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The Great Reboot

“…when you slowly begin to believe and understand your inherent worth, rest becomes possible in many ways.” ― Tricia Hersey, Rest Is Resistance: A Manifesto

For many, founding and running a business (or working at a scaling startup) puts their life on full throttle. Big sacrifices are made in the name of mission statements and in the name of promises of big returns. Often these sacrifices take a toll on our health, our relationships, and our mental well-being. When we sign up for the entrepreneurial roller coaster, there’s as much foreboding as there is excitement. It may be a wild ride, yet the specific twists and turns we have yet to discover for ourselves. Yet, this way to ride out entrepreneurship is just one ride in the work/life amusement park. Sometimes we don’t realize that we can choose to ride the rollercoaster of entrepreneurship; it’s an option, not a requirement. 

Savvy folks wonder about how to do the ride more sustainably. Perhaps, even with a sense of wholeness in one’s life. Jean Smart, founder of Penelope, opens up her conversation with Jerry with a wish for more joy. “How can I be and live differently in regard to my work?” she wonders. What does it take to have more fortitude and savor the wins along the way on the entrepreneur’s journey? 

When you boarded the rollercoaster of entrepreneurship, what is it that you signed up for? What did you leave behind? What did you assume about the ride you chose? How did your assumptions and beliefs about work influence your choosing? Looking at things now: What or how might you choose differently?

When we move fastly and furiously into the loops and twists of the entrepreneurial journey, we can lose ourselves in the ride if we’re not careful. All too often, the choice to board the roller coaster is made from a place of drive or need that isn’t entirely aligned with our truest self. Until we come into our wholeness, and look at our choice from that place, it’s easier for us to be manipulated by our internalized parts that drive us against our truest self and desires. 

The startup playbook often feels to folks like a model of doing more, faster, and faster. No time for rest. Yet, the alternative playbook is also available to us. It asks: How would you like to be in relationship to this entrepreneurial adventure? What do you know about how you like to work best? What supports you in feeling your aliveness moment to moment, and day to day? How do you manage your energy? What do healthy interpersonal relationships look and feel like for you? What do you need to be present for this work and for your life? 

“Presence isn’t a routine in our lives,” notes Rick Rubin. “It’s a way of calling ourselves back to another way of being in the world by opening up to our senses and tuning into what we feel.” 

In her grand manifesto, Rest is Resistance, author and founder of The Nap Ministry, Tricia Hersey reminds us that “Justice looks like space to rest.” Her’s is a manifesto for another way of being in the world in which we know our worth and know we are worthy of rest for our own well-being and for the well-being (and longevity) of our work in the world. 

What would be different if you approached your work choices from a place grounded in a sense of self-worth? How many of the choices made around your job, company, or career are based on a belief that you are ‘not enough’ or valuable outside of your accomplishments and bank accounts?

At Reboot, we believe that in our work lies the possibility of the full realization of human potential. Work doesn’t have to destroy us. Work can be the way we achieve our fullest selves.

 “You were not just born to center your entire existence on work and labor,” Hersey tells us. “You were born to heal, to grow, to be of service to yourself and community, to practice, to experiment, to create, to have space, to dream, and to connect.” 

Talk about a great reboot on how we consider work within the scope of our whole life, and how that perspective can take us off the roller coaster. No one worries about the business quite the way a founder does. Yet, as founders we can decide how we’d like to show up for our entrepreneurial endeavors. 

Consider these questions for reflection:

  • What are the highs and lows of your entrepreneurial journey?
  • How do you manage the emotional ups and downs of entrepreneurship?
  • What is your purpose in entrepreneurship?
  • How do you stay focused on your purpose when things get tough?
  • What are your responsibilities as a leader?
  • How do you represent your community or identity in your work?
  • How do you take a step back and gain perspective on the rollercoaster of entrepreneurship?
  • What advice would you give to other entrepreneurs who are feeling burnt out?


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