Interested in starting your own entrepreneurial journey in personal development but unsure what to expect? Then read up on our interview with Caitlin Drago, founder of Inspire Improv and Coaching Inc., located in Macedon, NY, USA.

What's your business, and who are your customers?

My company is Inspire Improv and Coaching Inc. I work with organizations to create cultures of empathy, creativity, and trust, beginning with how they communicate and connect. As a certified leadership coach and trained actor, I facilitate programs (in-person and virtual) that focus on communication, collaboration, and teamwork, using improvisation as a platform for interactive learning.

Tell us about yourself

I started as an actor, which taught me to be present, self-aware, empathetic, and prioritize connection with others. Improv taught me to listen and deal with the unexpected in positive ways. I knew that these were skills that everyone could benefit from, not just actors/improvisers, and I wanted to share that knowledge! I am motivated every day by the power that, at a base level, improv has to teach us to listen to and value one another.

What's your biggest accomplishment as a business owner?

Asking teams to do improv together, especially when it is over Zoom, is a big ask. I pride myself on my ability to create a space where people feel safe and supported as they step out of their comfort zone and try something new, all while learning, laughing, and bonding with one another.

What's one of the hardest things that come with being a business owner?

Covid? I wanted to keep it out of this, but it’s the truth, and I know that I sit in a position of privilege in so many ways. Being a business owner with two kids (6 and 2) during a global pandemic has not been easy. My partner and I have had to take turns focusing on our respective businesses and caring for our family. I’ve had to give myself grace when my “big plans” for 2020 didn’t quite come to fruition because of something I had no control over. Being a business owner means pivoting and re-inventing while staying true to your mission and those you serve, even if it means letting go of your “big plans.”

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Do something each day that energizes and inspires you.
  2. Learn when to delegate, especially if you are a solopreneur. There are things you could “figure out,” but there is a line between spending a week “figuring it out” when you could have paid an expert to do it (a lot better) in an hour.
  3. Make marketing a priority, even if it is simply reaching out to one contact in a day. It is easy to get caught up delivering work and neglect to continue to plant seeds. Making marketing a priority ensures that once you are done with one project, there is another behind it.

Is there anything else you'd like to share?

Get yourself into an improv class; if it scares you, know that improv isn’t about being “funny,” the goals are to listen, be present and create together. Because of the rules (Yes! There are rules!), you will laugh together! Research shows that laughing together builds trust, helps us deal with stress, and allows for more creative thinking. Who couldn’t use more of that!?

Where can people find you and your business?


If you like what you've read here and have your own story as a solopreneur that you'd like to share, then email; we'd love to feature your journey on these pages.

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