In his remarkable book about turning obstacles into opportunities, respected author and speaker Ryan Holiday uses examples from the Stoics (aka, third-century philosophers) who saw an obstacle as something to overcome. In fact, they realized it was actually a signpost: the impediment could, after being moved, initiate and promote success.
The Stoics persevered and changed their tactics, Holiday says, sometimes to win a war or subdue an enemy. Modern innovators can learn a similar lesson. An obstacle could be a personal crisis in life, a lawsuit, or even a total failure at a start-up–but it could also help you find direction. By pivoting when you meet an obstacle instead of just crumpling by the side of the road, a few erstwhile leaders have found success. And so can you! Here are a few obstacles you might face and how real companies turned the roadblock into an opportunity.
1. People are not using your app the way you intended
It’s tough when you make a new mobile app and find out no one is using it. Did you know theInstagram app started as a location-sharing social network called Burbn? Holiday told me about how the company founders were disappointed when they found out how users only liked the photo aspects. It was a pretty big hurdle, especially given all the work they had already done. The founders had an all-hands meeting and announced a major pivot. “They had the humility to retool the entire premise of their app,” he says. “Burbn wasn’t going to light the world on fire so they pivoted instead.”
2. Your product does not fit a market sgement
It’s a curious thing about start-ups. The ones that blow us away the most often start out lagging in the mire of market confusion. We don’t know what to do with apps like Snapchator Tumblr. Holiday told me Airbnb is a good example of how finding a market is such a major obstacle…and such a major motivator. Inventing something no one understands, uses, or can even categorize might be a good thing. Still, Airbnb had to keep iterating until they found an untapped market and capitalized on it. They had to persist. “AirBnB could have settled on their first idea, which was basically letting people crash on your couch and feeding them breakfast, but that wouldn’t have been much of a business,” he says.
3. You are not sure how to lead
Holiday mentioned an interesting catchphrase in his book. Soldiers in WWII used to refer to a famous German field general and say “Where Rommel is, there is the front.” Founders of companies might not always feel that way, but maybe they should (minus the world domination part and the insane blitzkrieg tactics).
“All great leaders like Jeff Bezos lead from the front,” says Holiday. “You have to know your product better than anyone else and have the confidence of your employees to support your vision. But you can create an obstacle in your business when you start to believe that you have to do everything, all of the time. You have to trust the people you’ve hired and let them do their jobs. Being that overbearing type of leader is also a mistake strategically, because as a company you’ll become too rigid and unable to innovate.”
4. You have reached the end of your own ability
I have struggled with this obstacle my whole life–it’s a pretty big one! In my writing and in my business management, there are certain functions–let’s say taxes, accounting, or anything having to do with numbers–that are constantly blocking my progress. Holiday says that’s when it would be best to develop and focus my energy even more.
“Thomas Jefferson was quiet and reserved, and purportedly had a speech impediment,” says Holiday. “He wanted to be a politician, but he was a terrible public speaker, which was basically a requirement back then. But instead of complaining about his fate he started channeling all his energy into his writing. And he ended up writing the Declaration of Independence in a single draft.”
5. Fate blocks your success
I’ve interviewed hundreds if not thousands of founders in my career. The one obstacle that comes up again and again is fate (and providence). Maybe it’s because so many entrepreneurs are micro-managers at heart (a nice way of saying they are controllers). Theydon’t like to accept no and tend to persevere through any trial, but sometimes fate deals a different hand. Is that when you should stop? Holiday says no–it is better to accept the randomness of life and keep going even when the obstacle seems insurmountable.
“The Stoics had a great name for this attitude. They called it the art of acquiescence,” he says. “The ancients used the word ‘fate’ a lot more than we are comfortable with today. This idea, this ‘amor fati–a love of fate’ was critical to their success in a much more capricious world that they lived in. Today, because of advances in technology, we think that the world submits to our every demand and that just isn’t the case.”
6. The obstacle seems like an advantage
One of my own take-aways from the book is that an obstacle is just that: it is an impediment that’s blocking the road to success. Too many companies try to explain away an obstacle or even turn it into an advantage when it’s really just dressing up a pig. Facebook did this early on when users complained about how the social net uses personal information–they explained the obstacle away and said it was for our own good.
“Facebook in my opinion has bad leadership,” says Holiday. “It’s egotistical and it is often evil. Certainly Mark Zuckerberg is bold but he is also often conscienceless. Eventually, your customers or fans are going to find out about whatever you’re trying to hide and its going to hurt your brand. You see this a lot in PR crises where instead of taking the hit, being honest, and maybe turning it into something positive, they do a fake apology.”
How about you? What’s your obstacle right now?