Work on the Weekends Only If You’re Learning Something Useful

Man Reading By Candlelight by Rembrandt Peale/Artvee

My latest at Fast Company started with venture capitalist Jordan Kong’s tweet that rocked the Twittersphere, “Unpopular opinion: the best thing young people can do early in their careers is to work on the weekends.”

If I were watching myself from, let’s say, a security camera, I’d look like I was working on the weekends for most of the 2010s. It started in college, when I made a little bit of money writing blog posts on the weekends. I was never alone at the library—a lot of students study on the weekend—so it never felt weird. 

After I graduated, I just didn’t stop. In some ways, I felt like I’d squandered a lot of my youth, so I actually really became motivated to work harder. I wanted to develop all sorts of skills, and I started a business. I spent a lot of my weekends working. I’d visit my friends and then leave them while they watched the soccer game or played FIFA so I could go to work. I’d invite friends to work with me, which they often did. 

During these weekends, I’d probably be working on—or in (there’s a difference!)—my editorial studio, compiling quotes from Kanye or Chamath, or writing at Medium. Maybe I’d be learning new skills, like how to use a scraping tool to crunch data, or building Ryan Leslie’s first website for the business that would become Superphone. I’m still living it. In fact, I actually wrote that piece for Fast Company on the weekend!

Why Some People Hate Working on the Weekends

Still, Kong was correct that the opinion would be unpopular. Many disagreed:

Responses range from descriptions of working on the weekend as a “never-ending wealth-chasing capitalist hellscape” (source), 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” (source), to “sell yourself body and soul for companies that don’t even bother with your mental, physical and financial well being” (source).

It’s not exactly rocket science: different people have different relationships with, and experiences of, work. I have fun with work, and I’d never call it a “hellscape”—but I can understand why somebody else wouldn’t have fun. I think the most important excerpt I wrote was this part, on how different people experience work differently:

Work means something different to everyone, which is why Kong’s tweet polarized. For example, The Futur CEO Chris Do tweets, “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 6 years. Thoughts?”

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

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

In other words, the responses weren’t from those who have found—or are frankly afforded the luxury of finding—a calling greater than money. If I were to guess, they’d probably settle for a comfortable physical and mental work environment if it were handed to them, as described in 1843, but that path might seem unattainable. 

The Nuances of Working Hard

Y Combinator founder Paul Graham took to his own blog to pen a response, based on the timing I’m guessing he was inspired by Kong’s tweet. The conclusion is on point, I just wished he moved it up:

Working hard is not just a dial you turn up to 11. It’s a complicated, dynamic system that has to be tuned just right at each point. You have to understand the shape of real work, see clearly what kind you’re best suited for, aim as close to the true core of it as you can, accurately judge at each moment both what you’re capable of and how you’re doing, and put in as many hours each day as you can without harming the quality of the result. This network is too complicated to trick. But if you’re consistently honest and clear-sighted, it will automatically assume an optimal shape, and you’ll be productive in a way few people are.

Similarly, based on Graham’s reflection, I considered my own upbringing and my current multi-hyphenate mix of work:

I loved books, and my parents made sure I could read plenty for fun (I would finish a book at the bookstore, and borrow the maximum 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 well enough 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, amongst many other things.

In an ideal world, everyone would make money loving what they do and doing what they love. I think working on weekends and evenings to move your career path into that direction is an admirable thing. I would also understand if you didn’t want to do that—after all, if you’ve just turned 30, it’s “only” another 35 years until retirement. 

Navigate Your Career Path On Your Weekends

Still, I stand by my edit of Kong’s tweet at the end of my piece in Fast Company, “The best thing young people can do early in their careers is to learn skills that excite and fulfill them on the weekends.” You could say, “Herbert, you’re just talking about hobbies,” and it certainly can be—but it can also mean developing a skill that gets you to where you want to go financially as well. Or just breaking through a creative block, or figuring out what your passion really is.

Consider programmer and VC Casey Caruso, who worked at Google during the day, and took on a VC role on evenings and weekends. Sometimes, you don’t have the skills to make your passion your career yet. Or maybe, in order to make ends meet, you can’t go all-in on your dream career path yet.

On average, we’ll each spend 80,000 hours in our work life. There’s good sense in using your spare, non-work, time to set your work situation up so that one day you might enjoy work more. There is no perfect career, but work as a whole doesn’t have to suck. Don’t let anyone tell you otherwise.

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