October 19, 2020 13 min read
Good writing can boil a big idea down to its essence, or stretch a fleeting moment into a universal experience. Once a thought is on the page, you can come back to it. You can relate to it, or define yourself against it.
Being able to articulate ideas about business is vital, but learning to write about yourself can take your entrepreneurial storytelling to a whole new level. For one, editors like me usually prefer to read business stories that are framed by personal anecdotes, something happening in the news, or some reality outside of business. After all, businesses serve a purpose in the real world. Business stories are people stories, so the better you are at writing about humans, the better you will be at writing about business. You are the human you know best. And if it’s ever occurred to you that you might want to get to know yourself better, writing honestly about your life is one of the most effective ways to do that.
Although journaling is an excellent jumping-off point for personal writing, that’s not what I’m talking about here. Journaling is something that you do just for yourself. Here I am suggesting that it’s useful for entrepreneurs to learn to write about themselves for the consumption of others — whether or not they ever actually show their work to anyone. Writing about yourself for others is a skill that requires remaining true to yourself while creating something your readers will find value in — a balancing act inherent to entrepreneurship.
Entrepreneurs should try their hand at creative nonfiction: mostly memoir and personal essays. They are different forms, but there’s lots of overlap. Personal essays are shorter and more contained. Memoirs are book-length personal narratives. Sometimes they span the entirety of a person’s life, from childhood to the present day. Sometimes they focus on one time period. But both forms are most successful when there is a distinct “I” character guiding readers through the narrative, driving toward some self-discovery.
Below are some entrepreneur-relevant instructions on writing from some of today’s most admired nonfiction practitioners and teachers — along with a few insights from my own experience — and some tips on how to get started.
“What do you know to be true?”
In her classic book on writing, Bird by Bird, Anne Lamott says, “The very first thing I tell my new students on the first day of a workshop is that good writing is about telling the truth. We are a species that needs and wants to understand who we are. Sheep lice do not seem to share this longing, which is one reason they write so little. But we do. We have so much we want to say and figure out.”
In The Situation and the Story, Vivian Gornick writes, “Truth in a memoir is achieved when the reader comes to believe that the writer is working hard to engage with the experience at hand. What happened to the writer is not what matters; what matters is the large sense that the writer is able to make of what happened.”
In case you’re still not convinced, Hemingway famously said, “All you have to do is write one true sentence. Write the truest sentence that you know.”
And at the end of most interviews, Oprah asks her signature question: “What do you know to be true?”
Maybe, when you sit down to write or envision yourself in an armchair across from Oprah, you have an iron-clad truth at the ready. But maybe, if you’re like me, you’re not sure what you know to be true, all the time.
That’s totally fine, because that’s what writing can help you figure out. You start out feeling around in the dark, and sometimes you write things that are untrue — they could be narratives that you’ve told yourself for years. But once you hit on something true, you’ll know, and other people will too. Developing a nose for truth hones our ability to recognize ideas — business or otherwise — that will speak to other people. And when other people believe you’re onto something true, they’re much more likely to buy what you’re selling or follow your lead.
To write is to “try”
The word entrepreneur is from the French entreprendre, which means “to undertake.” The word essay comes from the French verb essayer, which means “to try.” A personal essay is an attempt to find meaning in an experience or feeling. Good essays show the writer grappling with an idea, either by way of action or analysis. While the internet has ushered in a gaggle of “oversharing” personal essays that trade in shock value, these are not usually good examples of the form, because they don’t attempt to find meaning beyond “this crazy thing happened to me!” Really, the only requirement of an essay is that the writer ends the piece in a slightly different place — emotionally, or intellectually — than she began it. After all, if you’re offering to take the reader for a ride, the least you can do is go somewhere.
There are obvious parallels between the entrepreneurial instinct to “undertake” an unproven business idea and being willing to “try” on the page. For most writers, one of the most daunting and thrilling things about writing is that when they sit down at the desk, they don’t really know where they’re going to end up. They may have unearthed a memory, stumbled on a kernel of a concept, or witnessed an interesting scene, but they don’t usually know what to make of it just yet. The vulnerability of making something out of a personal experience is excellent practice for following your entrepreneurial instincts, and taking risks on ideas while mercilessly examining your own vantage point.
Perfectionism is where action goes to die
Plenty of entrepreneurs know that nothing will stop your venture from getting off the ground like perfectionism. Don’t get me wrong: Attention to detail is important, as is questioning your built-in assumptions. But all of that is for later, during the editing process. The belief that something has to be perfect before you put it out there is how good ideas die before they see the light of day. It’s understandable; failure is scary. But what’s even scarier than failure to most perfectionists (hello there) is mediocrity. Elizabeth Gilbert, the author of Eat Pray Love and Big Magic, has said that, “Perfectionism is what I call the haute couture, high-end version of fear. It’s just fear in really good shoes. But it’s still fear.”
