How to Break Through Your Fear of Success
I then came across an exercise that changed my life. The exercise was simple. It was a set of questions that walked me through to an understanding of my core fear and of what exactly was the limiting belief that was holding me back.
It first asked: What do you want?
I want my software company to thrive. I want to have a hundred employees working for me so that we can serve more people, have more customers, make more money, and turn ToutApp into a revenue-generating machine.
It then asked: What would you have to do to get what you want?
I knew exactly what I had to do. We had to make our current customers successful. We had to expand our feature set, uplevel our messaging, become more aggressive about getting our word out, and, most importantly, we had to expand our sales capacity so we could sell more.
I knew the answers! What was holding me back, I wondered?
Surely enough, it then asked: What could go wrong if you did those things?
I felt a knot in my stomach.
The software might not scale.
We might hire people who may not be good at what they do.
We might have to hire WAY MORE people, and then I’d have to manage all of them!
We might run out of money.
We might find out that our software is not great and the broader market doesn’t want it.
We would have to find a way to support all those customers.
We would have to find a way to educate all these customers on how to use the software, and that might be harder to do for mass adoption versus for the early adopters we have now.
Competitors might start copying us, and then we’d lose our position in the market and get trumped.
I may not be good enough to build a software that so many people would want!
The list went on…. Within minutes, I had listed a full page of things that would go horribly wrong if we were to become successful. It was a wake-up call for me. There I was, toiling away, my team was toiling away, and yet all of these things were subconsciously pulling me back from achieving success -- because I was afraid of all the things I would have to deal with if we were successful!
The exercise was unrelenting and unapologetic. It then asked: You’re now successful. Those problems that are your demons are now real. How would you overcome those problems, given your newfound success?
As you might imagine: I had an answer for every single problem I was deeply afraid of.
More customers meant more revenues, meant more dry powder.
More customers, more revenue, meant more employees who could help solve problems.
More growth meant more investment dollars coming in.
More revenues and more investment dollars meant I could hire smarter people to solve problems and help manage more employees.
The exercise then asked: If you are NOT successful, what would happen?
Death. I answered. We would die, we would fail, it wouldn’t matter anyway.
It then asked: If you ARE successful, what are the positive things that would happen?
I would thrive. My employees would thrive. We could deliver MORE for our customers. Our customers would thrive. It would be WIN-WIN-WIN for everyone involved. Our wildest dreams could come true and all our effort would be WORTH IT.
The exercise finished with… What’re you waiting for?
What was I waiting for?! What was I afraid of?! The worst-case scenario was our failure, which was assured if we didn’t do the things necessary to achieve success anyway.
By the middle of 2012, shortly after I completed this exercise, we doubled the number of employees to a whopping eight people on a single day.
By the end of 2012, we sold so much software, we did a pre-emptive Series A round of $3.3m from Jackson Square Ventures to help support and accelerate our growth.
Through 2013, we grew the company 300% in a single year, increased to 40 employees, and raised another $15m from Andreessen Horowitz.
Through 2015, we grew the company again, to nearly 80 people, and through twists and turns (which I’ll leave for another time) we sold the company in 2017 to Marketo, a market leader in the space.
The exercise made me realize two important things about living a proactive life:
Without doing the basics, such as setting goals, practicing Belief and Discipline, and having a sense of urgency, failure is guaranteed.
However, even with doing those things, we may be walking around with subconscious programming in our minds because of our environment or upbringing that may sabotage our own success.
It’s unbelievable, isn't it? We could be working tirelessly toward our goals, could wholeheartedly want to be successful, and yet our subconscious programming could be actively working AGAINST us to sabotage our forward momentum. When I felt like I was pushing ahead but there was an imaginary hand pushing back against forward momentum, I wasn’t wrong. I felt the right thing! The “hand” was my own fear of success, it was my feeling like I didn’t deserve success. It was my feeling that I wasn’t enough.
What are the limiting beliefs and fears that are holding you back from your path to success?
Was it being taught at an early age that money is evil? Is it a fear of all the bigger problems you’ll have to solve tomorrow if you are successful today? Is it the memory of your parents telling you at an early age that you’re not good enough or doing something wrong? Is it friends or a significant other who is unsupportive of your dreams?
We all have these things in our life. It’s just that we’re not trained to identify these negative patterns in our lives as they work silently in the background to sabotage our hard work.
Now, I don’t mind failing because I got the market trends wrong. Or because I miscalculated a strategic move. Or I made a poor business decision. I can own that. I can learn from that. I can come back stronger than ever from that. But to sabotage myself because of my own fears? That is simply unacceptable.
Throughout the rest of this book, I will help you craft a life strategy and a proactive plan. But before we delve into that, I want you to follow the same exercise that I followed, in order to identify the subconscious fears deviously holding you back from the life you deserve.