Fear and Thinking Too Lean

Earlier this month we held the first Trajectify Live Business Growth Conference. More than 50 entrepreneurs and professionals got together for a day of learning, sharing, and connecting. Presentations were really high quality, fast-paced without a lot of whitespace. I kicked off this day to set the theme and motivate open minds. I drew on my experience growing eight companies, combined with the observations of dozens of others I’ve helped, to identify the biggest challenge and how to shift your perspective to be able to do big things. Here’s some of what I shared.

Limitations of Lean Thinking

Entrepreneurs are often told to think “Lean.” Take lots of small steps, doing a series of short iterations of launching and learning, making progress by taking each bit of learning one step of a time into the next iteration. You won’t do any one big thing before you go onto the next.

My challenge with lean is that as much as it’s a great philosophy for when you are starting out, you lose the ability to leap when you think about really big things. How do you do things that can’t be done in a one or two week sprint, the things that are too big to put on a little post it and stick to your bathroom mirror? In order to grow, you need to have a mindset of leaping, planning and doing big things, and then to figure out how to land after you take that leap.

I named Trajectify specifically to communicate this. In order to achieve success on a big leap, you need momentum (traction) and to have a trajectory (scale). You must know where it is that you are going to land on the other side of the chasm, and plan the trajectory to get there. Launching and learning is important, but you don’t achieve success until you are able to leap and land.


Why Don’t We Leap More?

Lean is really comfortable for most entrepreneurs. Consider what happens when your trajectory isn’t good enough to land. We might fall into the chasm. We are afraid to take these leaps because we could get hurt. Fear takes over.

I have a problem with fear. It is an emotion. I’m not advocating that you control your emotions, you need to be aware of them and embrace them. Recognizing that fear is an emotion that you might have, do you want to let a feeling control how you build a business or reach a goal? Think of fears you’ve had in your life and ask yourself how many of them every actually came true? Very few, if any. Fear is a feeling that you have, it’s not a projection of what’s going to happen.


It’s difficult to not feel fear. Maybe we can harness it, making it a motivator.

You’ve heard Tony Robbins say, “If you want to take the island, burn the boats.” (It’s certainly meme-able, and he did it with more expletives.) The story references Spanish Conquistador Hernan Cortes in 1520 attempting to conquer Mexico. He told his troops to burn the boats so they couldn’t retreat - winning the battle was the only option, failing to do so would be deadly (literally). Cortes did win, but I wonder if it was more because they were ruthless conquistadors, not because they didn’t have an escape or retreat.

A few years ago, I read a post on Medium from a startup founder. They received an investment to build the company, started out strong, developed some revenue, and then failed! He shares that they were supposed to get acquired, but the deal fell through and they had no alternatives. Being without a backup or alternatives is a dangerous trajectory. They had to get this one deal done and if they didn’t, the company falls into the chasm.

If you are afraid to fail, does that motivate you to take big leaps? No. It’s more likely to have you make reckless or impulsive decisions, increasing the odds of failure. Fear should not be a motivator.

While I was COO of CDNOW, a public company, there were market shifts (the start of the dotcom bust) that forced us to take a leap. We made plans to merge with Columbia House, a private company owned by Sony and Time Warner. On the last day they were able to terminate the deal, Sony and Time Warner backed out. It was nearly devastating. To a team, motivated by fear, this could have been a deadly fall into the chasm. We had backup plans, one to sell the company to another party, another to restructure. We pursued both in parallel, distracting, but not deadly. We sold to Bertelsmann as the cornerstone of their new e-commerce group and preserved $150M in revenue and 500 jobs. (A couple of years later, Bertelsmann did change their strategy and decided to shut it all down, a different lesson for a another story sometime.)

The leaps of merging with Columbia House, and it having fail, and the risks in the plans that followed, certainly did make us fearful about our ability to land and succeed. We didn’t let that fear drive how we were going to continue to build the business.

Out of Your Comfort Zone

The Jewish New Year 5779 was earlier this month. I went to a new synagogue, hearing new rabbis and new sermons. It made me wonder if I should hire Rabbis as coaches. Perhaps some of the clergy or leaders of faith in your life help positively shape your perspectives?

One of the Rabbis shared a story in his sermon of a man who asked G-d for $5,000. When you think of G-d, you probably assume he has an infinite bank account, so why not ask for $10,000 or $10,000,000. Why only $5,000? The person in the story doesn’t ask for more because they self-imposed limits. When we do not ask for $10,000,000, it is because we are trying to be kind or humble. But why not try and make the big leap? Another Rabbi the following day said, “You’re not living until you are out of your comfort zone.”

We need to focus on dreams and push our fears aside. Jordan Zimmerman, a speaker at the 10X conference, said “Chase your dreams, not your fears.” Whether we are planning our business, our careers, or our personal lives, we need to be prepared - and comfortable - to take leaps towards our dream. Forget our fears, accept them as emotions, and leap forward.