How Entrepreneurs Can Turn Obstacles into Opportunities

October 3, 2023 Book Reviews, Personal Branding 1 comment

Hit a roadblock in growing your small business lately? You are not alone.

Virtually all entrepreneurs and small business owners have encountered trials and tribulations in our start-up journeys.

From huge and seemingly insurmountable challenges, to daily slip-ups and failures, obstacles are a regular feature of life as an entrepreneur.

The question, however, is this:

How can start-up and Small Medium Enterprise (SME) founders like you turn your obstacles into opportunities?

In this article, I will summarize key lessons from the book The Obstacle Is The Way—The Timeless Art of Turning Trials into Triumph by bestselling author Ryan Holiday.

Inspired by the Stoics like Roman emperor Marcus Aurelius, and Greek philosophers Epictetus and Seneca, the book outlines useful ways for us to think about, act upon, and endure the obstacles come along our way.

Ready to tap on the wisdom of the ancients?

#1 Perception — How To Think About Obstacles

The first part of the book covered the right ways to think about obstacles that hit our path to success.

Here we learn how John D. Rockefeller maintained “unflappable coolness under pressure” to seize economic opportunities during the Panic of 1857. Aged 25 then, he got investors to invest approximately US$500,000 in the right oil wells, but later returned the money as the opportunity didn’t feel right then.

Rockefeller’s ability to stay rational and disciplined allowed him to seize advantage from the obstacles in his life. It eventually allowed him to control 90 percent of the oil market 20 years after that first crisis.

To see the opportunity within the obstacle, consider taking these steps.

a) Stay Above the Fray

Keep yourself above the obstace. Recognise that you have the power to turn an unjust or negative situation into a positive.

“Choose not to be harmed—and you won’t feel harmed. Don’t feel harmed—and you haven’t been.” — Marcus Aurelius

b) Control Your Nerves

Stay calm, even-handed and cool in all situations. Shake off the bad stuff as it happens, and continue as though nothing happened.

c) Manage Your Emotions

Defeat emotions with logic. Ask yourself questions to get to the root causes. Apply your resourcefulness to solving that crisis, rather than go ballistic.

After all, what’s the worst than can possibly happen to your business?

d) Be Objective

Be an observer and not a perceiver. See events for what they are—free of distractions, exaggerations and misperceptions.

Give yourself clarity, not sympathy.

e) Change Your Perspective

When George Clooney changed his perspective from thinking that producers and directors don’t like him to the fact that “they need to find somebody, and they’re all hoping that the next person to walk in the room is the right somebody,” he made himself the solution to their problem. He then projected himself as the “man for the job” rather than showcase his acting skills.

Like Clooney, you too can interpret things correctly with the right context and framing.

f) Is It Up To You?

Follow the adage of the Serenity Prayer:

God, grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference.

The things that we can change are our emotions, our judgements, our creativity, our attitude, our perspective, our desires, our decisions, and our determination. Everything else is fair game.

g) Be in the Present

Focus your energies and attention on each idea, each job, each task, and each obstacle right at the present moment. Catch your mind when it wanders, and live in the moment.

f) Think Like Steve Jobs

Heard of Steve Jobs’ famed “reality distortion field?” Part motivation and part sheer drive and ambition, it is the notion that almost everything can be malleable with the right vision and work ethic.

g) Find the Nugget in the Dirt

Whatever doesn’t kill you will make you stronger. See how you can flip an obstacle in your business into a positive—use your constraints to outmaneuver your enemies and make you stronger.

#2 Action — What We Do During Difficulties

Taking the right action can turn an adversarial situation into an advantageous one.

Learn from Demosthenes, who was born sickly and frail with a debilitating speech impediment. Cheated of his inheritance by guardians, he made it his life mission to get it back.

Rather than bemoan his fate, he devised exercises to improve his voice—including filling his mouth with pebbles while speaking, and running up steep inclines while rehearing full speeches! The end result was that he became “the voice of Athens” and one of the greatest orator of his age.

a) Get Going with Energy

Throw yourself into your enterprise with your full ardour. Get the momentum, and stay there—right at the battle front. Pursue it with bravery and courage.

b) Be Persistent

Persistence lies in chipping away at all the different possibilities, finding out what doesn’t work—and what does—and slowly chiseling away at the problem until it is gone.

It is how Thomas Edison invented the light bulb—by testing with six thousand different filaments. And how Ulysses S. Grant eventually won the critical battle for Vicksburg in Mississippi—by leaving behind his supplies, living off the land, and taking town after town along the way.

c) Iterate Repeatedly

Failure is a feature. Use each obstacle, each mistake, each complaint, and each slippage to improve your business.

Failure shows us the way by showing us what isn’t the way.

d) Follow the Process

Take it a step at a time. Follow through. Excel at each task in your business as they come along.

This means taking it a milestone at a time. Even mammoth tasks can be dealt with this way—a bite at a time.

e) Do Your Job Well

Pursue every endeavour with the same fervour and energy: hard work, honesty, and helping others as best as you can.

While the goal is important, it is vital that every part—especially the work that nobody sees—is done right and done well, with pride and dedication.

f) Pursue Pragmatism

“I don’t care if the cat is black or white, so long as it catches mice.” — Deng Xiaoping

Whatever works and whatever gets the job done. That should be your mantra. Think progress, not perfection.

g) Consider Flank Attacks

Sometimes, using a bypass route may work better than tackling a competitor head-on. Embrace this for your enterprise, and approach what Holiday called “the line of least expectation.”

h) Turn Obstacles on Themselves

Use an obstacle against itself, like Martin Luther King Jr who met “physical force with soul force” when he marshalled his followers to use the power of peace against evil.