The thing about writing is that when you first sit down to do it, first drafts are almost always mediocre (at best). Every single time you set out to capture a feeling, image or an idea, you must quiet all the bullies in your brain saying, “That’s dumb. That’s cliche! Why do you think you have something to say about that?” It’s a fact that every thought you put to paper will not be brilliant, but in order to even find out if you have something good, you must muzzle the real or imagined haters.
In Bird by Bird, Lamott says, “Perfectionism means that you try desperately not to leave so much mess to clean up. But clutter and mess show us that life is being lived. Clutter is wonderfully fertile ground — you can still discover new treasures under all those piles, clean things up, edit things out, fix things, get a grip. Tidiness suggests that something is as good as it’s going to get. Tidiness makes me think of held breath, of suspended animation, while writing needs to breathe and move.”
Learning to be curious about yourself opens you up to feedback
In his book To Show and to Tell, the essayist Phillip Lopate writes that “it’s an observable fact that most people don’t like themselves, in spite of being decent-enough human beings.” As a person in the world, Lopate thinks this is unfortunate. But as a writing teacher, he sees this as a huge setback, because “an odor of self-disgust mars many performances” of would-be writers. “The proper alternative to self-dislike,” he writes, “is not being pleased with oneself — a smug complacency that comes across as equally distasteful — but being curious about oneself. I am convinced that self-amusement is a discipline that can be learned.”
Learning to be curious about and amused by yourself (and your shortcomings) is an excellent way to put some space between you and your ego. If you stop taking all your flaws so seriously and being so hard on yourself, you’ll probably find it easier to receive critical feedback — a skill that is incredibly important to starting or running a successful business.
Where to start: “Apply your ass to the chair”
Every book you ever read about writing will tell you that the first rule is simply to prioritize it. In her book The Art of Memoir, Mary Karr writes, “Just apply your ass to the chair (as someone wise once said, a writer’s only requirement) and for fifteen or twenty minutes, practice getting your attention out of your head, down to some wider expanse in your chest or solar plexus — a place less self-conscious or skittery or scared. The idea is to unclench your mind’s claws. So don’t judge how your mind might jet around. If you just watch it, eventually you’ll start identifying a little bit with that detached, watcher self and less with your prattling head.”
Related: Easy Reading Is Damn Hard Writing
If this practice sounds a lot like meditation — an important routine for entrepreneurs from Jack Dorsey to Ariana Huffington — that’s because it is. Your first draft of a story about your life is like cleaning out the attic; you need to get all the crap out there and see it on the page to start tossing things out and deciding which dusty relics to polish. This isn’t so different from getting comfortable with brainstorming in business. If you have the self-discipline to put aside time for loosening your mind and seeing yourself at a remove, it can result in all kinds of inspired ideas.
You (and your experiences) are not too weird, or too boring
In To Show and to Tell, Lopate says that getting people to start writing about themselves often involves helping them clear one of two psychological hurdles:
a) “I am so weird that I could never tell on the page what is really secretly going on in my mind.”
b) “I am so boring, nothing ever happens to me out of the ordinary, so who would want to read about me?”
Lopate goes on to say that, “Both extremes are rooted in shame, and both reflect a lack of worldliness. The first response (‘I am so weird’) exaggerates how isolated one is in those ‘wicked, wicked thoughts of mine,’ to quote Nietzche, instead of recognizing that everyone has strange, surreal, or immoral notions. The second response (‘My life is so boring and I’m so boring’) requires a reeducation so that one can be brought to acknowledge just those moments in the day, in our loves and friendships, in our family dynamics, in our historical epoch, in our interactions with the natural world, that remain genuinely perplexing, vexing, uncanny, luminous, unresolved. In short, one must be nudged to recognize that life remains a mystery — even one’s so-called boring life.”
Learning to recognize your thoughts and experiences for what they are — relatable to others, but also unique to you if you take the time to really drill down into the specifics, and your emotional responses to daily occurences — is a useful skill for entrepreneurs who are figuring out how to brand their businesses. When marketing yourself to customers or clients, you want prospects to know who you are and trust that you “get” them, but you also want to stand out in the crowd by telling a story that is distinct and unexpected.
Finding the moral point of view, or, your purpose
In Bird by Bird, Lamott writes about the importance of what she calls “the moral point of view.” When people hear the word “moral” these days, they tend to think of a scolding nun, but what Lamott is really talking about is purpose. “If you find that you start a number of stories or pieces that you don’t ever bother finishing, that you lose interest or faith in them along the way, it may be that there is nothing at their center about which you care passionately. You need to put yourself at their center, you and what you believe to be true or right. The core, ethical concepts in which you most passionately believe are the language in which you are writing.”
Whether you are writing about your life or building a business, if you think the message at the center of the story matters, or that the business is meeting an important need in the world, you’ll keep working to make it better.
And usually, the more you write about your life, certain themes, questions, or takeaways will surface, again and again. You may realize these refrains have defined, crippled, or inspired you throughout your life, and those revelations can take time to grapple with. But once you have that self-knowledge in place, you can build it into a purpose. And if you’re an entrepreneur, you just might find a way to put that purpose to use.