8 min read

How to Get Swagger

I have a confession. It’s something I’ve never really admitted to anyone… One of my biggest lifelong problems has been a lack of SWAGGER.
How to Get Swagger
Photo by Karsten Winegeart / Unsplash

I have a confession. It’s something I’ve never really admitted to anyone…

One of my biggest lifelong problems has been a lack of SWAGGER.

Swagger is excessive confidence. A lack of swagger can be a problem because it prevents you from living your fullest potential. If you feel you deserve swagger, you can have it! It’s a mindset. But most people do not love themselves enough to stop their endless mental criticizing, or they’re terrified of being judged by their peers, so they only show tiny bursts of swagger. Their confidence is held in a restraint, only expressing itself when it’s socially appropriate.

I’ve always been confident, but it’s always been grounded or muted by humility and a fear of being obnoxious to others. Even though I always wanted to express an OVERFLOWING confidence that radiates from my being — a confidence that flows through the way I walk and talk — I’d still hold back…

I remember when I was 16, at the height of my pitching career. I had great control of the ball, I was throwing in the high 70’s, and I could outthink any hitter at the plate. I was able to get in people’s heads, and easily sink into my element at the mound. I loved it.

After a game, my mom mentioned that another parent said they wished I had some swagger.

I was taken aback. Hadn’t I won the game? Wasn’t I good?

Of course I was, but I could be GREAT… If I’d only just owned who I was and truly embraced my own greatness, instead of constantly playing it careful, wondering “What if I mess up?”

There was another pitcher on our team who had swagger. He took big, casual, pigeon-toed strides whenever he walked out to the mound. He’d flash a smile at hitters, knowing he’d have the pleasure of humiliating them in front of their team.

This guy KNEW, in every fiber of his being, that he was better than everyone. He could throw the ball so ridiculously fast. And today, he actually plays in the majors, and makes $500,000 per year throwing a ball.

And he epitomized swagger to me. He was arrogant and he never said a nice thing to anyone. I hated him because he was a JERK, so I automatically labeled all people with excessive confidence as JERKS. And I made it a point to be his opposite — someone who was talented, but that everyone liked. I never wanted to be a jerk.

This fear of not upsetting people has been a recurring theme in almost every area of my life. It’s been the bottleneck that’s prevented me from behaving the way I want to.

I am REALLY good at a lot of things. In fact, anytime I really set my mind to something, I accomplish it. I’ve done this over and over, and even though I always do well, I also know that I can do better. But I often DON’T TRY, because what often holds me back is a fear of leaning in too far. A fear of swagger.

I value humility. I avoid taking the spotlight. I don’t showboat. I don’t like making anyone uncomfortable or resentful toward me. I like to be kind, to make people feel good about themselves, to feel SAFE around me for being who they are.

And yet, there’s a deep part of me that resents that safety. And I find it creeping into my life in odd ways. I know I should be leaning in more, confidently going for bigger gains and bigger risks at every step, in every area of my life. To express who I am, fearlessly, and make no apologies for it (is it any wonder I was drawn to work with guys like Tim Ferriss, Tucker Max and Ramit Sethi? Three individuals who are unapologetically confident, who I could learn from and practice my own swagger with by playing the man behind the curtain?)

At the core, a lack of swagger has put a ceiling on my life. That might seem crazy to you if you think I’m “the man” for having done a bunch of stuff that you wish you could do. But to me, I know that there have been so many times where I’ve mentally put the emergency brake on with my own thoughts of self-doubt and restraint. My mind continually clips my wings right before I spread them.

This lack of swagger is a feeble MINDSET that tells me to play it safe, tiptoe around risks, apologize if I make too much of a show or if I’m too noisy, or if I charge too much, or if I’m too aggressive and make an uncomfortable move, or if I upset someone I care about. It’s the voice that tells me I’ll probably get rejected or lose or die, before anything’s even happened.

I’ve struggled with having swagger my whole life. I thought if I just kept showing up, working hard, slowly building up my confidence bit by bit, then maybe I could someday have a big breakthrough and embrace my swagger. I thought that was the only way I could EARN swagger.

Until very recently.

Oh, nooo… I felt the blood drain from my face. I was sure I was going to throw up and cry at the same time. My ex-girlfriend was on a date with another guy, right in front of me.

It’d been 4 months since we’d broken up. I’d spent months grieving the end of our relationship. I’d really loved the girl, but we both needed space so we could get our lives in order. I was finally feeling like I was ready to move on, and believed I’d made peace with the situation.

Nope. There I was, wanting to run away and hide.

And I did. I rushed out of the building, gasping for a huge breath of fresh air and the safety of being an anonymous person on the city street again.

