How to keep my resume active during sabbatical? So I can get back on the PE/VC career treadmill

If you're willing to wait until year-end because you're eyeballing the Senior Associate promote, you have a lot of calendar runway to set yourself up to do this really well.

One ideal outcome is to take an EIR or Venture Partner role at a venture fund. How the decision to offer this is made will vary from fund to fund, but it boils down to how well the partners know or trust or regard the person.

The best way to make a strong first impression is to get a referral from a founder in someone's portfolio who you've invested in and been helpful to. If you put $25k into a guy's company and help him tighten up his board deck for two cycles, or help him polish half a dozen job descriptions he's about to post, or help interview applicants for his bizops or finops team, or source him an amazing candidate he closes and is happy with ... he's gonna sing your praises. 

So you could do that with three or four companies, and it's up to you to decide whether you do in support of a personal angel check or just for love of the game. I've said it often on here: the best way to get a job is to do that job as free work, because someone will invariably rope you into that job just because they can see you're performant and motivated.

If you got the checks out the door in the next couple of months, you could do this for three or four months and still be ahead of the holidays when asking founders to put you in touch with their investors.

It's pretty straightforward at that point. Tell people your story.

You obviously are no slouch if you progressed from boutique to upper middle market sector specialist fund, so string it together as your current position was nothing other than a happily early arrival to a position that was always your goal. You've always wanted to be in a position of freedom where you could critically evaluate opportunities at the intersection of your robust financial skill-set, passion for technology, (and ideally, domain familiarity in XYZ). Or something to that effect. And you're so glad John or Bryan or Hunter connected you, he spoke really strongly about how similar you are to their firm's approach to low-ego portfolio support, rolling their sleeves up and helping with anything.

Don't try to close the whole thing in one conversation. It's a win if your first conversation is simply a strong positive impression and a happy agreement to keep talking. Follow that up with the basics. Send them interesting things you read or listen to. Ask if there are any portfolio companies where you might be valuable. Crush it with any intro the same way you did for the companies you invested in or were helping from before. After 3-6 months of this, you can be pretty explicit about how interesting this is and whether there's a way explore this more formally.

A lot of early or mid-stage firms that do the EIR or similar role are paying a low six-figure base salary. This obviously comes out of management fees and can be a disincentive. You're comfortable living off of savings, so I'd be pretty explicit about simply wanting the legitimacy of the title and the email address.

This then grants you the optionality of two paths. You have the operator route, where you either join a company in the portfolio as a senior hire (and you can arrange this with the founders as heavily tilted toward equity since you don't have the salary need) or get paired with someone the firm knows as a co-founder. You also have the investor route, where this is a 12-month trial for a partner role.

You can run this process with multiple firms simultaneously. Find a place with people you respect as investors and like as people. If you're comfortable with the idea of getting off 'the track' altogether, take your time. There's nothing wrong with a gap on your LinkedIn from January to July 2023 before the start date of an EIR or Venture Partner position. 

I lean away from the LLC thing discussed in other comments. The only value of that is a track record in the event you wanted to raise external capital in a microfund strategy or syndicate type of thing. It's not going to add any real legitimacy from the perspective of anyone in private equity you're interviewing with if you were trying to return to the industry. 

You have a position many people only dream of achieving. Congrats on all your success so far. This is the fun part; you get to decide not just what you want to do, but how. I encourage you to be thoughtful and considered in how you choose to spend your time from now on.