Structured Exit Strategies Before Search: Asset or Anchor?

June 09, 2025

by a searcher from Harvard University - Harvard Business School in Washington, DC, USA

I’m in the planning stage to launch a self-funded search and considering whether/ how best to structure a thoughtful transition from my current role. I’ve seen most searchers exit cold turkey (which obviously does a lot to focus the mind), but have heard of others who negotiate phased transitions or part-time advisory gigs to buy time and runway. I’d love to hear how people in this community have approached this: Were you able to negotiate paid transition support while launching your search? Did it help - or did it dilute your energy and commitment? Any creative win-wins you’ve seen for employer + searcher? I’m especially interested in cases where people made the transition itself part of their edge, whether by de-risking cash flow or preserving narrative strength. Thoughts?

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Reply by an investor
from Karel De Grote Hogeschool in Belgium

Thanks for mentioning ^redacted‌. Sure I will give my honest opinion here. I don’t think there’s a one size fits all answer to your delicate topic, but I do think people gloss over the cost of dilution. A structured exit can “look” strategic, but in practice, it often ends up being a stall. I know a few searchers who negotiated part-time gigs or advisory retainers to “buy time,” and honestly, most of them ended up dragging their feet. The income extended their timeline, but it didn’t actually reduce the pressure, it just spread it out. Search is already a slog at times; doing it at 60% attention makes it even harder to build conviction and momentum. That said, if you can make the exit part of the search thesis, it’s a different story. A friend of mine spun his consulting work into a wedge: he advised a small industrial services company and used that to (a) map the competitive landscape, (b) access customer contacts, and (c) position himself credibly when talking to brokers in the space. He set a hard deadline for when the consulting would end, and stuck to it. It worked, but because it was integrated into his narrative, not just income padding. The bigger question to ask yourself is: Am I buying optionality, or am I building leverage?* If it’s optionality, be honest about what that will cost you in commitment and progress. If it’s leverage, great. Define the terms, set a deadline, and make sure it moves the ball forward. If you’re close to launching and the only thing in your way is cleanly exiting, my personal take is, rip the band-aid. You’ll never feel fully ready, and you’ll thank yourself 3 months in when your calendar is yours and your identity is no longer split between “searcher” and “still-kinda-employed.” Happy to chat 1:1 if it’s helpful. I think the messy middle of the transition is actually one of the most under-discussed parts of self-funded search.

Reply by a searcher
from University of Venice in 36100 Vicenza VI, Italia

Hi Mark, I had a similar approach in order to maxime cash flow and lowering the risk of a self funded (and not very traditional) search. I basically started my own consulting company moving from Big 4 strategy advisory practice in a financial district to an indipendent boutique located in a province of Italy rich in SMEs I am originally from. While providing consulting services I started looking for a corporate to join and to do a generational transition and I gradually shifted to this full time job. To be honest this is not a proper SF even if it has many points of contacts. Please also note that in my opinion such as approach requires more time and lower the focus and eventually leads to different type of deals (with pros and cons) in comparison to traditional SF. Ciao, Giacomo

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