I was in town having a drink with an associate when the oddest thing happened: She started talking about things she had done for me. It was weird, unprompted and out of context. The strange part was that they were a couple simple acts she did behind the scenes, like giving a co-sign to a colleague and such. Why did she feel suddenly compelled to let me know? I showed my appreciation by buying the next round, but the rest of the night took an awkward tenor. I haven't reached out to her since.
The truth is, there is little to be gained by telling people everything you've done for them. In fact, if you feel compelled to tell someone, you either a) did things way out of your comfort zone to help them and feel like they owe you or b) think you are a pivotal part of their current success and feel like they owe you. In other words, it's all about your needs, not theirs. The real root of your feelings is based on the intention you had in the first place. To paraphrase Robert Greene's The 48 Laws of Power, the best thing gained from reminding someone everything you've done for them is resentment.
I love giving back as a board member, as an official (and unofficial) startup advisor, and as an overall mentor, but each and every interaction is within a certain set of parameters.
I don't want to support others so they will owe me, but so they will prosper. Here is my basic foundation for helping others:
Consider it mutual, because it is mutual: If you are an entrepreneur, then you will need something from someone every single day. When I was a journalist in Silicon Valley, I connected with many VCs, thought leaders and entrepreneurs... who were the same people I talked to when I launched and later sold my startup Cuddlr and who will be part of the same folks I lean on when I do my next venture. I will need them, and they will need me.
Decide immediately if you want credit: If you want someone to know about your helping hand, then be upfront as soon as possible. There are certain instances where I'll give someone a heads up about a recommendation I gave in their favor, but generally I'm not fulfilled by direct credit. However, if I feel like there should be acknowledgement, I am as forthcoming and as honest as possible. The worst case scenario is someone expecting credit well after the deed is done - and that can build old resentment in the doer and new resentment in the receiver.
Assume you will work with them again: If you plan on having a long career, then you should just assume that you will work with every single businessperson you encounter multiple times. The cocksure among us are happy to brag about burning bridges, but the more focused your business, the higher chance you'll need to cross those same bridges sooner than you think - and the power you yield over another's progress today could easily change.
Always present it as a partnership: If you help a colleague today, then you get the pride in seeing them do well, the insight in helping them strategize their unique business, and the trust of a future ally. The reverse holds true, too. Consider helping someone as a healthy, mutual exchange rather than a one way street, as it will push you to consider them a valuable connection in the future. Viewing them as a charity case is both unnecessarily condescending and amazingly short sighted.