Embracing the Shadows: Strategies to Rise from the Depths of Change

Photo by Rui Bandeira.

“I just want this to be over,” I confessed to my friend during the complexities of my divorce. I was exhausted, and couldn’t see the light at the end of the tunnel. It wasn’t the first time I found myself in a dark pit- both personally, as well as a leader. From managing the recall of a drug on the global market or building a crucial transformational team, I'd faced these challenges before.

This shadowy place is a well known phenomenon. Seth Godin labels it "the dip," that phase between starting and mastery. In the hero’s journey, Joseph Campbell terms it the Abyss, a realm of death and rebirth. Mystics refer to it as the dark night of the soul.

No matter how many times you go through cycles of major change, you can’t avoid these dark spells. The intensity and duration vary for each individual. For some, it can be a series of "mini life crises" over a few days. For others, like Mother Teresa of Calcutta, it can span decades.

It’s usually a hidden struggle, one we don’t really share with others when we’re in it. At a Lean Start Up conference, I witnessed an interview with Arlan Hamilton, a successful black female venture capitalist. She was asked about the time when she was homelessness, sleeping in the San Francisco airport. She immediately dispelled any romantic notions of that time (I paraphrase from memory): “It was very painful. If you had walked by me while I was homeless, you wouldn't have stopped to asked me about it. We’re only talking about it now because I’m successful.”

I’d also rather talk about the excitement of starting something new, or wait until I’ve emerged on the other side to distill the wisdom. And yet, I’m going through it right now, as I continue to forge a new life and career between Portugal and the US. So I’m going to share practical approaches that are working for me to alleviate and emerge from the dark pit. I’m experimenting with writing from experience, rather than about it, per the wisdom of Thomas Hübl. I hope this helps me connect better with anyone else who might be going through a similar experience.

The way out of a dark pit is to dive right in

Upon leaving the corporate world, my plan was to continue coaching leaders and teams independently, a seemingly natural transition after 12 years of coaching. After the excitement of engaging my first clients, something shifted. I enjoyed the coaching sessions themselves, but outside of that, I was put off by all things coaching. What used to be invigorating work became a slog. My interest in what makes humans tick waned. I would easily get irritated around other coaches, and I was delaying the renewal of one of my credentials, criticizing the bureaucracy involved.

How could I build a coaching practice when I no longer enjoyed coaching? Did this make me a bad coach? If not coaching, what else was I going to do?

Ginny Rometty, former IBM CEO, shared a profound insight in a 2017 interview, reflecting on the formidable task of transforming IBM from a hardware to a services company, and enduring 20 consecutive quarters of falling revenue:

You have to have passion. And you have to have clarity. But I think the most difficult thing is perseverance.

The (re)solution to the dark pit is within it, and you need steadfastness to find it. Sensing what is happening inside your body through the practice of interoception is very helpful in three ways: one, it helps you be aware and regulate your nervous system through the discomfort of the pit. Two, it provides you with data to help uncover what is at the root of the dip (fears, beliefs, past experiences). The body doesn't lie. I recommend free writing or drawing about these sensations, or moving freely to instrumental music. Pay attention to any images or symbols that appear in your mind as you go through the process. These are messages from your unconscious mind. You don’t need to arrive at a logical conclusion, just observe and take note. Three, by staying with your experience, it will gradually shift to something else- usually, an inkling of new energy prompting you to look up, or shift direction.

Five steps to finding your way out of a pit

One of those energy shifts directed my attention to a neglected book on my shelf "Learning to Learn and the Navigation of Moods" by Gloria Flores, of Pluralistic Networks. And this book was just what I needed to chart my way out of the pit, in the form of five questions:

1) Why do I want to learn / do this? What will I be able to do that was not possible before?

“Does the world really need one more coach?”. I’ve been asking this question for the past couple of years. Revisiting my intentions by writing them down, by hand, on a piece of paper slows down the mind and involves the body in the reflection. I wrote down my purpose again (bringing light to dark places), and recalled times when I had had a lasting impact. Some of the images from my interoception clicked. I realized that I wanted to be more of a guide, and less of a coach.

2) What unproductive mood am I in? What assessments am I making? What are the standards behind those assessments? Do I need new ones?

One of the most useful tools of the book is a list of the typical moods we experience when we are learning something new. These moods reflect our attitudes, standards, expectations, and judgments about success. Here’s a summary of those moods adapted from the book:

Seeing my arrogance, confusion, and insecurity called out on the book’s pages helped me recognize that all of this was a normal part of the journey. I did not have to fix myself. But I could examine and question the bar I was setting for myself, and others. And a desire to discover a new way to be a helpful guide.

