The Failure Paradox

Unlearning the False Narrative of Entrepreneurship

By Jimi T Hardee

Screencap of a post shared unironically in our CEO’s LinkedIn feed. Post reads: “THE WILL TO SUCCEED ABOVE ALL ELSE. #entrepreneur #startups #winningthe20s.

Screencap of a post shared unironically in our CEO’s LinkedIn feed. Post reads: “THE WILL TO SUCCEED ABOVE ALL ELSE. #entrepreneur #startups #winningthe20s.

“What will you do if the business fails?”

As I contemplated my answer I took a deep sip of what was honestly a pretty mediocre cappuccino and looked across the steel mesh table at my friend sitting opposite me. We were outside of a cafe and I had just finished telling her about the fledgling startup I had begun volunteering my time with, in the hope of escaping my unremarkable life. Her expression was a mix of interest and concern.

I placed my cup and saucer down on the table and listened to the sounds of downtown Santa Cruz bustling around us. I was trying to think of an answer that would make me sound wise and self-assured, like I got this question all the time.

“You just can’t think about it.” I finally replied. “You have to believe it’s going to work out and do everything you can to make it happen.”

This was the first time anyone had asked me about the possibility of failure, though it certainly wasn’t the last. Whether it came from my mother and father or any of the countless peers who had to endure me prattling on endlessly about my work at NuLeaf for the last 3 years, whenever the question was asked my answer was more or less the same: ‘You can’t think about failure.’ An answer that could have come from ‘The Basic Bro’s Startup Survival Guide.’

I think I used to believe this platitude once, but our CEO, Rachel, upon hearing me regurgitate my tried-and-true answer to the failure question, had her own thoughts on the matter.


“Expecting failure not to plague you is unrealistic,”

Said Rachel, rolling her eyes at me. “Maybe in the first year I didn’t think about failure but, I mean, we’ve almost run out of money. How do you not think about failing in that situation? It would be irresponsible.”

I was a little taken aback when I heard this. My idea of an entrepreneur after living in Silicon Valley for 10 years was that of a uniquely insightful and shrewd influencer. I had a portrait in my head of some Elon Musk-ian fantasy person who always seemed to know something other people didn’t, paving the road to the future from some grandiose vision. So ingrained in me was this concept that through sheer force of will, you had to make your business work. As if startups only fail because their founders didn’t believe hard enough.

To hear someone I respected as a business leader brush off these accepted standards was a little jarring. Surely you wouldn’t start a company if you thought it was going to fail, so where was this coming from?    “If you are obsessed with keeping up the appearance of success, you are just opening yourself up to a blind spot.” Rachel elaborated. “When we almost ran out of money, we pivoted to a sales-based model and honestly if we hadn’t done that a) we wouldn’t have money in the bank and b) we wouldn’t be attracting investors.”

We had indeed nearly run out of money the previous year and were in desperate need of a cash infusion at the time. What I remember more about this time though, is that the atmosphere of the business hadn’t changed. There was a possibility of the company going under but we all understood that possibility and took measures to prevent it from becoming a reality (to great effect if I do say so myself). 

A startup who has never contemplated failure is ill-equipped to face it when the time comes. To right the ship when it starts going down, you need to be realistic about the fact that the ship is sinking. Simply put, to avoid failure you have to think about it. You need to be able to identify why your business is failing and address the issues before they become insurmountable.


“Learn to rest, not to quit”

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This is the phrase that helped me realize that the ‘failure is not an option’ attitude is not only shortsighted, but ultimately harmful to the startup culture in general, and to the entrepreneurs themselves. This lesson did not come easily for me, as I would have to learn it first hand.

A few months ago I had what can only be described as a nervous breakdown. I had been working with NuLeaf for about 2 years at this point while attending school in pursuit of a Computer Science degree (this did not work out). I had also just started working a retail job to make ends meet, all this proved to be too much of an undertaking. I probably realized within a few weeks that I was stretching myself too thin, but I had a voice somewhere in the back of my head telling me “failure is not an option.” 

The true blue success story of the bootstrap mentality would be as follows: I gritted my teeth, put my nose to the grindstone, and worked harder than I ever had before. I slept 4 hours a night and worked 80 hours a week and kept up that hustle until I was rich and successful and drowned in champagne. This is not what happened.

The reality is that I fell into a state of executive dysfunction, fell behind on my tasks, and eventually buckled under the weight of my anxiety. After about a month of this, I was on the verge of resigning my position at NuLeaf and returning to the unremarkable life I had been so desperate to escape from in the first place. In the midst of a contentious and not altogether pleasant conversation with Rachel regarding my less than stellar performance in the preceding weeks, the question I knew had been coming arose: 

“so, what do you want to do?”

I sat speechless on the grey upholstered couch opposite my computer monitor, the screen littered with tabs of unfinished work. My desk chair had long since been abandoned in the course of our conversation, as I paced the room trying to articulate my situation. I didn’t know what to say. I looked down at my phone screen as the call time ticked away our silence. My cat looked up at me from the floor, as if he too were waiting for a response. Finally, Rachel broke the silence with a quote.

“If you get tired learn to rest, not to quit.”

She told me to take a leave of absence and return in a month if I wanted to continue. During the interim period I reflected on the quote (which is attributed to the street artist Banksy if you are curious) and on what I felt at the time was my own failure. 

What I realized is that fear of failure had paralyzed me with indecision. My long held belief in willing and working and believing that I would succeed, without consideration of failure, had not served me. If I had accepted the possibility of my imminent failure, I could have taken proactive steps to address it. Instead I stayed the course and tried to convince myself that through sheer force of will I could make it work.

Unlearning toxicity

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When I returned to work, I was armed with the knowledge that has become vital to my health in business and indeed in life: just because a belief is popular doesn’t mean it is right. This is something I think most people understand on an academic level, but understanding it and internalizing it are very different things. We can know that the “failure is not an option” mentality is unhealthy, but that doesn’t stop us from believing it and perpetuating the cycle of toxicity.

The startup culture is defined by disruption, pursuing success through innovation such that your industry is irreversibly changed. Changes to the status quo define the most successful entrepreneurs. Still, even as we innovate in one area we can find ourselves falling into old traps of toxic business culture in others. To unlearn toxicity, we have to constantly question ourselves and our beliefs. If you really want to disrupt the status quo,  it isn’t enough to create innovative technology, you must also create an innovative business. 

The fear of failing deters entrepreneurs from innovating and adopting new attitudes towards our business culture. We know the old ways have worked in the past, so it is tempting not to rock the boat too much even if it is harmful to our business, our industry, or our own mental health. But what defines entrepreneurs more than anything else is our ability to look at the old ways and say “we can do better.”

It’s not always easy to unlearn toxicity, or even identify it within one’s business or oneself. I wish I could provide you with a handy guide for creating a more enlightened corporate culture but the reality is: we’re in uncharted territory. The best we can do is think critically about why we believe what we believe. If you don’t have an answer, it may be time to abandon that belief. This is how I reconciled my beliefs regarding failure. When asked “what if your business fails?” I still rely on an old platitude, just one that perhaps isn’t so harmful:

“Success is not final. Failure is not fatal; it is the courage to continue that counts.”

-Sir Winston Churchill