To Climb “But” Hill You Need Strong “WHY” Shoes

6 min readJul 29, 2022

Hearing “No” is hard. Even if the “no” is said politely — “no, thank you.” or “let’s hold off on this for now” — it’s still hard.

Each of us is trying to create something in this life — we enter the world each day trying to leave it a little bit better than it was that morning. Some of us do this in the boardroom, others in the classroom, and others on the streets — and everything in between. We live in a world of constant content — we can pick up our device and watch, hear about, or scroll through anything about just about anything. It feels overwhelming — especially for those of us who want to create helpful, meaningful work.

On days where I google the term “mindfulness” and come across thousands upon thousands of search results, it is hard not to think that my work, perhaps, isn’t adding that much. This usually happens on days where I have heard that an application I have submitted, a manuscript I have worked on, or a proposal I have sent in — has been rejected. Someone, for some reason, on the other end “loved it, but…” — “You’re amazing, but…” is a refrain I’ve heard over the years of building this work, and this year, I have come to realize that the process of creating can feel very much like an arduous climb, of what I now like to call — “But Hill”.

But Hill is a steep, jagged, rocky path carved into the side of a mountain where it is both intensely hot and humid, and also rains all the time. Oh, and also, there are a lot of exposed roots and tiny pebbles that get into your shoes. And snakes. Lots of snakes. But Hill is unpleasant, it is disheartening to face, and it is — sadly — a necessary climb for any kind of growth. So how do we do it? How do we get on up there and climb that big ol’ But Hill — sometimes every single day? We need to have strong “WHY” shoes.

What are “WHY” shoes? They are the deep, core, spiritually resonant reasons for why you do what you do — for why you get up every single day and contribute to the world. These reasons are solid, deep, and unique to you. If you ask any teacher, for example, why she goes into the classroom every day, very few — if any — will say “for the money.” If you ask an artist why they create over and over again, despite the possibility of years — or maybe decades — without anyone knowing of their work, you will not get the answer “for the fame.” I’m pretty sure Vincent Van Gogh didn’t cut his ear off to become a Tik Tok star.

Your WHY Shoes have to be indestructible. They have to be water resistant, blister repellant, have good grip, and also be incredibly comfortable. Your WHY shoes need to be soft enough for you to land on them every time you are facing But Hill. If you are a teacher, and your WHY Shoes are the love that you feel when you see your students grow — incredible. If you are a community leader, and your WHY Shoes are the rush you feel when you lead a successful effort — cool. If you are working with underserved communities, and your WHY Shoes are the knowledge that every single day, you are helping make someone’s life a little better- — yes! Whatever your WHY Shoes are made of, they better be strong enough to get up But Hill — over, and over again.

I climb But Hill a lot, especially as I am once again beginning to share my work with wider audiences. This year -I have been given the opportunity to climb But Hill many times. From conversations with schools, to submitting writing, to applying for grants and fellowships — But Hill has shown up a lot.

“We were impressed by your background and application, but…”

“You really are such a powerful writer, but…”

“This does sound so great, but…”

“Thank you for submitting such powerful work. We were very moved, but…”

These are real — copy and pasted from emails I have received. I am sharing them because I believe that there is absolutely no shame in trying — and not succeeding. Struggle is to be expected in a long journey — which is what life is — but giving up is just not an option. Some of them are actually quite nice at first, and then there’s the “but”…

Another way to think about But Hill, is to think of the other side — “Not Yet Valley” — hearing a no doesn’t mean give up forever. It actually means: Rethink — Review — Reflect — and Reset. When someone says they love your work, and then follow it up with a “but” — it means something didn’t quite click. Maybe it is energetic, maybe it is in the wording of your proposal, or maybe — it just isn’t the right time.

Every time, I found myself, again, standing at the bottom of But Hill, and asking myself the question, “why should I climb this again?” The answer doesn’t always come easily, sometimes I wonder if I am better off with more “traditional” forms of work. Then, I remember that I am wearing my “WHY” Shoes.

My WHY shoes are the now hundreds of letters, emails, and testimonials I have received from kids, parents, and communities about the impact of the work. I think about the kid who was so afraid to socialize they hid in their closet — who now has emotional and professional stability in their 20s. I think about the kid who was too anxious to go to school, who is now thriving in high school. I think about the kids — so many of them — who were hiding mental struggles — who learned the language that gave them inner strength, and the ability to really help themselves. I think about the kids — now adults -who still write to me about how they use the tools I taught them. My WHY shoes are filled with the knowledge that I can help others lead lives with less suffering, with more emotional strength, and with tremendous potential.

The truth is, for every email that had a ‘but’ in it, there have been so so many that have had “and” — the ultimate connector.

“We love this work, and we feel this is so important for our school community, and…”

“Thank you for submitting such powerful writing. We were so moved, and…”

The “and” is the gentle, sloping downhill on the other side of But Hill. It passes through Not Yet Valley and ends up in “Now is the time” village — and guess what?

We all get there.

It might look different for each of us. We are not all going to be giving TED Talks (although, hey, i’m not against it), but we are all going to make a difference in this world. Our individual contribution might feel small — we cannot all be presidents, CEOs, principals, heads of state, billionaires…but we can all be contributors. We can all be creators, supporters, friends, healers, and allies. We can kiss boo-boos, innovate in our spaces, and make rocking music. We can climb again and again.

But Hill is rough to face, and sturdy WHY shoes will make the journey bearable.

What are your WHY shoes made of?