The past year has been one of change for me.

6 min read Original article ↗

TechStars Demo Day, November 2012

One year later: counterintuitive observations about people

Not to mention, my first post on Medium!

Alex Schiff

The past year has been one of change for me. I left the University of Michigan early, raised money for my startup Fetchnotes, and moved to Boston to do an accelerator called TechStars. I spent an extended stay back in Michigan during what would have been my senior year, and then came back to Boston. For me, the most interesting part of the journey has been the human component. A handful of things stuck out as counterintuitive, and given that today is Yom Kippur, a Jewish holiday for atonement and reflection, I thought posting this would be timely.

No one feels as awkward about yourself as you do.

“That girl saw me looking at her, she must think I’m so weird now,” “Everyone in the audience can tell how nervous I am standing up here,” “I’m saying um and uh so much,” “I’m not making eye contact.”

We often project our insecurities on other people, when in reality they’re too busy thinking about their own to notice yours. And if it turns out you’re actually as awkward as you think you are, big deal. Awkward people are endearing — go up and say hi to someone anyway. As outgoing and extroverted as I am, I don’t do enough of this.

We’re generally terrible at empathy.

It’s shockingly difficult for people to decouple themselves from their experience. For example, I forget that as the public face of the company, I have a lot more conversations with other people and take in more feedback/advice than the rest of the team. In doing so, my thinking subtlely evolves on how to describe our value, what strategies we should be employing, etc., and over time the difference can be quite significant. If I don’t relay that to the rest of the team, there can be a big gap in how we look at the same information.

Across all sorts of situations, I’ll find myself thinking, “How can you not agree with me about this?” or “How can you be so naive?” I forget that they haven’t had the same experience as I have, nor have I had theirs. It’s okay to disagree.

(For more thoughts on this, research “The Curse of Knowledge”http://en.wikipedia.org/wiki/Curse_of_knowledge)

Our lives look way different on the outside.

We have blinders when we think about others’ lives, too. Every so often, someone tells me, “I’ve been following you on Facebook and it looks like your life is so incredible!” I post interesting stories that happen to me, good news about my company and photos of going exploring around Boston. It probably looks like some fantasy adventure. That’s because I don’t believe in bitching to social networks when something isn’t going well.

Yes, I’m pretty fortunate in my life. But you don’t see the extremely difficult conversations I’ve had to have with close friends, or the nights I’ve laid awake stressed out about any number of things. Like most 22-year-olds, I have the same BS to deal with about making friends in a new city, missing old ones and pretending to be an adult. I try to remember that when I look at other people’s lives with a limited perspective.

Compliments and genuinely giving a shit go further than you think.

For reasons unknown, I’ve always been awkward about giving/receiving compliments. In the last year (especially more recently), I’ve made a concerted effort to change that, and it’s had a very positive impact on my relationships.

Compliments, however, are just flattery if not coming from an honest place. You’d be amazed at how rare it is for people to show that they genuinely give a shit about another person’s well-being. The two nicest compliments I’ve ever received have been when I IMed a friend to see how she was feeling because I knew she was sick, and when I emailed an acquaintance to congratulate her on a new job when I saw her LinkedIN was updated. I had no expectations or motive. Both were floored that I took the time to reach out.

It’s not always words, either. Because families were an interesting market my company was considering targeting, Katie Rae (one of the managing directors of TechStars Boston) made our team “The Five Love Languages.” It discusses how there are generally five ways that people show affection for one another: words of affirmation, physical touch, gifts, quality time and acts of service. Depending on the person and relationship, you might be trying to show someone you value them by saying so, when doing something for them, or spending quality time with them, would mean a lot more. Understanding this nuance can save a lot of stress and turmoil.

There is zero downside to persistence. Err on the side of annoying.

When it comes to trying to get someone else to do something for or with you, there are only two types of people:

1) People who are going to do it
2) People who aren’t going to do it

Without fail, the people who are annoyed by you following up were never going to do what you wanted in the first place. The investor that gets annoyed by you following up was never going to fund you. The person that gets annoyed when you call because they didn’t respond to your text about plans tonight was never going to go out with you in the first place. The reporter that gets annoyed by your follow up emails was never going to write about you.

By the same token, people are busy and have other things going on. The people that were actually going to do something with you appreciate when you follow up, because it means that they didn’t miss out on an opportunity. More often than not, they were just busy and your message got lost. I actually know a non-insignificant number of people that ignore first emails from people because “if they don’t care enough to follow up, they’re not worth my time.”

With this in mind, there’s literally no downside to persistence. The people you piss off were never going to do what you wanted anyway, and the people who were are going to value you that much more.

Be persistent. Be memorable.