Embracing Life’s Pivots & Facing the Unknown (Season 2 Ep. 6)

On the show, Jess catches up with her dear friend Afenya Montgomery, founder and CEO of The iCAN Collective, which is a creative space in Chicago designed for coworking, community and content creation for black women. Afenya and Jess giggle and laugh a lot in this episode just catching up and sharing stories about how they feel like lifetimes have gone by since they first met in 2019. Spoiler alert, they do talk about how they've never actually met in person yet they've been each other's Instagram hype girls for years.

Afenya shares her story of how she made the leap into entrepreneurship after making the hard decision to leave a career that she really loved. They talk about having faith that you always land on your feet, Afenya’s failing forward moments and a lot more in between. As you listen we hope it sparks joyful moments as you think about catching up with your old friend and reminiscing on how far you both have come.

What can you expect from this episode:

  • [4:02 - 7:00] Afenya and Jess talk about how they met in 2019 and how amazing it has been seeing each other grow even from afar. Afenya dives into what she imagined for herself growing up. She shares the story on how she transitioned and grew in the nursing and healthcare field, and the spark that r steered her toward the diversity and inclusion space.

  • [7:24 - 11:37] Jess and Afenya highlight their similarities of having a dream to move to New York City to work in fashion. We get to hear the details on Afenya’s early passion for the fashion industry and how that changed after learning more about herself. Jess resonates with Afenya’s story of when she was in fashion PR and working in the restaurants industry. 

  • [14:49- 23:38] We get to hear Afenya and Jess bring to light the power of being a quiet force when it comes to being an extroverted introvert. Afenya talks about how understanding herself more helped her in her entrepreneurship journey. She also talks about what it was like to leave an industry like nursing that was so rewarding to her. 

  • [23:38 - 34:09] Afenya shares what The iCAN Collective is and what officially made her decide to take the jump on launching her business. Afenya breaks down for us how she was emotionally and financially when starting The iCAN Collective. She dives into how her idea came to be in 2016, that she got to implement her coworking space for events (pre-pandemic) and how her organization's purpose evolved with time. She talks about the support from her coach at the time that helped her narrow her focus to helping women. 

  • [34:50 - 39:43] We hear about how Afenya diversifies revenue for her space and the effects she experienced when COVID hit. She shares how she overcame the pandemic and grew during a time of uncertainty. She shares how her introverted side took over and she leveraged the need for more intimate events after so many shutdowns in Chicago. 

  • [39:49 - 41:33] Lastly, Afenya answers Jess’ question on what she would say  when writing a love letter to her past self knowing she was going to get into serious unknowns. Afenya highlights the value of failing forward and how embracing that has brought so much to her life, especially when she stepped into the unknown.

Where can you find Afenya and iCAN Collective : 

The iCAN Collective

[email protected]

IG theicancollective

FB The iCan Collective

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Marketing Funnel: The Nurture Phase

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Co-founder Adventures & Finding Solutions for Moms Everywhere (Season 2 Ep. 5)