How To Build Your Self-Esteem & Stop Approval-Seeking For Good

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Insecurity makes singlehood feel like the plague. It foments anxiety and jealousy and feeds every other negative emotion that destroys a relationship. But even though it can seem unattainable, total security is just one friendship away.

That might be hard for you to believe, especially if you’ve been burdened with insecurity for years. I wouldn’t have believed it either…not if I hadn’t experienced it for myself.

My case of insecurity—AKA, insanity.

I was an insecure man. Except that my case was so bad, we can just call it what it really was: insanity.

I couldn’t meet a girl without obsessing over whether she thought I was handsome or charming enough. It didn’t matter if I had a girlfriend, or even a fiancée—I needed external confirmation of my attractiveness to make up for the inner security I lacked. And it made me do some crazy things.

Like cheat on a loyal partner.

And play the part of a homewrecker.

And obsess and obsess over relationships to the exclusion of everything else: progress in a career, most specifically. I ended up being fully dependent on my parents till the age of 25.

I had it bad. And with each relationship, it got worse—until it got so bad that I actually thought about checking in to a mental hospital after the last breakup. When the worst of it passed, I faced a choice: I could either latch on to another relationship and lose my mind (again), or I could figure out this business of being single, retain sanity, and possibly even grow as a person.

Though impossible-seeming, the latter option made me feel saner just thinking about it. So, I took my vow of relationship abstinence: one year. New me. Let’s go.

That was in 2014.

Now, saying you’re going to be single for a year and actually doing it are two separate things. Because making the decision to be whole doesn’t actually make you whole; it just gives you the chance to make better decisions. And to make better decisions, you have to overcome obstacles.

For me, that obstacle was Stephanie.

Gorgeous, 5-foot-11, athletic, hilarious, warmhearted, and lively, she was an all-around amazing human being. I could go on and on and still not describe the first tenth of how exceptional this woman was. Through a shared love of volleyball, we became close friends.

Steph and I hung out, ate dinner together, and did all the things that would normally have preceded a romantic escalation. But I was bound to my commitment. And even though I was tempted to take things further with Stephanie, I kept it friendly.

I still had the same insecure thoughts as always: Am I good enough? Does she actually like me? Am I’m handsome enough for her? But this time, things were different. I couldn’t just pounce on Steph to assuage my insecurity. I had to actually grow up. I did that by confronting my thoughts.

How I conquered insecurity through mindfulness.

Back in the dark ages (before I turned 23), I didn’t know that I could take control of my thoughts. But when I started my year of being single, I also dove deep into self-improvement. Mindfulness has been a huge part of that journey.

So, I had my morning and evening routines: affirmations, journaling, meditation. They helped me to change my thoughts. And without them, Stephanie would’ve been one more in a long line of heartbreaks. I would’ve sunk back into the same patterns of insecurity. Instead, here's what I did differently:

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1. I noticed my thoughts.

One day, after a beautiful hike together in the Jemez Mountains, I caught myself longing to kiss Stephanie. Then the longing turned into negativity: "She wouldn’t want me in a thousand years—I’m not good enough—" Blah blah fricking blah. Same old insecure story.

I felt miserable. Then I wanted to call her and confirm my value through a good conversation. THEN, I took some mindful breaths and realized what was going on. I was feeding the wolf of insecurity.

2. I changed the thoughts.

When I became aware that I was feeding the wrong wolf, I changed my thoughts. I fed myself the affirmations that I practiced morning and night—"I’m worthy, I’m beautiful, I’m good, I am independent, I am lovable." Reversing the negative thoughts seemed impossible at first, but they soon became my focus. Then the empty feeling in my stomach receded. Then I was OK. But more than being OK, I had confronted and beaten the enemy of insecurity, which had always bested me before. I was victorious.

But that was just one battle.

3. I prayed for Stephanie.

Especially after spending quality time with her, the wolf of insecurity would come howling at my door. And since there are only so many affirmations a man can do, I prayed for her.

I asked God to give her all the qualities I was striving for to become successfully single. I prayed for her future husband. I prayed for my future wife. And in the prayer, I shifted my focus from poor, unlovable me to being so secure in myself that I could actually pray for others. Not only did I instantly elevate myself, separating myself from the insecure vibes, but I learned how to think outside of myself—even and especially under duress.

As time went on, and as my friendship with Stephanie grew more intimate, the wolf would howl more and more loudly. But as I learned to rely on mindfulness and prayer—not Steph’s opinion of me—I got stronger and stronger. And eventually I slaughtered that wolf. It was a damn good thing I did, too.

Because I could see beyond her opinion of me, instead of being desperate for her approval, I got to know Stephanie a little better. And I started noticing lots of behaviors and beliefs that didn’t align with my new values. She ate unhealthy food and smoked. She drank excessively. She wasn’t fully committed to personal improvement. She didn’t believe in herself.

None of those things would’ve been a blip on my radar if I had bonded sexually with Stephanie. And, in that case, all of those things would’ve been justifications to withdraw my love from her after the honeymoon phase. That would’ve demeaned her and made me feel worse about myself. But that’s not the way it happened.

Not only did I not fall into the trap of conditional romance, but I came out with more security, more confidence, and more purpose than I had to begin with. And it’s all because I chose to remain friends with Stephanie—just to do it with integrity this time.

My friendship with Stephanie eventually petered out. She wasn’t into self-improvement, which was my whole reason for being. But I am so grateful for her because, through her beauty and her friendship, I challenged myself to become secure. And instead of feeling regret and jealousy and every other awful feeling I'd generally experience at the end of a bad relationship, I have nothing but appreciation for her. And pride for my actions.

Over the last couple of years, I’ve built on the security I created through my first platonic friendship with a woman. Now, I couldn't care less if a woman thinks I’m sexy. I have other things on my mind. I’m too busy living my life and creating value that inspires other people to become successfully single.

Want more insights on how to level up your life? Check out your August horoscope, then learn the three simple tips that'll totally transform your communication.

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