Several months ago, I was going through a very busy time in my work. I was embroiled in a series of really packed weeks, and I started fantasizing about this magical land where everything would be peaceful and I could escape all the stresses of entrepreneurship.
For some reason, these fantasies coalesced into an intense desire to go to the Poconos. I really latched onto the idea; my brain was convinced it would be the solution to the hectic past few weeks.
Even though fantasies of the Poconos were taking over my daily life, I wouldn't have pulled the trigger if it hadn't been for my friend Chris Castiglione, co-founder of the coding education site One Month and Adjunct Professor at Columbia Business School.
After listening to me daydream about the Poconos for weeks on end, Chris stepped in on my behalf. He booked the trip.
As it turned out, the Poconos were not the magical solution I'd thought they would be. Contrary to what we'd read, Strasburg, PA did not present as the new Brooklyn. We stayed in a really weird hotel room. One night I ended up sleeping outside in a hammock, and then it rained.
Still, it was a great experience because Chris had seen how desperate I was for some time away from the entrepreneurial grind, and he'd made sure that I got it. Ultimately, we had a good time and made some good memories. I returned to NYC feeling ready to get back to work, which is exactly what I'd needed.
That's the kind of friend Chris is, and it's why he's played such a big role in my entrepreneurial success over the years with BarBend. Not only is he there for me as a fellow entrepreneur when I need professional advice, but he also helps me step away from it all. Paradoxically, the time we spend disengaged from entrepreneurship has turned out to be a major contributor to my business success.
"Yes, And": How Goofing Off Together Makes Me a Better Entrepreneur
Chris and I met four or five years ago through a mutual entrepreneur friend. We were both helping out with her company, and we hit it off at a work party. We became fast friends, and we've watched each other grow in tremendous ways over the past few years.
Our companies have both grown on similar time frames, so we've been able to navigate everything that entails together--from raising money, to hiring people, attracting customers, creating a great workplace culture, and sorting out exactly what we're responsible for as CEOs. (Hint: everything.)
Throughout it all, Chris has been a person I can turn to for advice and reflection. In his work at One Month, I've seen how great Chris is at optimizing how he runs his business. There are so many little things I can ask him about, knowing that he's already done it or knows somebody who's done it. As an entrepreneur, there's no one to tell you what to do. So when you talk to someone who's done it already, it's invaluable.
When I need to talk through something, Chris is there. This is true not just when it comes to business, but in many aspects of life. A large part of what makes Chris such a powerful force in my career is that he helps me get away from it sometimes--whether that means taking a spontaneous trip to the Poconos, shooting our own web series, playing ukulele covers of popular songs, or otherwise distracting me from entrepreneurial life. Having that person who can be there when you're dialed in to work and when you're dialed out is really valuable.
Our shared background in improv might help explain why the time we spend goofing off ends up enabling our entrepreneurship. A staple of improv is a "yes, and" mentality, in which you adopt a default attitude of rolling with whatever comes up rather than immediately shutting down zany ideas or perspectives.
As Chris puts it, "[Our friendship] is like having someone who you can have fun with and is always open to your ideas. It gives you a sense of trust and allows you to be vulnerable. I think that just happens to extend to business."
For example, we used to do something called "The Bet" to motivate ourselves. We'd bet each other in quarters that we could do certain things and set up major penalties if either of us failed to follow through. One of our bets was that Chris would get into Sundance (he's not a filmmaker), and that I would write a comedy musical. Both of us failed. As our penalty, we had to go to SOHO and do an over-the-top model shoot. So that happened.
It might sound like pure silliness, but this "yes, and" mentality is a major motivational tool. As Chris puts it, "We have these audacious goals sometimes, and it helps to have somebody willing to put a lot on the line. Sprinting beside somebody else is really useful, especially when you're an entrepreneur."