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The Entrepreneur’s Hero’s Journey: Stage 6 — Tests, Allies, and Enemies
- Dr. MJ Yang
- 4 days ago
- 5 min read
This blog is part of The Entrepreneur’s Hero’s Journey, a 12-month Entrepreneurship series in 2026 that explores business ownership through a Jungian lens, drawing on Joseph Campbell’s (1949/2008) Hero’s Journey and the twelve stages refined by Christopher Vogler (2007). Each post corresponds to one stage of this inner journey, offering a reflective map to help entrepreneurs recognize where they are and understand entrepreneurship as an evolving process of individuation.
12 Stages of the Entrepreneur's Hero's Journey
Departure (For the Aspiring)
Initiation (For the Active)
Stage 6 — Tests, Allies, and Enemies
Stage 7 — Approach to the Innermost Cave
Stage 8 — Ordeal
Stage 9 — Reward
The Return (For the Established)
Stage 10 — The Road Back
Stage 11 — Resurrection
Stage 12 — Returning with the Elixir
Following Stage 5 — Crossing the First Threshold, the entrepreneur has committed to the journey and entered unfamiliar territory. What comes next is not mastery, but learning.
The Real Journey Begins
In The Entrepreneur’s Hero’s Journey: Tests, Allies, and Enemies, the entrepreneur begins learning through direct experience.
The business is no longer simply an idea. The threshold has been crossed, and the realities of entrepreneurship start to unfold. This stage introduces the challenges, relationships, and obstacles that shape both the business and the entrepreneur.
While earlier stages focused primarily on preparation and commitment, this stage focuses on adaptation.
The entrepreneur begins discovering that growth often happens through experiences that cannot be fully predicted or controlled.
Tests, Allies, and Enemies in the Entrepreneur's Hero's Journey
In the Hero’s Journey, this stage represents a period of adjustment to a new world.
The hero learns how things work through experimentation, mistakes, and unexpected encounters.
For entrepreneurs, this often means discovering:
What works and what does not
Which strategies fit their strengths
Who supports their growth
What obstacles repeatedly emerge
At this stage, success becomes less about having the perfect plan and more about developing the ability to learn and adapt.
The entrepreneur begins building knowledge not only through reflection, but through lived experience.
What Tests Look Like for Entrepreneurs
Many people imagine that entrepreneurship is defined by a few major decisions.
In reality, growth often unfolds through a series of smaller, everyday challenges.
Entrepreneurs may encounter:
Difficulty attracting clients
Marketing efforts that do not generate results
Financial uncertainty
Rejection or lack of response
Slow business growth
Decision fatigue
Impostor syndrome
Competing personal and professional responsibilities
These experiences can feel discouraging, especially for capable and high-achieving individuals who are accustomed to competence in other areas of life.
Yet tests serve an important purpose.
They reveal strengths, expose weaknesses, and help entrepreneurs develop skills that cannot be learned through theory alone. Every challenge asks a deeper question:“Who are you becoming through this experience?”
The answer often matters as much as the outcome itself.
The Importance of Allies
Entrepreneurship is frequently portrayed as an independent pursuit. While initiative and self-reliance are important, few sustainable businesses are built entirely alone. This is where allies become essential.
Allies may include:
Mentors
Therapists
Coaches
Professional peers
Referral partners
Friends and family members
These relationships provide more than practical support.
They offer:
Encouragement during setbacks
Perspective during uncertainty
Accountability during difficult periods
Emotional support when challenges feel overwhelming
Sometimes an ally's greatest contribution is helping entrepreneurs remember their purpose when self-doubt begins to take over. The entrepreneurial journey may be personal, but it does not have to be isolated.
Understanding “Enemies”
The word enemy can sound dramatic. In entrepreneurship, enemies are often not people. More commonly, they take the form of internal obstacles that repeatedly interfere with growth.
These may include:
Perfectionism
Fear of visibility
Self-doubt
Chronic comparison
Burnout
Unrealistic expectations
Fear of failure
Fear of success
External challenges also exist:
Economic uncertainty
Market competition
Limited resources
Unexpected setbacks
However, many entrepreneurs discover that the most persistent obstacles are internal rather than external. The experiences that create the greatest frustration often point toward areas that require deeper attention and growth.
The Psychology of Tests, Allies, and Enemies
From a Jungian perspective, this stage often activates aspects of the Shadow. The Shadow contains qualities, emotions, and experiences that remain outside conscious awareness or are difficult to acknowledge.
Entrepreneurship may bring forward:
Insecurity
Envy
Vulnerability
Fear
Anger
Self-criticism
These experiences can feel uncomfortable, especially for individuals who are accustomed to being capable, prepared, and successful. Yet shadow material emerges for a reason.
The entrepreneurial journey creates opportunities to encounter previously hidden parts of the self. The goal is not to eliminate these experiences. The goal is to develop a more conscious relationship with them.
Growth becomes possible when we learn to understand these reactions rather than simply fight against them.
Why This Stage Feels Messy
Many entrepreneurs expect progress to be linear. This stage teaches otherwise.
Growth often looks like:
Progress followed by setbacks
Confidence followed by doubt
Momentum followed by stagnation
Clarity followed by confusion
The unpredictability can be frustrating. Yet these fluctuations are not necessarily signs that something is wrong. They are often signs that learning is occurring.
Entrepreneurship rarely unfolds in a straight line.
Instead, it develops through cycles of experimentation, reflection, adjustment, and growth.
What Entrepreneurs Learn Here
The lessons of this stage extend far beyond business skills.
Entrepreneurs often begin developing:
Resilience
Adaptability
Discernment
Emotional regulation
Healthy boundaries
Sustainable decision-making
These capacities become increasingly important as the journey continues. The entrepreneur is not simply building a business. They are developing the psychological foundation needed to navigate future challenges.
Why This Stage Matters
Tests reveal capabilities.
Allies reveal support.
Enemies reveal growth edges.
Together, these experiences help transform an entrepreneur from someone pursuing a business into someone becoming a leader.
This stage teaches that success is not only measured by outcomes. It is also shaped by how entrepreneurs respond to challenges, cultivate relationships, and develop greater self-awareness.
Reflection Questions for Entrepreneurs
What challenge keeps appearing in your entrepreneurial journey?
Who are your most important allies right now?
What internal obstacle creates the greatest friction?
What lesson might your current struggle be teaching you?
How are these experiences shaping who you are becoming?
Reflection can help transform everyday challenges into opportunities for growth and learning.
Transition Toward Stage 7 — Approach to the Innermost Cave
As entrepreneurs gain experience, deeper challenges begin to emerge.
The journey gradually shifts from learning how to navigate the external world toward confronting more personally meaningful fears, vulnerabilities, and uncertainties.
This leads to Stage 7 — Approach to the Innermost Cave, where entrepreneurs prepare to face a challenge that feels especially significant and transformative.
Closing Reflection
The entrepreneurial journey is not shaped solely by success.
It is shaped by the tests that challenge us, the allies who support us, and the obstacles that reveal who we are becoming.
Each encounter offers an opportunity to grow—not only as an entrepreneur, but as a person.
The journey continues.
