Generous but not boundary-less

Nov 03, 2025

Like most of us, I get asked to do, or participate in, a lot of different things. In any given month this could look like being asked to contribute an essay, appear virtually at a book club, offer my expertise to a student, or travel to another continent to present a lecture. Despite my years of experience fielding these kinds of requests, I still find myself flip-flopping from full-on yes in some cases, to outright no in others, without feeling great about either of these decisions.

Sometimes I head into a meeting to talk about an opportunity in a very defensive posture: I’m so skeptical of what might be proposed that I’m poised to immediately reject it. Other times I seem to forget how to ask questions and just say yes to things that sound simple enough but often have hidden pitfalls. I don’t like the miserly version of myself nor the inevitably resentful one.

I wish I had the perfect formula for knowing what to say yes, no, or maybe to, but I still haven’t come up with that magic math. Ahead of a recent meeting, though, I did find it helpful to say to myself that I could be “generous, but not boundary-less.”

This phrase reminds me to tap into a side of me that I like - being generous - while also nudging me not to forget that being overly generous is likely to lead to feelings of regret and annoyance.

I think some of us were raised to believe, or absorbed from wider cultural messages, the idea that true generosity is boundless, as if putting a limit on it erased the entire giving spirit of the interaction.

Maybe because of this, we might sometimes lean far in the other direction, saying no to everything because it’s cleaner and easier than a “yes, but” or “yes, if…”.

I’ve also spent a lot of time trying to pre-define my boundaries around these various kinds of asks: how much money I’ll ask for, the time commitment I’m willing to make, how many meetings I’ll be present for, and more. It seems like good advice, to have such a rubric. But I can’t think of one time it was actually useful in guiding my decision.

This is because every situation is unique in some way and there just aren’t any rules (i.e., boundaries) that I can universally apply. I also want to leave space for doing something just because I feel like it, even if it “violates” my pre-set boundaries. After all, I’m ultimately only accountable to myself, not to some imaginary “boundaries jury” judging me for not sticking to my imagined fee structure.

So for now I’ll go forward with “generous, not boundary-less” as a guiding principle with enough flexibility to make context-specific choices, and a reminder that being generous with my time and energy doesn’t mean being without limits.

Perfectly Cromulent

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