The Doubting Entrepreneur

There’s one thing of which I’m certain . . . I think. Have you ever had this kind of feeling? We entrepreneurs are a pretty confident lot. We are scrappy and tough. There’s nothing we can’t do including leaping over tall buildings in a single bound. Throw us a challenge and we’ll whip it with one hand tied behind our back and blindfolded to boot. Right? Well, maybe. And most of the time.

Entrepreneurs have several “thought enemies,” one of them being gnawing and nagging doubts. Here’s a not-so-fictional example. Let’s say that things have been going pretty well in our business and we’ve had some nice wins along the way. Then we hit a little speed bump – perhaps a contract doesn’t get signed that we thought we had in the bag. Or an important customer stops doing business with us. In other words, we get knocked off our game a bit. That part we can handle with aplomb as we go on to sign another contract or we fix the problem with our important customer. It’s what happens next that can be perplexing.

After we’ve been bucked off the horse so to speak, we begin to have feelings of doubt. For example, we are ready to introduce a new product or service, but we wonder if it might flop. In the past, we would have launched without any trepidation, but now it feels different. Could something else go wrong that that might cause everything to come unraveled? We know that these gnawing and nagging doubts aren’t healthy and could become self-fulfilling prophecies. Yet still they are there and hard to push out of our mind.

Why is our confidence shaken, and doubts have entered the picture? I’ve thought about all of the times this has happened in my life and believe it centers on a rather recent failure in the past. The earlier example that I gave where the contract or customer was lost illustrates this notion. Coming off of a failure makes us wary and more sensitive. As entrepreneurs we have winning in our DNA. Failure is for losers. And yet we do fail, and we do lose. Sure, we’re resilient, but we can’t ignore what it felt like to fail and lose, and we don’t want to experience it again. And so, we’re vulnerable to doubt and uncertainty. Subconsciously we’re thinking, “I’m sure what I’m doing now is going to work, but if it doesn’t, I don’t want to be hurt again.” We find ourselves moving forward but wondering . . . always wondering when the other shoe will drop.

Here’s what I’ve learned about myself when these insidious doubts start creeping into my consciousness. I step back and take inventory of all of the positive successes that I know lay in front of me. I may have just lost a deal, but there are ten more that I believe with all my heart will succeed. Now here’s the key – even if only half of the ten deals actually succeed, I’m still way, way ahead. In other words, I’m not looking at the glass half full, but I’m looking at multiple glasses and every one of them is overflowing. Immediately my mindset changes and all is right with my world again. I’ve accepted the fact that I had a prior setback. I’ve accepted the fact that I’ll have more setbacks in the future. But I know that the pluses will always far outweigh the minuses and the winning score will be in my favor – overwhelmingly!

Gnawing and nagging doubts are usually a product of a recent failure. We get past such feelings by looking at the scoreboard and realizing that we are way ahead in the game. Ultimately this makes us unbeatable.

This blog is being written in tandem with my book, “An Entrepreneur’s Words to Live By,” available on Amazon.com in paperback and Kindle (My Book), as well as being available in all of the other major eBook formats.

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