Entrepreneurs tend to be optimists.
And that optimism inspires persistence and creative thinking—two key traits of success. But entrepreneurial optimism can also lead to sticking with an idea or a venture longer than is beneficial. Every new creative solution we come up with is a chance to assert a belief that this time will be different. We cycle through idea after idea, letting optimism carry us into an uncertain (and unpromising) future.
I’ve picked up and moved across the country twice. The first time, I moved out to Oregon after my divorce. I had left all of the stuff I’d accumulated during our brief marriage, as well as some stuff I’d collected in my early adult life, with him. Part of that decision was shaped like “fresh start!” and the other part of that decision was punishing myself for not being able to make my marriage work. I still wish I had the vintage dish set I left behind.
When I moved to Oregon, I took whatever I could fit in my Ford Focus hatchback and left the rest at my mother’s house where I’d licked my wounds. My mom was also moving out of the state for the first time in her life. Between my mom, my step-dad, my brother, and me, we were collectively letting go of quite a bit. After we’d all left the house for a final time, haulers came to take away the odds and ends of furniture we left. They were artifacts of another life, another set of dreams. We didn’t need them anymore.
After three years in Oregon, I moved back to Pennsylvania. Again, I filled my Ford Focus with what I could fit from a new life with a new soon-to-be husband. Together, we had donated or sold all of our furniture, books, and clothing. I remember standing in the empty apartment we left, wishing I could have gotten the red wine stain out of the cream carpet. There were things we thought we’d miss in the carloads we’d given away. But we were also excited about the prospect of starting fresh, beginning again together.
The thing about moving cross-country is that it provides the opportunity to indulge a sense of optimism that, at least for me, I don’t feel moving across town. When I move across town, I pack about 60% of my stuff neatly and strategically. The remaining 40% gets thrown haphazardly into boxes. When I empty out the junk drawer or the back closet, I’m prone to shoving all the contents into an NPR tote bag—which may or may not ever leave the trunk of my car. While there is a day and time when I can no longer go back to the house or apartment I’d been living in, the whole process of moving doesn’t feel very final. Same life, different address—for good or for bad.
Moving cross-country, on the other hand, feels like a chance to start from scratch. You leave behind the people, places, and stuff of one life and start a new life. There is excitement, sadness, and anxiety all at once. Above all, at least for me, there’s the optimistic hope that this time will be different. Even now, I dream about our next cross-country move five years from, and still, I hope this time will be different. Optimism keeps me moving forward.
I’m not sentimental.
Leaving my stuff at the Goodwill drop-off doesn’t phase me. But what I’ve come to realize is that leaving behind my stuff, my apartment, or even my chosen family isn’t the same as beginning again. No matter how far the move is, no matter how final it seems to pack up that last box or lock the door one last time, there is a part of me that continues to hold on, just like that red wine stain. What I hold on to, though, isn’t what’s past—it’s potential and possibility. I hold on to old goals. I hold on to the identity I hope to one day inhabit. I hold on to what I’ve learned with an eye for how it will benefit me in the future. Some of that is good—the root of growth. But I can’t help suspecting that some of what I hold on to holds me back.
Inertia is a powerful force.
We are all objects in motion, staying in motion. Even when we feel “stuck,” as we so often complain, we’re stuck going through the motions. When we’re not stuck, inertia often appears as a set of moves—idea after idea, strategy after strategy—that we hope will make a difference in the distance to our goals. My friend Sarah Avenir put it this way when examining her own tendency to allow the inertia of optimism to move her:
Fifteen or even five years ago, I would have absolutely identified with the passionate, impulsive nature of the visionary—someone who’s good at kindling fires but bad at keeping them burning. My natural bent is to pour myself totally into some grand pursuit (and if I’m being honest, to run hard and fast away from outcomes I dread).
But at some point, that changed. My unflagging optimism and determination to push hard toward possibility became a liability rather than a strength. It wasn’t wisdom that convinced me to change as much as my inability to force myself to do things anymore. If I could have kept going in the way that came naturally, I would have.
The inertia of optimism: I’m certainly guilty of going with the flow, by which I mean that I’ve optimistically maintained my course long after I realized I was headed in the wrong direction. When Sarah writes that if she could have kept going she would have, I feel that in my bones. The inertia of optimism is the same force that keeps me moving from one place to the next. It’s the same force that inspires a new marketing strategy or offer idea and lets me say, “This time will be different.” I go and go and go until I can’t. It’s easier that way.
People tell me that they wished they had my energy or fecundity. What they don’t know is that my ability to keep coming up with something new isn’t generative—it’s inertial. What is set in motion stays in motion.
