Why the perfect is so often the enemy of the good
Key Takeaways
One of the most striking aspects of Sarah Wynn-Williams’s best-selling memoir, Careless People, about her years at Meta, is the way she portrays Sheryl San
⚡ Quick Answer
This guide covers why the perfect is so often the enemy of the good with practical tips and strategies.
🎯 Key Takeaways
- Master the fundamentals - Learn the core principles
- Practice consistently - Regular practice improves skills
- Apply techniques - Put learning into action
One of the most striking aspects of Sarah Wynn-Williams’s best-selling memoir, Careless People, about her years at Meta, is the way she portrays Sheryl Sandberg. Contrary to Sandberg’s carefully crafted public image as a levelheaded advocate for working women and their families, she is shown to be narcissistic, mercurial, and hypocritical.
Whether you see Wynn-Williams's book as an important exposé of Big Tech culture or a hit job by a disgruntled former employee, it’s hard to escape the sense that Sandberg’s public persona was more fantasy than reality. The image of a fabulously wealthy executive and doting mother living her best life every hour of the day was always a bit over the top.
There is clearly something unhealthy about the idealized images that we are constantly inundated with, as well as those equally curated versions that so many feel compelled to post on social media. Beyond the obvious psychological toll, the pressure to project constant perfection undermines the gritty, unglamorous work required to perform at a high level.
The value of hacking away
We’re all familiar with the eureka moment from the movies. The hero, when confronted with a seemingly insurmountable challenge, suddenly stops and has a moment of epiphany. He slams his fist on the table—he's finally got it. The camera pushes in tight on his determined face as a montage depicting a frenzy of activity plays out, bringing the plan to life.
As anybody who is involved with creative work will tell you, that’s a myth. Things don’t really work that way. Sometimes you get hit with an idea while driving your car or something, and might stop to write down a few notes. But most of the time you’re just hacking away, working and reworking ideas, most of which don’t amount to much.
Kevin Ashton, the tremendously creative engineer who came up with the idea for RFID chips, put it well in his book, How to Fly a Horse: “Creation is a long journey,” he wrote, “where most turns are wrong and most ends are dead. The most important thing creators do is work. The most important thing they don’t do is quit.”
One of the most useful things anybody ever told me about creativity is that “you have to let the muse know that you’re serious.” You have to be there, every day, doing the crap work until you come across something worthwhile. Most people never do that, because crap takes courage. You have to dare to be crap.
The power of doing the minimum
One of the best ideas I’ve ever had came to me at the end of college. I had been a Division I wrestler, so I never had much trouble staying in shape. But now I was embarking on a professional life that I knew would involve a lot of sitting in an office. I had seen friends who went completely to pot after just a few years.
The idea I had was to commit to working out five minutes a day—without fail. Of course, five minutes a day wouldn’t keep me in shape, but it would make sure that I showed up, and that’s half the battle. I later learned that Jake Tapper has a similar idea about writing. He commits to writing 15 minutes per day, and he’s written a number of bestsellers.
The truth is that people don’t get out of shape because they go to the gym and don’t work out hard enough. They get out of shape because things happen in their lives and they don’t go for two weeks and that somehow turns into 10 years. The same is true about writing, learning a language, or almost anything else: Do the minimum and the maximum will take care of itself.
Of course, in our hyper-optimized theatrical world, we rarely hear that basic truth. Our social media feeds are full of “gonzo workouts,” wacky diets, and “secrets” that will unlock a more successful, fulfilling life. But the truth is that while going extreme might feel rewarding for a few weeks or even a few months, in the long run it’s consistency that matters.
So don’t fall for internet hype and FOMO. If you want to achieve something meaningful, think about what’s the minimum you can commit to and start there. The more you lower the activation energy, the more consistently you’ll be able to try new things and push the envelope.
Sometimes you need to not be productive
Like most people, I occasionally get blocked, which is incredibly frustrating. While sometimes my mind seems to be positively buzzing with ideas, other times I either feel that my brain is stuck in molasses or I’m fixated on something going on in my life and no new ideas seem to be able to work their way in.
In both cases, I’ve found that the best way to get over these difficult periods is to not worry about them and do my best to relax and quiet my mind. That’s more difficult than it sounds, because being blocked can be maddening. But sometimes the most productive thing you can do is to recognize when to stop struggling.
My friend Lu Ann Cahn wrote a great book about this called I Dare Me. Hitting middle age and feeling stuck in her job as an Emmy-winning TV news anchor, she set out on a mission to do something new every day for a year. What she found was the simple act of doing something different—even just taking a different route to work—rewires and refreshes your brain.
So when you’re feeling stuck on a project, the best thing to do is often to step away and do something else, at least for a few hours. Meet a friend for coffee, go to the gym, read a book, watch a movie, or do whatever will help you take your mind off of what you’re doing. I’ve found that once I stop trying to force ideas, they can start flowing again.
Learning to muddle through
You don’t have to go far to find someone advising you to “live your perfect life”: from self-help books and TED Talks urging us to “find our why” to people posting pictures of their spouses and children on social media while praising the perfection and nonstop joy their loved ones bring them—and then, strangely enough, announcing their divorce six months later.
Compare that to how best-selling author and TV anchor Fareed Zakaria describes his work: “Thinking and writing are inextricably intertwined,” he says. “When I begin to write, I realize that my ‘thoughts’ are usually a jumble of half-baked, incoherent impulses strung together with gaping logical holes between them.”
That’s much closer to reality. Whether it’s writing a book or starting a business, you start off with an idea and that idea is always wrong. Sometimes you’re off by a little, and sometimes you’re off by a lot, but it’s always wrong. Your job isn't to be right, but to embark on a Bayesian process of becoming less wrong over time. Eventually, you get it to the point that it can impact the world.
The truth is that the world is a messy place. Marriages are hard. Kids are frustrating. Even stories of incredible success often contain within them tales of heartbreaking desperation. That’s why we need to look at the carefully cultivated images of perfection with a jaded eye, because they will distract us from the necessary struggles required to do something worthwhile.
Not all who wander are lost.
❓ Frequently Asked Questions
Q1: How do I get started with why the perfect is so often the enemy of the good?
A: Begin by understanding the basics, then practice regularly with feedback.
📚 References & Sources
- Toastmasters International - Leading organization for public speaking and leadership