Entrepreneurs are eternal optimists, but we struggle too

Entrepreneurs are eternal optimists, but we struggle too

At a recent event for Phoenix tech leaders, fellow entrepreneur Adam Toren and I were catching up over beers. Adam waved to a friend across the room. Gabe walked over to join us.

“Hey Gabe. How’s it going?” Adam asked.

“Great!” Gabe said with a smile.

Not knowing about any recent events at his startup company, DUUL, I played with him a little. “So that means it sucked until today, right?” I asked. Gabe and I had talked on the phone last year, but we had never met.

Instead of the chuckle I expected, Gabe looked at me with a serious look of surprise.

“Yeah, it literally sucked until earlier this afternoon. How did you know?”

He explained a few of the brutal challenges he faced in recent months: pivoting to a different business model, laying off some of his team, difficulties raising money and a lawsuit by a disgruntled co-founder. It felt like nothing but big obstacles and impending doom, until just that afternoon.

“At 2:00 this afternoon, we closed a $30 thousand deal that is bringing cash into the company. It totally validates our new strategy. We’re back on track!” he shared.

In the last few months since then, Gabe’s company has grown revenue, added thousands of new customers and initiated partnership discussions. They are moving forward and have new successes.

But it almost didn’t happen. And it felt like “slow death” for a while, according to Gabe. Now it’s just normal ups and downs.

Truth is, almost every entrepreneur and CEO is experiencing both “Things are going great!” and “I’m dealing with some serious challenges that are really hard” at the same time.

I have had over 100 deep coaching conversations with CEOs in the last year. “If I call you and and I’m crying, you’ll know it’s me,” one CEO told me. No I won’t. I can’t think of any entrepreneur, startup founder, small business owner, or CEO with 500 employees who isn’t grappling with really hard issues. “All’s well” is the rare exception in business these days, even in big companies. We are all grappling with hard questions, struggles, crises, self-doubt, frustration and anxieties, but that’s not what people see, or what we share.

Everyone is still fantastic on Facebook, amazing on Instagram and “doing great!” when you meet them in person. All we see is the good stuff, so we don’t want to look like the only leader having problems. We aren’t sharing the hard stuff with many people, let alone in public.

Aren’t we supposed to look like we know what we’re doing while we are making it up?

I plead guilty. I say “I’m doing great!” when asked. I post only good news on Facebook. Yet I’ve got similar challenges. I’m working hard to create a new business, write a book, find a scalable business model and learn what works and doesn’t work in the new world. Every day I discover something I don’t know and wonder if I can do it all–because it’s hard, and as with most new ventures, is taking longer than I wanted. Like most people, I’m my own worst enemy and occasionally have to dig myself out of negative thoughts.

I still love it. I’m making progress and “doing great”–and wouldn’t trade it for anything. People are surprised when I share my challenges with them, especially young entrepreneurs. “Really, I thought you had it all figured out.” Um, not entirely, and the landscape is constantly evolving. But I’m consistently working on it and I’m not stopping.

Most people don’t want to hear your troubles, it seems. Your employees, customers, partners and family mostly want to hear the good stuff. And entrepreneurs are generally optimists with thick skins and a high tolerance for pain. We aren’t grumpy grousers. The stuff that keeps us up at night? Let’s not talk about that so much.

So when you meet another entrepreneur and “it’s going great!” for them but it isn’t going so great for you, just remind yourself that everyone who is running a business is dealing with hard stuff. It’s just not the first thing they talk about.

Even if you are doing great, remember that the landscape evolves and life happens. Enjoy the good times, but be prepared to deal with challenges that will surely come.

You’re not crazy and you’re not the only one.

Keep going.