Beyond Your Comfort Zone

The first time you venture forth to lead in the unknown world of high-potential startups, you will definitely be moving outside your comfort zone. Fear and self-doubt are normal, despite enormous pressure to pretend you are not experiencing them.

A first-time founder will inevitably spend much of their journey outside their comfort zone because there are so many things to learn when building a company from scratch. No single person has all the skillsets and experiences required to do all the work and solve all the problems you will face. 

Being a startup leader driving innovation means you will, to the best of your ability, be forging new paths into the unknown. That means you will frequently be uncomfortable and uncertain. Yet, I can say, both from my own experience and from my conversations with many first-time founders, that if you feel times of fear, uncertainty, and doubt (FUD) along the way, you are not alone:

• I remember my first set of business cards with CEO printed on them. I stared at them, feeling a bit like a fraud. Was I qualified to do this?
  
  
• I remember when I first started fundraising for a startup. I was uncertain about what to include in a fundraising pitch, baffled as I tried to learn the unwritten fundraising rules, and mystified by the norms and terminology in a term sheet. I had not yet learned what was important or how to discuss it with potential investors. Learning from my mistakes was not fun.
  
  
• Later, after raising $20+ million and developing a product that we could beta-test, I remember my feelings of angst and doubt every time I drove into the company parking lot. Looking around at all the cars made me feel the anxious weight of the responsibility of ensuring I made good enough decisions about what was essential to keep all those people employed and able to make their car payments and take care of their families.
  
  
• I remember the first time I had to terminate a poor-performing employee and had to figure out all the legal, IT, and logistical aspects without the support of a larger organization.
  
  
• And so on…and on…and on…

And, yet, you cannot give in to those feelings. Instead, you have to keep learning, growing, stretching, and recruiting help to find a way to solve the problem(s) at hand and move the company forward.

I wish I could tell you that if you decide to become a serial entrepreneur, you will be able to stay inside your newly developed comfort zone, but, alas, that has not been my experience. Each and every new venture I have undertaken has come with new technologies, new customers, and new learning curves. Here are some tips and techniques I have found helpful and commended to others to succeed in spite of the reality that most startups fail and startup founders are constantly tackling new problems outside their comfort zones:

• Carefully pick co-founders to complement you. This is one of the great values of having a team to tackle the problems that must be solved. By having a broader set of skills available, your team will be better positioned to successfully tackle the problems at hand. You do not need to solve everything on your own.
  
  
• Know that sometimes you will make mistakes. When you do, step back, assess the damage, gather better information, and adjust.
  
  
• Ask for help. Sometimes someone on your team is better equipped in some area, so hang onto your humility and make sure you ask for assistance and input. Use others as sounding boards. Cultivate mentors and advisors to provide insight. Remember that even when you ask for help, you still have to integrate the input into the rest of your information and perspective as a startup leader.
  
  
• Embrace learning and growth. Every problem you solve successfully will add to your experience bank and build your confidence. However, you will not be perfect, so focus on learning from your mistakes and doing better the next time. The very nature of a startup involves lots of learning, so keep cultivating your ability to venture into the unknown and get up to speed as a master entrepreneurial skill.

• Educate your gut and then trust your instincts when you have to make tough decisions. You will have to make many decisions in a fog of partial information, so I think of gathering whatever partial information might be possible as educating my gut. Then, I judge when I can make a decision that balances risks and potential rewards before making the best call I can and committing to a direction.
  
  
• Give yourself grace when you sometimes feel like a fraud and that you are making it up as you go along (many times you are!). Imposter syndrome is a common experience.
  
  
• Remember to count your blessings. It is much harder to be anxious when focusing on gratitude.

Now, several startups later, I have learned much along the way, and I have what feels like infinitely more confidence, yet there are still moments when FUD strikes, and I am confronted by something new to learn. Yet, building startups remains exciting, so I still find myself boldly stepping outside my comfort zone, seeking to learn fast enough to keep one step ahead of those who are looking to me for leadership. If you want to lead high-potential startups, you must find that the excitement of going where no one has gone before dominates the FUD you must go through along the way.