Dig Your Heels In
Business conversations for professionals who build on their own terms.
Dig Your Heels In is a business podcast for professionals who resist shortcuts and build careers and companies on their own terms. Episodes cover leadership, entrepreneurship, and the decisions that define long-term professional success. The channel speaks directly to B2B practitioners who value substance over speed.
Women leaders overcome doubt to reshape male-dominated industries
Nine episodes showcase female executives, founders, and innovators across tech, healthcare, construction, and manufacturing who share how mentorship, intentional storytelling, and visibility drive career momentum in traditionally male spaces.
Dig Your Heels In argues that imposter syndrome and gender imbalance in technical and industrial fields are surmountable through mentorship, intentional exposure, and deliberate narrative work. The channel backs this belief by featuring named women leaders who explicitly describe how these mechanisms—from Megan MacDonald's solid mentorship at Hello Alice to Amy Czuchlewski's decision to speak up in tech—enabled them to move past self-doubt and advance.
Drawn from Dig Your Heels In: A Working Women’s Series wi… and 2 more →
“The best way to solve challenges in healthcare is working in systems.”
YiDing Yu, CMO at Olive
By the numbers
What the channel argues
Who and what shows up
Megan MacDonald
Chief Strategy Officer, Hello Alice
Describes how mentorship overcame imposter syndrome and advanced her to C-suite at a female-led company.
YiDing Yu
CMO at Olive, practicing physician, published researcher, serial entrepreneur
Demonstrates how combining medicine, politics, and technology creates career leverage to solve systemic healthcare challenges.
Amy Czuchlewski
Computer Engineer, University of Michigan graduate
Articulates how early exposure to engineering prevented internalization of gender as a barrier and motivated speaking up in tech.
Allison Grealis
President and Founder, Women in Manufacturing Association
Leverages 22 years of trade association experience to address systemic gender imbalance in manufacturing through organizational advocacy.
Jolene Delisle
Founder and Head Creative, The Working Assembly
Pioneered one-on-one consulting for female founders using storytelling to help brands refine and market themselves across life cycles.
Questions this channel answers
How do female leaders overcome imposter syndrome?
Solid mentorship and faith-building in one's education, experience, and accomplishments help women leaders move past doubt, as Megan MacDonald experienced at Hello Alice.
Dig Your Heels In: A Working Women’s Series with Megan M… →How can women bring diverse interests into a single career?
YiDing Yu combined her interests in medicine, politics, and technology by recognizing that solving systemic healthcare challenges required working in technology-enabled systems.
Dig Your Heels In: A Working Woman’s Series with YiDing … →How does early exposure shape women's relationship to male-dominated fields?
Amy Czuchlewski's early exposure to engineering prevented her from realizing women were in the minority, blinding her from the gender hurdle in her future career.
Dig Your Heels In: A Working Woman’s Series with Amy Czu… →Why is storytelling critical for female founders?
Jolene Delisle recognized that brands must refine, synthesize, and market themselves through storytelling across their life cycles, which she built into The Working Assembly's consulting model for female founders.
Dig Your Heels In: A Working Woman’s Series with Jolene … →What organizational approaches can address gender imbalance in male-dominated industries?
Allison Grealis founded the Women in Manufacturing Association to support, promote, and inspire women in a male-dominated sector, applying 22 years of trade association expertise.
Dig Your Heels In: A Working Woman’s Series with Allison… →Best place to start
Dig Your Heels In: A Working Women’s Series with Megan MacDonaldIntroduces the channel's core theme: how mentorship overcomes imposter syndrome and enables advancement to C-suite roles.
Dig Your Heels In: A Working Woman’s Series with Allison GrealisShows how deep industry experience becomes a tool for systemic change in male-dominated sectors through organized advocacy.Industry context
Imposter syndrome disproportionately affects capable professionals and founders, particularly those from underrepresented groups. Mentorship programs have emerged as a structured approach to address these self-doubt barriers and build confidence in career advancement.
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