3) What moods would be more productive?

Once you've identified unproductive moods, the book provides a whole list of antidote moods you can cultivate for constructive learning. Here's a glimpse:

Wonder and perplexity. I had been so focused on performing and doing things right, that I had lost the curiosity I had felt since I was a teenager about the inner workings of the human psyche. I recalled the pleasure I felt as a young person, reading Agatha Christie mystery novels: not knowing was always a bigger thrill than finding out who did it.

4) What actions can I take to shift to these moods?

Here are some suggestions that worked for me to specifically cultivate wonder, ambition, and confidence:

Make art: In my new keynote, I discuss how art- not business- gives leaders the edge in navigating the complexity of change. Being a polymath, ie, having breadth and depth in different areas and integrating that knowledge, is what gives you the adaptability and intuition needed for breakthroughs. Case in point, research has shown that art fosters scientific success. A Nobel Prize winner is 7,5 times more likely to be a craftsperson (eg, woodworking, glassblowing) and 22 times more likely to be a dancer or performer than a general scientist! During my pit, I choreographed a new flamenco dance solo and learned how to cross-stitch (exhibit A below!). Playing, failing, making something with my hands and moving my body generated vitality and sustained states of flow. Life felt more integrated. I got new exciting new ideas for my work, such as crafting this new keynote where I bring business and flamenco together.

My new hobby!

Work with your nature, not against it: Understanding our creative and productive peaks throughout the day makes a difference. Dr. Andrew Huberman shares this piece of fascinating research on his Huberman Lab podcast: we are most productive 30 minutes, 3 hours and 11 hours after we wake up. I finally understood why traditional business hours don’t work for me. I refine my schedule to leverage my energy even more, and also followed his advice to get 5-20 minutes of outdoor time in the morning.

Help someone else: A friend on a recovery journey told me that whenever he feels anxious and wants to reach towards the addiction, he helps someone instead - even if it's just washing the dishes at home. My dad had a transient ischemic attack (TIA) recently. He’s been writing his memoirs for the past 12 years or so, and lately he’s been struggling to make progress, staring at his laptop trying to edit an 800 page document. One day, I secretly got the file from his computer, created a cover, and had the whole thing printed and bound. The moment he opened the box and saw his work on paper is something I will never forget. A small act that brought him weeks of joy, and filled my heart with the possibility of feeling this useful to others, again.

Go on a content diet: Albert Einstein once said, "Reading after a certain age diverts the mind too much from its creative pursuits." Inspired by this, I stopped consuming any content related to coaching, wellbeing, or self-improvement. The lack of input allowed my mind to rest. I got interested in the treasure trove of content I already have. As I browsed through my materials, memories of working with clients and colleagues rekindled, and I find myself slowly falling back in love with the work.

5) Is there someone who could mentor me? Practice with me?

This is the final question, and a very important one.

I reached out to Eric Nehrlich, a fellow coach and author of You Have a Choice. Eric transitioned into solopreneurship a few years ago. I shared how low I felt about coaching, and the impending renewal of my certification. "Don’t renew it!”, he said. “Who are you trying to be? If a potential client says that they won’t work with you unless you have that certification, is that a client you really want to work with?". Sometimes, you need a friend to give you permission to do what you want to do. Eric played that role for me, and I am eternally grateful.

It's also helpful to interact with people who have moved past the pit. My friend and former colleague, Melissa Williams, left her full-time job to launch her own company Simply Patient. Her mission is to simplify the drug launch process for patients. Melissa described the promise of what lies beyond the pit: when you stop working to fulfil the vision and performance standards that someone else defined, you finally uncover your own. Melissa's words inspired me:

The joy I'm feeling right now is incredible. Simply Patient is this expression that is uniquely me. Me in the focus of the business, me in the way I'm executing, me in the structured yet flexible approaches, me in the community that has helped bring it to this point with input and encouragement. I love it so much!

Love is what awaits you on the other side of the pit.

True love is rich, complex and beautiful. It keeps evolving. There will always be dips, pits, and dark nights. As Ken Wilber explains in A Brief History of Everything:

There is a price to be paid for every evolutionary step forward. Old problems are solved or defused, only to introduce new and sometimes more complex difficulties.

I like thinking of these pits on the journey of change as the cavities inside my heart. Those powerful places that propel my blood and life forward.

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