Why Leaders Retreat


by Luke Entrup

My stomach was queasy. I had so much stress in my body that I couldn’t move my neck. I wasn’t sleeping much. My nervous system was on high alert. My adrenal system was taxed. My fitness routine vanished. I was having dreams (and the occasional nightmare) about work.

I was doing exactly what was needed to help navigate the organization through a series of crises but the toll it took on me was great.  

I had just joined the leadership team of a healthcare organization. My mandate was to lead innovation initiatives, introduce new technologies, and to build and open a new innovation center. This was to be a creative, fun role within a company known for innovation.  

However, shortly after I joined, a major labor dispute ensued. Instead of leading innovation efforts to improve patient care, I found myself leading culture building initiatives, facilitating employee engagement meetings, helping to assuage employee dissatisfaction, and finding fiscally responsible ways to improve the employee experience.

As soon as things appeared to have calmed ever so slightly, disaster struck. On the morning after Christmas, an arsonist burned down the organization's original, flagship health facility. This led to a new crisis -- one in which I was now scrambling to find temporary medical facilities as quickly as possible. The facility served about 4,000 of the region’s most vulnerable souls in a fairly remote area. We moved to secure medical “RVs”, modular buildings, and temporary office space so the team could provide medical and mental health care to patients who rely on the facility as a lifeline for healthcare and social connection.  

After many intense months, the labor dispute resolved. The day after the temporary medical building opened to replace the burned out clinics, I drove the winding country roads of Sonoma County until I arrived at a retreat center… and took a deep breath for the first time in months.  

The first day, my nervous system unwound a bit from the slower pace. My stomach was soothed by the warm ginger soup. On the second day, my mind began to clear. There was a spacious schedule and nowhere for me to be. My body relaxed and strengthened from the yoga and light martial arts. For the first time in months, I didn’t have to make any decisions, no one was looking to me for answers. After a few more days the colors seemed brighter. My headache lifted. I could move my neck again. I settled back into myself and, ever so slowly, new ideas began to come to me: some about my work with the company, some about how I had chosen to set up my life.

I’ve been on many retreats over many years. Some of the most impactful have come after an intense push with my work or during times of transition.  

When we remove ourselves from our day-to-day life, our habits, unconscious patterns, well-worn communication methods, and familiar faces and places, we will see with fresh eyes the choices we’ve made about how we set up our lives. Meditation and contemplative practices allow us to quiet our minds; then we realize the deeper truth of who we have become. Sometimes this awareness is painful. Sometimes it gives us joy. It is always fruitful. 

The unconscious parts of our minds save mental energy by letting us fall into habits and patterns. To become conscious requires making mindful, deliberate choices about how we spend our days and what we think about. Retreat is a powerful place to reset our habits, to update our beliefs about what is possible.

Retreat is a remarkable tool for inspiring innovation and creativity in an individual or team. As a student (and teacher) of innovation, I find that novel, powerful ideas often come from changing the context for how we view a problem. Retreat provides the space for this context shift to occur.

As I sat in silence and let all of the noise in my mind settle, I stretched and breathed into the recesses of my tired and sore back. I ate nourishing organic foods and took in the beauty of the forest. After several days of disconnecting from others, waking up with the sun, going to sleep when I was tired, I started to watch the movie that was my life. Rather than feeling like it was directing me, I started having thoughts about how to make changes in my life. I started having inspiring visions for a new business endeavor. I was contemplating creative ways to solve some challenging problems within the company. After about six days the ideas were coming furiously. I felt like ideas were being given to me. A new startup idea. A potential partnership I didn’t notice, right in front of me. A long-term strategy for scaling innovation. An exit strategy.

For me, retreat is the place where I connect with my deeper essence, the parts of me that are easy to lose touch of during periods of hustle and execution. Retreat is a vital tool for having a clear and inspired purpose. Retreats can be solo or guided experiences. Different situations require distinct tools.

There are different types of retreats:

  • Mindfulness retreats focus on meditation and contemplative practices such as yoga, tai chi, and breath practices. They are often quiet and slow in pace. The are great for relaxation, gaining depth, and cultivating presence.

  • Personal growth retreats offer a place to make shifts in our self-limiting beliefs and emotional baggage. They usually focus on developing a sense of personal empowerment. They are often more interactive and cathartic.  

  • Visioning retreats provide a venue to redefine one’s life purpose. They are useful during periods of transition. They often include some element of a personal mission statement, credo or life plan through a series of guided visualizations.  

  • Solo retreats might focus on any of these aspects and include long periods of being alone. Being alone allows us to unravel our external attachments and turns our awareness towards our internal landscape.  

Some of the best retreats combine elements of each and include others not yet mentioned.  

Retreat as the Hero’s Journey

Some of the most impactful retreats follow an arc of the Hero’s Journey as described by Joseph Campbell. This arc includes a Separation and detachment from our daily routines, cell phones, and old beliefs. This is followed by what Campbell calls the Ordeal - a place to face whatever we need to change in order to become the better version of ourselves. This means facing parts of ourselves we would rather keep in the shadows. Finally, there is the Return or reintegration. This is where we make plans for sustaining the changes we desire and build a structure that supports our own evolution.

As an executive coach, I find retreats to be a powerful way for my clients to stay sharp and to grow. Taking time to recharge and evolve gives us the ability to see our lives, our roles, and our companies with fresh eyes, a relaxed body, and a new perspective. The sense of possibility we experience through retreat is a potent catalyst for personal growth and effectively leading others.  
Luke Entrup is an executive coach and strategic consultant at Evolution. He has spent much of the last twenty years designing and facilitating leadership retreats. He works primarily with founders and executives of high-growth startups, helping them scale their culture and leadership capabilities. His next retreat, DEEP, is in Maui in October.  

DEEP is a four-day, three-night transformational retreat. It is designed to provide meaningful personal and professional change for leaders of startups and early-stage companies. Participants will be invited to unplug from their daily routines and to be skillfully guided through a series of experiential adventures. It will include nourishing meals and connection to the splendor of Maui. You can learn more about DEEP, here.