Bourbon. Neat. With a Side of Ice.

Bar Scene


“Bourbon. Neat. With a side of ice.”

A few months ago a client of mine ordered this as we pulled ourselves up to the bar. More importantly, the conversation that followed gave me perspective in how I think about my business – and how I think about life.

When I lost my “normal nine-to-five” job almost 4 years ago, I quickly became an entrepreneur. Less because I wanted to actually run my own business and more because I didn’t want to continue to do work I hated. Work that didn’t get me excited. Work that I couldn’t pour absolutely everything into. Work that didn’t feel like work.

Then things picked up. And they picked up fast. I made a lot of money and and I’m still doing well, but it wasn’t until I sat down, sipped bourbon, and had a conversation about the ebb and flow of being a business owner that I stopped being motivated by fear and started being motivated by confidence and passion. 

In this month’s issue of Inc Magazine, there’s an excellent article titled “The Psychological Price of Entrepreneurship”. The article clearly articulates this ebb and flow – this roller-coaster – I experience and we as entrepreneurs experience every single day. The analogy they use is one of a man riding a lion…

“People look at him and think, This guy’s really got it together! He’s brave!” says Thomas. “And the man riding the lion is thinking, How the hell did I get on a lion, and how do I keep from getting eaten?”

I read this over and over again and thought about Tess Vigeland’s talk at World Domination Summit that echoed this “wild ride” from surviving to thriving.

From Surviving to Thriving. The Entrepreneurial Roller-Coaster

One day you sign on a big client and feel like a badass – totally unstoppable and validated. Then a couple days go by and no one calls – no new clients come through the door, no one likes or retweets your blog post, and you immediately fall into the mindset of “Oh shit, who was I kidding? This was a joke and I clearly don’t have what it takes to run a business.”

From the outside looking in – this seems like a completely ridiculous line of thinking. I tell myself, “You’re making good money – working with amazing clients – and have built an amazing team of people who are working with me and believe in my vision and the vision of our company.”

But as insane as it may seem – the more you find success, the more that fear seems to find you. The more you start to tell yourself that it’s too good to be true.

For so long, I let this battle of success and fear overwhelm me. I let the success go to my head and let the fear of failure bring me down – way down. Then, a man much older and wiser shared his perspective on running a business for the past 20 years.

And somehow, it all came back to the bourbon with a side of ice.

Managing the Ebb and Flow

As we sat at the bar, I shared my plight of the entrepreneurial roller-coaster and was quickly met not with a “you’re crazy” response, but rather, a voice of agreement and understanding. Having run a publishing company for the past two decades, my drinking partner and client shared his insight into his own roller-coaster ride. He shared some of his greatest successes and most epic failures – which included losing huge clients and laying off over half of his team.

What I learned through our conversation was beautifully articulated metaphorically through the drink he ordered. Entrepreneurs don’t neglect the ebb and flow of the day to day – that’s impossible. Rather, they manage it – they tame it. They don’t let the ups go to their head and they don’t let the downs pivot them into a downward spiral of fear, doubt, and depression.

A neat bourbon may be way too strong and intense. Put bourbon on ice and it’ll get watered down and lose its flavor. But by ordering it neat with a side of ice, you can tame – manage – the cocktail as you see fit. Add a couple cubes of ice if you want – when you want. Suddenly you’re in control of upping the intensity or smoothing things out.

Entrepreneurs find themselves on the lion wondering how the hell to get off – all while pretending to know exactly what they’re doing.

Successful entrepreneurs master the art of riding the lion. The fear of being eaten is no longer the motivator to stay on. It’s the excitement – the challenge – of continuing to ride – that keeps them going.

The entrepreneurs and leaders you respect and admire aren’t without their highs and lows, they’re just incredibly effective at managing those highs and lows. The intense, exciting moments and the slower, weaker lulls – through it all, they, we, keep moving forward. We stay on the roller-coaster. We keep riding our lions.