I found my purpose hiking up Mount Greylock

Path to Purpose

How my hike up Mount Greylock gave me clarity to focus on my dreams

“My route lay up a long and spacious valley called the Bellows, because the winds rush up or down it with violence in storms, sloping up to the very clouds between the principal range and a lower mountain. It seemed a road for the pilgrim to enter upon who would climb to the gates of heaven.”

–Henry David Thoreau

A few months back, I decided to build a brand new wellness venture (more on THAT later).

Running a consultancy full-time and launching a new startup is challenging. So when a very large advertising agency (a business partner) offered to buy my company, I thought, this is perfect! I won’t have to run my business–I’ll be a strategic advisor. I’d be able to focus more time on the startup (or so I thought).

I kept thinking to myself PEOPLE would be so impressed and that became a motivating factor. We’d have big press releases and my days of hibernating would be over. I somehow convinced myself that this deal was the only way to prove myself before announcing the startup. Things were in motion–I had the paperwork…the lawyers were reviewing.

On September 15, four days before my birthday, I woke up and realized I did not actually feel good about the deal.

There were too many conversations with the C.E.O. of the other company, where I had to convince him my company was worth more and I was worth more. They kept adding my personal time into the contingency without more compensation. You know how sometimes you’re on fire and radiate charisma? I wasted one of those days repeating myself over and over to him. The worst part is I had skipped a startup investor conference. Over and over I chose to spend my time trying to make this deal better for me vs. feeding my startup. But…I wanted the “glory,” the press release. The outside validation. But, did I? The deal was starting to feel like a tether to the consulting world, an anchor. Something blocking the path of my dream. Want to know what happens when you spend your days trying to convince people of your worth? You start to feel insecure.

Stepping Away to Gain Clarity

For whatever reason, I kept thinking my life was at a transition point very similar to back in 1995, after graduating UMass Amherst. I knew I was focusing on the wrong things, and felt I knew my purpose, but was too scared to pursue it 100%. It took a day off, and a long hike on Mount Greylock 24 years ago to spark a new path. That hike prompted me to go to grad school…which propelled the move to San Francisco, and my becoming an entrepreneur.

It was time for that kind of re-set, again, 23 years later.

Magic Happens on Mount Greylock

North Adams, Massachusetts is a tad less than three hours from Cambridge, MA, but a world away in terms of culture and kindness.

I chose a place at the bottom of the mountains, with suspension bridges spanning “The Beyond Place”–an Algonquin term for the Hoosic River. Yes. This is a magical part of the world, understated, with a quiet elegance, woods and rocky cliffs and wild streams.

On my actual birthday, Dalton (my dog) and I took on Mount Greylock–famed for being, the inspiration for the white whale in Moby Dick, the school for American witches and wizards (aka Ilvermorny)–if you can’t see it, you’re a muggle ;), and, of course, was an inspiration for Thoreau.

We walked 6 hours up and 4.5 hours down, an entire day of trekking, thinking, and getting clarity.

What a beautiful day, 63 degrees, crisp–the perfect Fall day, the type of day that reminds me of being a student and *knowing* you can change the world. You’re one with nature, the path opens into sunlight, and the slight breeze coasts you forward. Except…Greylock can be fickle/moody, and seems to like throwing all four seasons in the span of a hike at the mere mortals who dare to trek his surface. We experienced nasty vine-whips of wind, cold bouts of shadows and a few moments of actual…trepidation (N.B.: I dislike like 5-foot tall grass). Dalton and I were alone except for the trees and birds, and whatever animals lived beneath the surface. Overall it was peaceful and empowering.

Hiking is my Headspace App

Halfway up the path we sprawled on a rock, gulping water, bathed in a sunbeam which enveloped the trees and leaves on the ground. A red-tailed hawk circled above, and it was silent. I felt as if the entire world belonged to us, and whatever dreams we brewed.

Hiking in general is my Headspace/Calm/Yoga–I feel it is a metaphor for the journey of life. You can choose your path, but whatever way you go, it’s not supposed to be EASY, or simple, or a padded leather seat limo ride. It’s supposed to be full of twists and turns. Perhaps an unexpected stream and wet socks. Yet also, moments of pure bliss. It’s a hike, and you have to be 100% fully present the entire time.

Mount Greylock is how I got the answers I needed. When we arrived at the summit, we could see 90+ miles into budding fall foliage; mountains, rivers, streams, church steeples and red barns, a perfect, clear view. I knew what I needed to do, what my purpose was, and which path I needed to take to be aligned with it. The perfect birthday gift.

Finding the Path: What Do We Want?

Everyone has heard this saying–what would you do if you didn’t need money, and you could pursue anything you want. What is your purpose in life? The one thing that is so entirely you. The answer to that is usually closer to what you’d be happiest doing, but so many dismiss it. We operate out of fear–we think, there is no way we could earn a living doing that, or we tell ourselves it would be too difficult to change direction. There’s a Paulo Coehlo quote from “The Alchemist,” that reads, “When you want something, all the universe conspires in helping you to achieve it.” In my experience, this is true–it’s not woowoo or crazy–it’s when you’re aligned with your passions and your dreams and you pursue them. When people see that, they help. You find others like you, who pursue their purpose.

When you want something, all the universe conspires in helping you to achieve it.

Paulo Coehlo

My Purpose is Wellbeing

Dalton finding his purpose on a suspension bridge.

I love pursuing wellness and all things related to wellbeing, and I’ve actually known this for a long time–it’s what fueled my last startup back in 2008, it’s what fueled me teaching Aerobics through college and in San Francisco at the YMCA. It’s what attracted me to a certain entrepreneur in SF who was always optimizing his health. It’s what has fueled me to be a lifelong vegetarian, and pursue work that gives me freedom with my schedule. Of course, it’s also why I’m building a new wellness startup.

Align Your Actions With Your Purpose

Yeah, I mean it is obvious, right? But the thing is, it wasn’t–not until I was on a rock, taking a breather on the Bellows Pipe trail on Mount Greylock. The past 3 months I worked almost fulltime on consulting clients, and spent my spare time on paperwork for the sale of my company. No significant progress had been made with my new startup idea, because I hadn’t given it any fuel. I was spending all my time feeding the wrong people, places, and pursuits. All of this was deeply misaligned with my goals, and my true passion.

When I returned from my trip, I refused the sale of my company.

I realized I could hire someone to “be me” at the consultancy and I’d be able to step back, or, I’d find the right buyer who appreciated my goals. By walking away from the deal I could focus on the startup. Walking away had an added benefit, too: by leaving behind “partners” who didn’t fully value me, I started valuing myself more. I have become more confident and more determined.

Here I want to give some credit to Z, my cousin and friend, who helped me see the truth, and realize how much time and energy I was spending on things that were not aligned with my goals.

Onwards With Purpose

My muscles were sore, even a few days after I returned from the Berkshires, and my head hurt, too. My journal was filled with Jackson-Pollocky looking scramblings. I was like a cranky 3-year old who didn’t get enough sleep, but was on the plane to Disney World. This is the what happens when you know what you must do, and you decide to pursue it.

2 weeks ago I hiked that mountain and turned down the deal…and I feel alive. I haven’t figured everything out yet–but I see a path opening up before me. Friends and helpful people are showing up to propel me forward, and I am more content and driven.

Sometimes all we need is to step back and gain some perspective, and sometimes, we need 11 hours on a mountain full of magic.

In the past 2 weeks more progress has been made on the startup than in the prior 3 months. I’ll announce THAT soon. Onwards!