The Limitations of Resiliency Alone

“Hustle, stick to it, the pain will eventually pay off.” The quivers of many self-proclaimed business gurus are filled with these paper-bullet admonitions. ‘More pain, more gain”—we treat the capacity to endure pain as its own special currency—the more you endure, the more currency you accumulate to tip the scales of success in your favor.

It’s from this ability to endure pain in the never-ending gauntlet of challenges that we convince ourselves of our heroic qualities. We treat the entrepreneur as a virtuous Don Quixote character slugging her or his way through the unrelenting headwinds of difficulty and failure.

Of course, it is true startups are indeed not easy. The onslaught of challenges they present is indeed unrelenting. The road less traveled is laden with an onslaught of obstacles. This is a dimension of most difficult tasks though.

This is also what makes hard endeavors so transformational. Over and over we are dropped into deep water and left to flounder. However slowly we learn to swim. In doing so, the obstacles we face become a catalytic source of personal growth.

Startups have the quality of being a perpetual sink or swim simulation. ‘I didn’t know how to do x, so I just had to figure it out.’ This is what I regularly hear from successful founders. Facing the many obstacles you will face, you simply have to learn more and more to stay in the game.

Resilience is the obvious foundation of startup survival. It is an important foundation, for no other reason than it extends the time horizon you have to actually learn enough lessons to eventually succeed. Through resilience you allow yourself to get more reps, and make the adaptations to gain some competency in your craft.

Resilience is an essential ingredient in the formation of wisdom. When things get difficult, however, it is tempting to tap out early. Countless talented people give up on their visions. When we are headed down the wrong path why not change course, or even better yet, go back to the drawing board and just approach things with fresh eyes?

There is nothing wrong with giving up on a particular idea. While giving up on a single venture can be a sign of maturity and wisdom, we often do so at the expense of something much greater. ‘I don’t have what it takes, I am not cut out for this.’ This is the refrain of so many defeated founders searching for the nearest startup offramp.

Perhaps as it stands today, with your current skillsets, you may not have what it takes to carry your current project over the finish line, but you are not born with some fatal flaw that precludes you from ever achieving your goals. You are not static, neither are your skills.

By staying in the game you buy the opportunity to grow into the person that could eventually succeed. When you hit the eject button too early though, you are inadvertently making a decision to arrest your own development.
We don’t acquire knowledge through osmosis though. Resiliency alone though is not sufficient to attain wisdom. The capacity to endure failure is no virtue unless it is coupled with deliberate introspection and analysis of why we have fallen short when we do.

When we deliberately analyze our failures and missteps, we can start to build an arsenal of expertise—it is these experiences that we milk for wisdom. It is in fact this awareness and self-analysis, not age or experience, that leads to wisdom. Without this deliberate analysis of our shortcomings, we are just wittingly submitting ourselves to repeat the same mistakes.

Rest assured startups will quickly expose your shortcomings. It certainly did for me. We all start ill-prepared to lead a new enterprise. There is no school to be an entrepreneur so you’re learning everything in real-time.

I started my first company with very little insight into what it meant to run a business. I was gravely ill-equipped to lead a successful company. The list of my weaknesses as a founder could be written in volumes, while my strengths may have barely been able to fill an index card. At nearly every decision point, it felt like I made the wrong decision.

I was a beginner, and stepping onto the stage as a beginner can be painfully embarrassing as all of your warts and blemishes are transparent for everyone to see.

One particular source of insecurity for me was my ability to deliver a pitch for my company. Like many introverted founders, I experience a tremendous amount of anxiety around delivering presentations and public speaking. As such, I spend hours preparing for presentations leaving nothing to chance, and not letting my anxiety have an opportunity to creep to the surface.

On one occasion I attended a mastermind meetup, which I had volunteered to pitch my company. In attendance, that evening was one of LA’s biggest celebrity venture capitalists. I was scheduled to speak right after the investor. He had everyone in the group rapt at his every word. Then it was my turn to present—queue the crickets.

In less than a second into addressing the group a surge of adrenaline shot through my body. I’ve experienced this surge of adrenaline just as I was about to speak to an audience a thousand times. I could hear my heart beating what seemed like a million beats per minute, and well, the rest was history. When that adrenaline spikes, it becomes incredibly difficult for me to keep a linear train of thought. My mind spastically follows every tangent down a rabbit hole. That became clear to everyone in the audience. I was talking incoherently, and as the crowd looked at me befuddled, my nervousness just compounded.

When it was time to get feedback, the VC chimed in by saying something like it was one of the worst presentations he had experienced. I am sure he may have offered a more constructive critique, but I was still shellshocked and in the doldrums of what I perceived to be a catastrophe, and none of that got through.

To make matters worse, days after the presentation, I received a phone call from a friend who was not in attendance but got word of my presentation. He told me I shouldn’t apply to be part of the VC’s incubator. My performance was so bad I got a rejection to an incubator that I had not applied to, nor had any intention of applying to—a gratuitous reminder of how bad my presentation was.

