Fear, Anxiety and Showing Up

Fear, Anxiety and Showing Up

Anxiety is something I’ve struggled with since I was a kid. I can vividly remember sitting in my second grade classroom, the day after failing to complete an “important” homework assignment, anxiously awaiting homework collection, rising discomfort in my chest, feeling increasingly short of breath, until I asked to go to the restroom, hoping not being physically present to turn in my homework would magically exempt me from the inevitable ZERO in the grade book.

Common Worries For Me

The stresses and uncertainties of life as a startup CEO often exacerbate the problem. To illustrate, here are a few fears and anxieties I have lost sleep over in the last year:

  • Will this funding round ever close?
  • Why do I keep making the same mistakes?
  • Was that product launch a waste of time and money?
  • Are we spending money too quickly?
  • Are we not spending money quickly enough?
  • When I make this ask, will I get laughed out of the room?
  • Will we get paid for this big contract?
  • What if I get everything I want and I still feel this way?
  • Am I doomed?

Some of these track more closely to reality than others. I can assure you I’ve felt all of them as deeply real and deeply troubling over the past year.

Fear is a Signal

I have a friend who says, “Feelings aren’t facts.”

In response, I have another friend who says, “Maybe not. But, they are signals.”

What do these feelings of fear and anxiety signal to me? For starters, they signal that I too often believe a false reality: that I am the master of my destiny and that my worth and the company’s worth rise and fall with results that I can control.

What Works For Me

One of the few things that I’ve found that helps is to pray for the power and willingness to show up for the next challenge, the stamina to diligently and sacrificially work and then to show up, in my fear and weakness.

I am confident that hard work and being in the right place at the right time are crucial elements for success (however you define success), but that anxiety is a feeble motivator and is ultimately self-centering and counterproductive. I heard someone say that fear is a mile high and a mile wide and paper thin. I have generally found this to be true.

Another thing that helps release me from fear and anxiety is talking about it with friends.

Instances of success that I’ve had personally and professionally always result from some mixture of showing up for a fortuitous (or, more accurately, grace-filled) moment that I couldn’t have predicted and working hard leading up to that moment. These include things like getting into Harvard, starting FaithStreet, meeting my wife and many other personal and professional moments.

Deep down, I guess my fear and anxiety is a result of not believing that God is going to take care of me, of not enjoying the reality of His victory over sin and death.

I hope to write more about this issue in the future.


Investor Brad Feld has written a lot on his own experiences with the topic, which I recommend checking out: https://www.feld.com/archives/tag/anxiety

Here’s another piece by Pastor Scott Sauls worth checking out: https://www.thegospelcoalition.org/article/anxiety-and-depression-my-strange-friends/