Evolve Your Path

Megan Flanagan

For people who've realized the path they were on no longer fits who they're becoming. Evolve Your Path is a podcast about nonlinear careers and portfolio lives — hosted by Megan Flanagan, career coach, business strategist, and ultrarunner. Join us as we explore moments of tension: burnout, reinvention, career pivots, and designing work more intentionally. Through conversations with coaches, founders, and creative leaders, we talk about building sustainable businesses, navigating multiple income streams, and what it takes to evolve your path over time — without losing yourself in the process.

  1. Riding the Waves of Freelance with Emily Hollender

    3. MÄRZ

    Riding the Waves of Freelance with Emily Hollender

    In this episode, Megan hosts Emily Hollender, a marketing and community-building expert, to explore how passions like surfing influence personal well-being and professional success. They dive into strategies for transitioning to freelance work, building authentic client relationships, and navigating the challenges of entrepreneurship with confidence. About Emily: Emily Hollender is a brand marketing and community-building leader with over a decade of experience driving growth at category-defining startups, including Rent the Runway, The Wing, and Tia. She's best known for building and scaling RTR's Campus Ambassador Program, launching The Wing's Digital Membership, and driving Tia's Go-to-Market expansion. Currently, through her fractional marketing practice, Next Wave Marketing, Emily partners with early-stage consumer brands to unlock sustainable, community-led growth. She also teaches the popular Maven course From Full-Time to Fractional: A Step-by-Step Launch Playbook for Senior Leaders, equipping experienced operators with the tools to launch successful independent practices. In this episode: Emily shares her journey from corporate startups to freelance community strategistHow surfing fosters grounding, resilience, and community connectionCommon misconceptions about marketing and how to define your nicheStrategies for acquiring first clients through authentic networkingManaging imposter syndrome and self-doubt as a fractional professionalThe importance of clear scope, outcome alignment, and setting boundariesInsights into creating impactful messaging and evolving your personal brandHow to test new markets and opportunities without overcomplicating brandingPractical tips for overcoming mindset blocks and taking small, actionable stepsThe value of community and relationships in business growth and fulfillmentLinks: About Emily: www.emilyhollender.com / https://www.linkedin.com/in/emily-hollender/ Fractional Practice: www.nextwave.marketing Sign up for Emily's Maven Course: https://maven.com/emily-hollender/full-time-to-fractional?promoCode=EVOLVE25 Promo Code: EVOLVE25 Resources: Blue Crush – Inspiring film about women surfersToxic Grit by Amanda Getz – Navigating a portfolio careerSetting the Table by Danny Meyer – Relationship-focused leadershipOld Girls ClubThis episode offers actionable insights for freelancers, entrepreneurs, and anyone interested in blending personal passions with professional pursuits to craft a fulfilling, resilient career.

    54 Min.
  2. 24. FEB.

    Self-Reflecting in Your Career Transitions with Julia Cohen

    In this episode of the Evolve Your Path podcast, host Megan Flanagan speaks with career coach Julia Cohen about navigating career transitions, identifying personal values, and the challenges of the current job market. Julia shares her non-linear career journey, emphasizing the importance of aligning one's work with personal passions and values. They discuss the significance of self-reflection in career choices, the role of coaching in personal development, and practical strategies for job seekers, including interview preparation and creative approaches to job searching. The conversation highlights the need for patience and kindness during the job search process, as well as the importance of being proactive and resourceful in finding opportunities. Guest Bio: Julia Cohen is a certified career coach with 12 years of experience in operations and product management before transitioning into coaching. She now works with professionals across industries who are navigating what’s next — whether they’re exploring a career pivot, seeking work that better aligns with their values, returning to the workforce after a break, or stepping into a new leadership role. Her goal is to help you gain clarity, rebuild confidence, and take practical steps toward a career that feels fulfilling and sustainable. Chapters: 00:00 Navigating Career Journeys 03:20 Defining Personal Success 06:18 Identifying Values and Interests 09:15 Career Coaching Insights 11:46 Long-Term Career Planning 14:31 Current Job Market Challenges 17:20 Interview Preparation Strategies 20:06 Cutting Through the Noise 22:57 Creative Job Search Strategies 25:33 Final Thoughts and Advice 28:25 Introduction to Evolve Your Path Podcast 28:50 Transitioning and Resources for Growth Connect with Julia: LinkedIn Follow Evolve Your Path: Substack Instagram Apply to join our Slack Community!

