The Catch-22 of Success and Self-Confidence (Issue #5)
An unexpected way to break the cycle
It seems impossible to be successful without some degree of confidence. But how can you be confident without achieving some degree of success?
It’s a chicken and egg dilemma. When you see a successful, confident person, what came first? The self-confidence or the success?
I remember going to school with someone who seemingly had it all. They were smart, wealthy, attractive, gifted athletically, and had tons of friends.
But, they also were gifted with a series of disastrous relationships. One failed after another. Each time, the partner walked all over them and treated them like crap.
I found it baffling. We were talking about the latest crash and burn one day, and I said, “Why do you put up with that? You’re a catch. You don’t need to put up with that.”
As the conversation unfolded, I realized they felt unworthy of love and a good relationship. They completely lacked the self-confidence I assumed they had, and falsely projected. They were the one who felt lucky that someone would go out with them.
I had already experienced my fair share of massive failures in school, work, and life. I had failed relationships, too.
I remember thinking to myself, “Damn. If that person who has it all still doesn’t feel confident, what chance do I have? I’m screwed.”
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Ironically, once I felt like I didn’t have a chance at big success anyway, I think I began taking an almost perverse pleasure in shooting for the moon and failing. My internal pep talk wasn’t, “I can do anything!”
It was more like, “Eh, who gives a sh*t. Might as well go for it. What’s the worst that can happen?”
But, an odd thing happened. I failed often, but I also began succeeding. Not a lot, but just enough to keep churning ahead and making progress in life.
Enough to marry a woman who is way out of my league. Enough to get into grad school after being put on academic probation a few years before. Enough to land a job at my dream company.
To this day, I don’t feel like I have what I would consider classic self-confidence. I know what’s true about myself, but I also accept what I never will be. However, I no longer care about those flaws. I’ve experienced so many failures, yet I’ve come out the other side and survived.
“You gain strength, courage, and confidence by every experience in which you really stop to look fear in the face. You are able to say to yourself, ‘I lived through this horror. I can take the next thing that comes along.’”
— Eleanor Roosevelt
I keep churning and striving. So, is that what confidence is? Perhaps.
Recognizing true confidence
With age comes perspective and, hopefully, some wisdom. You can see behind the masks that everyone wears. You look under the layers of projected identity that people have constructed.
You recognize true self-confidence — the people who are calm, hardworking, generous, and surprisingly humble. You also know when someone is bluffing. You grow weary of the people who are continually bragging, dominating every conversation, and one-upping everyone in the room with their stories of how they saved the day (yet again).
You should know that there are people who seemingly “have it all,” yet they lack confidence. Despite their big mouths and even bigger stories, they don’t believe in themselves.
The people who surround themselves with the shiny trappings of success are rarely as successful as they seem.
That person wearing the latest designer clothing and sitting in a new luxury car at the stoplight next to you? They’re in debt up to their eyeballs, hate their job, and have to go into work every day and kiss their boss’ a$$.
This other person wearing a T-shirt and jeans, sitting in a beat-up car? They retired at 40, are worth millions, and have zero debt.
Think I’m full of it with this observation?
Warren Buffett has a net worth of over $80B, yet he still lives in the same modest home he purchased in the 1950s. He stops at McDonald’s to spend about $3 for breakfast on his way to the office.
On the other hand, Bernard Ebbers fraudulently racked up over $1B in debt so that he could buy yachts, a shipyard, a ranch, etc. He had all the trappings of a wealthy and successful person, but it was all fake. Ultimately, he was sentenced to 25 years in prison for a record $11B accounting fraud.
Confidence doesn’t come from external validation or from the usual superficial indicators of success. It isn’t about your good looks. Endless amounts of money and fancy titles won’t give you self-confidence either.
“Confidence is not, ‘They will like me’. Confidence instead is, ‘I’ll be fine if they don’t’.”
— Christina Grimmie
Ironically, becoming more successful in life and career may make you feel more insecure (Hawley, Katherine. “I — What Is Impostor Syndrome?.” Aristotelian Society Supplementary Volume 93.1 (2019)). You feel like a fraud and impostor. Everyone is going to find out that you’re not that talented. You’re going to lose it all.
But what does create confidence?
Confidence doesn’t come with achievement. It comes with striving and believing in what you can do.
Be confident that you will learn how to do something.
Be confident that you will work hard.
Be confident in your grit and determination.
I’ve talked about uncovering your core truths before. Digging deep and claiming what is true about you and can never be taken away — making that the basis for your self-confidence and banishing your impostor syndrome.
Confidence and calmness also come with accepting what you are not, will never have, and never will be. Pushing that crap to the side, out of your mind, and out of your life.
If I don’t give a damn about doing something, I can’t lack self-confidence in doing it well. It doesn’t even register on my scale of talents, abilities, and skills.
Nope, I will never be a great basketball player. I don’t care about that either. It means nothing in my life. I don’t suffer from some damaged sense of self or lack of confidence in my basketball skills, because I don’t give a damn about it.
Mark Manson talks about becoming comfortable with failure, rejection, and pain. The most confident people aren’t brimming with self-confidence because they believe they will always succeed and never fail. Their confidence stems from the fact that they accept that failure is an option, and they know they can survive it and come back.
Confident people don’t say, “I’m going to win” every time.
They say, “I’m going to give it my best and, no matter what happens, it’s going to be ok.”
“I think that the power is the principle. The principle of moving forward, as though you have the confidence to move forward, eventually gives you confidence when you look back and see what you’ve done.”
— Robert Downey, Jr.
It would be foolish — and confidence-destroying — to assume and expect 100% success. Failure is inevitable. If you base your confidence on bravado and proclamations of eternal success, you’re in for a rude awakening.
Break the cycle by claiming what you can own
As Fred Kofman points out in Conscious Business: How to Build Value Through Values (affiliate link), we focus too much on outcomes. We lose confidence in ourselves, become demoralized, and even grow angry when we don’t win, succeed, or change someone’s mind.
But you can’t control the outcome. You shouldn’t force others to do your bidding (not ethically, anyway). You won’t be able to bend the environment to your will. However, you can control your values, actions, and effort. Focus on what you can do and let your confidence flow naturally from the belief in your actions.
Do more and say less.
Learn more and brag less.
Fail more and expect less.
Give more and take less.
Save more and buy less.
The most unexpected way to break the cycle of “confidence requiring success” is to become comfortable with failure and rejection. Base your self-confidence on your core truths, grit, and determination. Don’t focus on success, achievements, or any other external markers of success.
Once you accomplish that transformation, nothing can take your confidence away from you.
Larry Cornett received his Ph.D. in Psychology from Rice University. He spent decades in the Silicon Valley tech industry as a designer, Design leader, Product executive, and startup founder. He eventually left the corporate world to start a coaching practice and now lives in Northern California near Lake Tahoe with his wife and children, and a gigantic Great Dane. He does his best to share advice to help others create their own invincible lives. He’s also on Twitter @cornett.