The Long Drive — The True Story About Being a CEO

When I started my first company, I couldn’t wait to give out my business card. It had a glossy white finish. It had rounded corners. Most importantly, it had “Zack Parker, CEO” printed on the bottom right. I was anxious to update my Gmail signature with my new title and add my new job description to my LinkedIn profile. I was young, naive and armed with a Vistaprint box full of 1,000 business cards.

Fast forward a few years — I’m dealing with hiring/firing decisions, handling an audit from the IRS and hearing “no” from potential customers and investors over and over again. Those glossy white business cards no longer brought me the same fuzzy feelings that they once had.

Being a CEO can be one of the most rewarding positions in the world when things are going well. You’re on top of the world, surfing a tsunami of swagger. However, when things don’t go as planned, your uncertainty quickly morphs into anxiety. The job of a CEO is about managing self-doubt, internalizing pressure and driving for countless hours thinking about your company. Alone.

As I drive across the lower level of the Bay Bridge heading towards Southern California, I’m reciting my pitch to the various investors and potential customers I’m about to meet. As CEO, I’m perpetually in “pitch mode,” answering a barrage of questions about why our product needs to exist and who it’s for. I’m like a boxer defending himself against an array of punches. During these pitches, I mask the utter chaos inside of our startup in fear of being exposed as a rookie. If I let my guard down, then I’m unprotected and I’ll get knocked out.

I’m always selling. Always pitching. As I head east on I-580, I call my mom and tell her a pitch that makes her believe my company will make me stable and secure. I call my teammates and tell them a pitch about when the company “takes off,” we’ll all be on a beautiful island somewhere drinking rum out of coconuts. I merge onto I-5 South oozing with optimism and I run through my pitch to investors about how our company goes from a five-person team to a $100 million business. Each pitch is delivered with complete conviction. My guard is up.

In Southern California, I’m pitching from sunup to sundown. It’s like being on a job interview for days on end. Before each pitch, I remind myself that this could be the one. But sometimes I just want it all to stop. Cold turkey. I want to be real and tell everybody how terrible the last few weeks have been and how I’m doubting if there’s even a need for our product in the market. However, I never share this with anybody in fear that I might be venting to the wrong person (my next potential investor, customer, hire, etc.). So rather than admit this truth to anybody, I decide to internalize it and let the pressure build. The pressure gains momentum right in the dead center of my chest beneath my sternum. It has the type of momentum I want my company to have.

On my lonely 8-hour drive back home on the I-5, I think about why I’m coming back from Southern California empty handed. I fill up my gas tank at Arco and get In-N-Out Burger in Santa Clarita and look around at all of the happy people eating their Double-Doubles. I tell myself that their contentment from the cheeseburgers will be short-lived because they too are battling with their own internal struggles and doubts. I bet their guard is up about something. As I slurp my milkshake down, I think about how creative and driven I’ve been with my business development, but the doors just don’t seem to be opening. Back on the road, the smell of cow manure singes my nose hairs and I think about all of those empty promises and unsigned contracts. Every CEO knows these dark days. If you don’t hear about them, that’s because they too are in “pitch mode.”

I drive straight on the I-5 for hours and listen to podcasts about successful CEOs like Mark Zuckerberg, Sir Richard Branson and Elon Musk. They make it seem so easy. So glamorous. They’re like ducks on a pond that look calm on the surface, but underneath the water I’m sure they’re paddling like hell. They all share the story of their “breakthrough moment.” I pass the Altamont windmills on I-580 and I tell myself that my moment is coming. Days turn into weeks and weeks turn into months, until my confidence lays limp in the gutter. The same place those business cards will end up.

Will I be a CEO again? Of course. The entrepreneurial game runs in my blood. I’m addicted to it. That pressure that drives me insane is the same pressure that propels me forward. When I find the next idea and the right team, then there’s no denying that I’ll jump right back in. I can’t wait to tell my mom that “the band is gonna make it.” I can’t wait to tell my teammates that “success is right around the corner.” I’ll be chugging my own Kool-Aid. I’ll be in pitch mode nonstop until those dark days turn into dark months. After months of preparation, I’ll once again pull off of the I-5 and approach my next pitch and look down at those three little letters on my business card and smile. I’ll pass that glossy white card with the rounded corners into the hands of my potential customer. All of my fears and doubts will have succumbed. Then, I’ll put my guard up and remind myself, this could be the one.

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