    29 Min.
  3. 20. FEB.

    Find Your Poetic State with Bryan Collins

    Join coach Bryan Collins of Poetic State to discover how embracing your unique identity, cultivating vulnerability, and visualizing future success can transform your personal and professional life. In this episode, we explore the power of authenticity, the importance of meaningful connection, and practical frameworks for unsticking yourself in a world full of possibilities. Key topics: The role of authentic branding and messaging in building trust and connectionHow embracing your 'weird' or unconventional qualities fosters greatnessThe metaphor of life as a "space in a hole in the wall" practice for unique identityThe significance of “moon boarding” and visual mood-boarding for envisioning goalsStrategies for identifying when you’re truly stuck and how coaching maintains momentumThe impact of future visualization: acting like your successful selfThe importance of humility, vulnerability, and self-awareness in creative reinventionHow creatives process decision-making amid abundant possibilitiesOvercoming scarcity mindset to attract the right clients and opportunitiesThe benefits of ongoing maintenance and routine in personal developmentResources: Moonboarding — For creating inspired visual goalsFuture Self Visualization Techniques — Practical ways to activate future successBook: Atomic Habits by James Clear — Building habits for routine maintenanceConnect with Bryan: LinkedIn Poetic State - coaching & website Connect with Evolve Your Path: Substack Instagram Slack Channel

    45 Min.
  4. 17. FEB.

    The Future of Work & Going Fractional 101 with Natalie Hoop

    In this episode, Megan Flanagan interviews Natalie Hoop, a leader in the fractional consulting space. They discuss the journey into fractional work, the changing landscape of careers, and the importance of community and networking. Natalie shares her insights on the misconceptions surrounding fractional roles, the reality of finding clients, and the need for individuals to take ownership of their careers. The conversation also touches on the future of work, emphasizing the rise of freelance and fractional opportunities, and the importance of work-life balance. Notable quotes: "Career paths are not linear; embrace change." "You are the CEO of your own career." "Job stability is a myth in today's market." Chapters: 00:00 Introduction to Fractional Leadership 02:52 The Journey into Fractional Work 05:43 Career Evolution and the Changing Job Market 08:59 Redefining Job Stability and Career Ownership 11:58 The Reality of Starting a Fractional Business 14:46 Misconceptions About Fractional Work 18:03 Finding Clients and Building Relationships 20:51 What's Broken in Job Hunting 23:50 The Future of Work: Freelance and Fractional Roles 26:37 Navigating the Shift to Fractional Work 29:52 Personal Growth and Work-Life Balance 32:43 Conclusion and Resources Connect with Natalie: LinkedIn https://www.nataliehoop.com Connect with the Evolve Your Path community: Apply to join the EYP slack community Join our Women in Transition cohort in March Find the podcast blog posts

