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Connecting Solo-Preneurs: Michelle Calcagni, Founder of Lady Boss Collective

Published on 01/23/2020

You are the Founder of Lady Boss Collective, which brings women solo-preneurs together for support, guidance, and inspiration. What need did you see that you were trying to fulfill?

It started with my own experience as an entrepreneur. Within the first couple of months, I realized that although I love many aspects of being on my own, it can be incredibly isolating. You need a group of champions around you who understand what you’re experiencing and give you the companionship, insight, and encouragement that powers your success (professionally and personally). Beyond that, I wanted to do something that brings women together in a positive context – there’s nothing more powerful than women standing together to create a better world. It’s truly awe-inspiring.

Who is a good candidate for Lady Boss Collective and how does membership work?

The Members who get the most from the experience combine key attributes (fewer than 10 employees, primary owner, etc.) with a commitment to making time to engage at our monthly in-person meet-ups and on our online forums. More than anything, Members agree to a shared set of responsibilities that create environments full of authenticity, open-mindedness and empathy. You can read more about our Member Requirements and Member Responsibilities on our website. Our first Members provided great perspective so we could be sure to get these cornerstones right.

Membership is based on small (6-8 women) cohorts that connect in person and online. Lady Boss Collective curates the groups and provides a wide range of tools to encourage conversation and share ideas. Each cohort is led by a Member, which creates an environment that balances mutual sharing with a focus on creating value for the time that is invested.  Beyond the cohorts, we are planning special events, online tool access, Member discounts and other resources.


Can you share one or two examples of women who have participated in Lady Boss Collective and how it has helped them?

Absolutely – just look at the testimonials on our website! What I love is that the conversations at meetups vary so much that there is always something new to learn and share – and everyone can take different learnings from a single conversation. We’ve talked about business topics as straightforward as creating a social media plan or updating your LinkedIn profiles, and have also gone deeper with conversations about reluctance around self-promotion, the prevalence of imposter syndrome and how to know when you need to return to a “day job.” I believe that at its core, Lady Boss reminds Members that your entrepreneurial journey isn’t a solo one and you have an army of caring people on your side who want you to be happy and fulfilled in your work.


What’s your best advice to women solo-preneurs?

Invest time and energy in understanding what makes you happy and how you define success. Sometimes we forget that these things change over time and we miss opportunities to stretch ourselves, to try new things, or to celebrate what we’re already doing. I know I’ve made that mistake myself and am glad I have friends and colleagues to remind me when I’ve gone off-path! I know this work isn’t always easy, especially if it brings new ideas to light or means letting go of long-held ideas, but once you have this clarity, you’ll be amazed by the army of wonderful people and experiences that will become part of your journey and will help you sustain your momentum as you move forward.


What are some of your favorite resources for women solo-preneurs?

Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships by Marshall Rosenberg
Life Reimagined: The Science, Art, and Opportunity of Midlife by Barbara Bradley Hagerty
Good and Mad: The Revolutionary Power of Women’s Anger by Rebecca Traister
The Essential Calvin and Hobbes: a Calvin and Hobbes Treasury (my go-to for distraction)

Your Professional Decline Is Coming (Much) Sooner Than You Think
Women Over 50

Unf*ck Your Brain
Freakonomics Radio
Dolly Parton’s America

IN Balance Chicago Women’s Network (Indiana University alumnae but similar options are available for many universities)

Headspace (meditation)
Flipboard (easy access to a wide range of content)
YouTube (for at-home yoga)

The bullet journal is the best organizational tool I’ve found
The Happiness Test


Connect with Michelle Calcagni:
Email: Michelle@ladybosscollective.org
Website: www.ladybosscollective.org
Instagram: @lady_boss_collective
LinkedIn (personal)
LinkedIn (Lady Boss Collective)


Michelle’s career includes a wide range of business and philanthropic activities, all of which came together when she created Lady Boss Collective in 2017. This mission-driven organization brings women entrepreneurs together for support, guidance and inspiration. Inspired by her own experience, Michelle tested the Lady Boss Collective concept for over two years before launching the organization to the public in fall 2019. By creating this unique community, Michelle combines her professional experience with a passion for connecting women around the world so they can support each other’s success.

Michelle’s background includes everything from start-up firms to publicly traded Fortune 200 public companies to non-profit organizations, where she has a proven track record of successfully developing and implementing integrated marketing, communications and business strategies that drive results. Organizational effectiveness has also been a focus, founded in Michelle’s work through multiple reorganization, transformation and mergers/acquisition projects. She has a unique understanding of the global marketplace, having served in multiple global leadership roles and as an expatriate in Europe, Asia and South America.

In 2016, after a successful career primarily spent with publicly traded companies, Michelle decided to change her path by creating PhoneBox Group. This multi-discipline business consultancy leverages her broad global network to bring projects to life for small- and medium-sized businesses in the US, Europe and Asia. Going from leadership roles in Fortune 500 companies to leading a small business has allowed her to shape an organization that reflects her values and her commitment to working with women-owned businesses as clients or as partners.

Michelle balances her professional activities with a strong commitment to giving back. She is active in the Chicago community, where she served as a Board Member for the Career Transitions Center of Chicago, is a member of Indiana University’s IN Balance Women’s Network planning committee and serves as a Supermentor for the Good Food Accelerator. Michelle is also an experienced public speaker and instructor, sharing her experiences and insights with audiences in the United States and abroad.

HeleneTStelian Musing
I’m Hélène Stelian, the Midlife Mentor with a passion for facilitating personal development in women 40+. Through my THRIVE Courses, I help introspective, curious, action-oriented women 40+ deepen their journeys of self-discovery and growth—and create their next chapter with courage and intention.



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