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.

“Don’t You Know Who I Am?!”

The actor, Alec Baldwin, purportedly was riding his bike the wrong way near Union Square in New York and was stopped by police officers. After uttering some profanities, he produced this gem, “Don’t you know who I am?” We’ve all heard this before. Someone isn’t getting his or her way and so they play the “Don’t you know who I am” card. This statement is reflective of the ultimate entitlement mentality. Entrepreneurs are often on the road to success – sometimes in a big way. This success may lead to wealth, fame and power. What it doesn’t produce is entitlement.

Let’s define entitlement a bit more clearly. There are certain circumstances where entitlement is perfectly legitimate. For example, suppose we pay through the nose to fly first class on an airline. There are perks that inure to our benefit when we pay extra for them. Similarly, if we pay a premium for a luxury automobile, there will likely be some special treatment that we receive at the dealership when we arrive for service. Again, we are entitled to this special treatment because we paid for it.

Now, contrast this with the guy who always parks his luxury car in a “no parking” zone. Or the woman in an expensive mink coat who cuts in line at the grocery store or the theater. Or in 2009 when a young woman ordered a hamburger in a fast food restaurant and upon asking her name for the order, she replied to the server, “You don’t recognize me? I’m Miley Cyrus!” I don’t know about you, but I cringe when I witness this kind of behavior. This type of entitlement mentality is not the legitimate kind.

As leaders we’re role models whether we like it or not. Our team members are watching every move we make. If we happen to be in the public eye, there are many more eyeballs and ears that are taking notice of everything we are doing and saying. Oh, and they are judging us AND our organization at the same time. It’s one thing to have a great deal of self-confidence and assertiveness – this is entirely necessary to succeed in today’s rough and tumble world of commerce. But the line is crossed when that self-confidence and assertiveness becomes boorish, arrogant and aggressive.

The whole issue is one of self-esteem. The way we see ourselves comes from within and not from the outer. It’s probably no secret that people who are shoving their fame, fortune or power in the face of others, are acting from a feeling of low self-esteem. Sometimes the resulting sense of misplaced entitlement leads to destructive actions such as heaving drinking, drug use, gambling, extramarital affairs and other sorts of outrageous behaviors.

There’s absolutely nothing wrong with driving a luxury automobile, wearing expensive jewelry and clothing, or being on a magazine cover. It’s how we feel about ourselves and how we treat others that matters most. Country singer Dolly Parton is one of the nicest and most humble mega-stars on the planet. Soccer star David Beckham is super polite, and actress Jennifer Lawrence is known for being very down-to-earth and easy to work with. There’s no doubt that all three are members of the rich and famous class. And yet they aren’t overcompensating for their insecurities (and they may not have any) by displaying an attitude of entitlement. They, and many others like them are gracious and put others first.

Our station in life is not a rung on a ladder. Instead, it’s simply a stepping stone that is part of a long and winding journey. Each of us is on a similar journey. When we offer a helping hand to others our lives are enriched.

You can also listen to a weekly audio podcast of my blog. What you hear will be different than what you read in this blog. Subscribe on iTunes or wherever you get your podcasts. You can also click on this link – Click here to listen to Audio Episode 62 – 2300 Feet and No Ropes!

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.