We entrepreneurs are on a long strange trip, (fist bump Jerry Garcia), and while we love to dream, we’re also realists. We know that our chosen road has bumps and cracks, and potholes and sinkholes and that we must deal with them as they come along. Over time, we become pretty good at manoeuvring, sometimes through and sometimes around, sometimes as an ace pilot and sometimes with our eyes shut and hearts in our mouths, (gasp-fully) hoping that they are temporary, and that soon the road will be smooth again.

But what if smooth is an illusion? What if instead of being our stable and underlying reality, it is actually a siren lulling us into a state of artificial security, meanwhile causing us to veer dangerously off course into the deep ravines? What if the problems that we look at askance, and deny, and pray do not exist are actually the road we are supposed to be on? What if we are not supposed to be comfortable? What if problems are the only real signposts along this otherwise pitch black (would it kill them to turn on those damn street lights) journey of ours?

Smarter people have talked about this, of course. Ancient Stoics like Seneca and Epictetus explain that self knowledge is key and that being emotionally resilient to misfortune is virtuous. Nassim Nicholas Taleb, in his book, ‘Anti Fragile’, tells us about the advantages of being the opposite of fragile, and how systems that are shocked can actually get better. There is that outstanding TED talk by Luvvie Ajayi called, “Get comfortable with being uncomfortable”, and the rather wonderful book, “The Obstacle is the Way,” by Ryan Holiday. Successful entrepreneurs like Tim Ferris, also a proponent of Stoicism, credits a system called “Fear Setting”, that he does once a month, as a major reason for his major business and personal successes.

I decided to make this past June my ‘Month of living Uncomfortably’. I would actively look for problems to solve, and take action on situations that I had avoided, neglected, procrastinated and conveniently forgotten. You know, stuff like looking rationally and unemotionally at a spreadsheet that says one of my businesses is doing shite, or resolving issues (without resorting to violence) with an ex business partner who screwed me over, or asking a business favour from someone I don’t particularly care for, or laying off someone I’ve kept around far longer than sensible, (sorry! please don’t hate me!), or dealing with some government *insert favourite expletive* bureaucratic paperwork that has absolutely no relevance whatsover to anything or anyone in our solar system.

Stuff like that.

I decided to replace my first thought in the morning, “Yay! Breakfast Time!” with, “What one problem or uncomfortable situation can I take action on today?”

Why did I do this?

Allow me to explain:

What if you had a choice between doing burpees and lifting a nice, heavy, beautiful cold pint of Guinness? Well, they both involve muscle strength but the ale is refreshing and makes you feel so good. It has this wonderful black color and the foam rests elegantly on the top just so. Did you know that Guinness is actually good for you? It has all these essential vitamins and barley and it makes your world bright, happy and optimistic and you forget all your problems.

What was I saying?

Right, about June being my month of doing something that could be psychologically classified semi masochistic.

Anyway, I’m happy to report that I survived, kind of, and writing about this from the shelter of July, I’m able to safely reflect and tell you what I learned:

1. Attitude is Adjusted: Attitude matters. Like, a lot. Panic doesn’t help. Getting angry, crying, and calling for your mama doesn’t help. Being calm, reasonable, logical, and that serenity prayer thing where understanding what’s in your control and what isn’t, is the only way to go. And patience of course. Patience with the situation and especially with yourself
2. Action Leads to Inspiration: I never quite felt like taking action, especially the first few days, because once I started looking for problems, they began to appear everywhere. They even got together and began making babies. Were they always there? Or was this some strange cognitive perception thing? Anyway, since I had made this my theme and all, I managed to override my default procrastinator mode and decided to take action. And once I started and successfully resolved one thing, I immediately wanted to move to the next issue. My confidence improved, my energy increased and my anxiety reduced. So inspiration did not lead to action, rather, inspiration was just a by-product of taking action. Go figure.
3. Skills and Knowledge Get Updated: I quickly found out that I lacked a lot of the skills necessary to solve the problems I encountered. I had also neglected to keep up with the knowledge I thought I had. Things had changed so damn fast since I was younger and I had become lazy and comfortably dumb. But strangely, this made me pretty excited because it meant that the problems weren’t actually insurmountable. I just had to download a patch or a new program into my brain, and much of this is easily and cheaply available. As for the more involved, specialised stuff that I didn’t really want to get into, I could outsource them to an expert. I was able to focus on the solution rather than obsess about the problem.
4. Multitasking is Dumb : I’m a man of limited attention at the best of times, and using what little I have to do five things at once — which is impossible anyway because we’re really just doing them one by one but with less effectiveness — would often quickly deplete my well of focus. But by prioritising and taking on issues small and large as individual projects, my mind was forced to hyper focus and lo and behold, I actually got shit done. You can always be more productive, you can always try harder. Always. And what was surprising to me was how much potential expansion space there actually is out there. So much time is wasted during the day, so much focus on things that are inconsequential and irrelevant, and we willingly let our mind which is our primary accomplishment tool, get hijacked by BS.
5. It’s Ok to Fail : Focusing on tough situations, trying to solve difficult problems, getting comfortable with the uncomfortable, all this means that I am going to fail a lot. But If I’m in it for the long haul, then failure is simply more data that can be used to increase my chances of achieving my objectives. Yes it isn’t very pleasant. Feels like crap really, but then again isn’t this a normal part of business? Isn’t slipping and sliding and then gripping again something that we entrepreneurs do? Failure is just another uncomfortable feeling to get comfortable with.

So that was it.

You can lift up that beautiful Guinness now.

I know it maybe doesn’t sound like much for a lot of the entrepreneurs out there. After all, there are many among us who thrive on challenges and obstacles.

But there are also a lot of us who don’t particularly love problems, and want them to just go away so that things can go back to being smooth agan.

The thing is though, the moment we decided to start our own businesses and to orient ourselves towards our goals, that very moment also gave birth to our own personalized and ever changing landscape, a terrain that tests us and demands that we grow in ways we never imagined.

I definitely didn’t go sky diving, do a TED talk or champion world free trade. But in my own little way, using a small flash light, I tripped and stumbled against what I thought were externally created impediments and instead, I found myself lighting up neglected caverns of my mind, discovering new pathways leading to panoramic vistas and fresh view points of existence.

Perhaps hidden deep within us, underneath our ambition to fundraise and desire for exit strategies, behind our dreams of creation and disruption, this is our real reason for becoming entrepreneurs.