Comfortable with Uncertainty

Getting Comfortable with Uncertainty

It was five months ago exactly when I showed up in Chicago for my first real business meeting about my new startup idea. The weekend prior was rainy, so naturally, I spent 28 hours creating my initial business plan and pitch deck in my own little startup-weekend bedroom. I felt prepared, excited and nervous as I presented to a friend of a friend in hopes of getting honest feedback and gaining valuable connections.

As soon as I was finished, he gave me his thoughts and I couldn’t have been more appreciative and willing to listen. “This timeline is incredibly optimistic. You should consider another logo. A board of advisors would be a good idea. You need to bootstrap your costs. Investors what to see a credible team.”

But the thing that really hit home was when he said that he had interviewed hundreds of startup founders and the one thing that all of the successful founders had in common was their comfort level with ambiguity. As he analyzed my perfectly prepared binder with labeled tabs and spreadsheets of optimistic sales, he asked how I felt about ambiguity. At the time, I wasn’t really sure. All of my decisions up until that point, were made because I wanted them that way, not because something hadn’t worked out as planned.

As time has gone by, I’ve discovered that I will never be completely prepared for this lifestyle. I will never know exactly what to do or have the answers to every question. Each person I meet with will always give mixed advice and opinions that I have to take with a grain of salt and ultimately make the right (and sometimes wrong) decisions in an effort to keep pushing forward. I will always have to carve out a percentage of my day to learn, read, listen and grow.

But now, at least I know that my level of comfort with uncertainty is much higher than when I started. I jumped. Three short months ago. I jumped with complete passion and ambition to make this idea a reality.

This roller coaster is just getting started but it’s all about that moment at the top when you can see above everything else, feel the cool breeze on your face with a knot in your stomach and excitement for the next wave of momentum to keep you going.

Let’s Take Notes

Blogs and books from experienced entrepreneurs are really the best way to start learning. So, if you have the desire to pursue a startup idea but don’t know where to begin, here are a few resources to help.

  • Both Sides of the Table – Startup Advice – Mark Suster is a two time entrepreneur that turned VC. He blogs about being both the entrepreneur and the VC and provides very valuable information.
  • Venture Hacks – Although it hasn’t had much progress lately, this blog is full of amazing advice from seasoned founders and investors.
  • On Startups – This blog provides insightful information for entrepreneurs from “14 Ways to be a Great Startup CEO” to “How to Get Media Coverage for Your Startup”
  • Technori – Based out of Chicago, this blog features interviews with startup founders as well as advice and tips relating to technology, business and entrepreneurship in general.
  • Steve Blank Startup Tools – This is an absolute list of every resource for you to use at any stage of your startup journey. Seriously, this could take you months to get through but it would be well worth the time.

And lastly, I’ve provided a few prior blog posts with great value:

As always, keep moving forward but don’t forget to enjoy the ride.