The Stoic Path to Entrepreneurship

In 2013, I made a tough decision to leave my comfortable job and a steady paycheck to start my journey as an entrepreneur. Fortunately, I was able to partner with a financial firm whose CEO chose to take me under his wing and mentored me to help me build my own agency. Being part of his inner circle was a great accomplishment, as he only selected a few individuals to coach. Most people would assume that the value of the mentorship was the business knowledge he imparted. Surprisingly, he taught me concepts that I later discovered were rooted in Stoic principles. 

In this paper, I will be sharing some of the concepts that I have applied over the years and have had an impact on not only my business but also my personal life. These concepts have helped me build a framework that has enabled me to coach hundreds of agents in the financial space, and I still use them today. Based on my experience, I believe that Stoicism can play a significant role for entrepreneurs seeking success on their journey and can also put them on a path of the prokopton. 

Control

Transitioning from being an employee to an entrepreneur can be a challenging process with the introduction of new experiences, responsibilities, and an elevated level of self-accountability that can lead to an increased sense of stress, fear, anxiety, and many other unwanted emotions. 

For example, most entrepreneurs will experience missed appointments that can lead to a variety of negative emotions. One remedy would be to take inventory of circumstances that could occur in advance and create a list of what is within our control and what is not. A list may look like this: 

Out of my control: 
The client attending the appointment 
The client answering the phone 
The client responding 
The client booking another appointment 

Within my control: 
My attempt to call the client back 
My attempt to follow up with the client 
What I attempt to say if the client answers 

In the future, when an appointment is missed, the list can be used as a guide to help focus on the next steps before emotions take over. Entrepreneurs can apply this helpful tool to various situations, such as clients not proceeding with a sale, dealing with customer complaints, agents quitting, and more. Epictetus had a similar perspective when he wrote, “So in life our first job is this, to divide and distinguish things into two categories: externals I cannot control, but the choices I make with regard to them I do control” (Epictetus, 2008, p.111).

In addition to gaining clarity of what is within our control, another helpful tool is to develop the discipline of how we interpret circumstances. We cannot control thoughts from entering our minds, but we can control how we interpret them. To my surprise, Marcus Aurelius wrote something similar, “External things are not the problem. It’s your assessment of them. Which you can erase right now” (Aurelius, 2002, p.110). 

For instance, businesses will likely offer a product or service through a sales process, usually ending with a client deciding whether to move forward. Initially, most entrepreneurs will have difficulty dealing with rejection, which can lead to discomfort around future client meetings. A solution to this would be reframing rejection as an opportunity to learn a new lesson. Moving forward, this can reshape the way entrepreneurs view their subsequent encounters. The practice of reframing circumstances can help form habits around the value judgments we attach to our thoughts, a tool within our control. 

Sellars points out a similar viewpoint, “The passage from Epictetus said the following. It argued that the impressions we receive that present external objects to us are not within our control. We do not have the power to choose them; instead, they force themselves on us. However, we do have the power to choose whether to assent to these impressions or not” (Sellars p. 93). 

Being Present

As entrepreneurs continue their journey and gain experience, they may find it harder to be present as they dwell on the past and worry about the future, creating fear and anxiety. For example, anyone who consistently has clients declining their offer will most likely recall those memories and anticipate a negative outcome for future appointments. 

Seneca captured this when he wrote, “Fear keeps pace with hope. Nor does their so moving together surprise me; both belong to a mind in suspense, to a mind in a state of anxiety through looking into the future. Both are mainly due to projecting our thoughts far ahead of us instead of adapting ourselves to the present. Thus, it is that foresight, the greatest blessing humanity has been given, is transformed into a curse” (Seneca, 2004, p.38). 

As I noted, taking inventory of what is within our control and changing how we interpret thoughts are effective ways to overcome this. Similarly, developing the discipline to focus on the present can be another effective tool. Marcus illustrated the importance of being present when he wrote, “If you can cut free of impressions that cling to the mind, free of the future and the past—can make yourself, as Empedocles says, “a sphere rejoicing in its perfect stillness,” and concentrate on living what can be lived, then you can spend the time you have left in tranquillity. And in kindness. And at peace with the spirit within you” (Aurelius, 2002, p.162). 

