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Why Writing About Your Life Makes You a Better Entrepreneur



October 19, 2020 13 min read

There are many reasons that writing is a worthwhile pursuit for entrepreneurs. 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.

Learning to articulate ideas about business is great, but learning to write about yourself can take your entrepreneurial thinking (and writing) 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. 

Related: The Entrepreneur’s Guide to Writing a Book

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.

Related: How Writing Regularly Can Improve Your Creativity and Clarity


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The Trump campaign celebrated a growth record that Democrats downplayed.



The White House celebrated economic growth numbers for the third quarter released on Thursday, even as Joseph R. Biden Jr.’s presidential campaign sought to throw cold water on the report — the last major data release leading up to the Nov. 3 election — and warned that the economic recovery was losing steam.

The economy grew at a record pace last quarter, but the upswing was a partial bounce-back after an enormous decline and left the economy smaller than it was before the pandemic. The White House took no notice of those glum caveats.

“This record economic growth is absolute validation of President Trump’s policies, which create jobs and opportunities for Americans in every corner of the country,” Mr. Trump’s re-election campaign said in a statement, highlighting a rebound of 33.1 percent at an annualized rate. Mr. Trump heralded the data on Twitter, posting that he was “so glad” that the number had come out before Election Day.

The annualized rate that the White House emphasized extrapolates growth numbers as if the current pace held up for a year, and risks overstating big swings. Because the economy’s growth has been so volatile amid the pandemic, economists have urged focusing on quarterly numbers.

Those showed a 7.4 percent gain in the third quarter. That rebound, by far the biggest since reliable statistics began after World War II, still leaves the economy short of its pre-pandemic levels. The pace of recovery has also slowed, and now coronavirus cases are rising again across much of the United States, raising the prospect of further pullback.

“The recovery is stalling out, thanks to Trump’s refusal to have a serious plan to deal with Covid or to pass a new economic relief plan for workers, small businesses and communities,” Mr. Biden’s campaign said in a release ahead of Thursday’s report. The rebound was widely expected, and the campaign characterized it as “a partial return from a catastrophic hit.”

Economists have warned that the recovery could face serious roadblocks ahead. Temporary measures meant to shore up households and businesses — including unemployment insurance supplements and forgivable loans — have run dry. Swaths of the service sector remain shut down as the virus continues to spread, and job losses that were temporary are increasingly turning permanent.

“With coronavirus infections hitting a record high in recent days and any additional fiscal stimulus unlikely to arrive until, at the earliest, the start of next year, further progress will be much slower,” Paul Ashworth, chief United States economist at Capital Economics, wrote in a note following the report.


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Black and Hispanic workers, especially women, lag in the U.S. economic recovery.



The surge in economic output in the third quarter set a record, but the recovery isn’t reaching everyone.

Economists have long warned that aggregate statistics like gross domestic product can obscure important differences beneath the surface. In the aftermath of the last recession, for example, G.D.P. returned to its previous level in early 2011, even as poverty rates remained high and the unemployment rate for Black Americans was above 15 percent.

Aggregate statistics could be even more misleading during the current crisis. The job losses in the initial months of the pandemic disproportionately struck low-wage service workers, many of them Black and Hispanic women. Service-sector jobs have been slow to return, while school closings are keeping many parents, especially mothers, from returning to work. Nearly half a million Hispanic women have left the labor force over the last three months.

“If we’re thinking that the economy is recovering completely and uniformly, that is simply not the case,” said Michelle Holder, an economist at John Jay College in New York. “This rebound is unevenly distributed along racial and gender lines.”

The G.D.P. report released Thursday doesn’t break down the data by race, sex or income. But other sources make the disparities clear. A pair of studies by researchers at the Urban Institute released this week found that Black and Hispanic adults were more likely to have lost jobs or income since March, and were twice as likely as white adults to experience food insecurity in September.

The financial impact of the pandemic hit many of the families that were least able to afford it, even as white-collar workers were largely spared, said Michael Karpman, an Urban Institute researcher and one of the studies’ authors.

