Leave it on the Mountain: The Power of Letting Go

I went on a hike in Colorado a few years back, where the guide promised us a meditation at the top of the trail. I remember it so clearly, and not because the view was especially dramatic or peaceful. The experience is still crystal clear to me because the prompt she gave us when we sat down to meditate was so powerful. She asked us to think about something we wanted to leave on the mountain - it could be a thought, a belief, an expectation, or a memory. To this day, my wife and I still say, “leave it on the mountain,” when we realize it’s time to let go of something that we’ve been carrying for too long or that is no longer serving us. 

Letting go can be hard, but it’s a huge part of transition. I see it all the time in my work with Teamshares, supporting former owners who have sold their companies and are transitioning out of their businesses and into their next stage. It goes without saying that selling a business is exhilarating. I’ve been there, and yes, it’s deeply satisfying to extract value from something that you’ve worked so hard to build and grow. But what’s much less talked about (and which I’ve also experienced) is that a transaction contains within it a kind of loss. Part of moving on from even the most successful exit is recognizing that you are closing a chapter of your life. You can acknowledge all the business gave you (financial rewards, recognition, community), but you may also need to mourn that the experience is ending. AJ Wasserstein at Yale School of Management, in his excellent case study, What’s Next: The Entrepreneur’s Epilogue and the Paradox of Success, explains it this way: when an entrepreneur exits a business, they lose their sense of structure, purpose, and identity, all of which have been tied up in their company.

Learning to let go - and this holds true whether you are moving on from a company, career, or relationship - can be challenging. Holding on to the past is comforting. In the case of many founders and senior executives I know, it’s hard to see where the business ends, and the person begins, which can make the act of separating the two even more daunting. But holding on can also hold us back. Oftentimes, we need to let go in order to create real space between what came before and to honestly contemplate what lies ahead - even if that future appears murky, unclear, uncomfortable even. In other words, sometimes you might just need to put down that particular activity, identity, or story about yourself. Leave it on the proverbial mountain. And who knows? You might just feel a little lighter when you do.