The very act of Marcus writing that passage down in his Meditations was one way he stayed present, which was also a form of therapy by managing his internal dialogue as renowned scholar Pierre Hadot concludes, “It appears indeed that, unlike other Hypomnema, the Meditations of Marcus Aurelius are ‘spiritual exercises,’ practiced according to a certain method” (Hadot, 1995, p.11). 

Writing can be a mindful practice that provides introspection and helps entrepreneurs stay grounded in the present moment and cultivate self-awareness. As mentioned before, creating a list of circumstances can also play another role by practicing premeditatio malorum or negative visualization, which is a process that contemplates future hardship or losses. This exercise can prepare one mentally for different outcomes, such as declining offers, canceled appointments, and many more, thereby reducing anxiety about the future. Chris Fisher, appointed Scholarch of the College of Stoic Philosophers and author of the Stoicism on Fire podcast, wrote, “The Stoic practice of premeditaio malorum helps to keep us on the path of virtue toward true freedom and well-being,” Additionally, Chris wrote, “While the practice of premeditatio malorum has us consider events in the future, its purpose is to prepare our minds for life in the present moment. As Stoicism teaches, the present is all we have, and we do not know how much time we are allotted” (Fisher, 2022b). 

Morning and evening reflection can also be an opportunity to appreciate the present by practicing gratitude. With all the negative experiences, entrepreneurs will almost always find positives, explicitly focusing on self-improvement gained from lessons learned, people who supported them along the way, mentorship, and anything they may have taken for granted. 

To take it a step further, embracing amor fati, Latin for the love of fate, is an idea often associated with Stoicism that not only accepts what happens but actively loves it. We can see an example of this when Epictetus wrote: “Seek not that the things which happen should happen as you wish; but wish the things which happen to be as they are, and you will have a tranquil flow of life” (Epictetus, 2008, p.5) and Marcus shared the same views in Mediations: “The things ordained for you—teach yourself to be at one with those. And the people who share them with you—treat them with love. With real love” (Aurelius, 2002, p.77). Love of fate is an important topic related to living according to nature that we will discuss further. 

Character 

Entrepreneurship involves interaction with various people, such as customers, colleagues, supporters, staff, and leadership. A person’s character plays a crucial role in these interactions, directly influencing how people perceive their trustworthiness and ability to maintain relationships. Entrepreneurs often feel disheartened when someone views them as untrustworthy or points out character flaws. However, we cannot control others’ perceptions of us, but we can control how we carry ourselves. 

Chris describes good character as all that is needed for our well-being. The Stoics argued our well-being can only depend on the virtues of wisdom, justice, courage, and temperance because they are the only things entirely up to us (Fisher, 2021a). Therefore, I will make the case that every entrepreneur should choose the same four foundational virtues for their development. Marcus held these virtues in high regard, as he wrote, “If, at some point in your life, you should come across anything better than justice, honesty, self-control, courage—than a mind satisfied that it has succeeded in enabling you to act rationally, and satisfied to accept what’s beyond its control—if you find anything better than that, embrace it without reservations” (Aurelius, 2002, p.30).

Courage is one of the four virtues commonly associated with entrepreneurship because most entrepreneurs take on challenges with a high risk of failure. Additionally, their income is dependent on their personal or team’s performance and production. If their goals are unmet, it could mean no income for them. 

Moreover, entrepreneurs will need the courage to handle moral issues like standing up for what is right, facing competition, progressing through the unknown land, and facing mental challenges like fear and anxiety. 

Epictetus understood the importance of courage as he wrote, “Furthermore, you have inner strengths that enable you to bear up with difficulties of every kind. You have been given fortitude, courage and patience. Why should I worry about what happens if I am armed with the virtue of fortitude? Nothing can trouble or upset me, or even seem annoying. Instead of meeting misfortune with groans and tears, I will call upon the faculty especially provided to deal with it” (Epictetus, 2008, p. 39). Without courage, success would be improbable. 

