Crushing Your Fear Of Failure: Using Stoicism To Thrive At Your Startup

Working in a startup is inherently risky. You need the courage to conquer your fear of failure in order to succeed as a leader.

Ben Bashaw

Ben Bashaw

Published: Apr 24, 2019

The ancient philosophy of stoicism, originally used by ancient leaders to help endure the hardships and anxieties of daily life, is experiencing a resurgence among today's tech leaders and startup employees.

Working in a startup is inherently risky. When you are building new products, testing new ideas, and operating in an environment where a mistake could mean the end of your company or job, the “what ifs” can easily overwhelm you. However, a great paradox is that you need the courage to take risks and need to learn to conquer your fear of failure in order to succeed in a startup or as a startup leader.

From CEOs to investors, people across tech and the startup ecosystem have turned towards stoicism to find comfort in the face of fear and actually thrive in spite of it.

Face Your Worst Fears

There are many ways to negotiate with and mitigate the effects of fear, but stoicism offers one of the clearest methods for dealing with your fear by pushing through what you fear most — an essential heuristic for a startup where postponing decisions out of fear of failure is even more dangerous than making a risky decision.

The ancient stoics constantly reminded themselves and their followers that we are all mortal and only have a short time to make an impact on the world. Confronting the fear of death head-on and accepting, rather than denying, it allowed the Stoics to be more productive and courageous in their daily lives.

“Let us prepare our minds as if we’d come to the very end of life. Let us postpone nothing. Let us balance life’s books each day,” Seneca wrote. “The one who puts the finishing touches on their life each day is never short of time.”

By confronting the fear of death, Seneca proposes, you will be more productive and never run out of time to accomplish your goals and tasks. For people who fail to confront their fears, Seneca writes that “life is very short and anxious.” You can't accomplish your goals if you continuously put off action out of fear and anxiety. The first step to reaching the goals you set is confronting your fears.

Ancient philosophers aren't the only ones who have found the value in contemplating death and facing their worst fears. CEOs such as Steve Jobs and Jeff Bezos also take a stoic approach to putting their fears in the perspective of either personal or company mortality.

In 2005, Steve Jobs gave a commencement speech at Stanford in which he discussed how reflecting on his own mortality allowed him to conquer his fears of failure. “Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life” Jobs said. “Because almost everything — all external expectations, all pride, all fear of embarrassment or failure — these things just fall away in the face of death, leaving only what is truly important.”


Steve Jobs giving his famous Stanford Commencement address in 2005

As the founder and CEO of Apple, Jobs had to take on considerable risk and build wildly ambitious products in order to succeed. To overcome his fears that these products and initiatives would fail, Jobs relied on the old stoic practice of contemplating his mortality to help put those fears in perspective. In the context of impending death, the outcomes of mistakes and failures at Apple didn't seem as serious or scary. As a result, Jobs was able to focus on executing projects without being distracted or hindered by fear of failure.

During an all-hands meeting at Amazon, Jeff Bezos once calmly stated that “Amazon is not too big to fail… In fact, I predict one day Amazon will fail. Amazon will go bankrupt. If you look at large companies, their lifespans tend to be 30-plus years, not a hundred-plus years.”

Bezos went on to explain, “If we start to focus on ourselves, instead of focusing on our customers, that will be the beginning of the end… We have to try and delay that day for as long as possible.” The thought of Amazon going bankrupt wasn't meant to send employees into a panic. Instead, Bezos used Amazon's ultimate end as a way to motivate his employees to look past all their other fears and anxieties about competitors and focus only on what matters most — keeping a customer-first mentality.

If you can come to grips with the existential risks you face at work, whether that's your company going out of business or your job being eliminated, the other risks that stand in your way to success will seem easily surmountable by comparison.

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Preparing For Failure

Like startup founders who knew that their companies could find themselves in a crisis at any moment, the Stoics believed that their wealth and stature could be stripped away from them at any time. However, the Stoics believed that a wise person would always be prepared for such drastic swings of misfortune because they'd visualize the events that could lead to what they fear and prepare themselves in advance.

The Stoics used times of peace and tranquility to prepare themselves for failure. “It is in times of security that the spirit should be preparing itself to deal with difficult times” Seneca wrote. “while fortune is bestowing favors on it then is the time for it to be strengthened against her rebuffs.”

For people like Seneca this oftentimes meant preparing for the event of loosing all wealth and becoming poor. Even though he was one of the richest men in all of Rome, Seneca would walk around in worn-out clothes, eat simple meals, and spend very little money. By visualizing and practicing poverty, Seneca was able to gain confidence in his ability to withstand the event he feared.

The act of visualizing and preparing for failure is something that people across the tech industry have taken up as a part of their own daily lives and as a part of their companies' standard practices. Tim Ferris, an entrepreneur and angel investor, urges people to document their fears as meticulously as they document their goals.


When Tim was starting his first business, he had a tough time delegating responsibility. He was overwhelmed by stress and anxiety about taking any time off and the need to control projects; as a result, he worked around the clock without ever taking a day off.

Drawing strength from Seneca and the Stoics, who he knew found value in visualizing their fears, he began to document all the “what ifs” that ran through his head every day, followed by all the things he could do to prevent those “what ifs” from happening, and all the things he could do to recover from those events if they did happen.

Taking a vacation and letting his team take on more responsibility in his absence was something that Tim could not have done without this practice of documenting his fears. By writing out his fears and thinking through ways to address all the things he feared about taking a vacation, he made himself comfortable enough with the idea to go ahead and do it.

