Where the Road Bends

#003: Holly Whitaker - Respecting the Order of Life

Episode Summary

In our third conversation, I talk with New York Times-bestselling author and speaker Holly Whitaker. She’s known for her work in the field of addiction recovery and her focus on the intersection of wellness, feminism, and personal growth. In 2021, she was fired from Tempest, the addiction recovery company she founded and poured her life into. This thrust her into a period of grieving, introspection, and transition. In this conversation, we discussed various topics such as the connection between one's identity and their company, how to navigate major life transitions, reframing ambition and purpose, embracing wonder and waiting for things to unfold, and acknowledging that everyone is in recovery.

Episode Notes

FEB 24 • 1 hour 5 minutes 50 seconds

WTRB Episode #003: Holly Whitaker and Respecting the Order of Life

The third guest on WTRB is Holy Whitaker, a New York Times bestselling author, and speaker. Her book "Quit Like a Woman: The Radical Choice to Not Drink in a Culture Obsessed with Alcohol," was published in 2019 and has received praise for its fresh perspective on sobriety and addiction.

In this episode we covered:

On the other side of her transition, Holly discovered that addiction and recovery are part of her story but no longer her identity. And this experience inspired her to step into her power as a writer, launch a Substack called Recovering, and work on a new book about being lost rather than sobriety.

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Listen now on Apple, Spotify, Simplecast.

To sign up for the newsletter and podcast visit https://www.wheretheroadbends.fm/

Where to find Steve Schlafman:

• Website: https://www.schlaf.co/  

• Twitter: @Schlaf

• Facebook: Steve Schlafman

• LinkedIn: Steve Schlafman

Where to find information on Holly Whitaker:

• Website: www.hollywhitaker.com

• Instagram: @holly


Where to find information on Holly’s writing:

Substack:  Recovering Newsletter

Email Course: The Mantra Project – 40 days of Sobriety

Book: Quit Like a Woman: The Radical choice to Not Drink in a Culture Obsessed with Alcohol




In this episode, we cover:

(00:00) Holly Soundbite

(00:17) Steve’s introduction about Holly

(01:44) Beginning of the interview

(02:10) Steve and Holly’s connection

(03:00) 2019 / 2020 – A hectic time - closing a Series A and a house at the same time

(03:30) The calling to have a social impact in the space of Recovery

(04:30) On writing and becoming a new author

(05:50) Fitting personal life amid trying to juggle it all

(06:35) Covid impact on life and business

(07:30) Relieved – the gift of stopping and tuning into the woods

(07:58) The weight of using your personality to build a company and sell a book

(09:00) After raising $20M – achieving the dream – it was still so empty

(10:41) How much of a difference of outward success and how you feel in the inside

(11:02) July 2020, “I don’t want to be CEO anymore”

(11:40) What Holly was longing for

(12:20) Holly is a creator – replacing herself as a CEO

(13:20) Identity and story of company are deeply intertwined

(14:15) Holly using herself as the way forward to create the narrative around recovery and her company

(15:35) Leaving Tempest - April 2021 – Going on sabbatical

(19:10) Committed to not jumping on ‘the next thing’

(19:45) Holly gives herself space for the first time

(21:00) Staying in the middle – and finding meaning and worth without creating something validating

(21:37) The moment that Tempest was going to close – confronting “I failed”

(22:28)  A dinner – everyone had a great job – the only thing that matters is that “I am here”

(23:34) Steve walking away from running his own VC

(24:02) Steve’s year of stillness

(24:27) Navigating the liminal space – experiencing a ‘lifequake’ after Tempest

(27:30) So much happening and nothing happening at all

(28:20) Being in the messiness but trusting and expecting how things unfold

(29:05) It’s all ambiguous – we create structure for safety

(30:15) Trying to get to the feeling of fullness

(30:50) Getting to the Present Moment

(31:04) Big transformations and big learnings for Holly – You don’t have to have a purpose.

(32:45) Waiting for an external event to give yourself a moment of contentment

(34:00) The simple moments in life – no other purpose really matters

(34:30) It matters more how you move throughout your day that creates massive change

(36:15) Finding purpose and meaning in work is a lie 

(37:28) Satisfaction is obtained more by your orientation to the world

(37:50) A story of a famous editor

(39:15) The feeling like you need to outdo yourself – how Holly use to view ambition

(40:55) Looking at ambition in multiple dimensions of life

(42:25) How Holly has channeled her energy over the last two years

(43:28) The anti-ambitious period of Holly’s life

(46:00) Allowing for life to happen “through you”

(47:30) Surfing and feeling sucked under

(48:07) Life is too precious to not have fun – learning to not hold life so tightly

(49:50) Taking advantage of existing – how you view your life and future

(51:42) Discussion on self-improvement – the notion we are broken and need healing

(52:10) Different structures that serve us at different times

(52:55) All tools become weapons – even self-improvement

(54:05) When going through grief, loss, and transition – self-improvement becomes oppressive

(54:50) Self improvement as a form of self-aggression

(56:00) Embracing the ugly – everyone is in recovery

(56:50) How you move through the steps of recovery

(58:10) What is addiction? – Are we all addicted? – The things we are addicted to

(59:15) Recovery – as an essence of finding something lost – and compelled to change for the better

(1:02:00) Last question – Mistakes make us human

(1:02:30) Humanity – acceptance and forgiveness of our mistakes

(1:03:15) How you can find Holly Whitaker on the internet – Substack on Recovering

(1:04:25) Where you can find more information about Steve

Stay curious and keep exploring the winding road of life.


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