A special thank you to our esteemed panelists, Gale Wilkinson, Lori Igleski and Kate Bensen for sharing their career paths and transitions in cultivating an enriching and impactful portfolio life that aligns with their values and purpose.
Too often, our identities become narrowly defined by what we do for work, while the passions, interests, and values that truly inspire us get pushed to the margins. That’s why cultivating a portfolio life, one that’s intentionally diversified across personal and professional dimensions, is so powerful.
It is a conversation you will not want to miss, as Kate, Gale and Lori share their personal journeys, pivotal moments, lessons learned, and practical takeaways that reshaped how they define success and fulfillment in their lives.
We are sharing key takeaways in our recap below, but there is much more to learn from the recording.
KEY TAKEAWAYS
Creating Your Portfolio Life
Whether you view them as pillars or pieces of your pies, the components of your portfolio life can include:
- Vocational/professional, income generating
- Educational learning
- Spiritual growth
- Avocation: recreation, play, health and wellness
- Relationships: family and friends, community
- Philanthropy/giving back: time and talent donations
Small Steps To Move Forward
In the midst of uncertainty and change, pause and be open to the new possibilities that this might create for you versus getting stuck with what was and is no longer. Learn to say no so you can say yes to what matters. And avoid the negative self-talk, follow your intuition and give yourself permission to do something for yourself versus others!
And as Lori Igleski shared, “Use joy as a primary filter between a yes and a no for a new opportunity.”
This is not a solo journey.
The decisions will be yours to make, and this journey can feel lonely. However, there are many people, especially women, who often have these same feelings, as we have a broader sense of self and seek fulfillment. Lean on your network and stay in community with others to work through this journey.
Your portfolio evolves.
What you say “yes” to and how you spend your time should be in alignment with your purpose. It’s essential to pause and reflect: Does the way you invest your energy, attention, and resources truly honor your core values and the life you’re meant to live?
Use your head, heart and gut as you think through to make decisions. Just because you can do something doesn’t mean you should do something.
Be intentional.
Having a portfolio life is a mindset. You can always cultivate your portfolio life – even before you are in a place to fully execute it. And a portfolio life is not just for the “lucky to do so.” Live your life today so you can live it the way you want to tomorrow when some of your responsibilities shift and you have space to do so. This includes being intentional with your finances to support these portfolio life choices that can bring you greater joy and fulfill your legacy.
Be ambitious about everything in your life not just your career!
ADDITIONAL RESOURCES
Books
The Middlescence Manifesto: Igniting the passion of midlife, by Barbara Waxman
Portfolio Life: The New Path to Work, Purpose, and Passion After 50: David Corbett
The Portfolio Life, by Christina Wallace
The Second Mountain: The Quest for a Moral Life, by David Brooks
Podcasts
You can also find interviews, wherever you get your podcasts, with any of the authors about their books that were identified in our program.
About Our Speakers
Kate Bensen is an independent director for MicroMetl Corporation, the leading USA manufacturer of HVAC accessories and equipment. Prior to that, Kate served as CEO of The Chicago Network for 10 years, where she led the transformation of the organization to one that successfully empowers women to lead. Prior to the Network, Kate led strategy for Conlon Public Strategies and was a corporate and public finance partner at the law firm Schiff Hardin LLP (now known as ArentFox Schiff).
Kate is a member of the board of the Admiral at the Lake, a leading CCRC in Chicago, where she chairs the Governance Committee and also chairs the Governance Committee at the Private Directors Association Chicago Chapter. She is on the board of Chikaming Open Lands, a land conservation organization and a Co-Coordinator for Interfaith Action of Southwest Michigan.
Kate is a member of the Commercial Club, Economic Club, Graham School Council (University of Chicago) and the Chicago Innovation Advisory Board. She is also a judge for the Chicago Innovation Awards. Her board work focuses on governance and leadership succession. Kate has received the Chicago Women in Innovation Award, the inaugural 2020 Women on Boards Champion of Women Award and the University of Chicago’s Alumni Service Medal.
Kate holds an AB in economics from the University of Chicago and a JD from Loyola University of Chicago School of Law.
LinkedIn: http://www.linkedin.com/in/katebensen
Gale Wilkinson is the founder and Managing Partner at VITALIZE, a seed stage venture capital fund invested in transformative WorkTech software. Previously, Wilkinson founded IrishAngels, one of the largest angel groups in the world. Gale has led over $80M in early-stage deals across 150+ portfolio companies and is also an active angel investor.
Wilkinson is the author of Samson’s Story – A Tale of Pet Loss Grief, Love, Hope, and Magic. She is also an animal communicator where she telepathically speaks with animals to help their owners learn more about their pets’ wants and needs. She recently started a dog rescue called Gale Loves Dogs and has saved seven dogs so far with aspirations to re-imagine ways to fix animal over-population in shelters. To fund this vision, Wilkinson is opening a short-term rental property near Nashville where friends and colleagues can connect in a nature setting just 30 minutes outside the city.
Wilkinson received a BBA with honors from Notre Dame and an MBA with honors from the University of Chicago Booth School of Business. Wilkinson enjoys public speaking, design, teaching, and connecting. Her inspirations include energy work, vintage and antique pieces, dogs, horses, and nature. You can find her on YouTube, Instagram, TikTok, or Facebook @galelovesdogs. She lives in Nashville and Chicago with her husband and three dogs, Murphy, Lark, and Baby NoNo.
LinkedIn: https://www.linkedin.com/in/galevc/
Lori Igleski is the Founder of Heart-Led Ventures LLC, and a sought-after strategic advisor to C-Suite leaders facing transformational change. Over her three-decade career in financial services, she led over 35 significant merger & acquisition integrations, business reorganizations, significant process changes and technology implementations impacting hundreds of thousands of employees and millions of customers. She has led process and technology transformations that improved risk visibility, streamlined operational processes, and enabled scalable back-office efficiency. A strong risk manager, sales team leader and data analytics champion; Lori is well positioned to lead change in a variety of complex situations.
Over the past fifteen years, Lori has started two independent consulting businesses focused on strategic advisory and transformational change. Through her firm, she also served as the fractional Chief Credit and Administrative Officer for a community bank struggling under a number of regulatory orders. Lori helped transform the risk management culture and operational processes resulting in significant improved business results and ultimately one of the highest merger premiums paid in a community bank transaction. Today Lori advises CEO’s on a variety of Go To Market strategies, workplace issues and using company-generated data to improve decision-making and business insights.
In addition to her consulting practice Lori serves on the board of directors of SmartBiz Bank N.A., a former Fintech who originates SBA loans across the country. She also provides executive advisory support to C-Suite executives in transition and serves on other non-profit boards.
Lori is a frequent panelist and speaker advocating for women leaders, entrepreneurs and investors. She was recognized by Crain’s Chicago Business as a Notable Woman in Commercial Banking in 2018. She is a 2003 Leadership Greater Chicago Fellow.
LinkedIn: https://www.linkedin.com/in/heartledventures/
Please let us know if you would like to have a conversation with us. Email the CAP STRAT Women’s Forum with any questions at womensforum@capstratig.com! Or call us at 630.320.5100.