The second virtue, justice, is essential for entrepreneurs. It involves always doing the right thing and treating others fairly, with kindness and respect. Without this virtue, entrepreneurs may focus on making money over the needs of others and possibly break the rules for personal gain. This ultimately leads to their downfall. 

The virtue of justice goes beyond individuals and contributes to the common good of others. It means actively doing good, helping those in need, and showing compassion to society. Chris highlights this process as a part of Stoic ethics, “Oikeiosis begins with the orientation toward self-preservation and then expands as a human matures to include one’s family, society, and humanity as a whole” (Fisher, 2022a). 

Marcus emphasized the significance of justice as the cornerstone of all other virtues when he wrote, “Hence Justice, which is the source of all the other virtues. For how could we do what justice requires if we are distracted by things that don’t matter, if we are naive, gullible, inconstant” (Aurelius, 2002, p.150). When entrepreneurs become successful, my opinion is that they have a social responsibility to create a positive impact on the world. 

The next virtue, temperance, will be required for entrepreneurs to prevent self-sabotage. The lack of temperance alone can bring down a successful business and hurt others. Seneca wrote, “People who know no self-restraint lead stormy and disordered lives, passing their time in a state of fear commensurate with the injuries they do to others, never able to relax” (Seneca, 2004, p.196). Entrepreneurs who experience a sudden increase in income may find it challenging to maintain self-control. The availability of money can lead to an urge to indulge in desires and impulses, which, in turn, can lead to issues like drug and alcohol abuse, reckless spending, and uncontrollable emotions. 

Therefore, entrepreneurs must exercise caution and the virtue of temperance to avoid such pitfalls. As Marcus wrote, “We need to master the art of acquiescence. We need to pay attention to our impulses, making sure they don’t go unmoderated, that they benefit others, that they’re worthy of us. We need to steer clear of desire in any form and not try to avoid what’s beyond our control” (Aurelius, 2002, p.157). 

The final virtue, wisdom, acts as a guide for the other virtues. Wisdom is not only about acquiring knowledge but also about applying it correctly. Without understanding, having too much courage may lead someone to make poor decisions. For instance, without moderating their courage, entrepreneurs might convince clients to invest in something where the risk far outweighs the reward, causing them to lose their investment. 

Simultaneously, wisdom provides clarity for entrepreneurs on how to do the right thing when helping clients, like placing their needs above making a commission. It will also give the right way to help new agents by having compassion, empathizing with their situations and struggles, and finding a way to guide them. Beyond business, wisdom will also provide entrepreneurs with a sense of responsibility to their community and society, making a positive contribution. 

Furthermore, as income increases, entrepreneurs will know to exercise wisdom to avoid excessive spending on material possessions. They will see the importance of practicing self-restraint and how to save and allocate money for financial stability. 

Seneca wrote, “No one can lead a happy life, or even one that is bearable, without the pursuit of wisdom, and that the perfection of wisdom is what makes the happy life, although even the beginnings of wisdom make life bearable. Yet this conviction, clear as it is, needs to be strengthened and given deeper roots through daily reflection; making noble resolutions is not as important as keeping the resolutions you have made already. You have to persevere and fortify your pertinacity until the will to good becomes a disposition to good” (Seneca, 2004, p.63) 

Wisdom is also a big part of understanding Nature and the natural order of things and living in harmony with it. The Stoics believed that four virtues were essential to forming the ideal character of a Stoic sage. These virtues were not separate traits but interdependent aspects of a single ethical approach to life. By cultivating these virtues, one could achieve eudaimonia, often translated as happiness or flourishing. The goal of living in harmony with nature and reason is achieved by practicing these virtues. 

Entrepreneurial Nature 

The previous emphasis was on the practical implementation of various Stoic principles that are relevant and easy to comprehend. But the most crucial and integral idea that may take some time for entrepreneurs to grasp is the notion of living in accordance with nature. This centers on aligning one’s life with the rational order and principles that govern the universe. While some may disregard this aspect, it is essential for those who wish to benefit from practicing traditional Stoicism.