Like any embarrassment, I stewed on it for a couple of days. ‘Pitching is stupid—either the product is good or it isn’t,’ I would tell myself. Or ‘the numbers should speak for themselves.’ A torrent of resentments flooded my thoughts. At that moment it would have been comforting to indulge those resentments and absolve myself of my shortcomings as a speaker.

It is a well-known adage to play to your strengths rather than build on your weaknesses. This is true for the most part, but weakness, when framed through the perspective of a career, can be a real anchor. Your weaknesses become the ceiling of your potential.

In my case, if I didn’t overcome my stage fright and learn to be a better communicator, it would be hard to be taken seriously and would always be a roadblock to reaching my goals of building a company.

While it is comforting to look back at failure and riddle off the misfortunes that ultimately scuttled us, it’s not as easy as understanding how we as individuals contributed to our own failure. What areas have our shortcomings become roadblocks to our success? The reality is we can’t do anything about misfortune, but we can equip ourselves with more knowledge and insight to tackle future obstacles.

I ultimately hired a speech coach to help me overcome this challenge. I learned skills to slow down and be more present as I spoke. It’s something I constantly have to work at. To this day every time I present a get a surge of adrenaline that is slightly disorienting, but each time I put in the reps, I get a little better at it and it becomes less and less of a weakness.

This deliberate self-examination and self-awareness are the ways we persevere over the hurdles we face so we don’t have to face them over and over again. In sports, we go back to the film to see where we need to adjust; in the military, after-action reports are used to analyze what went wrong in a failed mission and make sure grave mistakes are not repeated.

The more frequently we can check-in, analyze your performance, and make adjustments, the faster we can catch ourselves from drifting off course.
The Roman emperor Marcus Aurelius noted in his journal, “These are the characteristics of the rational soul: self-awareness, self-examination, and self-determination. It reaps its own harvest…It succeeds its own purpose…” Aurelius is telling himself to look inward, examine yourself critically, and ultimately make decisions based on the principles derived from that self-examination.

Aurelius maintained a practice of writing these axioms in his journal. He did so not because he was a master of these principles, but because he was prodding himself to live up to them.

The journals of the comedian Gary Shandling provide a perfect example of this purposeful self-examination. In Judd Apatow’s HBO documentary on Shandling, he turns the spotlight on the comedian’s journals and reveals how much Shandling leaned into his journal to scrutinize his performance and breakthrough the troughs of being a beginner during the early stage of his career.

His journals were riddled with mantras of encouragement to be resilient. He would say things like, ‘Do it. You are ready. Work. Be a comedian,’ or, ‘each day I will gain strength. Each day I will become more determined’ in order to stoke resilience and purpose as he was undergoing a monumental task of breaking into the comedy scene.

In his self-analysis, he would land on principles that would shape his performance. “The secret is to be myself,” he would write to himself. “Use everything you’ve got to be funny. I can still use more of myself, more voices, more faces, more characters, more attitude, more presence.”

He even had the humility to draw on the performance of others to model his own act. He would say things like, “I saw Jeff Altman kill, kill like I never have. This is not a comparison, there was something to learn.”

After dealing with a bad set due to a heckler, he would go to his journal and devise a strategy for the next time. “Dealing with a heckler: Relate to the audience, not to the heckler. Tie heckler into existing material,” he would write in his journal.

This was all while he was learning to develop his own comedic voice. “No one realizes that they want to hear Elvis, so it is with material. It doesn’t matter if it is like someone else’s, it is merely a vehicle to be Garry. The more you are Garry and the less you worry about the song you are singing, the more you’ll be yourself,” he wrote as more and more clarity would come to his work.

It was neverending. He always was fine-tuning his performance—as we are never fine-tuning ourselves as entrepreneurs. “I need to work on my space work,” he reminded himself. “Commit to killing. Commit to the performance!”

We all have hecklers, we all have bad performances, we all are trying to access our authentic voice or leadership style, and we all have the capacity to learn from these things to push ourselves to grow. When we have setbacks we have to use those setbacks as material for the daily lessons of our self-education.

If you were to read my journal you might see things like, “That meeting unraveled quickly, you need to make sure to send out an agenda to make sure we don’t lose focus.” Or “you were nervous during that presentation. Remember to slow down.” Or “you weren’t assertive when dealing with that individual, make it a priority to clarify your thoughts tomorrow.” Or “You spent too much time on that activity, and it is a distraction for your main purpose right now. Carve out more time to code, and less time for meetings. Be okay with saying no to people.”

This is not self-flagellation—there’s no virtue in being unnecessarily critical of yourself. It’s a process of perpetual fine-tuning that keeps us on the right course.

We use our failures not to define ourselves as lesser, but as the material to catapult our understanding of how to move forward. And with the actual success of any given venture subject to the whim of outside forces, the growth that we gain from this perpetual fine-tuning through self-analysis and awareness is indeed the non-monetary dividend that makes the experience priceless—it is the currency that really matters. That is the currency that will actually tip the scales in our favor.