You Know Your Values, Now What?
Alana Winter spent 25 years building a national video distribution business before realizing she'd built something successful without ever asking herself what she actually valued. In this episode, Alana and Maricella talk about being raised by a serial entrepreneur dad who taught her to control her destiny, the moment the business became a grind and she didn't know who she was without it, and the three-year process of figuring out her own core values, and how she helps leaders do the same in a much shorter time frame. They get into the difference between needs, values, and your why (and why most people confuse all three), what she means by "the how matters less than the what," and her story about the bathroom attendant at the Beacon Theater that made me tear up.
About Alana Winter:
Alana Winter is an executive coach, facilitator, and serial entrepreneur who helps leaders navigate the moments when outward success no longer matches their inner truth.
After building and running businesses for more than 25 years, including a nationwide video distribution company and the internationally covered Stiletto Spy School and MI6 Academy, Alana found herself in the disorienting space that comes after a major chapter ends. That experience led her into a deep exploration of identity, core values, and what it really means to build a life and business from the inside out.
Today, Alana works with founders, CEOs, executive teams, and leadership groups around the world, helping them clarify their values, communicate more honestly, make better decisions, and lead with greater self-awareness. Her work blends psychology, lived entrepreneurial experience, and a highly intuitive ability to see the patterns beneath the surface.
She holds a B.A. in psychology from Wesleyan University and has worked with thousands of leaders through EO, YPO, WPO, Chief, and private executive coaching engagements. Her work has been featured by NPR, The Today Show, The Wall Street Journal, Psychology Today, and other major media outlets.
Show Notes:
(00:00) - Nothing To Do Identity
(00:21) - Show Intro And Premise
(00:52) - Purpose Values Episode Setup
(02:05) - Meet Alana Winter
(04:54) - Childhood Dreams Icebreaker
(06:19) - Raised To Be Entrepreneur
(07:37) - Building Video Distribution
(13:10) - Meaning Fades Business Grind
(16:16) - Betrayal And Embezzlement
(23:09) - Burnout Signs And Body
(25:57) - After the Exit Void
(28:09) - Meaning Over Opportunity
(30:33) - Purpose Work for Kids
(33:34) - Three Year Values Quest
(38:15) - Values Needs Why Framework
(44:20) - Living Values Anywhere
(47:16) - Clarity Becomes a Calling
(50:06) - Advice for the Goo Phase
(52:18) - Podcast Closing
