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Keeping a work diary is an outlet for self-doubt and inner turmoil.
THE ANXIOUS MIND

If you’ve got a big career goal, you need to start keeping a work diary

By Sarah Todd

There’s nothing more satisfying than reading a good book. But if you happen to be struggling to bring your own literary dreams to fruition, the experience can also be oddly discouraging. As Anne Lamott explains in her much-beloved essay, “Shitty First Drafts” (pdf), “People tend to look at successful writers who are getting their books published and maybe even doing well financially and think that they sit down at their desks every morning feeling like a million dollars, feeling great about who they are and how much talent they have and what a great story they have to tell.”

Nothing could be further from the truth, as Lamott explains. Plenty of great writers—not to mention CEOs and scientists and academics and inventors and artists and entrepreneurs—are absolutely wracked with self-doubt, so much so that they can become paralyzed by the weight of their ambitions.

So how can a person deal with the psychological tumult that comes with tackling a major (and scary) new career goal? One good option is to start a work diary like John Steinbeck, the author of one of the true great American novels and, as his journal reveals, a big-time neurotic.

While Steinbeck was writing The Grapes of Wrath—the 1939 novel tells the story of Oklahoma tenant farmers seeking a new life in California after suffering from the dual catastrophes of severe drought and the Great Depression—he was simultaneously pouring all his anxieties about his creative endeavor into a diary which later was published as Working Days: The Journals of The Grapes of Wrath. As Maria Popova explains in an article for Brainpickings, the journal functioned as “at once a tool of self-discipline (he vowed to write in it every single weekday, and did, declaring in one of the first entries: “Work is the only good thing.”), a pacing mechanism (he gave himself seven months to complete the book, anticipated it would actually take only 100 days, and finished it in under five months, averaging 2,000 words per day, longhand, not including the diary), and a sounding board for much-needed positive self-talk in the face of constant doubt.”

It’s that last point—Steinbeck’s constant, craven self-doubt—that really comes through in his work diaries. “My many weaknesses are beginning to show their heads,” he writes in one passage highlighted by Popova. “I simply must get this thing out of my system. I’m not a writer. I’ve been fooling myself and other people.”

Steinbeck’s case of imposter syndrome is complicated. Like many a visionary, he has utter faith in his idea, which he sees as somehow separate from himself, yet despairs of his ability to do it justice. “If only I could do this book properly it would be one of the really fine books and a truly American book,” he writes. “But I am assailed with my own ignorance and inability.”

You might imagine that a journal that consists largely of the author bemoaning his own faults would get old fast, and so it does. A Publishers Weekly review of Steinbeck’s diary includes a helpful warning that “the repetitiveness and at times boring nature of the journal may deter general readers.” But that’s just fine; Steinbeck never intended his diary to be a fun beach read. He was spewing his insecurities onto the page in order to exorcise them, so that he could free himself to write the book he had inside.

Personal growth is perhaps the most important outcome of keeping a work diary, according to Harvard Business School professor Teresa Amabile and psychologist Steven Kramer, co-authors of the book The Progress Principle. As they explain in an article for the Harvard Business Review, they asked more than 200 knowledge workers to write in a diary for no more than 10 minutes a day while working on a complex project. While the participants said the exercise helped them stay focused and organized, they were especially struck by the psychological revelations that occurred to them as they wrote.

“I saw that my comments seemed to reflect a pessimistic tone which, in retrospect, may have been unwarranted. I now try to approach projects with a more optimistic frame of mind,” one participant told Amabile and Kramer. Another noted, “This daily ritual was very helpful in making me more aware of how I should be motivating and interacting with the team.” In pouring our ruminations about a big project into a work diary, we may become more aware of thought patterns that are holding us back, or recurring habits that make interactions with colleagues unnecessarily tense.

Blake Mycoskie, founder of the shoe company TOMS, says that keeping a diary when he was starting out gave him an outlet for the insecurities he otherwise felt he couldn’t express. “It became a form of therapy for me as an early entrepreneur, when things were really tough … and you didn’t want to tell anyone because you always had to show this air of confidence,” Mycoskie said in 2017. “So then at night I could be scribbling about how concerned I was.”

Another variation of a work diary is Morning Pages, the ritual introduced to the world by Julia Cameron, author of the book The Artist’s Way, which counts entrepreneur Tim Ferriss, Billions co-creator and showrunner Brian Koppelman, and Weezer’s Rivers Cuomo as devotees. Cameron advises people to write 750 words a day each morning, shortly after waking up—jotting down whatever comes to mind and using the journal entries as “spiritual windshield wipers” that will clear away “muddy, maddening, confusing thoughts” and allow us to approach creative work with clearer minds.

As with Steinbeck’s work diary, the primary benefit of the practice seems to lie in externalizing our inner turmoil. Morning Pages “freed me from [my] perfectionism,” Koppelman told the Wall Street Journal in 2018, noting that he didn’t start writing until he was 30 because “my knowledge that I would fail to be as good as I wished as I was stopped me from doing the work.”

Keeping a diary can be a hard habit to maintain—not least if you’re a self-conscious type who shudders with embarrassment when confronted with a record of your own vulnerability in black and white. (Steinbeck himself struggled with the ritual, noting,  “I have tried to keep diaries before but they don’t work out because of the necessity to be honest. In matters where there is no definite truth, I gravitate toward the opposite.”) One possibility, if you’d rather not read back over your struggles, is to fill a notebook’s pages and then throw it away, a practice recommended by Quartz reporter Ephrat Livni.

However you choose to cope, it seems that the need to keep a work diary is proportionate to the amount of neuroses you’re contending with. It may be that 91% of our anxieties never come true, but there’s no doubt that—as Koppelman discovered in his 20s—they can hold us back from even attempting to achieve our goals.

A diary, it seems, can help creative people of all stripes to make like Steinbeck and, in the words of Popova, “let the doubt happen but plow forward anyway.”