    41 Min.
  5. 10. FEB.

    Get Past "Stuck" and Say Yes to a Job You Love with Liz Cohen

    In this episode of Evolve Your Path, we welcome Liz Cohen, founder of Lizco Studio, a product design consultancy based in Golden, Colorado. Liz shares her journey from a coffee shop worker in Boston to a UX designer and product manager, revealing the challenges she faced in her early career. Despite her passion for design, Liz often felt misaligned with her roles, leading her to explore various paths until she found her niche in the startup scene. The conversation delves into her decision to leave a stable job and embrace entrepreneurship, highlighting the importance of networking and saying yes to opportunities that arise. As Liz recounts her experiences, she emphasizes the significance of trusting oneself and the value of community support. She discusses the challenges of starting her own business, including the struggle for work-life balance and the need to set boundaries with clients. Liz's story serves as an inspiration for those contemplating a career shift or entrepreneurial venture, encouraging listeners to embrace uncertainty and pursue their passions with confidence. Keywords: entrepreneurship, UX design, product management, career change, startup culture, design consultancy, networking, work-life balance, personal growth Notable quotes: "I always wanted a seat at the table." "I was at the lowest point of my career when I just sort of got pulled out of the trenches by just saying yes to things." "You might think you want a seat at a certain table and then you get to that table and it's not what you thought it was." "Trust yourself; you’ve made it this far, you can keep going." "Say yes to things that you're scared of or that you don't know if you can do." Chapters: 00:00 Welcome and Introduction 02:08 Early Career and Misalignment 10:56 The Decision to Leave 14:42 Moving to Colorado and New Opportunities 15:52 The Reality of Entrepreneurship 26:16 Building Lizco Studio 31:24 Challenges of Running a Business 40:57 Advice for Those in Transition 46:38 Introduction to Evolving Your Path 47:06 Coaching and Community Engagement Connect with Liz: https://www.linkedin.com/in/lizcohen1/ Join our Women in Transition Cohort, launching in March: https://forms.gle/8FJGyqDn2wA7YosD6 Read the latest podcast post: https://www.evolvedpotential.co/blog

    48 Min.
  6. 3. FEB.

    Build a Life and Career On Your Terms with Tomide Awe

    In this episode, we interview Tomide Awe, who shares her journey from a corporate career in management consulting and tech to building a portfolio career on her own terms. Tomide discusses the importance of education, the value of an MBA, and the necessity of questioning traditional career paths. She emphasizes the significance of mental health, the need for ruthless prioritization in managing multiple ventures, and the power of community support. Tomide's mission is to empower women to take control of their lives and live authentically, challenging societal expectations along the way. Keywords: career, entrepreneurship, personal growth, work-life balance, education, coaching, consulting, women empowerment, mental health, portfolio career Takeaways: Tomide's journey reflects the importance of taking things one step at a time. Education can be a tool for personal branding and career shifts. An MBA can be valuable for industry changes but not always necessary. Pushing back against societal expectations is crucial for personal happiness. Mental health should be prioritized over corporate success. Ruthless prioritization is key when managing multiple ventures. Living life on your own terms requires questioning existing beliefs. Discomfort can lead to significant personal growth and change. Building a supportive community is essential for navigating career transitions. Creating a platform for women to take control of their lives is a powerful mission. Chapters: 00:00 Introduction to Tomide Awe's Journey 03:01 Education and Career Path Insights 05:45 Questioning Traditional Paths and Personal Growth 09:02 Navigating Personal and Professional Life Changes 12:04 Rethinking Work and Life Balance 14:55 Challenging Assumptions and Beliefs 17:54 Building a Portfolio Career on Your Own Terms 20:48 Managing Multiple Ventures and Prioritization 23:49 Vision for 'On Your Terms' and Future Aspirations 26:55 Living Life on Your Own Terms Responsibly Connect with Tomide: LinkedIn Amplio Substack: On Your Terms Connect with EYP: Apply to join the Slack community Read the latest blog/podcast post

    47 Min.

Info

For people who've realized the path they were on no longer fits who they're becoming. Evolve Your Path is a podcast about nonlinear careers and portfolio lives — hosted by Megan Flanagan, career coach, business strategist, and ultrarunner. Join us as we explore moments of tension: burnout, reinvention, career pivots, and designing work more intentionally. Through conversations with coaches, founders, and creative leaders, we talk about building sustainable businesses, navigating multiple income streams, and what it takes to evolve your path over time — without losing yourself in the process.