Why I created a blog about doing hard things

“No man’s good by accident. Virtue has to be learnt.” —Seneca

Some of us dream of Elyssium. We point to the moon and see it in arm’s reach. We quit our comfortable jobs to embark on a new venture, or catch a Greyhound bus to Hollywood from somewhere in the obscurity of the Midwest to pursue our dreams of appearing on the silver screen, or wake up at dawn to train to compete at the highest levels. That’s the life we choose. We visualize, have purpose and execute.

These dreamers are the modern day Don Quixotes; jumping into the arena, scoffing at conventional wisdom, and taking the proverbial road less traveled. In every industry we find them and glorify their success, often times ad nauseam, but this of course is not the purpose of the blog. This is a blog about doing hard things.

When I started my company I had the fortune of befriending my own band of Don Quixotes. We were entrepreneurs starting our first software companies and we were all doing hard things.

Who were these folks? These were the best minds of their generation. They had all the right outward signals: Stanford Computer Science degrees, Y Combinator bound, former Google project managers. These Don Quixotes were the best at their respective crafts and Silicon Valley investors flocked to them with big checks in hand.

Outwardly these individuals were the paragons of success. They had accomplished so much of what folks on the sideline only could dream of. They built the product that users flocked to, got the venture capital check, and all the accolades that go along with that.

Inwardly, things couldn’t be more different. The same company that was just lauded in TechCrunch for being the next big thing was secretly struggling to not break apart at the seams. Founder feuds, seemingly insurmountable cash flow issues, dealing with legal threats from big companies, or simply working themselves to the bone to make something happen, each one faced it’s own seemingly existentialist threat.

For most of us first time founders, going to work seemed like going straight into a headwind. Some of us languished and some of us persevered. Depression and anxiety, isolation from the world and even self medication were all part of our respective stories.

How did we get here? These of course were the best and brightest; so much so that the biggest Silicon Valley firms had placed big bets on these twenty something prodigies.

It was clear that while we had enough courage to jump into the arena and were smart enough to master our respective crafts, we weren’t always mentally prepared to deal with gauntlet of challenges we faced.

There are tombs of articles on the subject of success. This is not an article on success. Challenge, failure, fear and perseverance are all elements in the path towards success, but for far too many we find ourselves crippled before we reach the ark of that path.

I am not interested in glorifying success, but instead share my story and contribute to a discourse on facing obstacles, fear, and failure. What I learned over the course of running my business was that doing hard things requires a mental resiliency and internal robustness that most of us are not naturally equipped with. We don’t get this training in the womb of our 9 to 5 jobs or in the halls of our universities.

The truth is we can only prepare ourselves for the obstacles that come with doing hard things by actually doing hard things. This is experiential learning not found in books. It’s knowledge only found in the arena.

I will avoid gushing cliche optimism because that of course is not realistic. The knowledge that we acquired while running our companies often came through some very painful experiences. It was neither gushy, nor fun. It was through relentless pragmatism and objectivity that we overcame our difficulties and it is with relentless pragmatism and objectivity that I write these series of articles.

The goal of these series of articles is simple: how do we build a mental framework that helps us see challenges as objectively as we can, flip failure on its head and persevere through the challenges that await us. It’s both the mean and the end.