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The Absolute best Three Classes Realized From All My Previous Jobs

The Best Lessons Learned From All My Past Jobs | Wit & Delight
Photo by Paweł Bukowski on Unsplash

I have four different versions of this post in various stages of completion on my desktop. This isn’t my first time sharing work lessons and I’ve had a ton of jobs to learn from, so I thought it would be easy. It wasn’t.

The first version covers my obsession with owning my own business, which began in elementary school. I wanted to start a magazine, so in third grade, I created a hundred-page Creative Writer document with bits and pieces of ideas and information I collected from around my tiny world so that, one day, I could shape my own plucky pre-teen publication. I started a boutique friendship bracelet business out of a Caboodle shoved inside my fourth-grade desk. Later, I had another idea for a girls-only lawn mowing business that would take advantage of my handwriting skills to make really pretty, bubble-lettered yard signs advertising our work. 

That walk down memory lane fed into my second half-finished essay where I tell the story about how, when faced with the question “What are your hobbies?” from a coworker after starting a new job, I realized I had no hobbies that hadn’t been monetized or maxed out. The more I thought about my entrepreneurial pursuits driven by…god, I don’t know what…I recalled a duo of articles covering the recent backslide of the girlboss and #bossbabe and felt relieved. (I won’t even get into my tech startup ideas.)

In my final piece, I thought about sharing some of the most ridiculous advice I’d been given after a decade working as a writer (And editor. And content designer. And copywriter. And content strategist. And journalist.) That turned into a rant about feedback from mostly older men, which probably wouldn’t help you, but was extremely cathartic for me.

So, where does that leave us? I may not know a lot, but I am starting to understand how to be a better advocate for myself and my work. Here’s what I’ve discovered. Perhaps I needed the fifteen-year head start to get here.

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Hone your personal work style.

I’ve spent a lot of time over the years studying how other creatives work, because I thought there must be One True Way to approach writing that would make it easier. Less painful. Faster. Better. And you can find a lot of material outlining others’ processes, to be sure. But one of the most important lessons I continue to learn is that you have to honor your own personal work style.

One of the most important lessons I continue to learn is that you have to honor your own personal work style. . . . How do you like to work? How do you do your best work? There is no wrong way. Only different ways.

Some people do all their best work in the morning. Some can do it while multitasking. Listening to loud music. Sitting at a communal table in their open office. I need complete silence. I need my desk clean and my inbox empty. If it’s dark, even better. It’s a lot. And I used to think it was inefficient. But would it have taken twice as long (or longer) if I’d tried to do it someone else’s way? It’s evolving. But it’s worth observing in yourself: how do you like to work? How do you do your best work? There is no wrong way. Only different ways.

You have to input to get output.

I am a writer, but I probably spend 70 percent of my time reading. A quick scan of the open tabs on my desktop confirms this. I used to think it was a coincidence that I struggled to put my thoughts down on paper until after I’d spent a lot of time absorbing literally anything else, but this quote from writer Ted Gioia (via the incredible Austin Kleon) put it all into focus for me:

“But I know for a fact I could not do what I do if I was not zealous in managing high-quality inputs into my mind every day of my life. That’s why I spend maybe two hours a day writing. I’m a writer. I spend two hours a day writing, but I spend three to four hours a day reading and two to three hours a day listening to music.

People think that that’s creating a problem in my schedule, but in fact, I say, “No, no, this is the reason why I’m able to do this. Because I have constant good-quality input.” That is the only reason why I can maintain the output.”

And I’d say this goes for folks in any role, not just creatives.” However you find yourself showing up these days, make sure you’re setting aside time outside of work for the things that will inspire, excite, and fuel you.

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Nobody wins in Hero Mode.

Speaking of time allocation, I would be remiss if I didn’t mention boundaries. When I started my first job, and actually, my first five jobs and attendant side projects, it was not uncommon for me to work full-time, and then come home and do more work. I was happy to do it. God, I had so much energy.

But before I realized it, opening up my laptop at home evolved from plucky (and, frankly, naive) extra credit to mandatory work. A coworker at a startup called the phenomenon, and our tendency to rise to the occasion, “Hero Mode.” As in, you will fly in to save the day—usually at a personal cost to you—to fix a problem that couldn’t possibly be put off until normal business hours. Sometimes this is necessary (your company’s website has crashed and it’s critical people can access it) but most of the time it isn’t (your manager has decided 10 p.m. is a good time to send edits on a document that doesn’t go to the client until tomorrow afternoon).

There’s give and take, to be sure, especially in these unprecedented times when almost everyone’s schedule is unrecognizable. But drawing a line between your work life and your personal life (pandemic or not) when possible is not selfish—it’s 100% necessary.

One of the best things we can do (myself included) is commit to continually learning, growing, and advocating for ourselves along the way. 

I wish I could say I had three different anecdotes to help pull this wild train of an essay into the station, but as it turns out, our careers are a process, not a destination. There’s always more to learn, and if you’re anything like me, it takes an assignment and a deadline to actually take the time to sit down and reflect. One of the best things we can do (myself included) is commit to continually learning, growing, and advocating for ourselves along the way. Let’s check back in, in another fifteen years, and see how we’ve done.


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