I’m a Beginner at the Wheel…Again

Learning to drive was...stressful.

I was 15 years old, with the driver’s seat pulled all the way forward so I could reach the wheel of my family’s little black Volkswagon Jetta. My parents were big fans of a stick shift, so that was my one and only option. I clumsily stopped and started, traversing slow circles around my local elementary school’s parking lot.

When we got out on the real road with other cars, there was so much to think about: Where are my hands? How fast am I going? What's that car over there doing? How much gas do I have? Are my high beams on? Did I check my blind spot?

I grew up in Vermont, where winding dirt roads and cow crossings were normal parts of everyday life. I had to learn a hill start and a Vermont T turn (it’s a thing) for my driving test.

There were so many things to monitor and adjust, so much effort and attention required for each and every moment at the wheel.

I’ve had my driver’s license for 22 years now, and when I slip into the front seat of my Subaru Crosstrek, Roxy, what happens next is pretty second nature. Often, I arrive at my destination as if waking up from a dream—so tuned into a podcast or my endless stream of thoughts or the endless steam of demands from the two goofballs in their carseats in the back that I think to myself: How did I even get here? 🤷🏽‍♀️

Driving now is pretty effortless.

Whenever I learn something new, it feels a lot like learning to drive. There are so many new variables to pay attention to, so many new habits to learn. There’s a lot of stopping and starting. And stalling out.

I feel that way as I navigate my career right now.

How much do I take on? Where do I put my focus and efforts? How do I challenge myself while also caring for my health and well-being? How do I balance my work with family life, my marriage, and my personal needs?

This summer, I embraced a slower pace. I hung up a sign in my office that said, “LET IT BE EASY” and didn’t hustle for meetings or new work. I coached a small set of new and return one on one clients, taught a cohort of leaders through Harvard, and spent as much time as possible curled up in an armchair with a cup of tea at my co-working space. I relished open blocks of time in my schedule for writing and projects I’ve been meaning to tackle but haven’t gotten around to as well as reading, embroidery, and quilting. It felt really good.

One day in early August I realized with surprise that I hadn’t felt work stress in several weeks. Woah. 🤯

For once, I've been operating with wide margins. I gave myself permission, for the summer, to let my capacity exceed what I took on. To have white space in my calendar, my mind, and my heart.

As we get closer to the fall, I'm wondering: What if I could keep this going? CAN I keep this going? Am I allowed? Am I even capable?

I mapped out September through December in post-it notes on my office wall and stared down all of the various to-dos. I took out my budget for the year and studied the numbers. I looked back at my work calendar from last fall, which was packed to the max with back to back meetings between school drop off and pick up.

I thought that leaving traditional full-time work in favor of starting my own business meant that I would define my path on my own terms. I stepped off of the forward and up linear career model to build something else entirely.

But business owners are susceptible to the “forward and up” linear narrative that pervades American culture, too. Grow! Scale! Build a team! More clients! More revenue! Fill your schedule!

I am constantly pushing these messages away and trying to hold true to what I actually believe: that work is about expressing myself, sharing my gifts in service of others, and sustaining an enjoyable life. ⬅️ That’s a radical thought in today’s world.

I told my therapist that I feel like a character in a movie, stuck in a room with walls that are closing in; I’m frantically searching for a way to prop the walls open and defend my sense of space.

She suggested that, instead, I take over the control board that powers those walls.

That’s what I’m trying to do as I plan for this fall: get really intentional about what opportunities I pursue and say yes to, what it means to preserve space for my creative practice of writing, how I set up a pipeline of meaningful work and manage my capacity, and how I make my health and wellbeing part of all the choices I make.

It feels a lot like being behind the wheel when I was 15: overwhelming. There are a lot of factors to pay attention to, and it feels effortful, not natural—yet.

I’ve been driving for 22 years and it’s become second nature. I’ve been navigating my career for almost as long and it still doesn’t feel effortless.

That’s because the career landscape keeps shifting. I’m driving to places I didn’t plan on going, and I’m finding my way as I roll along. I spent a long time learning the rules of the road. Now I’m giving myself permission to break them.

The thing is—I don’t actually believe that navigating my career will ever become second nature. I sure hope I never tune out behind the wheel and have to ask myself, “How did I get here?”

The important thing is, I’m in the driver’s seat. I’m paying attention, I’m asking questions, and I’m learning.

Are you?