Autumn, 2014: It should be impossible to feel like shit right now, and yet, somehow, I do…

On paper, my life is beyond perfect. My speaking tour sold out a month ago, and I’m getting standing ovations at most talks. I’m dating a model who has an advanced degree from one of the best universities in the world. My social life is filled with incredible friends and wild parties.

I have more external validation than any human could dream of.

Still, I feel inadequate. I feel like I don’t deserve any of the accolades or relationships. I fear that once people notice who I really am, everything will slip through my fingers. I’ll become a cautionary tale.

It’s like some omnipresent dread is following me around, whispering, “Jason, just wait, it’s all going to leave you the second they see who you really are. You’re a fake man. You don’t deserve this.”

***

Though many people find it hard to believe, I struggled with self-worth for most of my 20’s.

Though I was “successful,” I didn’t feel successful. I felt like a fraud. I felt like I was growing apart from the people I cared about who would leave me once they noticed how different I was from them. I worried that one day I’d wake up and find myself completely alone.

While intellectually I understood these concerns were nothing more than phantoms, they still possessed me.

I spent two years experimenting with (almost) every conceivable approach to developing self-worth and self-esteem.

Today, I’m no longer possessed by the phantoms that used to stalk me. When I go looking for them or when they rear their heads, I notice only an echo of their former presence. They no longer have the soul crushing grip they used to.

In this article, I’m going to explain how to develop a healthy sense of self-worth. In doing so, I’ll clear up a few common misconceptions while helping you avoid the traps that I fell into.

Before we begin…

I am not a psychologist. If you’ve been struggling with self-worth for a while, seek the assistance of a trained mental health professional, not a blogger.

Understanding self-worth (and dispelling a common misconception)

We tend to give ourselves what we feel we deserve. If you’re struggling with self-worth there’s a good chance that something deep inside of you has been tricked into believing that your needs, desires, and aspirations are unimportant especially when compared to everyone else’s.

Self-worth is not about your external situation. It’s common for someone to spend a fortune pampering herself, while still feeling like shit. On the flip side, plenty of people live quiet, minimal lives and feel amazing about it. Most of us have experience with both sides of this coin.

Self-worth is marked by feeling that the real you deserves to be loved and seen.

It’s about accepting and pursuing your true desires and knowing that even if you fail, you will be ok. It’s about leaning into the hard conversations and opening up to the people that matter. It’s about knowing that your needs matter. It’s about understanding when to be gentle with yourself and the world and when to be ruthless.

Your past, present, and future

I know that this is a controversial belief, but it seems simple to me: everything that happened in your past created the person you are in this moment.

Who you are right now will create the person you become in the future.

So, if you want to heal, begin by digging into your past so that you can improve your present. By improving your present, you will be able to improve your future.

Ignore the self-help gurus: real change comes from the inside out

It’s trendy in self-help to approach internal problems with formulaic external solutions.

Feeling unlovable? Repeat, “I love myself” over and over, and you’ll soon trick yourself into believing it!

Struggling with focus, anxiety, or discipline? Make sure your morning routine includes cold showers, meditation, 30 grams of protein, a microdose of LSD, lifting heavy at the gym, and Whim Hoff breathing. Then you’ll be optimized!

And I get it. This approach almost makes sense. It seems like you should be able to manipulate your external behavior in order to fix your internal problems.

Unfortunately, it doesn’t work. In fact, it’s a crock of shit. Real change happens from the inside out.

To merely change your external behaviors rather than confronting your inner demons is, at best, treating the symptoms instead of the causes. At worst, you’re putting whipped cream on dog shit and calling it an ice cream sundae.

To heal, you have to dig into your life story and shine a bright light on yourself.

The breadcrumb trail of recurring pain, tension, fear, and anxiety

In order to heal, you must lick your wounds. For some, this is easier said than done. Many of us have learned to adapt to our greatest pain instead of confronting and healing it. The trick is to look for recurring negative patterns in your life. That’s where your path begins.

Look for the little moments, obsessive thoughts, or unusually strong opinions that routinely make you feel inferior, afraid, or angry. Money, love, sex, appearance, status, food, intelligence, religion, fitness, and fame (or lack thereof) are all common culprits.

During a silent meditation retreat, I first noticed two problems that had been plaguing me for over a decade.

The first was a struggle to form healthy romantic relationships. I either dated women who I didn’t care about, or failed to open up to the women I had feelings for.

The second was intense anxiety around money. Regardless of my financial situation, I lived with constant fear that I was going to run out of money in the near future.