Sometimes, nonaction may be better than action. Or you can use the leverage from your obstacle against itself.

In short, judo rather than fencing.

i) Mentally Tight but Physically Loose

When encountering business setbacks, avoid reacting emotionally to them. Instead, rename it and claim it.

Deploy and channel the energies in your emotions towards your actions, so that you can be more fluid, more powerful, and more elegant.

j) Turn Offenses into “Teachable Moments”

If your business hits a nail on the road to success, use the disruption to navigate a new path. Turn that negative situation into a positive by asking yourself what opportunities does this problem present to you.

k) Be Prepared that You’ll Fail Anyway

Yes, you may eventually still hit an unscalable wall in your entrepreneurial journey. You can try everything, and still not overcome the obstacle.

This isn’t necessarily a bad thing. Just do your best, not the impossible.

#3 Will — Your Internal Power To Endure

Abraham Lincoln may be the most popular US President due to his work on the Emancipation Proclamation (releasing American slaves from their bondage). However, few knew that he has suffered and struggled through much of his life—losing his mother as a child, experiencing multiple defeats at the ballot boxes, and having bouts of depression.

Rather than give up and let go, Lincoln adopted the saying “This too shall pass” and built a strong inner fortress that girded him.

Like Lincoln, you too can adopt the Stoic maxim sustine et abstine which is to “bear and forbear.” Acknowledge the pain but plod on forward in your task.

a) Exercise to Strengthen Your Fortitude

So what if you’re handed an unfair set of cards in life? So what if you have less money to start up your business?

Remake yourself to overcome these drawbacks. Craft your spiritual strengthen through physical exercise, and your physical hardiness through mental practice.

And yes, learn the principles of deliberate practice to strengthen your craft.

b) Anticipate and Prepare for Disasters

Nobody wants to predict negative things, but preparing for a potential slip-up (aka a premortem) may actually give your business an advantage. Hope for the best but prepare for the worst.

Use this approach…

  • What if ______? Then we will ________
  • What if ______? Instead, we will just ________
  • What if ______? No problem, we can always _______

Better to be a pragmatic pessimist than an obtuse optimist.

c) Accept What Cannot Be Changed

Sometimes, the best way to deal with a problem in your business isn’t to go headlong against it but to accept it.

However, this doesn’t mean giving up. Rather, it means that you should change the way that you’ll get to your destination and the duration of your trip.

When the cause of the problem lies outside of our abilities to overcome them, it may be better to just move on.

d) Embrace Whatever Comes Your Way

When the sh*t hits the fence—as they inevitably do in any entrepreneurial venture—find a way to see the shine in it!

When Thomas Edison was 67, he returned home after dinner only to learn that a fire had broken out at his research and production campus. Fueled by the strange chemicals in the various buildings, green and yellow flames shot up six and seven stories high, threatening to destroy everything Edison had created in his life.

Instead of feeling devastated, Edison told his son: “Go get your mother and all her friends. They’ll never see a fire like this again.”

The goal here is not to mope and despair, but to embrace fate (Amor fati) and choose to face any tragedy forward with a smug little grin ?.

e) Pursue Perseverance

Perseverance is more than persistence (which is directed at one problem until it breaks).

Perseverance is the tenacity and staying power to play the long game. It is about determining to get to where you need to go, somehow, someway, and nothing will stop you.

It is a matter of will and endurance—the ability to hold on and hold steady come what may.

f) See Beyond Your Own Interests

Having a bigger other-centric goal helps you to persevere through your own personal discomfort. Focus on how you can help your fellow humans thrive and survive, and how you can create your little dent in the universe before it all ends.

In short, “If I can’t solve this for myself, how can I at least make this better for other people?”

(This is one of the central tenets for my company Cooler Insights.)

g) Mull Over Your Mortality

“Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.”—Steve Jobs

Thinking about death isn’t pleasant. However, it can be an extremely powerful way to focus your energies and prioritize on what truly matters.

h) If At First You Don’t Succeed…

Nature is a never ending cycle. Similarly, you need to consider how you can surpass one obstacle, one impediment, and one challenge after another. Again and again.

Each time you’ll learn something. You’ll also develop strength, wisdom and perspective.

Life as an entrepreneur is a marathon and not a sprint. Even if this current venture fails, dust yourself and then get ready for the next.


As an entrepreneur and business founder (read my story here), I’ve faced more than my fair share of obstacles.

What I found edifying about The Obstacle is The Way is how it uses timeless principles to teach valuable lessons in entrepreneurship.

I hope that this summary has been valuable for you. Do pick up a copy of the book if you can, its really worth its weight in gold!

The Obstacle is the Way: The Ancient Art of Turning Adversity to Advantage: Holiday Ryan: 9781781251485: Books

By Walter
Founder of Cooler Insights, I am a geek marketer with almost 24 years of senior management experience in marketing, public relations and strategic planning. Since becoming an entrepreneur 5 years ago, my team and I have helped 58 companies and over 2,200 trainees in digital marketing, focusing on content, social media and brand storytelling.

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