Leadership Is Hard — Use These Four Strategies to Overcome Adversity

Think about the most significant achievement in your life and how you made it happen. Was it easy, or was it hard?

Chances are, it was hard (or even extremely hard!), which is likely what made the achievement significant to you. Hard things tend to be worthwhile. Really hard things can be epic!

Yet, I’ve heard plenty of smart, capable leaders lament and wonder why things couldn’t be easier. I’ve witnessed others expend massive amounts of time and energy pursuing “easy wins” at the expense of a more significant accomplishment.

Although challenge and adversity seem to be required to manifest our greatest successes, we tend to either avoid or circumvent the very thing we should embrace and push through. 

For example, recall your first promotion into leadership. You may have thought something like, “Things will be easier for me now that I’m in charge,” but quickly realized that being an effective leader requires a lot of challenging work. Some choose to face the challenges while others look for an easy way—and we know how each of these two diverging storylines typically conclude.

If you aspire to accomplish anything significant, you must learn to love and appreciate adversity.

Adversity comes in many forms. It can be internal, requiring you to master your own mental game or external, necessitating you figure out how to deal with others. It can be involuntary, caused by factors you don’t control or voluntary, in the form of accepting a role or project with full knowledge of the challenges ahead.

Through my own experiences and those I’ve seen my coaching clients face over the past two decades, I’ve identified the following four strategies that help leaders aiming to accomplish great things stick with the challenges they face, work through and overcome adversity, and build resilience.

Embrace Failure

“I have not failed. I’ve just found 10,000 ways that won’t work.”  –Thomas Edison

Thomas Edison had it right: you must learn to embrace failure if you want to make your mark. Failure is part of every change process, and change is required to accomplish the most important things in work and life.

Think of any complex skill you’ve mastered––from riding a bike to hiring great people, or perhaps making a sale. How did you learn to do it? Trial and error had to be a part of the process and your ultimate success was built atop countless failures along the way. As such, it’s productive to look at failure as a building block of success rather than as a setback––though the latter is an easy default for many.

Accounting software company Intuit embodies the idea of embracing failures and recognizing them as opportunities. The company’s philosophy is that failure teaches powerful lessons and provides the seeds for future great ideas, so much so that they give an award for Best Failure and host periodic “failure parties” to reinforce their culture of experimentation and learning. Materials science company W.L. Gore & Associates, the manufacturer of windproof and breathable GoreTex fabric, provides another example, having long celebrated failed projects with beer or champagne as if they had been successful. Their leadership team views mistakes as a required element of its successful creative process.

How can you find rewards in the inevitable failures you’ll have on the way to your greatest successes? How can you help your team do the same? 

Consider It an Ordeal

“Be grateful for all ordeals, they are the shortest way to the Devine.” –The Mother (Mirra Richard)

In addition to considering inevitable failures as learning, to accomplish great things, you’ve got to muster the motivation to keep moving forward––regardless of the difficulties you encounter along the way. As I’ve written previously, decades of psychological research consistently identify Autonomy, Mastery, and Purpose as the keys to motivation and engagement. Autonomy is self-directedness and latitude regarding how to get work done, mastery is the opportunity to learn and gain expertise, and purpose is feeling part of something larger than oneself. You’ll activate all three when you reframe an extreme challenge as an ordeal or “rite of passage” instead.

In 2019, I opted into an extremely rigorous certification program in Neuro-Linguistic Programming (NLP). In addition to about fifty hours of preparatory work, I was required to travel from my home in New Jersey to Whistler, British Columbia for two eighteen-day blocks––one in the spring and one in the fall.  For those who haven’t made the journey, Whistler, BC is a beautiful place, but it’s particularly hard to get to from the Eastern United States! The travel and the time commitment, in and of themselves, were ordeals of sorts.

While there, my classmates and I worked long days in a windowless classroom and spent many late nights completing assignments. There were plenty of opportunities to quit the program (and at times, it was quite tempting, as this was the singular most challenging learning experience I’d ever faced in my life––university included!).

But instead, I reframed the whole experience as an ordeal.

I thought of how few people enrolled in––let alone successfully completed––the program. I thought of how much I could learn. I thought of the course as an opportunity for me to prove I could do it, even at the age of fifty-two, with a family and a coaching practice to run.