“A lot of people who were already in a precarious position before the pandemic are now in worse shape, whereas people who were better off have generally been faring better financially,” he said.

Federal relief programs, such as expanded unemployment benefits, helped offset the damage for many families in the first months of the pandemic. But those programs have mostly ended, and talks to revive them have stalled in Washington. With virus cases surging in much of the country, Mr. Karpman warned, the economic toll could increase.

“There could be a lot more hardship coming up this winter if there’s not more relief from Congress, with the impact falling disproportionately on Black and Hispanic workers and their families,” he said.


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Ant Challenged Beijing and Prospered. Now It Toes the Line.



As Jack Ma of Alibaba helped turn China into the world’s biggest e-commerce market over the past two decades, he was also vowing to pull off a more audacious transformation.

“If the banks don’t change, we’ll change the banks,” he said in 2008, decrying how hard it was for small businesses in China to borrow from government-run lenders.

“The financial industry needs disrupters,” he told People’s Daily, the official Communist Party newspaper, a few years later. His goal, he said, was to make banks and other state-owned enterprises “feel unwell.”

The scope of Mr. Ma’s success is becoming clearer. The vehicle for his financial-technology ambitions, an Alibaba spinoff called Ant Group, is preparing for the largest initial public offering on record. Ant is set to raise $34 billion by selling its shares to the public in Hong Kong and Shanghai, according to stock exchange documents released on Monday. After the listing, Ant would be worth around $310 billion, much more than many global banks.

The company is going public not as a scrappy upstart, but as a leviathan deeply dependent on the good will of the government Mr. Ma once relished prodding.

More than 730 million people use Ant’s Alipay app every month to pay for lunch, invest their savings and shop on credit. Yet Alipay’s size and importance have made it an inevitable target for China’s regulators, which have already brought its business to heel in certain areas.

These days, Ant talks mostly about creating partnerships with big banks, not disrupting or supplanting them. Several government-owned funds and institutions are Ant shareholders and stand to profit handsomely from the public offering.

The question now is how much higher Ant can fly without provoking the Chinese authorities into clipping its wings further.

Excitable investors see Ant as a buzzy internet innovator. The risk is that it becomes more like a heavily regulated “financial digital utility,” said Fraser Howie, the co-author of “Red Capitalism: The Fragile Financial Foundation of China’s Extraordinary Rise.”

“Utility stocks, as far as I remember, were not the ones to be seen as the most exciting,” Mr. Howie said.

Ant declined to comment, citing the quiet period demanded by regulators before its share sale.

The company has played give-and-take with Beijing for years. As smartphone payments became ubiquitous in China, Ant found itself managing huge piles of money in Alipay users’ virtual wallets. The central bank made it park those funds in special accounts where they would earn minimal interest.

After people piled into an easy-to-use investment fund inside Alipay, the government forced the fund to shed risk and lower returns. Regulators curbed a plan to use Alipay data as the basis for a credit-scoring system akin to Americans’ FICO scores.

China’s Supreme Court this summer capped interest rates for consumer loans, though it was unclear how the ceiling would apply to Ant. The central bank is preparing a new virtual currency that could compete against Alipay and another digital wallet, the messaging app WeChat, as an everyday payment tool.

Ant has learned ways of keeping the authorities on its side. Mr. Ma once boasted at the World Economic Forum in Davos, Switzerland, about never taking money from the Chinese government. Today, funds associated with China’s social security system, its sovereign wealth fund, a state-owned life insurance company and the national postal carrier hold stakes in Ant. The I.P.O. is likely to increase the value of their holdings considerably.

“That’s how the state gets its payoff,” Mr. Howie said. With Ant, he said, “the line between state-owned enterprise and private enterprise is highly, highly blurred.”

China, in less than two generations, went from having a state-planned financial system to being at the global vanguard of internet finance, with trillions of dollars in transactions being made on mobile devices each year. Alipay had a lot to do with it.

