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One of the most common questions I receive from my entrepreneurship students at Purdue is, “What gave you the confidence to start a business and quit your job?” I get it.
Every semester, they are exposed to my entrepreneurship journey with One Click. We spend time talking about nurturing an established company culture, analyzing a built-out customer acquisition strategy and selling the company. They see the results of 10-plus years of hard work. It’s difficult to know where to start.
I love the question and the conversation that follows, because the truth is that I never had the confidence to build an 85-person team, manufacture glasses in China and Taiwan, or figure out how to sell prescription eyeglasses online. Randy (my partner) and I didn’t start the company with any kind of confidence that we could build and grow, because we had never done it before. Confidence comes from repeated trials and errors and realizing you can overcome them to keep moving forward.
Several years into the business, after we had successfully navigated multiple stages of growth and too many trials to list here, we had the confidence required to tackle almost anything that came our way. But that isn’t how we started.
It was courage, rather than confidence, that helped us take that first step in building our business. And that courage was bolstered with a solid plan of action and an understanding of our worst-case scenario.
I’ve seen entrepreneurs who take a giant leap into entrepreneurship on blind courage alone. Sometimes it works out, but it’s kind of like running full speed into a brick wall again and again and hoping you can either break through or find a hole big enough to slip through. It’s risky, and you’ll likely end up with some breaks and bruises along the way. I liken this approach to watching my 2-year-old race down the driveway on his no-brakes balance bike, only to stop when his face hits the back of my car. A whole lot of courage, but not a lot of foresight. (His helmet saved the day.)
On the other hand, I’ve seen folks spend months or even years reworking plans and waiting until the plans feel perfect, or they feel ready. These entrepreneurs are trying to plan away any roadblocks or uncertainties, but that just isn’t possible. Or they spend time and money trying to build the perfect solution before they launch and allow other entrepreneurs the opportunity to get to market sooner with a product that will better solve the customer’s problem. It is the fantasy of a perfect plan that keeps these entrepreneurs from ever becoming successful entrepreneurs.
The truth is that the entire entrepreneurship journey is filled with uncertainty. And once the path feels certain, something comes to knock you off the path once again. But it is in these moments that the courage to move forward and the ability to both plan and react in real time help you build the confidence you need to continue moving forward.
In my experience, the more my courage to take on challenges evolved to confidence, the less time I needed to process, plan and react. Early in our journey, I often had to take a night to process the fact that we were in a crisis. That processing time became shorter and shorter the more experience I had with handling new challenges.
The third piece of the puzzle was understanding our worst-case scenario. It’s an exercise that we used repeatedly in our first few years to help us understand all the possible outcomes. If we realistically looked at the worst possible outcome for a decision, and we were OK with that outcome, that helped us feel more comfortable moving forward with the decision.
When we purchased SunglassWarehouse.com in 2005, it required us to empty our savings account and commit our nights and weekends to learning and building. The realistic worst-case scenario was losing our savings and losing out on time with our friends and family. It was a risk we were willing to take to test our entrepreneurship skills.
Turning courage into confidence doesn’t have a set timeline or a sexy 10-step plan. It happens through repeated chances to solve new problems and understanding how you react to failure. It comes from figuring out how to use that failure to your benefit, reflecting on your wins and giving yourself credit along the way.
If you’re ready to take that next step, wrap your courage around a solid plan and understand your best and worst possible outcomes, then get ready for the wild and crazy ride of entrepreneurship.•
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Stocklin is an angel investor and exited founder who currently teaches entrepreneurship at Purdue University.
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