Many business leaders use the same practice to prepare for failed projects and disaster events. One technique many companies use is something called a premortem meeting. Before a product or project even launches, teams will imagine that weeks down the road the project turns out to be a huge failure. From there, the team lists all the events that could bring about failure, what they could do to better prepare for that failure, and how to recover.

In one study of various fortune 500 companies who use premortem meetings, researchers found that the structured format of these meetings coaxes out worries and anxieties that had previously gone unmentioned. A lot of these worries, such as not having enough time to build a well functioning feature before the launch deadline ended up being incredibly important and also controllable. Moving back a deadline or accounting for review and testing time is a worry that is better when addressed at the beginning, rather than the end of a project.

In the competitive and fast-paced world of tech and startups, there is always the ever-present threat of new companies and new technologies putting your own out of business. Rather than letting these fears go unaddressed though, entrepreneurs employ the stoic technique of visualizing failure, and in the process become better prepared for it and less likely to encounter it.

Finding Value In Failure

Regardless of how well you prepare for failure, setbacks and roadblocks to success are inevitable. Especially in a startup, where best practices are still being uncovered and unforeseen challenges arise on a regular basis, failure is an experience you need to become comfortable with.

Of all the small businesses started in the U.S. in 2014, only about half were still in business by 2018. Among all startups that survive, only about 1% become “unicorn” companies. The odds are stacked against founders, and avoiding failure at some point is largely unavoidable.

When a business is starting out, they need to figure out how to build a product that successfully addresses a need their user base has, they need to compete with existing players, they need to build a team, and they need to secure investments to grow. Along this journey, there is a lot of room for error and usually the only way to get through it is to learn and adapt on the fly.

No one builds a business without encountering setbacks and failure. There is a learning curve as entrepreneurs search for the right product-market fit, the right marketing and sales strategies, and learn the ins and outs of their industry. Failure is a key part of that journey. Stoicism offers today's startup leaders a way to reframe how they relate to failure so that they can find value in it rather than dread it.

According to the Stoics, the anticipation of our fears is more harmful than the actual outcomes of the events we fear. Seneca, summing this viewpoint up nicely, wrote, “We are more often frightened than hurt; and we suffer more in imagination than in reality.” Separating your perceptions and emotions from the reality of a situation forms a core principal of stoicism.

The Stoics believed that you could control your reaction to a problem by simply repositioning your perception of that problem. Marcus Aurelius went so far as to say, “Choose not to be harmed — and you won’t feel harmed. Don’t feel harmed — and you haven’t been.” Through this lens, you could even view failure as something to be embraced rather than feared.

Entrepreneurs take a similar approach to talking about failure. It's commonplace now for business owners and managers to talk about how much they value failure. Muhtar Kent, the former CEO of Coca-Cola, said in a commencement speech that companies should celebrate their failures and that he regrets not doing so during his time at Coca-Cola.

“If I would do anything different in my 36 years of career, then it would be to create an atmosphere which allows mistakes, as you learn so much from mistakes” Kent wrote. “We are not bold enough to take enough risks, and risk is critical for success. We don't make enough mistakes.”

Jeff Bezos is another CEO who famously values failure. In his 2015 letter to Amazon shareholders, Bezos almost brags about the failures Amazon has had writing that “One area where I think we are especially distinctive is failure. I believe we are the best place in the world to fail (we have plenty of practice!), and failure and invention are inseparable twins”


The list of CEOs who talk about failure in a positive light could go on and on. The more important thing to note, however, is how positive framing of failure has helped each individual and each company stay resilient and motivated in the face of repeated failure.

Amazon, by Bezos's own admission, has experienced billions of dollars worth of failures. Bezos could have perceived these failures as serious impediments to success and as indicators that the company didn't have the potential to make the impact he had envisioned. Had Bezos taken this approach, he likely would have given up on projects like Amazon Marketplace, which only came about after two previous iterations — Auctions and zShops — failed.

Instead, Bezos chose to perceive his own failures and his company's failures as learning opportunities and necessary steps towards innovation. By reframing how he thinks about failure, Bezos makes every seemingly large setback an event to be embraced rather than ashamed or afraid of.

Within every failure a startup makes, there is a silver lining that can be used to make that business stronger. Something that separates the businesses that fail from the businesses that succeed is their leaders and their employees' ability to reframe how they think about failure. Those who can, like the Stoics, consciously control their reactions to problems by tweaking their perceptions will be able to find a silver lining. Those who can't will lose confidence and lose the courage they need to take necessary risks.

A Philosophy Tailor-Made For Startups

The hard facts of working at a startup or leading a company of your own is that failure is an inevitable experience. Not just small setbacks and mistakes, but big failures that threaten the viability of your company and your job security.

Within this setting you can either:

  1. Ignore your fears and likely miss indicating factors that you should pivot your plans and adjust to threats accordingly.
  2. Let your fear of failure paralyze you from taking action, and live in a constant state of anxiety
  3. Take a note from the stoics and learn to overcome your fear of failure

Stored within the ancient philosophy of stoicism, are helpful tips and practices any entrepreneur can take advantage of to thrive in a startup environment. Facing your worst fears puts failure in a manageable perspective, visualizing your fear better prepares you for the event of failure, and changing your perception of failure can help you learn and become stronger because of it.

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