Why Magic Happens When Your Back’s Against the Wall

If you read my first blog post—How Making Work Better Became My Passion—thanks for returning to read more about my journey. The Workify chapter actually began in late 2013, when my first stab at entrepreneurship was collapsing.

In September 2013, the writing was on the wall—my first attempt at the entrepreneurial dream was a failure. Similar to the stories of many other startup CEOs, the consequences seemed devastating, and there was no aspect of my life that was unaffected: my marriage, career plans, friendships, and my financial outlook. 

While I was picking up the pieces of my life, I realized I needed to give myself space to think about what just happened. How did I get here? What lessons did I learn? What were my successes? Where did I go wrong? What contributed to my failure? What were my fears? What was I blind to? What dreams were still worth holding on to?

I’m blessed to have mentors and friends who helped me work through the smoldering ashes. I debated whether or not I should go back to the corporate world, but a mentor clearly advised, “Don’t do it. If you can find the courage, stick with entrepreneurship. It won’t be easy, and it may get worse before it gets better.” I followed by asking for a job, which was immediately declined. I was told that I had to figure the situation out on my own.

My mentor was right. This predicament brought me to a big realization. Something magical happens in moments of desperation—when our backs are against the wall. You see this magic occur in sports when teams are down. I believe it also happens in business and leads to major breakthroughs, discoveries and innovation.

When there is no clear way out of a struggle, and people are hungry, momentous hurdles are overcome. The philosopher and Roman Emperor, Marcus Aurelius, wrote about this idea many centuries ago.

“The impediment to action advances action. What stands in the way becomes the way.” – Aurelius said. 

Through our obstacles, we often find our greatest successes. Why? Because there is no other way. I firmly committed to the entrepreneurial path that I started.

Do What You Are Afraid Of

With a renewed commitment to the entrepreneurial path, the question became: “What do I do now?”. The advice I was given was to focus on what I was most afraid of. This was easy –  sales! My first business died because I didn’t do a good enough job at creating a sales pipeline. Looking back, I realized I had some core fears around failure and rejection. I immediately reached out to my network and I began looking for a sales job in the startup world.

I worked for a local business-to-consumer (B2C) mobile startup for six months. This was a mobile app that targeted restaurants. Restaurants are constantly being sold to and are used to being sold “snake oil”, so I found myself in a hostile sales environment.

I had my teeth kicked in for six months, which was crucial for me. I walked away from this experience with some great clarity around three important things:

  1. I became desensitized to rejection
  2. I realized B2C is not my strong suit
  3. It confirmed I have good instincts to survive in a product-oriented business

These lessons were all important for their own unique reasons. Now, I could move forward with my mission, because I found my niche in B2B sales.

If you don’t quit, patience will work in your favor

When I left the mobile app company, for the first time in my life, I had no definitive plan. This was a scary place to be, but I was able to trust that things would work out.

I left my sales job on a Friday. Coincidentally, I met with my personal attorney to shut down my first business venture on that same day. He introduced me to a mutual connection, Dustin Wells, the CEO of Headspring, who was expanding his Austin-based software company to Dallas. That following Tuesday we had our first conversation, and a month later we had an agreement to launch a company together.

Dustin and I quickly realized that we had a lot in common. He saw value in my experience of having failed at entrepreneurship and my attitude toward the situation. We shared the passion to improve company culture, employee engagement, and make work better. Without this timely meeting, I wouldn’t have worked under Dustin as an entrepreneur-in-residence, launching me toward my mission with Workify.

This journey of finding success through failure was difficult and even painful at times. I’m reminded of this quote from Thomas Jefferson, a man who failed many times, at one point even seeing his high-earning factory burn down when he was 67-years-old.

Jefferson says: “Many of life’s failures are people who did not realize how close they were to success when they gave up.”

Or consider the story of Dr. Samuel P. Langley, former director of the Smithsonian Institute, who was ridiculed after several failed attempts at manned air flight. After years of humiliation and failure, Langley abandoned his dream of flight—only to see Orville and Wilbur Wright fly their plane in Kitty Hawk a few days later. What would have happened had Dr. Langley stuck with the work?

To anyone aspiring in any field, I offer these three lessons from my experience:

  1. You’re often closer to success than you realize. Don’t. Give. Up.
  2. Dive headfirst into the tasks that you are afraid of.
  3. Persistence always pays off. You may not be able to connect the dots immediately, but hindsight will always reveal that moving forward was the best decision.

If I didn’t heed the warning from my mentor to not give up, I’d likely be back in the corporate world—just another cog in the wheel. I wouldn’t be on my way toward making work better.

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