It’s not that I don’t like people, I just can’t stand small talk for more than a few minutes. I hate the idea of having to “make conversation” with somebody and I’m the type of person to be comfortable with silence in the presence of others.

I will also talk in great detail with complete strangers if we’ve hit it off on something specific. These are some of my favourite memories because they caught me off-guard in the moment. And being caught off-guard is a great learning lesson, if you let it be.

By recognizing that some of the most profound conversations I’ve had have come from taking a chance with a total stranger, I was able to see past the bullshit I had pigeon-holed myself into.

The truth is, I love people. And now I’m convinced almost everyone else does too.

As anti-social as I may view myself (it varies from mood to mood) the world around me is built and run by people. Yes, algorithms now dictate much too, but so much of our world is based around human relationships and connection. Even the algorithms are just trying to figure out what the relationships and connections can (or should) be for X to occur.

Uber, Lyft, Doordash, SkipTheDishes and Postmates are all algorithms, but they don’t work unless there’s an actual entity delivering your meals (although it won’t be people for long…) Beyond this, it’s the relationship that the Apps are able to make with you that determine their success. The way they choose to interact with you (push notifications, text messages, emails, etc.)

It’s the communication that makes or breaks a service in the long-run. And it’s the communication of the team that makes or breaks the long-term success of a start-up. Ceteris paribus, the company with better communication will steamroll the other.

And then the light clicked on – I wasn’t contributing positively to my team with regards to communication.

As a 1-man-marketing operation who was also doing analytics, web design, operations reports and budgeting cashflows, I had hidden myself away in my details. It seemed like a good rationalization at the time.

I convinced myself that the work I was doing was more important to get done by myself (I was surely the only one who could do it), to do it as quickly as possible (time is always of the essence at a start-up) and that I didn’t need to leave a record of it for others or communicate updates (nobody else was going to read them anyways, they were busy with their own work).

Writing it out, it’s pretty obvious this mentality was a mistake. But how could I have caught it in the moment? How will I prevent myself from doing it again in the future?

The first piece of advice I’ll offer is: Ask yourself why you made the decisions you did.

If it’s because you’re not interested in the work anymore, if you’ve been looking for an exit for the Nth time this month, if you hate where you work or if you are uninspired by what you do, maybe you should just walk away. Figure it out and move on, but understand that the company will likely continue without you. It could be successful or it could be your entire social group. Business is the lifeblood of more than just the economy.

On the other hand, if you wanted to succeed, but messed up thinking that you could do it alone (or some variation of this) then that’s a much different story. Icarus son, you have flown too close to Sol. But like a phoenix, You shall rise from the ashes.

Pick up your pride and come clean with all the people that you work directly with. Be open about the mistakes that you have made, and be clear about why they occurred. Do it as it relates to the work you do with this person.

Next, ask them about themselves and ask about the ways that they like to communicate. Then focus on their needs when you communicate with them.

Finally, actively work to communicate with your team consistently. I have to actively think about this (and I still don’t always do it) but I know that I feel better and perform better when I do.

The people who are aware that their sociability has an impact on those around them and try to make their environment better are the silent heroes of this post.

Writing this, I am reminded of the fact that I am endlessly fascinated by people. It is because things don’t fit together quite right that the puzzle is fun.

-Jake