Why My Day in the Woods Was My Most Productive Work Day Yet

On a hike with Mo Siegel, the founder of Celestial Seasonings, I asked him when in his career he was most happy. He replied that he is always happy as long as he feels “productive”. I think about this often. As an Enneagram Type 1 (the Reformer), I feel this way too. I get extreme satisfaction from staying disciplined and focused, and relentlessly checking things off my to-do list. It’s one of my best talents. I can visualize and diligently execute on elaborate, multi-tiered, multi-year to-do lists to achieve lofty goals. However, this strength can also be a detriment. Anything I perceive as a distraction from my to-do list feels stressful, and I have to constantly tell myself that unexpected, off-the-to-do-list opportunities are often the best opportunities. I was recently reminded of that.

I reluctantly signed up for an all-day hiking event to support a nonprofit called Walking Mountains. The organization inspires environmental stewardship and a love of science through experiential learning in the Colorado mountains. I love this organization, and it has been very supportive of our efforts at MergeLane. The event combined a lot of things I love—being outdoors, hiking, supporting environmental stewardship, and connecting with interesting people I can be beneficial to and vice versa. However, it was an eight-hour commitment. As the event approached, I looked at my inbox and all the things I could do with eight hours to move the needle with our MergeLane fund. I almost canceled. At the last minute, I said, “Just get in the car and see what today brings.” As my guilt increased over spending a day out of the office, I kept telling myself, “They’ve been so supportive of you. They are doing good work. Just get there and focus on supporting Walking Mountains. Feel like you’re having a productive day doing that.”

I started the hike and began talking with some Walking Mountains donors. Because I wanted to check off my “support Walking Mountains” to-do, I started asking them questions in the hope of reinforcing their support for the organization—questions like “Why did you choose to spend your time doing this today? Why are you interested in the environment? What in your childhood sparked your interest in science?” and so on. I started having this lovely conversation with a man named Bill George. Bill is the former CEO of Medtronic; an expert, author, and Harvard Business School professor on the topic of authentic leadership; and a strong supporter of women in leadership. As the general partner of a venture capital fund for high-potential startups and select venture capital funds led by authentic leaders and with at least one woman in leadership, I immediately saw the potential to gain from this connection. However, I was there to tick my “support Walking Mountains” checkbox. “Just give first,” I thought.

I started talking about Walking Mountains. I told him how much I appreciated his and his wife Penny’s donation, and why I think their support is making an impact. I encouraged him to articulate and hopefully strengthen his passion for the organization’s mission. I think it worked, and it seemed to trickle to a few of the other donors hiking with us as well. “Box checked,” I thought.

As we started downhill, I felt content. It felt nice to use my talents to benefit another organization and to “unplug” for the day. Then, Bill started asking me about my work. He seemed genuinely interested and introduced me to his wife, Penny, who is also a strong supporter of organizations like ours. He also told me about his books, Discover Your True North and Authentic Leadership. It was a very meaningful connection.

At the end of the event, I ran into an investor I’d been trying—unsuccessfully—to connect with for six months. I had a clear calendar for the rest of the day, and we both had an hour’s drive back home. “Would it be weird if I rode home with you?” I asked.

I found someone to drive my car home and rode home with him and his wife. They committed to invest in our fund. Another meaningful connection.

The next morning, I had an unexpected meeting cancellation and found myself with three hours of free time. The “should” in me said I should stay in the office and catch up on my to-do list. However, I really wanted to go for a hike. Because of the work I have been doing in Conscious Leadership, I am working to shift my focus from things I feel obligated to do, to things I feel inspired to do. I was itching to listen to Bill George’s True North book, and it was a beautiful Colorado day. I shut my laptop, downloaded the book, and went out for a hike. It was exactly what I needed. I had been thinking a lot about my leadership purpose and his book focuses on exactly that. By the end of the hike, I had a clear articulation in my head: I believe my leadership purpose is to help people achieve seemingly impossible things in a way that feels easy, fun and rewarding. I like to work with highly effective leaders who can push themselves beyond normal physical limitations, but often do so at the expense of their own health. I inspire these leaders to accomplish more without giving too much of themselves. I help them understand and operate in their zone of genius, increase their authenticity and self-awareness, and integrate physical fitness, the outdoors and activities they are passionate about into their work.

In roughly 24 hours, I used my talents to support a worthy cause, made a highly strategic and thought-provoking connection with a leading leadership expert, secured a new investor for our MergeLane fund, and defined my leadership purpose. This is far more than I would have achieved by staying in the office checking off my to do’s.

A few things lined up to enable these outcomes.

• I was operating in my zone of genius—asking insightful, thought-provoking questions and creating authentic connections with hard-to-access people in a way that is enjoyable and productive for all parties involved.
• I operated in my zone of genius while being physically active and outdoors—something I am increasingly a proponent of.
• I was in Vail, Colorado, a community with an extremely high density of potentially meaningful connections.
• I created room in my schedule for unexpected opportunities, thought, and creativity. My typical day would not have left time for me to ride home with that investor, for example.   
• I followed the principles of give first.  

This day occurred three months ago, but I am just checking off the to-do of writing this post now because I wanted to stay hyper-focused on recruiting for our MergeLane Funderator. I believe that was a smart move, and it leads me to my final reflection. My mastery of managing my to-do list is, and will continue to be, one of my greatest assets. Like everything in life, it is best in moderation.

Onward.