Overpass Experiences

The Eric Wroolie Blog

Preferring to Be Alone

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I’m sitting at the LaLuz Beach Resort in the Philippines by myself. For the past few days, my team and I have been hanging out here and having a good time and also discussing the future of the company. They left yesterday and I stayed another day.

Being Alone

I’m by myself and I’m fine with it.

In fact, I spend a lot of time by myself. One of my pleasures as a kid was going to to the movies by myself. Others thought it was sad, but I liked being able to walk from the cinema with thoughts of the movie swimming in my head and not filled with chatter or the opinions of others. I frequently like to be alone.

As a software developer, I spend a lot of time in pensive thought. This ability to embrace ‘aloneness’ and quiet is what has helped me learn everything I need to learn and tinker with all the code I want. I wonder if this is a trait of software developers. We’re often introverted and pensive.

This wasn’t easy as a kid though. Every parent-teacher meeting was like a “greatest hits” album and never changed regardless of which year it was or which teacher was saying it— “Eric is a good kid, but needs to apply himself and come out of his shell”. They always talked about my shell. I never understood why it wasn’t enough that I just learn what they were teaching. I had to perform too?

I’ve always had very few close friends. And I’m terrible about keeping in touch when I move on to new places or new jobs. My kids sometimes ask me “Dad, how come you don’t have any friends?” I just smile and say “I don’t need friends, I have you.” I’m close with family members and work colleagues where we share the same interests. And, there are a few who work their way in, but I’m not easy to be friends with. It’s probably one of my big failings.

I am probably the worst person in the world at making small-talk.

A few years ago, I read the book “Quiet: The Power of Introverts in a World that Can’t Stop Talking” by Susan Cain. That was the first time in my life where I felt like I might be normal. It sounds stupid, but I always thought there was something wrong with me. When we think of quiet recluses with few friends, we hear about mass murders and the Unabomber. The book is very funny. She talks about how it’s okay to cross the street to avoid talking to someone you know just because you don’t feel like talking. She talked about a lot of things I had been feeling my whole life.

I’m trying to be more outgoing. I’ve had jobs that required me to talk to people in large groups. For example, I worked as a narrator at Sea World of Texas and gave narrations on dolphins, penguins, etc over a microphone. That helped. I’m doing the daily Youtube videos now, where I am actually trying to open up a little and be honest about my own thoughts (even if they might expose vulnerabilities). I’m trying…

My big fear when starting Overpass was not whether or not it could be done. I know it can. My big fear was (and still is) that I am not the guy to do it. Maybe if I was outgoing and super-confident, I could do it. I can’t stand the arrogant “entrepreneurs” who seem to know very little but talk a lot— but I still envy them to some degree. I don’t want to become them. I want to be me and I want to see if I can make this work.

But…today… I’m just going to sit here by myself.

How to Kill Someone’s Dreams

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The easiest way to kill someone’s dreams is to question them as if they should have an answer. Ask a lot of questions about hypothetical situations and watch the doubt fill their face. “What will you do if you get sick and can’t pay the bills?” “What is your plan b if it does not work?” “Are you absolutely certain you want to be doing this?”

Sometimes, finally getting yourself to do what you’ve always known deep down you should be doing is hard. Sometimes it feels like everyone is against you. You are trying to coax that higher version of yourself to take centre stage. And there are so many who are asking questions and shining a light on the doubt you have.

But, the truth is no one is certain of anything. I can’t tell you how many times I’ve had people question me about what I would do when I left a job. And, it really scared me. But, sometimes, those people end up losing their “secure” job anyway. No one really knows.

I think I experienced this most when I left the Army. I was so unsure of whether I was doing the right thing that I continued going strong until the last day. I elected to attend PLDC (Primary Leadership Development Course) and the promotions board to get my E5 sargeant stripes even when others I entered with were just waiting to leave. I still wasn’t sure.

I had all my friends and colleagues wanting me to give them my life plan. “What are you going to do for work?” “Are you going to college?” “If you go to college, what will you do afterwards?” And the most I said “I don’t know” the more I doubted whether I was doing the right thing.

And the Army recruiter was just as bad. I still get angry when I think about it sometimes. They just had to put doubt into my head. They just had to hint that maybe I was not doing the right thing and my fear took over. I very nearly stayed in.

On one of the many times I left a full-time contract to pursue Overpass full-time, I got the same treatment. It wasn’t so much that people doubted I could do it (but many did) as much as it was their constant questions about whether I had “thought everything through.”

But sometimes, you don’t need an entire plan. You don’t need to know how to get from A to Z. You just need to focus on A to B first.

And then you leap.

And it’s scary.

And if you can get used to uncertainty, the world is yours.

The Turn on my morning Run

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My routine morning run can be 3.5 miles or 6 miles. I usually decide based on time before hand whether I can squeeze in the extra 20 minutes required for the full run. Sometimes, though, my 6-mile run becomes my 3.5-mile run halfway through.

My run is a big loop around town. The longer run is technically around two towns (but they’re small towns). The shorter run has a turn which, if I take it, will cut the run in half.

Many times, I start out for a six-mile and decide to cut it short because I don’t feel like running the longer run.

But the point of that decision … is a single turn. It’s at this one stupid intersection where I can turn and cut the run short.

I know that if I make it past that turn, I’ve committed to the full run.

So, I’ve noticed over the years that if my goal is to do the long run … I need to psyche myself up for that turn.

If I think about the longer run and how tired I will be … I won’t do it. On a cold wet morning at 6am, I just want to get back home and get warm and dry.

But … if I think about just running straight through that turn, it’s much easier. So that’s my goal in the mornings— to go straight at that turn. That’s an easier decision. Once I go straight, I’m committed to finishing the run.

I read this advice in a Twyla Thwarp book many years ago called “The Creative Habit”. She said that her goal in the morning was to get dressed in workout clothes and get in the cab for the gym. If she focused on the entire task of working out, it would demotivate her. So, the simple task of getting in a cab is what keeps her doing it.

I started doing the same after reading that book. I know that if I put on my running shorts in the morning, I won’t take them off afterwards without running at least a little.

Motivation, I’ve found, is making your decisions small enough to be manageable. Instead of “I’m going to run every day for the rest of my life”, it’s easier to say “I’m going to run today.”