Your Problem Might be the Key to your Success

Book: The Obstacle is the Way – Ryan Holiday
Concept: Problems can be turned into Opportunities

What if the big problem that you face today is actually the springboard to your greatest success?

In The Obstacle is the Way by Ryan Holiday, we learn that you can turn almost any problem into an advantage. But, only if you start thinking about your problem the right way. What you need is to reframe your problems and look for the opportunities inherent in them.

Reframe Your Obstacles

Why is it important to reframe problems? Couldn’t we just focus on solving our current problems? After all, once they are solved, it’s clear sailing, right?

But, this doesn’t work. We tell ourselves things like this but the truth is that problems and obstacles will never go away. All our problems will never be “solved”. No matter how far we progress, how much we accomplish, or how much money we make, we will find and face new problems.

A brief look at human history illustrates this very well. Our ancestors faced far worse problems than we do today and solved them. If you’re reading this, you will probably never worry about having food to eat or a bed to sleep in. Or, if you’re a parent in the developed world today, you can reasonably expect all your children to live to see 18 years old. However, in the year 1800, a staggering 43.3% of children would die before their 5th birthday.

But, even though humanity has solved so many serious problems, we still face plenty of problems and worry plenty about them. The reality of human existence is that problems are a part of it. Since problems aren’t going away, we need a framework for thinking about them. We must not shy away from them, sweep them under the rug, or live in denial.

We must, instead, look for ways to flip those problems into advantages. In fact, your current problem contains an advantage specifically for you.

The Advantage Built In to Your Biggest Problems

Intel CEO Andy Grove once stated that: “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”

Holiday says that this quote is equally true of individuals: “All great men and women used their greatest challenges as the fuel to achieve their success”, writes Holiday.

All those who were regarded as great individuals or great leaders faced tremendous challenges. Have you ever heard of a great general who led an army through a time of peace? Have you ever heard of a great politician who led a country during a period where nothing bad happened?

Any sailor can look good on a clear, calm day at sea. The great sailors are only separated from the terrible sailors on the stormy, terrifying days at sea.

At a minimum, this problem is an opportunity to show what kind of sailor you are. The worse the storm, the bigger the opportunity to better yourself and prove yourself. And, maybe, just maybe, this problem you face opens the door to new opportunities you never before considered.

Examples of Those Who Turned Weakness into Strength

Over 33% of all entrepreneurs are dyslexic, including billionaire Richard Branson. Dyslexia is almost twice as common in entrepreneurs as the general population.  Some estimates put the percentage of entrepreneurs with any learning disability as high as 50%. These entrepreneurs developed resilience and got used to overcoming difficulties early in life and it served them throughout their lives.

Actor Arnold Schwarzenegger was rejected repeatedly during auditions and told that he could never be an American movie actor due to his accent. The accent became the signature of Arnold and a key reason that he became one of the world’s most famous actors.

President Barack Obama turned both his own multi-racial background and the racial issues raised during his 2008 bid into a vision of hope, change, and a speech on race relations still considered to be one of the best in history. Arguably both Obama’s “disadvantages” ultimately made him more remarkable and fueled his meteoric rise to the White House.

President Donald Trump has been widely ridiculed and sometimes despised for the things he has said in his political career. This very criticism has only made him stronger with his base. Why? In large part, because Trump has leaned into the very things he has been criticized for rather than run away from them. He turned a disadvantage into the source of his strength with his constituency.

How to Start Turning Your Problem Around?

The simplest place to start turning your problem around is realizing that, just like the examples above, your problem may contain hidden advantages. What positives can you draw from your problem? Could a certain way of handling this problem maybe even make you better off than you were before?

I also highly recommend checking out The Obstacle is the Way on Amazon by clicking here.

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This post summarizes some concepts from The Obstacle is the Way by Ryan Holiday. Check out the full book, The Obstacle is the Way on Amazon by clicking here.


Trey Sharp is an entrepreneur & author in Huntsville, AL. Trey is the former owner/CEO of a Huntsville-based technology company, Sharp Communication, which was sold to Mobile Communications America in 2018. In 2016, Trey co-founded technology startup Tango Tango where he served as CEO for nearly 2 years. Trey still serves as an active board member and shareholder in the company. Trey also serves as an active Board Member for Urban Engine, an entrepreneurial nonprofit in Huntsville, AL dedicated to spurring the growth of startups in North Alabama. Trey is married to Claire Sharp and the couple has 4 children. Trey earned his Bachelor’s of Science in Business Administration from the University of Alabama-Huntsville in 2002.