

No - he should just own up to making a mistake and say that he always loved investing but was curious to try being an operator, but quickly realized it wasn’t for him and he wants to be an investor again for x,y,z reason. Basically quickly acknowledge that it wasn’t right and immediately jump into a “why PE” answer and focus on how much he enjoys PE and less on why being an operator isn’t a good fit. They don’t want to hear you complain about why operating sucks, they want you to know you’re actually committed to PE and want you to dismiss any concerns they might have that you aren’t willing to put in the work to do the job or that you weren’t good enough to get a lateral offer after your assoc program. 

It takes 1-2 decades of operating to have any amount of relevant “expertise”. So 1-2 years of it is basically a waste of time if you want to be an investor and not an operator. 

The longer you’re out of the game, the more rusty people assume you are and the more skepticism they have about your willingness to come back. 

 

Ya man I don’t really get it … TONS of hype around startups and ppl leaving left right and center but like I spent some time in between MBB and PE at a startup and it was a complete waste of time… way less learning,  on average signficantly less smart people and was just an annoying experience 


The tough part though is staying in PE is extremely hard so I am worried we are all kind of destined to mean revert back to startup but that’s besides the point 

 

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