COURAGE: Melissa Kiguwa
The Poetry of Entrepreneurship

It’s Women’s History Month, and we’re celebrating it by speaking with women entrepreneurs who are making history right now. Each of the women we’ve interviewed represents one of Ascentim’s values. We’re kicking the series off with COURAGE

I define courage as going outside your comfort zone and making bold moves, even when it might feel uncomfortable or scary. When there’s no guarantee of success, you push forward anyway. For me, Melissa Kiguwa is the very definition of a courageous woman making history

Meet Melissa Kiguwa


Melissa is the host of The Idealist Podcast and the founder of break*through, a next-generation platform that offers coaching, community, and collective wisdom from female executive coaches, investors, board members, entrepreneurs, and senior executives. I sat down with Melissa to learn why the self-described ‘unlikely entrepreneur’ launched her latest venture and what courage means to her. 

She got her start in journalism with her own radio and television shows that took her all over the world. For most of her life, Melissa also considered herself a poet. She has since decided that entrepreneurship is its own form of poetry. “I do love the complexity in that space,” she told me. “It’s just not necessarily on the page anymore.” 

During our conversation, Melissa reminded me of a funny thing about courage: you might not always feel courageous while doing it. In her words, you’re going down a path and you know that your idea might not be normal, it might be different. And there might be some red flags going up around you. Maybe your family doesn’t understand what you’re doing. Or you’re worried about the market, and whether someone’s already cornered your idea. There are so many things you need to ‘shush’ in order to keep going, get it done, and move forward. 

It might not feel courageous at all. But it absolutely looks like courage to anyone watching you. 

Melissa lights up when she talks about her latest and greatest adventure, break*through, which Ascentim is proud to be a part of. The idea came out of the significant amount of time Melissa spent in the female founder space and the frenetic, chaotic energy she felt coming out of it. As they were all wound up in trying to build their things, she wondered if there wasn’t a better, more compassionate way to do this: for themselves, for their teams, and for what they were building. 

Melissa previously owned another business; however, after bringing on the wrong partner, Melissa decided to wind down that business. She didn’t let that derail her, instead, she found the courage to make a different decision and launched break*through.

Listen as Melissa shares how she made a courageous pivot to what brings her joy.
Courage to Break Through

Melissa says, “As women, if we’re already going up against the status quo, if we’re already entering into spaces that aren’t necessarily friendly toward us, then we should take more liberties than we do. We should be able to be a bit more audacious than we are. What happens if we go outside the lines? We need a place to play with that idea.” 

break*through is that place. It was designed for women who have the audacity to want to explore how far they can stretch themselves to get to new levels of creativity and vision. Melissa’s vision is to help women see beyond where they are today and give them the staying power not to leave. She wants to support you and change the game for those around you. 

We talked about the importance of being ‘in the room’ – of trailblazers like Maxine Waters and Ruth Bader Ginsburg, who showed us how much it matters to be there in those spaces. “We’ve got to get in there,” Melissa says. “And we’ve got to stay.” 

To be clear, neither of us believes that ‘staying’ means a specific company, title, etc. You should never feel like you have to stay somewhere you are not valued or appreciated. Instead, Melissa describes staying as being able to flourish and actualize your own potential to its utmost. 

The Journal by Melissa Kiguwa

For anyone who needs a little help to get there, stay there, or flourish, Melissa invites you to email her directly – or you can check out her book, The*Journal. It’s a reflection tool that acts as a safe space to realize your own truth without reservations, without any concern for what someone else might think. Moreover, I found it an excellent map for the journey to self-discovery.

Melissa’s Advice

I asked Melissa what she would say to other female entrepreneurs out there trying to make it, and this is it: “If you have the courage to go forth and build something for yourself, and you have ideas about how that should look, I think that in and of itself is a thing of courage. I see the data all day long, and it’s pretty dismal for women, especially women of color. Not just in starting, but also in retaining the money. But courage is inevitable when you’re trying to make a life or a path for yourself.”

Entrepreneurship as Poetry

As our conversation came to a close, I couldn’t resist asking Melissa one last question about the poetry of entrepreneurship. What poem are you writing with break*through? 

“We are like an old love sonnet… a love sonnet to women and our power and all the things we can achieve in the world.” 

What greater inspiration could we have asked for during Women’s History Month? Click here to watch the full interview with Melissa.

Connect with Melissa

Lisa L. Baker - Certified Personal, Career, Success and Life Coach

Lisa L. Baker is a professional life coach, career strategist, and keynote speaker. Lisa is the founder of Ascentim – a Maryland-based coaching practice that utilizes a unique G.R.O.W. process to help clients gain clarity, realize new possibilities, overcome obstacles, and win at life. Lisa shows high-performing professionals how to Level Up and Live the Life of Their Dreams.

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