This year, as I’ve endeavored to work on my craft as a writer and podcaster, I made a point to embrace revision. Naturally, I am the kind of writer who can put down a publishable first draft in an hour or two. But I decided that “publishable” is not the same as “remarkable.” And so I revise.
The process of revision is an interruption to optimistic inertia.
While I’m writing in motion, I feel like, if I just keep writing, it’ll all work itself out. And that’s important. I have to keep writing to discover what I really want to say. When I write, as Anne Lamott would say, a “shitty first draft,” I free myself to explore all sorts of possibilities. I ramble on without regard for structure, discovering interesting questions and turns of phrase as I go.
But when I sit down to come up with a second draft, I bring more intention and thoughtfulness to the subject of the piece. Inevitably, that leads to cutting things out. Letting go of thoughts that intrigued me in the first go around. If all I end up doing is proofreading, I’m not revising. I’m letting optimistic inertia hold me back. Revising is a process of challenging questions and difficult decisions. Things will be left behind. Metaphors will hit the cutting room floor. This time it will be different.
That doesn’t mean I don’t hold on to pieces of what I created before. I often hold on to quite a lot. But my goal is to approach that second (or third, or fourth) draft with a different purpose: discovering what the piece actually has to say and molding it into that form. My goal is to let go of the writing—the words, the phrases, and sentences—and embrace the essence of the piece, even if I didn’t know what it was when I started.
The writer Kiese Laymon talks about revising as part of his writing and living process. He writes:
In my own sloppy work on and off the page, I was beginning to understand revision as a dynamic practice of revisitation premised on ethically reimagining the ingredients, scope and primary audience of one’s initial vision.
When I moved back to Pennsylvania, I didn’t ask many questions about where or how I wanted to live. I took the ingredients of my life as facts. The house I live in, the things I have easy access to, the people I’m surrounded by—those things haven’t changed much over the years when it really comes down to it. The location is a mere line edit. I’ve held on to these ingredients of my life like a sentence I really don’t want to cut. And so now I find myself tormented by where I live—namely, the incessant traffic and everything that comes with it—because I didn’t step back and make a true revision.
I’ll turn 40 in 2022, and I will have lived at my current address longer than any address I’ve lived at before. Coincidentally or not, I’m beginning to see more potential for revision than ever before. Not so much the wholesale scrapping of my current draft but an embrace of the essence of what I’m trying to do and say in the world. Who I want to be. What I want to experience. At this point in life and business, I know there is no such thing as a clean break or even a final draft. But I do know that each draft can get closer to the key question.
Earlier this year, I worked with a group of business owners on the “what’s next” vision of their businesses. At the beginning of the retreat, I led a guided visualization where I had them imagine packing their existing business into a box and putting it in a closet. I encouraged them to question everything about what they believed their business is. While we remained open to holding on to what they’d already built, our goal was to take a crack at a true second draft—not just a proofread version of the first.
As we begin to close out this year, I’m considering the things I want to let go of—as well as the ways in which I want to begin again. What will my next draft look like? How will I get closer to the essence of my own work? I’m reminded of this line from adrienne maree brown’s Emergent Strategy, “Everything we attempt, everything we do, is either growing up as its roots go deeper, or it’s decomposing, leaving its lessons in the soil for the next attempt.” What I choose to let go of can influence me without dragging me into the inertia of optimism.
We can interpret the information we have in all sorts of ways.
If we tend toward optimistic analysis and dogged persistence, it’s worth asking ourselves:
- What if I’m wrong?
- What if the data is actually telling me it’s time to let go?
- What if the signs actually point to clearing the slate and beginning again?
Those might be uncomfortable questions to sit with.
They’re certainly uncomfortable for me. But I think they’re vitally important to becoming a better leader and treating ourselves more humanely. Clearly, there’s a role for persistence in entrepreneurship. Maintaining faith in the possibility of success has been a key ingredient in building many great inventions and companies. So these questions of when to move on, let go, begin again—they’re open questions.
A final thought: our culture doesn’t think highly of people who change their minds. We call them flip-floppers. We expect our leaders to know what they believe and stick to it. As a business owner, it often feels easier to stick with what you’ve been doing. Less to explain, less need to admit you were wrong or that the timing was off. But, the way I see it, a business for humans has to make space for new information and different ways of seeing. We need to be able to change course and lead as people who are thoughtful instead of entrenched in old data.
It’s more than okay to revise your plans or throw a draft in the trash. Only by letting go can we begin again.