When I considered it through the lens of an ordeal, I was able to tap into all three motivational elements: autonomy, mastery, and purpose. As a result, I powered through and earned my Certified Trainer of Neuro-Linguistic Programming certificate. It was a tremendous accomplishment, and quite an ordeal, which is what made it one of the most significant achievements in my life.

With that in mind, how can you reframe an extreme challenge you’re facing as an ordeal, doubling down on autonomy, mastery, and purpose to see it through?

Find the Learning

“Challenges are gifts that force us to search for a new center of gravity. Don’t fight them. Just find a different way to stand.”  –Oprah Winfrey

When hardship arises––and it will––look for the lessons. Intuit, W.L. Gore & Associates, and each of my coaching clients have built cultures that equate struggle and failure with learning. This is a healthy approach on numerous fronts, the most meaningful of which is developing a growth mindset among your team. In her seminal book, Mindset: The New Psychology of Success, psychologist and Stanford professor Carol Dweck explores the differences between those with a fixed mindset and those with a growth mindset. While fixed mindset thinkers tend to withdraw from challenging tasks, those with a growth mindset typically persist much longer. The reason is that growth mindset thinkers believe the more they try, the more they’ll improve.

One way to accelerate learning from failure is to resist judgment and consider the new information (from the failure) as feedback. This concept is so powerful, it’s one of the ten presuppositions of NLP: “There is only feedback (no failure, only feedback.)” Think about how often you judge yourself or allow yourself to be judged by others when you grapple with something new! During times like these, words like “never,” “can’t,” “don’t,” and “won’t” flow like water from a poisoned spring.

The reality is that struggle and failure offer clues—new information about how to improve slightly on your next attempt. And if you look for the clues instead of drinking the poisoned water of judgement, they will appear—providing valuable lessons from which to learn.

Want proof? Think back to the last big challenge you surmounted. Now recall exactly how you finally broke through whatever was blocking your way. The odds are overwhelming that your breakthrough came as a direct result of feedback (or learning) from prior unsuccessful attempts. If you’d like to take a deeper dive into the process of change, you’ll find everything you need here.

What can you learn from a recent struggle or failure by thinking more deeply about the clues (information) you may have missed? Who on your team can you help convert their adversity into learning, growth, and wherewithal to press forward?

Seek Community

“If I have seen further, it is by standing on the shoulders of giants.”  –Isaac Newton

According to the American Psychological Association: “Many studies show that the primary factor in resilience is having caring and supportive relationships within and outside the family. Relationships that create love and trust, provide role models, and offer encouragement and reassurance, help bolster a person’s resilience.”

As you think about those in your life on whom you can rely when the going gets tough, note the purpose of this particular community isn’t to attend your pity party or to dissuade you from your challenging pursuit! Rather, these should be people who have already met the challenge you face themselves or who are committed to the same ordeal you’re taking on.

Purdue University resiliency researcher Elliot Friedman reinforces this further, saying: “The availability of social support in all its forms—instrumental support, emotional support, support with how you think about things—they all matter and help us in facing challenge.”

I’ve written and spoken extensively on how critical it is to periodically evaluate and upgrade your professional neighborhood to ensure you have the right professionals, mentors, advisors, and peers around you to help you get where you want to go. These same principles apply here. To learn more, check out hack #5 and the corresponding free tool in this article.

Who are the top ten people in the world with the capability to help you surmount your biggest challenges and accelerate your growth as a leader? What must you do to add some of them to your professional neighborhood?


“Show me someone who has done something worthwhile, and I’ll show you someone who has overcome adversity.”  –Lou Holtz

You’re reading this right now because you are on a journey to achieve something you consider worthwhile in your business, in your life, or in both. While energizing and exhilarating, it’s hard. It’s frustrating. It’s seemingly unfair at times.

But, as Lou Holtz said, nothing worthwhile or truly meaningful in life comes without some form of struggle.

That adversity is also your greatest source of inner strength, motivation, learning, and deeply meaningful connections to others. What matters most is how you respond to it––which, in turn, depends upon how you think. The strategies we’ve covered––embrace failure, consider it an ordeal, find the learning, and seek community––help stack the deck in favor of your success.

Use them deliberately and thoughtfully to find the right path and the resilience you require to create the change, the progress, and the results you seek. Along the way you’ll discover that, as Celine Dion once said: “In the moment that you think you can’t, you’ll discover that you can.”

Indeed, you can, and you will!


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