Holly Whitaker - Respecting the Order of Life
Holly Whitaker - Respecting the Order of Life
Greetings from the Upper East Side. Our newborn turned six months this week, so my wife and I celebrated the milestone by getting away for a night, heading uptown and checking out the Ellsworth Kelly exhibit at the MoMA. It reminded me how important it is for our relationship to prioritize alone time together away from our girls. It feels great to be a couple again, and change the dynamic from two parents trying to juggle a dozen balls at once.
I also want to celebrate a big milestone with you this week—I notified my existing coaching clients that I’m pivoting my practice to focus exclusively on “work-life transitions.” As I was going through that process, I noticed waves of resistance, because I love my clients and I’ve supported a handful of them for more than two years. I also have some fear because I’m leaving behind a “sure thing”— coaching founders and executives—for a path that’s filled with unknowns and unpredictability. Although it's scary to leave behind what's comfortable, I'm inspired to create something new that aligns with my values and help high performers manifest their next calling.
In other news! Where the Road Bends episode three is my conversation 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. She is the author of the best-selling book "Quit Like a Woman: The Radical Choice to Not Drink in a Culture Obsessed with Alcohol," which was published in 2019 and has received praise for its fresh perspective on sobriety and addiction.
Previously, Holly was the founder and CEO of Tempest, a digital platform that provides online recovery resources and community support for individuals seeking sobriety. In 2021 she stepped down from the CEO position after realizing that she was outside of her Zone of Genius and burnt out from trying to scale the business. Shortly after she hired a new CEO, she was fired from the company that she poured her life into for nearly eight years. This thrust her into a period of grieving, introspection, and transition.
Holly and I have been close friends for nearly a decade and have supported each other through several life chapters.
We covered a lot of ground in this conversation, including
How identity and a company you started can be intertwined and what it's like to have it taken away.
Navigating the chaos of major life transitions by creating space and allowing things to unfold.
The power of reframing ambition and purpose.
The importance of waiting, trusting the order of things, and embracing wonder.
Acknowledging that everyone is in recovery.
On the other side of her transition, Holly discovered that addiction and recovery are part of her story but no longer her identity. Her experiences inspired her to step into her power as a writer, and launch a Substack, Recovering. She’s now working on a new book about navigating our “lostness” in life.
I hope you enjoy this conversation with Holly!
🤔 For Contemplation - Your Inner Superhero
Think about a time when you felt like your best self–strong, capable, and ready to take on the world. What qualities did you embody in that moment? Were you courageous, kind, determined, creative, or something else?
Now, imagine that you have an inner superhero who represents those qualities.
What would you name this superhero, and what would their powers be?
How would this superhero show up in your life when you need them most?
What situation in your life could they help you with right now?
What action would they take?
Take some time to reflect on the superhero within you, and consider how you can channel that inner strength and resilience in your everyday life.
🌱 Seeds of Change
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Here are five things I’ve been pondering about personal evolutions, life transition and conscious change since last issue. If any resonate, please share them with those in your life.
😊 How We Feel
Earlier this year, I began using How We Feel, an emotional well-being journal created by The How We Feel Project, a nonprofit organization started by Pinterest founder Ben Silbermann, and managed by a team of scientists, designers, engineers, and therapists to help everyone better understand their own emotions. This beautifully designed app lets you “check in” to track your emotions, spot patterns as they appear over time, and learn new ways to help yourself in the moment.
By using the app regularly over the past six weeks, I have noticed significant improvements in my emotional literacy and my overall well-being. It has helped me become way more aware of my feelings and identify potential triggers for what the app calls “unpleasant” feelings. Through the journaling feature, I have been able to explore my emotions in depth and gain a deeper understanding of myself. The trends feature has also helped me see how my emotions shift throughout the day. If you aspire to prioritize your emotional intelligence and well-being, I highly recommend giving How We Feel a try for a few weeks. Download for iPhone and Android.
🧘 Identity-Based Habits
Earlier this week, I was working with one of my clients, a public company COO, who is in the middle of a career transition. As we discussed his work-life goals and desired behaviors related to his transition, I introduced him to the concept of identity-based habits. According to author James Clear, who popularized this concept in Atomic Habits, if you want to make lasting changes to your habits, you should engage in behaviors that "vote" for the identity you’re trying to create. For my client, we talked about how he could start identifying and behaving as the type of person who he wishes to become on the other side of the transition—creative and entrepreneurial. This is a concept I come back to over and over again for myself and my clients. Read on JamesClear.com
😲 The Power of Awe
Last week, my friend Scott Britton posted on Twitter that he believed our cultural definition of spirituality needs improvement. I explained to him that as I’ve gotten older I have begun to think of spirituality as the feeling of being connected to something bigger than myself. Another friend, Dave Bailey, chimed in that if spirituality is a “feeling,” then that emotion is likely awe, which can bolster our perception of happiness and well-being. Dave then shared this excellent, well-researched and actionable piece on Awe. It’s one of the best things I read all week. Read on NBCNews.com
🍃 Letting Go: When Is It Time?
I recently discovered This Jungian Life, a podcast featuring three prominent Jungian analysts who explore the topics of life, dreams, and personal growth. As I listened to their back catalog, I came across an episode on the essential topic of “letting go.” The hosts offer a powerful perspective on this subject, sharing that in the first half of life, we focus on developing our ego strength and achieving our dreams. However, as we encounter setbacks or experience the loss of relationships, dreams, or identities, it can be challenging to know when to persevere and when to let go. The hosts provide insightful reflections on when holding on becomes counterproductive, and when acceptance is the key to moving forward. Their show notes beautifully capture the complexity of this issue, posing the question, 'When does perseverance become pointless, or hope turn rancid in refusal to accept disappointment, defeat, or depression?' If you're struggling to let go of something in your life, this episode is for you." Listen on Spotify
⛰️ The Dilemma of Life's Paths
I’ve been appreciating the work of Kyle Kowalski, a solopreneur who discovered his life’s purpose after an existential crisis―synthesizing the art of living for students of life. He does this through Sloww.
A few weeks ago, he posted this thought-provoking thread along with this quote from neuroscientist and author, David Eagleman, and it made me immediately pause and reflect.
"A fact of life: to get good at one thing is to close the door on others. Because you possess only a single life, what you devote yourself to sends you down particular roads, while the other paths will forever remain untrodden by you. Thus, I began this book with one of my favorite quotations from the philosopher Martin Heidegger: 'Every man is born as many men and dies as a single one.'