I read a quote many years ago that stuck with me to this day. Maybe when I’m not waist deep in this I’ll be able to tell you if there’s any truth to it or not. It could just be one of those things that seasoned entrepreneurs tell bright-eyed entrepreneurs to make them feel better about the current shitstorm de jour. The more time that goes by though, the more certain I am that it’s solid advice.
“A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have” — Tim Ferriss
It’s so damn easy to put off the really difficult conversations until the always distant “tomorrow.” There are so many “important” things we need to do every day: fires to be put out, code to be written, sales to be closed, anything and everything to postpone the uncomfortable.
I am absolutely guilty of this. I put off very difficult conversations for so long that a company blew up in the process. I like to think that the more experienced me would have been able to navigate those disastrous seas, but I still find myself skirting around the uncomfortable from time to time. I now recognize this dance almost immediately and do whatever I can to address it.
A key point here is that often times there is no immediate answer. This is a really difficult conversation for a reason. If there was an easy answer, it would have been done and we would all move on. It’s critical to address it head-on, with or without a solution, and begin the dialogue.
Praising the awkwardness
Lately, I feel like every single week brings a new shitstorm. Is that progress? It certainly doesn’t feel like it, but maybe.
I don’t ever want to postpone the uncomfortable conversations that come with these shitstorms, and I feel that significant progress is being made in that regard. Progress is progress, and I’ll take it.
My business partner and I are having an on-going series of difficult conversations about what comes next. We’re building out these internal projects and crushing client work, but the immediate path forward isn’t so clear. We’ve been setting aside time to have these intense conversations, and I feel like it’s bringing us closer together with a deeper understanding of each other. I’m not sure how this will impact what’s to come, but I’m thankful that we are having these conversations.
I make sure to take a moment to recognize both of us for embracing the uncomfortable. It’s important to take a deep breath and recognize that we are better off having had the conversation regardless of the outcome.
There’s a completely separate dialogue with me, my partner and an entrepreneur where we’re attempting to squash an upcoming shitstorm while it is still in tropical storm status. In some regards three people is easier than two, and other times it’s exponentially more difficult. Regardless, whenever we call out the bullshit and move through the uncomfortableness, I always make sure to recognize us for it.
The recognition of our journey through uncomfortableville doesn’t make the conversation any easier or allow us to manifest a perfect solution, but it does make it ever so slightly less painful the next time we need to have one of these conversations. Good job. That sucked. You didn’t die. Progress.
Thriving in the Uncomfortable
If in fact the stoic Timothy Ferriss is correct, then I want to swim in the uncomfortable. If that’s what it takes to truly be successful, bring it. And besides, if things were always easy and comfortable, I’d probably get bored very quickly.
It’s not enough to recognize the shitstorm, talk about it and praise the talk. That’s entrepreneurship 101. That’s the bare minimum for survival.
I want to thrive in these situations. It’s the definition of antifragility. I want to be at my best when these situations are at their worst. I want to be able to lead from a place of clarity and calmness when the world is falling apart around me.
I’m definitely not there yet, but based on the number of extremely uncomfortable conversations that have been taking place recently, I would say I’m definitely on my way.