Expectations And Entitlements

Expectations are a mindfuck. Why? Because, many of us live inside our heads. And, many of us are ambitious. We don’t have much time. Everything should have arrived yesterday. In the relentless pursuit of our goals, we move fast, talk fast, write fast, and bounce from situation to situation, human to human, all in an elaborate dance (or sprint) to, as George Jefferson may say, “finally get a piece of the pie.”

In the world of startups, expectations are their own special kind of mindfuck. Lately, this topic has surfaced in more of my conversations in real life. So, it’s been on my mind more, and I have been trying to come up with an answer to this specific query:

“How can we all take a more zen-like approach to effectively deal with all the personalities, egos, nooks, and crannies around startups today?”

Here’s my answer: “We should never expect anything.”

Let that line swirl around your brain for a while. It’s important. I believe that so much of the stress, confusion, misunderstandings, grudges, dislikes, and everything else in between in the startup world is due, in large part, to the fact that we now live in a time where people just expect shit to work out, they expect others to behave a certain way, they expect things to follow a pattern that they deem is right.

There’s another word that neatly captures all of these characteristics: “Entitlement.”

I know this because, for a while, I carried many expectations. I expected that if I emailed someone out of the blue, they should write me back. Worse, I expected that if I met someone or even spent time with them, that they should write me back. I expected that after a bunch of interviews, I should be given a crack at a job, or maybe even a longer tryout. I expected that if I wrote a good post, on the merits, that the right people would find and read it. I expected that if I helped someone, they’d help back or at least acknowledge the effort. I expected that if someone granted me options that they wouldn’t reneg on them before the termination date.

For a while, I stepped out of my body and tried to assess why everyone else was wrong. It’s really easy to do this. And, it appeals to the reptilian neurons stuck in our brains. Eventually, however, I realized it wasn’t other peoples’ faults, or their wrongdoing — rather, it was me. It was my fault. It was I who had committed the original sin — I expected something.

I believe everyone in the startup ecosystem — investors and founders, operators and executives, journalists and bloggers — should never carry expectations or feel as if they’re entitled to something. Investors should never expect that if they worked with a potential star founder for 10 years that this founder would have the courtesy to call up his/her investor-buddy and invite them to invest in a new venture; rather, the investor should relentlessly pursue their contact and close the deal, fully expecting to miss the opportunity if they don’t push. Founders should not expect that they should be able to get a meeting with any investor, or that their cold email advances should warrant a reply. Handshake protocols don’t matter because the real world has its own protocol.

I challenge everyone to man up, to woman up…to take a step back and intellectually reason what they may be fairly entitled to, yet to not impose their own arbitrary moral constructs on others, let alone to expect anything of anyone else in any situation. We must realize everyone is different, everyone has their own limits, their own motives, their own communication style, and — specifically, this was hard for me to come to terms with — to not take the silence or indifference of others personally. Thankfully, there is a free market out there, and lots of healthy competition. There are people who will surprise us with their attentiveness, their willingness to go an extra mile for us, and their willingness to listen. Yet, some of the most helpful people won’t do more than listen, and that’s OK — we must not expect more of them. It’s dangerous to expect too many things, and therefore, perhaps, wiser to move through business and life being surprised by the outliers rather than beaten down by the masses — and the weight of our own entitlements.