This week I’d like to address the topic of fear and anxiety – something every entrepreneur will likely deal with. I am no expert, but as an entrepreneur I have spent my share of time reflecting on my fears. These are just some observations and notes on how I have come to deal with my anxieties and fears.

Understanding the root of my fears

In Star Wars, The Empire Strikes Back, Yoda is pure genius when he says

“Named must your Fear be, before banish it you can.”

Yoda, Star Wars Episode 3, Revenge of the Sith

What I interpret Yoda to mean is that you need to understand your fears before you can conquer them.

My own entrepreneurial anxieties are typically:

  • What if we don’t succeed? 
  • What if the opportunity cost of this venture is huge?
  • How will people perceive me and my skills if I were to fail?
  • Will I still be marketable at the end of this?

Once I named those fears, I had to reflect on their roots. I realized that a lot of these fears are driven by the fear of losing something that I am emotionally tied to – essentially the relative certainty of my routine, money, lifestyle and my ego. Once I understood the role and extent of these attachments, I started to work on trying to rationally detach myself from these as best as I can. This is a constant work in progress for me.

One thing that helped me better understand and rationalize the roots of my fears is the chapter on “Fear Setting” in Tim Ferris’ book – The Four Hour Work Week. The theme of the chapter is – What is the worst that could happen? At the end of that chapter, Tim has a section where he asks you to ponder such questions as – “Define your nightmare, the absolute worst that could happen if you did what you are considering?” and and “What steps could you take to repair the damage or get back on the upswing?” Reflecting on these questions and others in Tim’s book, helped inform me of the basis of my fears.

Avoiding analysis paralysis – Trying to take action in small steps

“Screw it. Let’s Do it!”

Title of the book by Sir Richard Branson

I just love the title of Richard Branson’s book and the sentiment because in my opinion, over analyzing something ultimately results in my contemplating all the worst possible outcomes. Fear then tends to prey on those thoughts, which inevitably leads to paralysis.

Now, I am not advocating jumping into something without thinking it through. I believe in calculated risk taking. A bit of analysis and gut check is required but beyond that I find that I benefit from taking action. By taking action, the mind starts to focus on whats next and has no time for fear. And the action generates excitement and more positive energy.

Another common mode I find myself in often is when I start over-thinking things and feel – Man! There is so much to be done! I’m not sure that I will be able to do all of this? Again this type of thought leads me to more paralysis. What works for me when I feel this way is to remind myself to take small steps. I have drilled the following quote (one of my absolute favorites) into my head and find myself repeating it many many times each week!

“Start by doing what’s necessary; then do what’s possible; and suddenly you are doing the impossible.”

Francis of Assisi

Thinking positively and placing myself in the right environment

Enough has been written and said about thinking positive by all the motivational speakers out there. I am in no position to preach except to say, that I have learned that it takes real effort to consciously work on thinking positively. I have been trying to make it a habit to monitor my head for any negative thoughts. When one comes along, I try to reflect on the root of the thought for a bit and try to actively remove it.

“In order to carry a positive action we must develop here a positive vision”

Dalai Lama

The other aspect to thinking positively that I have learned is that it is essential to put myself into environment that is positive. Misery loves company and I have seen how easy it is to get bogged down when the environment or sentiment around you is negative. So I try to actively remove myself from these environments and seek people who are forward thinking with positive attitudes. At the same time I don’t want people blowing smoke up my rear. Ideally, I seek to associate with those who are pragmatic, question my assumptions, provide thought provoking feedback who also have a can-do, supportive attitude.

Using fear to my advantage

Here is something that I recognized a while ago that I try now to drill into my children – “If you do not put yourself out of your comfort zone, you are not learning or gaining a new perspective or experience.”

I have realized that the thing that keeps me in my comfort zone is fear i.e. the uncertainty and doubt beyond my comfort zone. Consequently, I try to monitor my thoughts for any fears and ask myself the question – “What am I missing out on i.e. not learning, experiencing or gaining a new perspective on because of this fear?” I then try to take action to confront that fear head on. After all – That which does not kill us makes us stronger.

I think this is also what Tim Ferris has in his mind when he says

“What we fear doing most is usually what we most need to do”

Timothy Ferriss, The 4-hour Workweek

Anyway, this is the thinking that has repeatedly driven me to take the plunge and go work on my startup ideas. I try to apply it to other areas in my life as well. For example, it was also one of the reasons I decided to go skydiving. I was honestly afraid of stepping out of a I decided I had to step out of one. I am glad I did. It was a wonderful experience and it is now one less thing that I fear.