The Stoic Path to Entrepreneurship COSP
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ISSUE 54
A publication of the College of Stoic Philosophers
January 2024
The Stoic Path to Entrepreneurship
Matt Seibert
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
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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
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ISSUE 54
A publication of the College of Stoic Philosophers
January 2024
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
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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
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ISSUE 54
A publication of the College of Stoic Philosophers
January 2024
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
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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
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its control - if you
find anything better than that, embrace it without reservations” (Aurelius, 2002, p.30).
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ISSUE 54
A publication of the College of Stoic Philosophers
January 2024
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
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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).
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ISSUE 54
A publication of the College of Stoic Philosophers
January 2024
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
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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.
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ISSUE 54
A publication of the College of Stoic Philosophers
January 2024
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