The Catch-22 of Success and Self-Confidence

An unexpected way to break the cycle - Issue #14

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, it became clear to me that 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.


Embracing failure

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 along the lines of, “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 start to be able to see behind the masks that everyone wears. You see 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 to the right of 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 their beat-up car on the left? They retired at 40, are worth millions, and have zero debt.

Think I’m full of crap with this observation?

Warren Buffet 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.

Jeff Bezos is worth over $100B (even after the divorce). He was still driving a Honda Accord to work every day, after becoming a multibillionaire in 1999.

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 of 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 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 that they will always succeed and never fail. Their confidence stems from the fact that they accept that failure is an option, and they know that 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.


What I’ve been reading and writing

  • It’s an oldie, but a goodie. I’ve been hanging out at Barnes and Noble waiting for my son while he’s at an astronomy class. I noticed Mark Manson’s book sitting on a table, “The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life(affiliate link). I mean, how can you not enjoy this? “The people who don’t give a fuck about adversity or failure or embarrassing themselves or shitting the bed a few times. The people who just laugh and then do it anyway. Because they know it’s right. They know it’s more important than them and their own feelings and their own pride and their own needs. They say “Fuck it,” not to everything in life, but rather they say “Fuck it” to everything unimportant in life. They reserve their fucks for what truly fucking matters. Friends. Family. Purpose. Burritos.

  • In “Do you love where you live?,” I talk about the first principle of creating an Invincible Career. Having the freedom to decide where you live is one of the most significant factors that determine your lifestyle and happiness. If you don’t love where you live right now, what are you waiting for? Retirement? Life is too short to think that way. Note: If this article is locked behind Medium’s paywall for you, I will be re-sharing it in an upcoming newsletter soon.

  • It may seem like an easy question to answer, but most people fail when asked, “Why do want this job?” Their answer betrays that they really don’t understand what the job requires. Or, they are interested in working for the company, but not enthusiastic about the particular role. Finally, the kiss of death is to say something that makes it sound like the job is merely a stepping stone on your way to something more important.