Sandboxes and Transitions

When we reach our first 90 days at August, we have a tradition of writing a letter to former Day 1 at August selves, sharing our learnings, reassurances, and reflections. Here’s mine…

Dear Usha,

This is the beginning of something pretty cool and pretty amazing. Some part of you already knows that- that’s why you changed your whole life to be here.

The beginning will be the hardest part. The weather will suck, the city will seem cold and impersonal, everything will feel indifferent and apathetic for a while; all during a time when you’re feeling alone, raw, and broken open. It will suck, and you will stick it out anyway, because you’re pretty resilient.

Soon, though, the heat will abate and the wind will pick up, the city will start to remove its mask and reveal its magic.

You’ll discover, soon, that everything you’ve been working up to, all the seeds you’ve been planting, all the things you’ve been learning, and all of the hustling (so much hustling, I know, I remember), all of that has been leading up to this- this moment where you get to do incredible work, where you can imagine and re-imagine systems on a daily basis, where you hold space for real change and transformation in individuals, teams, and organizations every single day. You will get to learn and grow every single day, and you will get to live your purpose inside and out every day. Best of all, you will get to do that with a pretty special team, and together, you will get to make an incredible impact in the world.

At August, you will find the true promise of self-management. Together, we will create and re-create every day. We will design and re-design every day. We will play with imperfect ideas and incomplete thoughts and see how they brush up with reality. We will listen, constantly, to what is and isn’t working.

We will discover and play together. We will listen to each other. We will challenge each other. We will also have hard brushes with each other. We will be honest with each other. We will create together, we will tear it all down, and we will build it back up. Again and again. Together.

We will start to have some really tough conversations together. We will push each other to the edge of our comfort zones. We will push each other past our comfort zones. We will force each other to grow, listen, learn, examine, and reflect. We will share some pretty honest feedback with each other. Amidst the frustration and confusion we will hold each other in compassion, care, and friendship.

We will consider hard challenges. We will run into things that will stump all of us. We will ideate and ruminate and incubate. And when we’re not looking, we’ll find the unlock, the next step, and we’ll try it. We will meet incredible people doing incredible work in the world. We will get to listen to their stories. We’ll be amazed by how much they care about their work. We will help their teams understand each other better. We will help them build structure and clarity into their work.We’ll see clearly what they seem to be missing, and it’ll feel amazing to help.

You will be a bridge during an important growth point in the company. You will get to hold space for others as we learn from each other and integrate some productive tensions. You see the promise of structure, and the promise of culture. The promise of the outside, and the inside, the connection between the two, and implications of the two. You will get to connect a lot of dots, for yourself, and others. Better yet, you will get to action the insights to help transform things inside out.

This is a really special sandbox, and you’re now a part of it. You’ll find that to be an incredible gift, and a deep responsibility. Anytime you see that something isn’t right, or isn’t up to its fullest potential, you will feel the weight of that responsibility. Sometimes, it’ll be exciting and fun. Other times, it will require you to stand in deep discomfort. In both cases, you will be called to speak up, and listen well. You will have to ask for what you need, and sometimes that will take a lot of courage. But the amazing thing is, your team will respond, and you get to figure out together.

The beginning will be the hardest. You will feel more alone than ever before. You will also feel more free than you ever have. Some days that freedom will be enough to compensate for the loneliness. Some days it won’t. For those days when it isn’t enough, remember to reach out to the very special people you’re privileged to have in your life.

The fresh slate of a new beginning will be daunting sometimes. You will feel confused about who you are and what you want to create in your life. Sometimes that fresh slate will be liberating. You can let your authentic expression in unprecedented ways. Lean into all of it- the confusion, the excitement, the newness, the freedom, the joy, the sadness, the frustration, all of it. Let all of that in and through, and allow your life to emerge.

All of it is a privilege. Remember that. You get to be at the edge- at the edge of your deepest growth, at the edge of humanity’s deepest growth. You are at the edge of a movement, and you get to sense the way, and carve the path. Best of all, you get to do it as part of a really special team.

Brace yourself. It’s all pretty fucking amazing.

Sincerely,

90 days later Usha