Going Deep Inside The Mind Of An Entrepreneur Can Be Scary

The more I live this entrepreneurial life the more I realize how much of a psychological game it is.

I was reminded of it the other day as I watched this interview between Jason Calacanis and Jerry Colonna, a very well known CEO coach in the technology industry.  The 90 minute interview is incredible, they  cover many aspects of how he works with CEO’s and the issues they (we) deal with during the entrepreneurial journey.

There are so many things in this interview I want write about but one of the biggest things that stuck out to me was the idea of “chasing demons” with entrepreneurship.  Jerry and Jason both reveal how their Dad’s lost their jobs when they were young, and how greatly it impacted them, and still does to this day.   For both of them, they committed to never be dependent on a large company, since it could all be gone one day if you are fired.  Deeper, it was the feelings of inadequacy (or the fear of) which drove both to become successful in their pursuits.  It’s amazing and touching to hear them talk about their fears and doubts, and how they are rooted simply from watching their father’s struggles as they were young men.

I think this is something very important to understand.

Why are you so driven?

What demons are you chasing?

Jerry bravely mentions chasing demons is not necessarily bad – not knowing you are chasing demons is.  Not fully understanding who you are and why you are doing things is a scary place to be.

Another thing he points to is how ALL of us feel inadequate, regardless of financial stature and prominence.  He works with over 60 clients (many billionaires) and without fail he see’s highly successful individuals tearing themselves apart, comparing themselves to other founders who – quite frankly – got incredibly lucky with their outcomes.

He emphasizes how much random luck has to do with success in business.

His point: figure yourself out.  Determine who you are outside of your company, your family, and your city.  Once you get to the core of who you are you can fully embrace the life of entrepreneurship without the feeling of insecurity and doubt.

The lesson to take here is although it might be scary to face these demons, once you do you will open yourself up to a much happier entrepreneurial journey.

Entrepreneur, You Must Realize It’s Best To Live With Your Doubt

We all have doubts.  Knowing this truth, it’s better to come to grips and embrace it rather than run away from those doubts.  All they will do is haunt you.

I recently read an interesting post written by Franscisco Dao touching on the concept of living with doubt.  It’s very much worth the read.  This paragraph in particualar really struck me.

The truth is most entrepreneurs never overcome their doubt. In fact, the day you overcome all doubt is likely the day you become blinded by your delusions of control and perhaps even greatness. What entrepreneurs really learn to do is live with doubt. And learning to live with doubt, being able to accept doubt, is a much more powerful thing because it allows you to continue questioning assumptions while still moving forward in the face of uncertainty.

Living with doubt.

What does that mean?

I take it as instruction to embrace your fears and doubts; leaning into the pain of challenge instead of running away from it.  This mentality allows you to become truly authentic in your ways with yourself and other people.  It allows you to be fully human, to accept that you are not superman and you have troubles, challenges, struggles just like everyone else.  I hope you realize you can talk about your worries and fears with others.  It’s ok, it’s human.

Just this week I met with another entrepreneur looking for some direction and advice since he is going through the same “stuff” as I have been recently.  Namely, his startup is taking a bit longer to get off the ground and attaining a sustainable operation, so in the mean time he is seeing the end of his financial runway approaching – fast.  “What do I do?!” he was asking me.

No doubt, I am in the same boat.

Here’s what I told him:

To tell you the truth, more startup founders are in that boat than not.  Most founders are struggling with massive pressure from every angle of their life – business, family, friends, financial, social, etc – and are scared as to what will happen in the coming weeks, even if they don’t tell you.  You are not alone, you just have to navigate it.

The point I grabbed on to most from Francisco’s post is the fact that a majority of founders feel like frauds when the reflexively respond to people’s question of “how are things going?”  Inevitably, they say “Great!” “Crushing it” or something else that eludes BS confidence and fakery just so they can move on to a different topic.

But it’s ok.

It’s ok to be humble.  It’s ok to let your guard down.  It’s fine to say things like “things are tough dude!”and ask what they did when they found themselves in that situation.

Because you know what?  The truth is life is hard, especially as an entrepreneur.

Anything else is BS.

Living With Doubt And Uncertainty As An Entrepreneur

Entrepreneurial doubt can creep up on you like little critters in the night. One day you are on top of the world, thinking there’s nothing between you and 1 billion people touching your product. The next day you don’t know if you are still leading an actual company. Life can be pretty tough sometimes.

I have had my share of creeping doubt as of late, some worthy of mindshare and some not. But the biggest thing I have realized lately is that no matter what, shit hit fans. So it’s not a matter of when or how much hits the fan but more about how you deal with it. And you HAVE to figure out how to deal with it so you can continue on living and working towards your goals.

I have found 3 things really help me when times get rough:

Get Back to the Drawing Board

For a while there I was feeling very exhausted, lacking creativity and innovation at all points of the day. Seconds, as a company, has come to the point where we are growing (we’ve grown each and every month) but has obviously not found proper product/market fit necessary to take things to the next level. Not surprisingly, this was a very difficult feeling to experience. Results were not clear enough to shut down the business but it was also too foggy to continue the current plan. We had to make adjustments or risk losing the war.

So I finally had to force myself to break out of the rut, grab the marker and get back on the whiteboard. For those unaware, magical things happen at a whiteboard. Most products you are using today were wire framed on a board. Most of the successful companies you read about on Techcrunch and Mashable were conceived on one of those boards. It’s truly amazing what can be created when you place pen to board and allow it to lead you. Now, As a team or even just a few of us, we now regularly jump into sessions of brainstorm and idea generation. I will even lock myself in a room alone and just allow the entire board to engulf my thoughts… I will tell you some great new stuff is set to be released at the end of September and it’s all due to our energetic whiteboard sessions of this summer.

Get Back to Friends and Family

I recently have had the opportunity to spend more time with my family and it’s been a great. Long story short, as an interim roof I am staying with my sister and her 3 kids as I look for my next place. There was simply too much going on… I couldn’t deal with looking for another apartment and she kindly suggested I grab the spare room for a while. I though it was going to be a burden but it’s been a blessing. It’s amazing what is presented to you once you are in need of a miracle.

Also, looking back over the last few months I have been able to break away and spend some quality time with my friends. As a founder and dedicated entrepreneur, it’s quite easy to become so engulfed in pursuits I forget about the special people in my life. I am also blessed to have a solid group of friends from my youth and college years. These moments of getaway and relaxation are very re-energizing. I believe we will be lifelong friends so I feel the time with them is more of an investment rather than a expense on my life.

Get Back in Shape

My previous career was oriented around health and wellness, so health is a biggie for me. To be quite honest, I have really never been out of shape so my thoughts are more about the commitment and consistency of exercise over being overweight or out of shape. Though recently I noticed myself slacking on training and exercise. One day a week here… two days a week there. No patterns or schedule to depend on was really taking its toll on my physically as well as psychologically. And I started seeing and feeling the result.

So I determined to make a change. More importantly, i found a closer focus on running and working out more often and earlier (relatively) in the morning is keeping me aligned as my life is becoming more random and out of whack by the week. Even more interesting, the harder I push myself physically the more I push myself psychologically and mentally. Physical exercise is definitely the healthiest weapon against stress and I hope it stays that way throughout the rest of my life.

Creativity, Exercise and Friends and Family. These are all you need to stay aligned and deal with the uncertainty of entrepreneurship.