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You should never work on weekends unless you’re doing one thing

The author of Creative Doing explains how a polarizing tweet led him to examine how best to advance your professional life without obliterating your actual life.

You should never work on weekends unless you’re doing one thing
[Source photo: Filip Urban/Unsplash]
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Her words soared across the Twittersphere, inciting thousands of reactions: “Unpopular opinion: the best thing young people can do early in their careers is to work on the weekends.”

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If we wanted to be pedantic, we could call venture capitalist Jordan Kong’s tweet more of a hot take. But still, I agreed so much with it that I thought it would be one of those unpopular opinions that wasn’t that unpopular. I couldn’t have been more wrong.

Responses range from descriptions of working on the weekend as a “never-ending wealth-chasing capitalist hellscape,” to an inevitable path to “zero time with their friends and family . . .  zero social skills, have no life experiences, and suffer from mental burnout before 30,” to “sell yourself body and soul for companies that don’t even bother with your mental, physical, and financial well being.”

Y Combinator cofounder Paul Graham supported Kong’s tweet, noting responses that equated work with earning an income. He replied, “for the ambitious, they are far from identical.” Kong clarified that work “can mean different things: could be a project that you own at your day job, could be a new skill you need for advancement, could be a side hustle you love.” 

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I appreciate Beth Pickens’s phrasing a version of the same idea in Make Your Art No Matter What: Moving Beyond Creative Hurdles:

Can you consider the radical proposal that even if your work never pays you, it will still be a valuable and integral part of your life, for the rest of your life? What if your art gives you life and your employment pays for that life?

Work means something different to everyone, which is why Kong’s tweet was polarizing. For example, the Futur CEO Chris Do tweeted, “my wife and I can’t agree on this. Can you work hard and make sacrifices if you love the work you do? She only considers it work if you hate what you do. Therefore I haven’t been working [for] the last six years. Thoughts?”

Similarly, in 1843 Magazine, Ryan Avent writes that software and IT have made the workplace much more likable. He writes about the joys of flow, collaboration, and a sense of purposeful immersion. This is probably the case in most venture capitalists and technology offices, and even for some of the people who get to work from home. 

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Still, there are many who don’t get to work in this type of environment. I could put on my headphones and get into flow at a coffee shop or in a coworking space, but there were always others that made it possible—the baristas, the caretakers, and the drivers, among others. 

Therein lies the rub. The digital divide might cover hardware and internet access, but the diverging natures of work, and feelings of optimism or despair in the future, drove the strong responses to Kong’s tweet. It’s not necessarily ambitious to work on the weekend when it involves learning, autonomy, and feels fun. It’s easy

Venture capitalist Mark Suster wrote a post titled, “Is it Time for You to Earn or to Learn?” The frank truth is, many of us probably feel the need to do both. For example, there was a point when I worked at Lifehacker in what would be the last days of Gawker Media, where I was also running my editorial studio

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In my ideal world, I would be a full-time author. But writing is an unstable business. I inherently knew and felt the same as Kim’s Convenience lead actor Paul Sun-Hyung Lee and Donald Glover when they said they felt like they didn’t have chances to fail. I’ll quote Brenda Peterson quoting Edith Oliver at The New Yorker, “My deah (sic), you don’t mean to say that you actually live on your salary?” Many of us do, and that’s just the way it is. For me, I couldn’t risk not earning, but thanks to my friends and family, I also knew the essentiality of learning. 

So, I do marketing and writing simultaneously. At points, there is definitely a sense of brain overload. But it’s a common element in many jobs, it’s still a privilege to experience them while I was doing the thing I liked to do. It helped that marketing paid well, and I didn’t hate it.

Like Kong says, my marketing opportunities started compounding thanks to my work in my spare time. After writing dozens of articles for a Canadian tech publication—on weekends in college and for a summer—through my friend Keane’s introduction, I got a contract job with Xtreme Labs, which got bought for $65 million in 2013

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I didn’t own any equity, and I wasn’t even working that day so I missed the party. But I learned a lot, and I could easily pick up relatively well-paying freelance opportunities with that. I learned to negotiate, to price, and to write, all on the weekends. Spending less time making the same amount of money meant I could make more time to write.

For most of my childhood, my schedule was packed with classes. Sunday was for going to church and attending Sunday school. Monday to Friday I went to daycare and public school. Piano class would be on Thursday, but I practiced each assigned song six times every night. Friday nights were swimming. When I stopped swimming, my parents made me play floor hockey. On Saturdays, I went to Chinese and math classes. If I wanted to watch cartoons on Saturday morning, I’d have to wake up at 6:45 a.m.—the earliest time of the week—which I did happily. I was upset cartoons didn’t start earlier and usually turned on the TV to the end credits of That ’70s Show. If I woke up even earlier than that, I would draw pictures. 

My parents made it clear: I was privileged to have a chance to learn. I also knew that a lot of other kids who went to my daycare had a similar schedule with different mixes of classes—ballet, guitar, violin, Kumon, martial arts, and such.

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I loved books, and my parents made sure I could read plenty for fun (I would finish a book at the bookstore, and borrow a maximum of 50 books at the library). And I spent no shortage of time playing video games. But the structure and discipline my parents instilled in me was a huge asset that made earning and learning—working on the weekends—much easier than if I hadn’t had those habits.

I also know that none of the habits that serve my work ethic would matter if I didn’t enjoy my work. Given my temperament, I’m just not the type of person that can grind away for 14 hours a day, thirstily seeking out drops of joy in something that makes me feel miserable. These days, I still do things that might look like work on the weekends—writing at Medium, taking notes, figuring out GPT-3, and reading, among many other things.

Even after all of this, I still find myself agreeing with Kong. I would amend her tweet more carefully, by removing the vague elements and polarizing misunderstandings that made it go viral in the first place: “The best thing young people can do early in their careers is to learn skills that excite and fulfill them on the weekends.”

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Herbert Lui is the author of Creative Doing, a book of 50 prompts that unblock creativity for your work, hobby, or next career. He writes a newsletter that shares three great books every month. He is the editorial director at WorkOS and Wonder Shuttle.