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Successful People Are Often Square Pegs In Round Holes, Fuelled By Self Doubt


by Jack Colton, founder of SilentRich.com

The most successful people amongst us are oftentimes also the most conflicted, unpredictable and seem to habitually struggle with an almost debilitating battle with their own self-esteem. For better or for worse, true-bred entrepreneurs aren’t like other people. You have plenty of hard edges and abrasive eccentricities that serve as the true formula behind your successes. But if left unattended, they can also be the cause of your undoing.

There is a perpetual contradictory dance of empathy versus you being a complete sociopath. You can be the most reasonable and compassionate person possible – helping to care for others on a regular basis, but then won’t lose even a moment of sleep completely obliterating the unfortunate soul who made the mistake of standing in your way.

You can’t walk into any situation and see things as they are, but rather are entirely consumed with deconstructing how they got there and what can be done to make them as good as they should be. And instead of sitting idle in helpless frustration, you are fueled with the confidence to actually take action and to do the things necessary to change what you don’t like. Thus, these are the situations where your best opportunities are found and acted upon.

When you truly believe in something, even the most extreme risk won’t overly concern you. You’ll take things to the edge if you have to, jeopardizing everything. And if it comes down to it, you’ll jump off that edge and just figure it out on the way down. Having your back against this wall of assured destruction is often where you shine the brightest. This willingness to risk it all is what separates you from the people who want things, but who never have the stones to sacrifice what is necessary to achieve them.

You are relentlessly unattached to anything and will change your mind at a moment’s notice as new information comes into the picture, no matter the cost of time or investment. You know that the line to success is rarely a straight path, so being able to immediately pivot to such extremes is merely seen as altering the route to your same eventual destination.

High achievers tend to focus more on what they haven’t done versus what they have and are notoriously vulnerable for crippling self-doubt and having a nasty case of Impostor’s Syndrome. Your obsessive pursuit of perfection and constant attention to detail always have you second-guessing yourself, then wondering if others will finally find you to be a fraud. Seeing you as you actually see yourself, not as smart or as talented as you “should be.”

It seems that the only people immune to Impostor’s Syndrome are those who are perfectly comfortable being mediocre and living well below the uncompromising bar that you’ve set for yourself.

They can’t possibly understand that regardless of how much you have accomplished, how many pats on the back you’ve received or how much money you’ve made in the process, none of these things actually matter. Instead, you beat yourself up over what you haven’t done and wonder if everything you’ve pulled off up to this point was just luck. At your lowest moments just before it’s time to again perform, you ask yourself “what the fuck have I gotten myself into, how am I going to do something again that people will love?”

While inescapable self-doubt manifests itself differently in all successful people, oftentimes it originates from an undeniably difficult background that you’ve spent much of your life trying to overcome and compensate for. When you peel back your layers and the prickly protective shell that are essential to hiding your vulnerabilities from those who would seek to destroy you, you’ll often find your driving force to be the poverty you were raised in, the abusive relationships in your past, the adversity your family overcame, your tumultuous relationship with loved ones or any number of other things that for all intent and purposes just plain sucked.

To this I say, embrace your past and whatever your actual driving forces truly are. It’s why you are able to do what you do and has brought about every opportunity that you’ve ever taken advantage of.

There is a reason most people aren’t capable of doing the things that you do, they haven’t lived your life.


As Founder of SilentRich.com, Jack Colton has always had a passion and a knack for networking and connecting people who can help one another. Prior to Silent Rich, Mr. Colton founded and exited a number of successful online companies, including the popular Las Vegas tourism guide JackColton.com and Blackout Artist Management. Additionally, Colton serves as a mentor for Nevada-based startup incubator, StartupNV.


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