Personal | Jenn Chen

10 Lessons from 10 years of freelancing

Today, I celebrate a decade of freelancing/self-employment.

Something funny happens when you give notice at a job: people ask you what you’re going to do next. So when I put in my notice at Groupon a decade ago, after burning out twice, I did it because I was on the edge of a third burnout. I had enough saved up at the time and very few expenses so I was able to leave without thinking of what I’d do next. But because people kept asking, I ended up scrambling for an answer and blurted out, “I’m starting a business! I’m going to do coffee crawls!”

Wow, I was so naive. Fast forward through creating and ending that business, part-time jobs, a “full-time” client that paid me as a consultant, and offering and stopping services, here I am.

One decade is a long time. If you’ve been following along in my journey, you’ll know that I like to celebrate the wins, no matter how small. My freelance-versary is a big win: it’s marked in my calendar, I usually do something to celebrate it, and I write one of these posts to mark where I was in the journey. You can read my 9-year post from last year here.

Here are 10 lessons I’ve learned from 10 years of freelancing:

2022 Word: Intuition

My word for the year 2022 is “intuition.”

f**k email etiquette

Your emails don’t have to be long to be nice.

2021 Recap

Oh look, it’s the end of another year. A year that really feels like it’s only been three months long. I used to set a word of intention for the year with goals plus a year-end reflection on them. Obviously, 2020 didn’t count as a year. So, here we are for a 2021 recap.

Sprudgie nomination for Best Coffee Writing!

I’m honored to be nominated in the Best Coffee Writing category for this year’s Sprudgie awards. For those who are unfamiliar, the Sprudgies are the specialty coffee industry’s version of the Oscars except that everyone gets to vote.

On relief

I don’t know about you but this past weekend, it felt like I could take a full, deep breath for the first time in a long while. In October, I had been doing ok in terms of giving myself a break and not doomscrolling at all hours. Last week, though, I found myself attempting to work on the days I said I would work, staring at the computer screen, and then refreshing my Twitter feed for the umpteenth time that hour. The prolonged wait and experience of multiple Tuesdays in one week was bad for many people’s mental health.

How do you define success?

I’ve been watching “Emily in Paris” on Netflix and there was a line that stood out to me: “You live to work, we work to live,” a French person told Emily, his American colleague. Whether it’s success in your career or your life, we’re all influenced by where we grew up, our culture, and the influences of the people you surround yourself with.

Relearning how to work

When I first started out working for myself, I had issues with working. I was in a studio apartment in Chicago. My desk was one foot from my bed. My counter and stool was across from my fridge. Naps and snacks were so tempting and it didn’t help that my natural inclination was to be a night owl.

Giving yourself some grace

I’ve been grappling with the idea of “grace” lately. And not the religious or spiritual kind. As you might know, I moved to a new place three weeks ago. Since moving here, I’ve already gone on two trips. But to me, it feels like I’ve been here forever and why haven’t I already organized everything and put decor on the walls? If it was any other person, I’d tell them to take their time but since it’s me, I feel like I’m lacking that same patience and grace.

2020 Goals: Centered

Every year, I pick a word or phrase to focus on. It’s better than setting resolutions in my opinion. This year, I’m choosing “centered.” For me, this means that I want to make sure that I’m opting in to do work and hobbies that are central to who I am. I want to reinvest in myself and my worth. This goes for both physical and mental health.

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