I spent years attempting to solve these problems with behavioral change. I worked on being more vulnerable with my girlfriends, and I told myself, “Once I have X amount of money in my bank account then I can relax.”

It didn’t work. The vulnerability felt forced and hollow and even when I hit my savings goals, I remained insecure.

I realized that if I wanted to heal, I needed to dive deeper.

Leaning into the pain

Disclaimer: this process will be more effective if done with the help of a mental health professional. They have access to tools and techniques that laypeople – including life coaches – have never even heard of, let alone been trained in.

Once you’ve identified the parts of your life that need healing, follow their threads into your past.

Though cliche, digging into your childhood and adolescence will likely be fruitful. As I was healing, I had to wrestle with things that happened 25 years ago.

The best thing to do is to start with the wounds you’ve noticed and become curious about them. Ask yourself, “Why do I feel that way?” again, again and again.

Let’s say you notice that you often feel lonely during the weekends, even though you have a few people you regularly hang out with.

When you ask yourself why, you realize that you don’t actually enjoy spending time with these people very much. When you explore why you’re spending time with people you don’t like, you find that you’re afraid to ask people you do like to hang out. When you’re curious about that fear, you notice that you’re scared of being rejected by people you admire.

Eventually, you realize that whenever you asked your older siblings to play with you as a child, they repeatedly ignored your requests and made you feel left out.



Though you’re older now, there is an indelible link in your head between seeking the companionship of people you admire and rejection. Today, this link manifests as a reluctance to put yourself out there and leads to complicated feelings about relationships with your peers. A few (but by no means exhaustive) examples of potential root causes of low self-worth:

Abuse, trauma, rejection, and neglect that led you to believe your needs are unimportant

Emotional distance or ineptitude from people close to you, especially caretakers and confidantes from both your past and current relationships

Bullying by classmates, “friends,” or siblings

Living in a culture that doesn’t accept you, i.e. being gay in a very homophobic city or faith

Being exceptional or otherwise overtly different than most people in your community

Childhood or teenage health problems, such as obesity and bad acne

I know that digging into your past can be unpleasant and potentially jarring; it’s also the best path forward. Stay strong. You’re a warrior. By examining your past, you’re raising your self-awareness. Once you’ve found the roots of whatever is sabotaging your self-esteem, you can begin to heal.

Healing

The healing process looks different for different people.

For some, simply raising your awareness or performing a ritual for yourself will be enough.

Others will require a significant amount of help and intervention along the way.

Most fall somewhere between the two extremes.

Regardless, once you’ve noticed your old patterns and understood their roots, it’s time to feel the pain you’ve been avoiding. Allow it to ripple through your body. If needed, let it break you. Accept yourself as you are, not as you wish you were. Take your time here, this stuff is intense.

After you’ve done this, heal your wounds with new feelings and behaviors. Set stronger boundaries that prioritize your needs. Build healthy relationships on your terms. Seek comfort when you’re disturbed. Let go of past grievances.

And again, move slowly. This stuff is new for you. Be gentle with yourself.

As your sense of self improves, you’ll start to engage with the world differently than when you were insecure.

You’ll stop hanging out with some of your toxic friends. You’ll uncover natural confidence and compassion within. You’ll experiment with vulnerability and intimacy in ways that you never have before. You’ll be more comfortable with uncertainty. You’ll begin tackling some of your bolder dreams. You’ll spend more time indulging yourself in guilty pleasures (but they won’t feel so guilty anymore).

You’ll realize something that’s been hidden in plain sight the entire time: you are entirely worthy of love, respect, connection, and joy.

Postscript: A note on false healing and false sickness

Before we go, I want to warn you about two traps that people tend to fall into on the path towards healing their sense of self.

The first is the false healers that litter the path towards health. There are many life coaches, psychologists, and drugs (or plant medicines) that can make you feel healed, without actually healing you.

The true litmus test: do the positive feelings last?

If, after intense work, your sense of self-worth is dependent upon the healer you worked with, there’s a good chance that this person (or drug) was a false healer.

Your best bet? Cut your losses and find new approach to healing.

The second is the denial of your own health. This is a trap I fell into. When I finally found a steady sense of self-worth, I was afraid that it would be ephemeral. I struggled to accept my own health because it felt unfamiliar and I worried it was all smoke and mirrors. It wasn’t.

Here’s the deal: if you’ve done hard, earnest work on yourself, and if you’ve recruited the help of qualified professionals as needed, you can feel comfortable trusting the results.

And if you need to heal, I hope you start as soon as you can. I hope you spend as much time feeling great, allowing yourself to be seen, and living as vividly and lovingly as possible. You deserve it.