What scares me most.

People look at me and think "this guy has it all figured out."

30 years old. Sold his company. Built an audience. He's living the dream.

Yes, I'm incredibly grateful for all that I have. And I do believe deeply in my abilities. But I DO NOT have it figured out. And there's a whole list of things that scare the shit out of me.

I'm about to share my deepest fears with you. Many of these I've never opened up about.

But I just hope they make you feel seen & less alone as well all navigate this crazy thing called life.

What scares me the most? And what am I doing about it?

1. Doing things because I care what others think.

This one freaks me out because I know it lives within me. 14-year-old Alex is starving for acceptance. He wants to be loved. He wants to belong. He wants to know he’s “enough.” And guess what. Building businesses & creating content on social media offers him the hit of validation he’s wanted forever. Which is why I worry deeply about doing things for the wrong reasons.

How do I know I’m launching a new business because I love solving problems & building cool shit. Versus creating out of fear of losing relevancy as Morning Brew becomes less and less of my identity?

How do I know that I’m shooting 60 Second Startup (aka Shark Tank for the Internet) to give founders a platform to grow & give myself an outlet to be creative & scrappy. Versus posting on social to cash in on the dopamine hit of engagement & feel valued within a community of tech folks I’ve deemed “important.”

So, what am I doing about it?

Spending more time on things that offer me no external value. No monetary gain. No social currency. No feelings of acceptance. Things I only stick with because they fill me with childlike wonder & play. Building Lego typewriters. Learning “Oh When the Saints” on keyboard. Reading books that offer me zero professional utility.

2. Not being fully present to the people & experiences that matter most.

I’m addicted to my devices. It’s that simple. The line between productive & pointless is razor thin. And I’ve proven I don’t have the discipline to navigate this careful dance gracefully.

At my best, I use these tools like a magic wand to express myself creatively & build relationships with kind, brilliant people, which wouldn’t have been possible otherwise, At my worst, I use these vices as an adult binkie to self-sooth in the face of boredom, mental discomfort, and fear.

Of course, I am concerned about the impact that my devices have on my professional life. But of greater concern, is the impact on my personal life. I don’t want to be the guy who whips out his phone while he’s enjoying the simple, but beautiful moments with his wife. I don’t want to be the guy who gets lost in a doom scroll as his child makes a key developmental leap for the first & last time.

So, what am I doing about it?

Not trusting that I’ll be disciplined. Just as I don’t buy cookies, so I’m not tempted to eat the entire box in one sitting, I’ve started to approach technology in the same way. If I want to go on a walk with my wife & be fully present, I leave my phone at home. If I want to be focused during a meeting, I use my Mindsight lockbox & enable Freedom on my computer. I take away the urge to slip.

3. Not feeling fully & feeling deeply.

I want my life to be colored by the full rainbow of emotions. Belly laughs so deep that I lose all bodily function. Ugly cries only made possible by fully surrendering & authentically connecting. But I worry I’ll never get there. The last time I cried was when my dad passed away in 2013. I haven’t cried since & I fear I’ll never cry again. And while I used to judge myself for not being able to shed tears, my insecurity has changed as I’ve become more accepting of how I emote. Today, I don’t fear not crying for the sake of crying. I fear not crying because I fear that I’m not giving myself the permission to feel fully & deeply.

So, what am I doing about it?

Working to increase acceptance & awareness. This story that crying = feeling sadness deeply is exactly that…a story. I do believe I feel deeply, it just doesn’t show up in the same way that it may for others. For me, a lump in my throat or chills down my arms is the telltale sign.

But also, I know that there’s an opportunity to tap further into my feels & I believe that happens through awareness. The typical emotion lasts for 90 seconds, which means being present to & sitting in those feelings as soon as I notice them, rather than pushing them deep into my belly is the best way to create awareness that they exist.

4. Cancer.

I have multiple anxious cancer thoughts per week. 50% of men are diagnosed. Odds are I’ll have cancer in my lifetime. You can stack the deck in your favor through diet, exercise, and other lifestyle choices. But there is a staggering amount that is out of your control. I don’t like the feeling of not being able to control my fate & not having certainty around my health.

So, what am I doing about it?

One-part lifestyle. One-part knowledge. One-part surrender. It reminds me of the famous Serenity Prayer: “God, grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference.”

I have the courage to live a lifestyle that stacks the deck in my favor. Eating clean. Exercising daily. No smoking. Limited drinking. The obvious stuff. I have the courage to be an advocate for my health, most recently completing a full-body cancer detection MRI thanks to Ezra. But I also know so much is out of my control. And the best way to surrender is to shift fears about the future into energy dedicated to being present to & grateful for all that I have in this moment.

5. Dying early.

My dad passed at 46. My dad’s dad had a heart attack at 40. I worry deeply about following in their footsteps. And the irony of this fear isn’t lost on me. Should I die early, I’ll have no idea that I’ve passed. It’s simply the idea of missing out on the richness of life that I find so provoking. I feel deeply grateful for all that I have. My family. My close friends. My freedom to spend time as I choose. My health. I know I’ll lose all of this at some point. But I sure as hell hope it’s not soon.

So, what am I doing about it? See previous strategy above.

6. Squandering my potential.

I deeply fear that I am my greatest weakness. I know I have the ability to accomplish anything I dream up. Building a world-class business. Being a world-class family man. Contributing to a cause I believe deeply in supporting. But I worry the same creative, fast-firing, excitable brain that gives me the power to do great things, is the very thing that will keep me from reaching my ceiling. I’m highly distractible. I’m a killer procrastinator. The simple act of “doing the things I say I want to do” proves to be far from simple for me. Why can’t I just get out of my own way?

But then I just think to myself, “Alex stop taking yourself so fucking seriously.”

So, what am I doing about it?

First, following my energy. When I am energized, I am way more like a heat-seeking missile. Not to say I don’t procrastinate. None of us are perfect. But I find my temptation to disengage largely disappears.

Second, I give myself grace. Sure, I believe I can become more focused & more disciplined. Everyday I try to get 1% better at it. But, I also know I’m wired in a very particular way. What makes me a strong storyteller & inventor, is the same thing that makes me a little dodo bird-y. It’s another side of the same coin. My upside down.

And third, I curate the right environment to meet my potential. See my thoughts on removing temptation, above.

That’s what scares me.

So what scares you?