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3 Psychological Challenges Entrepreneurs Face, And How To Turn Them Into Strengths


Entrepreneurship can be an amazing vehicle for inner work.

Being an entrepreneur means bringing something into the world—something that’s an expression of who you are. As a result, companies often take on the personalities of their founders—for better or, as numerous documentaries and biopics now show, for worse.

Just like a company, a personality/ego that grows out of control will eventually implode. 

For entrepreneurs, self-reflection is the guardrail that keeps business growth and personal growth in parallel.

Growing a business will take you to the lightest and darkest parts of your psychology. Most of us instinctively resist going to the latter. But the more willingly you shine a light into your weaknesses and blind spots, the more developed a human—and leader—you’ll become.

3 key psychological areas for entrepreneurs to be aware of:

1. The primal nature of entrepreneurship

Entrepreneurship is a primal act: You eat what you kill. If your business does well, you do well, and so it’s tempting to view your business as you. This mentality activates our primal instincts for self-preservation.

  • Benefit: Drive. Nothing is more motivating than a personal investment, and no investment is more personal than an entrepreneur toward their business.
  • Risk: Personal investment easily becomes emotional investment. When it does, your quality of life is tied to the performance of your company. You get too high when the company succeeds, and too low when the company underperforms.
  • Best practice: Consciously decouple your identity from the business. The success or failure of any venture is not a reflection of its founder. Try to view your current project the way you will in retrospect, as one chapter in a much larger story.

2. Family dynamics

You know when you go home for Thanksgiving, and you find yourself falling back into the role you played in your family growing up? Family dynamics are deeply embedded in all of us—primarily with our caregivers (usually parents) and secondarily with our siblings.

Those dynamics often play out within companies, especially around hiring. We might have biases toward people that unconsciously remind us of our parents or siblings and present familiar dynamics.

  • Benefit: The roles we play in families often contribute to our natural strengths. Growing up, I was expected to do everything myself, not ask for help, and be self-sufficient. These are some of the foundational tools of being a CEO.
  • Risk: Family dynamics come with biases that compromise our judgment. If you hire people because they subconsciously remind you of parent or sibling relationships, you may end up hiring the wrong people.
  • Best practice: First, establish clear, objective hiring metrics. Be sure your leadership team has a common understanding of what they are. Privately, complement this with inner work to understand how family dynamics may give you biases and blind spots.

3. Primary strengths and shadow weaknesses

Psychologist Carl Jung pioneered the concept of the “shadow,” the part(s) of ourselves that we can’t see. 

Entrepreneurs’ shadows are on full display. For every strength that makes you a natural founder, good leader, critical thinker, you have a shadow weakness that tends to go unacknowledged. 

  • Benefit: Our primary strengths are the qualities we lean on to weather the storms of entrepreneurship. Growing up, my family moved every two to four years, so I became very adaptable. Especially in entrepreneurship, having the ability to pivot is a key strength.
  • Risk: But there’s a flip side to that strength. Beyond that two to four-year mark, I tend to get uncomfortable. The shadow of my natural adaptability is a fear of commitment and consistency—not such a good thing for the long-term process of bringing a business to life. 
  • Best practice: Therapy. Full-stop. The very nature of shadows is that we can’t see them without help. There’s a reason why millennials are the “therapy generation”: Therapy isn’t just about working through crises, it’s about seeing the full image of who you are.

Bottom line: Your inner work and entrepreneurial journey need to run in parallel. Whether a specific venture succeeds or fails matters less than whether you grow as a person. Equating success with superiority is just as dangerous as equating failure with inferiority. Personal growth is the stablest foundation for business growth.

Founder and CEO, Upscribe | Reformed Politico | Proud Immigrant

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