As Chris pointed out, “The ancient Stoics placed a rational, divine and providentially ordered cosmos at the center of their philosophical system and relied on it to guide their every thought, desire and action” (Fisher, 2021b). “The Stoics believed a portion of our rationality that permeates and orders the cosmos resides within each of us as our rational faculty. It’s that portion that we each possess that enables us to understand and live in agreement with nature” (Fisher, 2018a). Through this lens, entrepreneurs must live in harmony with nature in order to experience well-being and happiness in their journey. 

However, happiness will likely be disrupted for every entrepreneur when their desire for status, wealth, and success grows. I have witnessed this desire become an obsession and lead to unhealthy pursuits and addictions. This outcome can occur whenever we pursue or desire things beyond our control. 

Alternatively, Chris provides a solution on his podcast when he mentions, “The discipline of desire helps us understand our human nature and cosmic nature and how it guides what is natural to us, what we should desire, and what we should not fear. The solution is to stop desiring and fearing what is not up to us. Control what you can, your thoughts, desires, and intentions to act, and leave the rest to the providential cosmos” (Fisher, 2018a). 

The Stoics hold that the only thing worth pursuing is an excellent character or virtue, such as courage, justice, temperance, and wisdom, which are entirely within our control. This provides a framework for entrepreneurs to follow, giving them complete control to obtain the only thing that should be desired, which is a virtuous character. This perspective aligns with the idea of living according to nature. 

At the same time, external factors such as status, wealth, and success are considered indifferent and can be preferred or dispreferred but are not inherently good or bad. Epictetus wrote, “For who is there among us at this present time who cannot give a systematic account of what is good and bad? That some things are good, others bad, and others again indifferent; that the virtues and what partakes in the virtues are good, while things of the opposite nature are bad; and that wealth, health, and reputation are indifferent” (Epictetus, 2014, p.89) 

Lastly, one of the final hurdles entrepreneurs will inevitably encounter is dealing with the results of their actions and unforeseen events. As I mentioned, one practical approach to overcoming this challenge is consciously choosing how we interpret each outcome. However, while this strategy can be helpful, it may not always be sufficient in more challenging situations. As mentioned earlier, living according to nature allows us to accept and love every outcome (amor fati), as the Stoics did. 

On his podcast, Chris mentions, “The Stoics disciplined themselves to lovingly accept and wish for everything that happens because it is the action of the providential cosmos that brought those events about. This does not mean that we cannot attempt to prevent all tragedies. However, once they have happened, we are to love them. We must only focus on what is up to us and trust the rest to the providential cosmos” (Fisher, 2018a). Marcus expresses this by writing, “Everything suits me that suits your designs, O my universe. Nothing is too early or too late for me that is in your own good time. All is fruit for me that your seasons bring, O nature. All proceeds from you, all subsists in you, and to you all things return” (Aurelius, 2011, p.75). 

Finally, Chris reminds us that we do not have control over the external world and any authority of Nature and that whenever we have goals and desires outside of virtue, the providentially ordered cosmos may have a different plan in mind. “When we seek such ends with reservation, and without straining, we are prepared to accept and love whatever actually comes about” (Fisher, 2018b). 

The Prokopton Entrepreneur 

Chris has defined a prokopton as someone who practices Stoic principles while making progress on the Stoic path. He mentions progress can be made by focusing on applying the three Stoic disciplines: the discipline of assent, desire, and action, which I firmly believe can have a life-changing impact on all entrepreneurs (Fisher, 2015). 

To conclude, as I reflect on my journey and think about the thousands of entrepreneurs who have either quit or are still moving forward, I can’t help but notice the similarities between the paths of an entrepreneur and a prokopton. Both of them will face similar challenges that are external to them. However, they are also pursuing similar goals – a life of excellence and, ultimately, happiness. Little did I know, more than a decade ago, the CEO who helped me start my journey was also training me for my path of the prokopton.