Beyond The Trail: What A Long Hike Reveals About Stretch Goals

Sunday, I completed the longest hike of my life, 18+ miles across my beautiful city, San Francisco. My daughter Madeline and I started out just after 9:00 a.m. watching egrets take flight on the still, quiet San Francisco Bay at Candlestick Point. We made our way diagonally across the city via the Cross Town Trail, favoring parks, green spaces, and trails wherever possible, climbing to heights with gorgeous vistas, descending through eucalyptus forests that made us forget we were in a city, and ending some eight hours later—tired and sweaty but elated—at Land’s End overlooking the majestic Pacific Ocean. And now, as I nurse a few sore muscles and reflect on the experience, I can’t help but draw connections to leadership and goal-setting. The lessons are not new, but worth repeating.

Motivating Goal. We started with a clearly defined goal. For me, it was a stretch, but like all good stretch goals, it was challenging, achievable, and inspiring. I believed that I could do it, but it was beyond anything I had done before. Though I’m strong and have hiked quite a bit, eighteen miles is about four to five times the length of my typical urban hikes. Could I do it? Yes, I thought so. I was intrigued and knew I would feel proud if I did. My other daughter Margot had completed the trail a couple of weeks before, and so we were also fueled by a competitive spirit . If she could do it, so could we!

Monitoring and Feedback. Thanks to the wonders of GPS, activity-tracking watches, and apps like AllTrails, I was able to monitor and track our progress all along the route. At about 10 am, when we were 1.7 miles into what we thought would be 16.9 miles (it wound up being a bit longer thanks to some detours), I turned to my daughter and said, “We’re 10% of the way there.” Tracking our progress helped us stay informed and motivated and gave us an ongoing sense of accomplishment. And when we strayed from the path, my phone flashed a notification that we had deviated from the established route. In several instances, this alert ( real-time feedback ) helped us course-correct so we didn’t miss some of the hidden paths and other features of the trail. And when we chose to deviate from the route to go to our favorite noodle shop, we did it intentionally and with purpose.

Companionship. Although my goal was ostensibly an individual one, I don’t think I would have tackled the challenge without a friend and fellow traveler to share the journey with me. We were united by a shared purpose and commitment, and we supported and kept each other company along the way. At times we chatted and at other times we were in our own thoughts. Mostly we were in sync, having established a game-plan at the outset, but we also had different needs that required flexibility. At one point I asked her to slow a bit to accommodate my pace. Later, I waited for her while she stood in a long line at a coffee shop. I pointed out birds, she spotted lizards, and we both exclaimed at the views. And when we confronted yet another staircase mid-afternoon, and my legs felt like heavy hollow logs, her strength and determination helped me find mine. “We’ve got this,” we said more than once. The power of mutual validation.

Rest. By definition, a stretch goal is taxing—often both physically and mentally. You can’t go flat-out all the time. As Tony Schwartz and Jim Loehr point out in their classic Harvard Business Review article, “The Making of a Corporate Athlete,” to achieve sustained high performance, both athletes and professionals need periods of expending energy and periods of renewing energy. The oscillation between states is key. We planned our rest breaks from the start. The Cross Town Trail can be divided into three sections of roughly 6 miles, and at the end of the first and second we took extended breaks: iced lattes and snacks at 11:15 and a sit-down lunch at the noodle shop around 2:00. It was amazing how much those breaks renewed and revived us, and I am convinced that it was not just the calories and caffeine—it was truly resting our bodies—that allowed us to continue.

Surprises (Smell the Roses). Although my daughter and I were focused on our goal and tracked our progress along the map, what made the journey truly engaging and energizing was keeping our eyes open to the world around us. One of the joys of the hike was experiencing parts of the city that we had never seen: chain of beautiful greenways in Visitacion Valley ; the volunteer-made Steep Ravine Trail in a forest in the middle of the city; mosaic staircases taking us up hills too steep for roads and revealing views and perspectives we had never seen before in a city we know well. Each surprise was a source of energy. The principle of no surprises management (which holds that your manager or co-workers should never be blind-sided) notwithstanding, staying open to surprise and to changing your perspective is essential to being flexible and questioning your assumptions. Even the cliché of stopping to smell the roses revealed the surprisingly different scents of wide variety of roses found in the Golden Gate Park Rose Garden , reminding us of the subtle and rich diversity in the world around us. And despite what the media might say about San Francisco, it remains a rich and varied city full of beauty.

Of course, our goal—though a stretch for me personally—could be accomplished in a day. And unlike many business objectives in our complex world, we had a well-delineated map, street signs and trail markers. Most business OKRs and personal goals don’t come come with turn-by-turn directions. Instead, you have a desired outcome and a working hypothesis of how to get where you are going. But these uncertainties only underline the principles above: start with a clear and inspiring goal, actively monitor and seek feedback, work a team or a buddy, take time to rest and renew, and be open to surprises. These are not just lessons or principles, they are values that can guide an individual or team in pursuit of excellence. (Noodle soup helps, too!)

By Hanna Hart, Contributor