Managing Your Own Psychology: The Hardest Part Of Entrepreneurism

It was a sweltering mid-August day. I was in a post office with no AC, and I was feeling the heat.

Clock: ticking. Bank account: almost empty. Cofounders: gone. Patience: zero. Post office line: long. Phone numbers on hand: blurred. Headset: broken and frayed, just like my willpower. Cold call: answering machine. Repeat.

I felt like ripping my hair out. "Is this what my dream is supposed to feel like?"

But, how'd we get here?

After graduating from college, I decided to transform the volunteer organization my friends and I started into a high-growth NGO with a staff and funding. My parents generously agreed to support me for the summer, but not much more. And, I had a month left before I'd have to move back onto their couch.

I was feeling more optimistic, but my repeated fundraising failures had the organization with less than a month of cash left in the bank. It wasn't for lack of effort; see, I'd never raised money before, and these meetings were with (very busy) people two to three times my age and millions of times my net worth, so I didn't quite know where to start.

Mentors and advisors offered advice that helped me avoid the biggest tactical pitfalls, but honestly, I was in over my head.

"Why not?" I'd hesitantly ask the 5 percent of philanthropists who'd take my meetings then politely refuse to donate. (Not everybody was as enthusiastic about our idea to bring financial education to schools as I was.)

Answers varied, and meetings rarely lasted more than a few minutes. "You're too young." "I've never seen a student organization turn into a real nonprofit before — are you sure it can be done?" "You don't have experience." "Who else has funded you?"

Some of these folks were right. I didn't have experience, a network, other reputable funders or an impressive board. My pitch deck looked terrible. I was usually nervous, with sweaty palms, a flushed face and stuttering speech. Not the profile of someone you'd entrust with a big donation.

I'd return from a day of several failed donor meetings, my emotions beaten to a pulp, then stand outside our donated office space and try to swallow my feelings before facing my team. Because, in addition to raising money, I had to inspire and guide my colleagues, who were preparing the organization for a new school year of programs.

I felt like an impostor, shameful for my business impotence.

I was 22 and a clueless mess. I would grind my teeth at night; the dentist said it was "bad, real bad." On the nights I'd stop working before 9 pm, I'd make aggressive attempts at emotional homeopathy by burning through books on stoicism and stumbling desperately into aikido classes.

But, sometimes, stoicism and aikido weren't enough. I'd overeat to the point of sickness, work out to the point of injury and retreat inward, closing off even to my most loved ones. And, some days, like this sweltering mid-August day at the post office, the day of that month's 30th rejection, I'd bottom out and lose control of my emotions… because, well, I'm human.

Back to the post office

"Sir, I'm not going to sell you stamps if you're on the phone."

The postal worker behind the counter was annoyed by my rudeness, my desperate unwillingness to stop making cold calls even when trying to purchase stamps. So, she exercised her right to refuse me service.

"What? Seriously? I've just stood in line for half an hour in this sweltering place and you won't sell me stamps?"

"Sir, please hang up or leave," she said.

"Please leave a message after the tone," I heard in my right ear bud.

I hung up, immediately sensed my blood boiling and felt like punching through the glass. But, I didn't. I held it in, counted to 10, walked out of the post office and just stood there, breathing in the sun.

Then, there was another urge, this time to chuck my damn phone into the brick building across the street and watch it explode into smithereens. But, I didn't. I held it in, began counting to 10, got to three, then collapsed on the stairs outside the post office and felt like crying. But, the tears wouldn't come out.

"Am I broken?" I wondered.

I felt despondent, lost. What's the point of all this? I can't change the world. Who am I kidding? I get up and start wandering. Without thinking, I pull out my phone and check email. I'm addicted to email.

In my inbox, I see a subject line with the word "Congratulations" from the sender "Blackstone Charitable Foundation." I open it to find that one of the world's largest financial companies decided to give us a major grant for us to make our first hire. Now, I know the organization will survive, even if my personal bank account doesn't.

I breathe a sigh of relief. Then another one. Then another one. Then the tears start falling. The process of founding my company has handed me many moments like this. Moments packed with meaning and loaded with emotional G-force.

Work worth doing — work you care about, work that matters — will always be difficult. That's what makes it worth doing.

After that day, I kept building. I keep building today and will for the rest of my life. I love how hard it is. I'd do it all over again in a heartbeat. But, I just wish I'd known more about why exactly it was so difficult.

What nobody talks about

Before I "took the leap" to be an entrepreneur, I asked many leaders who I admired what their biggest challenges had been. Most of them spoke of tactical challenges, like hiring the right people, or having the right market timing.

A few of them talked about balancing their work lives with their personal lives. A couple of them talked about learning to be more patient or self-aware.

But none of them — and none of the books I read in the business section of Barnes and Noble — addressed the biggest unspoken challenge of trying to change the world: managing your own psychology.

Ben Horowitz, the legendary entrepreneur and investor, wrote a game-changing blog post on "managing your own psychology." He wrote about how when he was CEO, he slept like a baby, "waking up every two hours crying."

Sounds like insanity. Or entrepreneurial leadership.

If I could go back in time, here's what I'd tell myself about managing my psychology

To succeed, you have to invest yourself so fully in what you're doing that you become it and it becomes you. You have to exist in a way that your work is your art, your words are the voice of your soul, and your enterprise is the manifestation of your spirit.

Despite all the books, speeches, inspirational memes, tweets and Facebook posts about success, nobody talks about what's difficult about work worth doing.

We talk about best practices, networking tactics, business strategies and "leadership." But, the biggest challenges aren't the tough clients, bad deals, underperforming employees or the bad market conditions.

They're deeper and far more personal. They're inside your head.

That's why the journey of leadership and especially entrepreneurial leadership is not about a skillset or a buzzword. It's about building an inner sanctuary that enables you to navigate uncertainty with high character.

It's not about "positive thinking." It's about accepting the harsh reality of your circumstances (because if life's not giving you obstacles, you're getting cheated), feeling what you feel and then roaring into your day with whatever optimism, enthusiasm and confidence your can find (and some days, you're lacking, and that's okay).

Speaking of feelings, it's not about getting over your feelings. It's about embracing your emotions, understanding where they come from, and then transforming them into what you want them to be.

It's about owning and channeling your emotions rather than letting your emotions own and channel you. (Working with an emotional coach changed my life; I highly recommend it.)

It's not about happiness or pleasure. It's about meaning. It's about knowing that the world will throw hardships your way, then enjoying the inner journey of working through them.

It's definitely not about certainty. It's not about knowing or declaring or crafting your "identity" or your "brand" in a vacuum.

It's about letting life's stormy elements sculpt your bulky wooden block down into a mortal masterpiece, with you as the sole judge. Because, well, don't count on finding certainty in others' opinions.

Blackstone validated our organization with that first check. The hundreds of rejections and failures faded into the backdrop of my mind, and for the first time that summer, I felt that what I was doing did have potential in the eyes of the philanthropists that would fuel the organization's launch.

After that check, we went to all the people who had said "no" to our donation requests and many of them turned to "yes." We were off to the races. We earned our first stamp of credibility.

But, that stamp quickly faded, and if we had have rested on our laurels, rather than continue to hustle humbly, we would have been back to square one.

It's not about comparing your path to others'. It's about walking confidently to the beat of your own drum, unconcerned with the apparent rewards of peers' pursuits. We so often compare our behind-the-scenes to everyone else's highlight reels.

Accept the silent magnificence of your struggle, and remember how lucky you are to be alive, experiencing life with such intensity.

Wake in the morning with the zeal to live a story worth telling, and rest well at night, comfortable with your choice to pursue meaning over certainty.