The Hero’s Journey of the Entrepreneur

Written by: Sayre Darling

If you are having some sleepless nights, experiencing dark nights of the soul, and are still leaning into the possibility that the only way forward…that interests you at all…is to start your own business – CONGRATULATIONS! 

I know from experience what it takes to overcome your Fears, Uncertainties and Doubts (FUD), and, still feel the fire in your belly and take on the “hero’s journey” anyway.

Most entrepreneurs have lived some version of the hero’s journey. It is a journey that starts by abandoning the status quo and letting go of “what’s expected” in order to follow their own course, listen to their heart as well as their head, reinvent themselves, and find their own place in the world. 

silhouette of man standing near body of water during golden hour

That dream of following your own path and starting your own business as a solution to your current situation: the need to create “plan B”, the heartfelt desire to serve others, to give voice to your expertise, to become who you always wanted to be, and to have more control and secure your future – releases pent-up energy to push you forward. 

And, it can also get in your way of developing a successful business.

When the passion for the “hero’s journey”, at the core of any entrepreneur’s story, collides with your FUD (fears, uncertainties and doubts), you end up putting one foot on the gas and the other on the brakes at the same time. This, in part, contributes to more than half of the 500 million business start-ups created every year to failure.

The very journey that leads an entrepreneur forward can also be what gets in the way. Here are three critical points to understand how to minimize the collision between your hero’s journey and creating a successful business.

  1. Understanding the Hero’s Journey is Important – Mostly Just to You

Your history creates the context for your current story/perspective. And, unless you can move forward with no regrets, or personal baggage, you dilute your opportunities to create a valuable brand and inventive marketing and sales strategies because a part of you is still stuck in the past. Without thinking about it, the story about your new business that you share with your friends, colleagues and prospects contains some facts (and fiction) about your previous career, past accomplishments, and why you are doing something different. 

Trying to explain or justify your past as a rationale for your new business isn’t helpful, and doesn’t work. You can’t reclaim the past in the present or the future. 

Whatever your journey is, it is very important for you to remember at times when you get lost on your hero’s journey; but it’s important just to you. For others, your past is just something that just gets in the way of helping them alleviate their pain, save them time or, money or solve their problem. Where you start your story impacts your ability to either stay in conversation about what you are trying to create or get lost in a monologue about your past. So leave the past behind you.

2. Beginnings are Difficult: Your Response Can Make it More or Less Difficult

Beginning anything new is difficult, and, as author Patrick O’Neill’s describes in his book, “The Only Certain Freedom, the Transformative Journey of the Entrepreneur” life in a start-up is also chaotic.

Understanding this will help you manage your expectations, and give you the opportunity to respond, versus react to the chaos. Whether you react to everything that occurs and exhaust yourself in riding an emotional roller coaster, or you decide to respond, and meet it all as an opportunity to learn and grow, can help you challenge that can help weather the ups and downs as an entrepreneur. 

When we see the future as a friend and not a force bent on destroying us, we meet it with optimism. Along the way, amongst the chaos, the starts and stops, emotions, sleepless nights, and 1,000 virtual coffee meetings – you will find the next step to building your business.

You’ll also be better prepared for the entrepreneurial journey when you remember that life events continue to occur during this time as well. The trick is be resilient enough to live at the edge of tension created by building something new, creating a path forward – at times pulling ideas out of thin air, while continuing to make your life work – live in the present, pay the bills, and maintain relationships, often for much longer than you imagined?

3. As Much As You Are Focused on the Destination, Don’t Forget, It’s About the Journey

And when your hero’s journey gets long, doesn’t generate the response you want or the money you need on the schedule you need it, keep this in mind: In exchange for working for someone else, for the entrepreneur, it’s always about adjusting to the hero’s journey. Here are some tools you can count on to aid you on your own hero’s journey:

  • Answer the call
  • Befriend the risk
  • Trust yourself
  • Commit (No matter what)
  • Place meaning before money
  • Defeat the self-critic within you
  • Be the fool – have a vision beyond the current reality
  • Ask for help
  • Disrupt your thinking
  • Enjoy your freedom

For more information about the hero’s journey, check out Patrick O’Neill’s book, “The Only Certain Freedom, the Transformative Journey of the Entrepreneur” © 2018, Thunder Mountain, Toronto, (Only 146 pages, and available at

About the author:

Sayre Darling

Sayre Darling helps shift business owner’s perspectives from saying what they want to say, to figuring out what they need to say in order to be heard. As a small business owner for more than 25 years, Sayre has developed an approach to creating strategic, integrated and results-oriented external and internal marketing and communication programs uniquely suited to small business owners. 

Sayre has a Master’s in Business Communications (MBA with a communications focus) from the

University of Saint Thomas, Minneapolis, Bachelors of Arts in Journalism from the University of Nebraska-Lincoln, and she received her accreditation as a life coach from The Hudson Institute, Santa Barbara, Calif.

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