Alibaba created the service in the early 2000s to hold payments for online purchases in escrow. Its broader usefulness quickly became clear in a country that mostly missed out on the credit card era. Features were added and users piled in. It became impossible for regulators and banks not to see the app as a threat.

ImageAnt Group’s headquarters in Hangzhou, China.
Credit…Alex Plavevski/EPA, via Shutterstock

A big test came when Ant began making an offer to Alipay users: Park your money in a section of the app called Yu’ebao, which means “leftover treasure,” and we will pay you more than the low rates fixed by the government at banks.

People could invest as much or as little as they wanted, making them feel like they were putting their pocket change to use. Yu’ebao was a hit, becoming one of the world’s largest money market funds.

The banks were terrified. One commentator for a state broadcaster called the fund a “vampire” and a “parasite.”

Still, “all the main regulators remained unanimous in saying that this was a positive thing for the Chinese financial system,” said Martin Chorzempa, a research fellow at the Peterson Institute for International Economics in Washington.

“If you can’t actually reform the banks,” Mr. Chorzempa said, “you can inject more competition.”

But then came worries about shadowy, unregulated corners of finance and the dangers they posed to the wider economy. Today, Chinese regulators are tightening supervision of financial holding companies, Ant included. Beijing has kept close watch on the financial instruments that small lenders create out of their consumer loans and sell to investors. Such securities help Ant fund some of its lending. But they also amplify the blowup if too many of those loans aren’t repaid.

“Those kinds of derivative products are something the government is really concerned about,” said Tian X. Hou, founder of the research firm TH Data Capital. Given Ant’s size, she said, “the government should be concerned.”

The broader worry for China is about growing levels of household debt. Beijing wants to cultivate a consumer economy, but excessive borrowing could eventually weigh on people’s spending power. The names of two of Alipay’s popular credit functions, Huabei and Jiebei, are jaunty invitations to spend and borrow.

Huang Ling, 22, started using Huabei when she was in high school. At the time, she didn’t qualify for a credit card. With Huabei’s help, she bought a drone, a scooter, a laptop and more.

The credit line made her feel rich. It also made her realize that if she actually wanted to be rich, she had to get busy.

“Living beyond my means forced me to work harder,” Ms. Huang said.

First, she opened a clothing shop in her hometown, Nanchang, in southeastern China. Then she started an advertising company in the inland metropolis of Chongqing. When the business needed cash, she borrowed from Jiebei.

Online shopping became a way to soothe daily anxieties, and Ms. Huang sometimes racked up thousands of dollars in Huabei bills, which only made her even more anxious. When the pandemic slammed her business, she started falling behind on her payments. That cast her into a deep depression.

Finally, early this month, with her parents’ help, she paid off her debts and closed her Huabei and Jiebei accounts. She felt “elated,” she said.

China’s recent troubles with freewheeling online loan platforms have put the government under pressure to protect ordinary borrowers.

Ant is helped by the fact that its business lines up with many of the Chinese leadership’s priorities: encouraging entrepreneurship and financial inclusion, and expanding the middle class. This year, the company helped the eastern city of Hangzhou, where it is based, set up an early version of the government’s app-based system for dictating coronavirus quarantines.

Such coziness is bound to raise hackles overseas. In Washington, Chinese tech companies that are seen as close to the government are radioactive.

In January 2017, Eric Jing, then Ant’s chief executive, said the company aimed to be serving two billion users worldwide within a decade. Shortly after, Ant announced that it was acquiring the money transfer company MoneyGram to increase its U.S. footprint. By the following January, the deal was dead, thwarted by data security concerns.

More recently, top officials in the Trump administration have discussed whether to place Ant Group on the so-called entity list, which prohibits foreign companies from purchasing American products. Officials from the State Department have suggested that an interagency committee, which also includes officials from the departments of defense, commerce and energy, review Ant for the potential entity listing, according to three people familiar with the matter.

Ant does not talk much anymore about expanding in the United States.

Ana Swanson contributed reporting.


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