Let admiration be your compass
I sometimes say that I only have one piece of career advice: Think hard about who you might have to work with, because you are inevitably going to absorb their attributes over time. So you’d better pick colleagues and bosses who you’d be proud to become more and more like as time goes on.
If you buy that principle, then career (and friendship, and maybe even marriage) decisions become very simple — all you have to do is follow your sense of admiration. When your gut reaction to someone is “wow, I’d be a better man/woman/person if I were more like them”, that’s the direction to steer your ship. Job title, money, geography… all of that gets pushed to the periphery. And if you’re stuck deciding between two opportunities, this is the test you can use to break the tie.
“If you’re early on in your career and they give you a choice between a great mentor or higher pay, take the mentor every time. It’s not even close. And don‘t even think about leaving that mentor until your learning curve peaks.”
Stanley Druckenmiller (link)
A lot has been written about how the importance of finding a mentor (and being one), but with this lens, everyone you spend time with is — to a degree — your mentor. And in the same way that you shouldn’t take just anyone to be your mentor (a bad mentor is worse than no mentor) you really should be careful not to spend significant amounts of time with people who don’t stoke your sense of admiration.
That said, admiring someone doesn’t mean you’re enamored with everything about them. You shouldn’t scratch someone off your admiration list just because you detect one of their flaws. In fact you can admire someone while finding some aspects of them to be annoying and tiresome.
Rather, admiration stems from the detection of certain desirable qualities — do you see some things in this person that are truly exceptional, that you would aspire to reflect in your own personality and character? Would the world be a better, kinder place if you invested the effort to adopt some of these attributes & facilitating others adopting them from you? Conversely, if somebody gives you an icky or anxious feeling, if despite lots of positive qualities you can detect some core deficit in integrity or empathy, do you have the self-confidence to walk away when they offer you money and prestige?
Not to do the whole “VC feigns humility by gushing about their founders in public” thing, but I was thinking recently just how lucky I am to get to work with so many founders and CEOs who I truly look up to and wish I was more like. What an honor to have the work day filled with people who constantly show me by example how to be a better professional and better person.
This is of course not to say that if we’ve declined to invest in your company it’s because we don’t admire you. One of the most gut-wrenching parts of this job is passing on deals where the CEO is utterly fabulous but the opportunity is good but not great. That stinks. But we never, ever, ever* invest in founders we don’t admire, and that discipline has served us well.
I suppose this is part 3 of my career advice series (first post, second post), but truthfully this is the only thing that I always come back to as a core principle. Your compass may be different from mine, and that’s fine. But this is what works for me and it’s never steered me wrong.
*(well, not in a very long time at least.)