Wesley Ross

Always do the things you Fear the Most

Posted on Author Wesley RossPosted in life

As much as I don’t like to admit it, I consider myself an introvert.

My childhood was spent traveling around the world with my parents due to my dad’s job.

I’ve lived in North Carolina, Santa Barbara, Chicago & then going all the way over to Europe where I spent my teen years.

That forced me to change school every couple of years, which in turn meant changing my whole social circle over and over again.

Through that, I always felt like an outsider, even though I didn’t have problems making friends I never could develop a deep bond with anyone.

So I took an interest in things that didn’t need other people in order to avoid potential disappointment further down the line.

Over time that developed into a form of anxiety towards social gatherings and a general approach of avoiding making decisions outside of my comfort zone.

Developing bad habits over a long period of time can really go unnoticed until suddenly confronted by someone with a totally unbiased perspective.

I wish I could pinpoint who or what at the time drastically changed my outlook on how to go about getting the most out of life.

Below I’ll list some example of things I was “scared off” doing at the time and what was the outcome afterward:

Moving back to the United States on my own when I was 19 years old.

Reasons Not To:

  • My whole family is in Europe.
  • I don’t know anyone local.
  • Limited budget of $800 dollars.

The result:

  • I was able to get an early start in the tech industry, support myself by doing what I love & be independent of others.

Quitting my job & starting a company with a total stranger.

Reasons Not To:

  • I don’t know anything about building an internet company.
  • I don’t know the market we’re going after.
  • Didn’t finish school yet & chances of me coming back are slim

The result:

  • Learned more things about starting & running a business than any of the dozens of business books would have taught me.
  • Build great relationships with people that are my mentors till this day.

Joining 500 Startups in Mountain View, California.

Reasons Not To:

  • I have “comfortable” lifestyle & established network.
  • Just moved in with my girlfriend to our new apartment in New York.
  • The company I’m joining didn’t yet reach product market fit.

The result:

  • Met the most amazing group of individuals that have amazing drive and passion to go after the unknown.
  • Got to meet some of the industry giants I admired for years.
  • Realized that New York City, “ain’t all that”.

Those are just a couple of examples of where at the time of making the decision I was totally overthinking the consequences and fearing what might come if I make the wrong choice.

However, the more I look back at my life the more confident I am that the things I fear the most are the things that will benefit me the most.

So nowadays when I look at the things on my to-do list, I force myself to choose the ones I don’t want to do as the first ones to complete first.

TL;DR: Do things that scare you, first.