I walked back to my apartment under the moonlight, feeling angry and sad and sick all at once. I googled “Why does it feel like you’ve been punched in the gut when you see your ex with someone else.” I discovered there was a survival mechanism to the awful feeling in my stomach — it was my body’s way of saying “You’ve been kicked out of the group! Emergency! Fix this!”

Normally, I would have just sat around my apartment, stewing in rage, forcing myself to pretend nothing had happened. Then I would’ve grabbed alcohol and called up friends to go back out. But I didn’t do that.

I sat down, closed my eyes, and effortlessly found my brain coming up with reasons why I was grateful for what just happened. I meditated, focusing on my breath for 10 minutes. When I realized I was crying, I got back up, wrote down three great things that happened that day in my journal, and went to sleep.

During the two months prior, I’d been practicing gratitude. Every morning, I’d wake up and immediately write down three things I was grateful for. And before I fell asleep, I’d write down three amazing things that happened that day.

At first, I didn’t really buy into the practice. It was something a few friends had recommended to me, but I’d been doing it for a few weeks, and it didn’t seem to work.

Until that night, when I saw my ex. It had undoubtedly worked when I’d needed it most. Instead of filling my mind with a loop of thoughts that were angry and bitter and anxious and jealous, I was surprised to find it creating a thought loop of gratitude and love and compassion.Those thoughts weren’t even a choice; they’d become a HABIT.

And those thoughts radiated through my body. I physically felt my heart warming up and opening. There was another layer of love that I felt, for both her and the guy she was with. It was one that I’d never thought I’d really be able to explain (and I’m still not sure if I’m able to in writing). That feeling colored all of my thoughts. I believed that I was grateful to be alive, that everyone around me was me, my parents, my siblings, my extended family, my universe, all wrapped up together. Everyone and everything I came across were all deeply related. I knew all of their secrets and fears, and they knew mine — I felt comfortably naked, so I was able to greet them with love, joy, and playfulness. It put me in an intoxicating state of swagger, which lasted a couple days, and then it began to dissipate.

I’ve been reflecting a lot on how my HABITUAL THOUGHTS — what I’m constantly thinking — have determined my reality, all my life. From the best times, to the worst times. They’d colored my perception, telling me how to interpret and behave toward everything.

When I was landing dream job after dream job, I thought ALL THE TIME about how there was an abundance of opportunities, that the world was mine for the taking, and that I deserved what was coming to me.

When I was debilitated with anxiety and depression, I thought ALL THE TIME about how uncertain the future was, how big of a screw up I’d been in the past, how the world was conspiring against me, and how I was losing my mind and dying.

And whenever I’ve felt so much love and kinship with others, I am thinking ALL THE TIME about how lucky I am to be alive, how much fun the people around me are, how fortunate I am to be serving others, and how certain I am that we are all connected — that everything is one.

The reason I’ve never had swagger was because I HABITUALLY THOUGHT that swagger was a bad thing. I resisted it, because I believed that manifestations of unshakeable confidence were ugly and needed to be restrained. And yet, I secretly loved and desired that quality.

I think back on this year, and I have so many exciting things I want to share with you…

How I did standup for the first time ever, after keeping a secret joke journal for ten years… How I spoke to a group of 60 veterans and made a woman cry, saying I changed her life… How I saved a person’s life with an email… How I auditioned in front of Richard Linklater (director of Boyhood) and gave him my book… How I created my first online course…

How I won an improv competition… How I learned to play one of the hardest songs I know on guitar… How I learned to say “I love you” without fear… How I lost a client thousands of dollars, and made another client millions… How I’m helping a friend write 10 books in one month… How I taught a former professional basketball player how to get girls… How a Brazilian supermodel and Tony Robbins became interested in my book… How I’m going to release one of my favorite projects of all-time next year on Kickstarter…

I’m excited to share all of it with you. But so often, I’ve found myself holding back because I’d think, “Don’t brag about that, no one wants to hear it and you’ll just upset someone.” I’ve HABITUALLY THOUGHT that I ought to hold back.

You know how I got swagger?

I practiced gratitude and loving myself, every day. I earnestly made the effort — every single day — to love myself as much as I try to love others, to be grateful for what I have, and to really feel that gratitude while meditating. It almost sounds like a cliche now, because we’ve all heard this advice so many times. It took me a few months of daily practice before I really felt it, but it worked.

I don’t have it all of the time, but I know it’s there. I can feel it. Because I fill my THOUGHTS with gratitude, and the belief that I am living with intention, and how I have the power of the entire universe within. And after many years of telling myself that swagger was not acceptable, I am confident that I’m on the right track.