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How a series of career detours eventually led Dropbox’s Associate Editorial Director to her dream job

4 min read
Shayna Hodkin
  •  Jan 10, 2020
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Name: LaDonna Witmer Willems
Title: Associate Editorial Director
Company: Dropbox
Location: San Francisco CA, USA
Age: 40-mumble
Years in the design industry: 22


LaDonna’s story, in LaDonna’s words:

I started my life as a farm girl in rural Illinois and grew up milking goats and riding horses. Somewhere along the way, I realized I loved city life. I lived in Chicago for a while, but it wasn’t weird enough, so I relocated to San Francisco 20 years ago this month.

I am an avowed introvert, an Enneagram 4, a reader of sci-fi/fantasy, and a fan of dangly silver earrings and stompy black boots.

I’m married to a dude, and I’m a mother to a 9-year-old girl who loves dragons. We all live by Ocean Beach with our smooshy-faced dog, Vila (“vee-lah”), a bird named FeeBea, and a beta fish named Rusty.

[Read more: Why you need a weekly “craft time,” according to Atlassian’s design manager]

Her move from poetry to tech in ten steps:

  1. I don’t want to have a career, I just want to ride horses and doodle words.
  2. I guess I’d better study something “useful” because poetry doesn’t pay the bills.
  3. Journalism doesn’t pay the bills, either, and all this ambulance chasing for “newsworthy” stories makes me feel like a bad person.
  4. What is this copywriting thing? Oh, I get to name paint colors? Rad.
  5. I’ll just sit in this corner and write by myself, please and thanks.
  6. Now people want me to manage people? I guess if I’m managing other writers, that will be ok? As long as I still get to write.
  7. Oh now I’m director-ing, with more people and more meetings. But I still get to write. And I’m getting paid to travel to Australia and Japan and Scotland and India and Bolivia and write about it. Not too shabby.
  8. I’m actually really digging this whole voice thing. Telling brands who they are and what they should sound like and how they should talk about themselves. Cool, cool, cool.
  9. Tech wants to hire me? I don’t know if tech and I have anything in common, but these particular people seem like good people, so I’ll give it a whirl. Also, free food.
  10. OMG I really love it here. We’re doing crazy creative work. And I’m still traveling the world, only now I get to talk to people about finding their own personal voice and telling their own stories. No one ever told me this kind of job existed!

On life after layoff:

I have been laid off more times than I can count. Getting laid off might not be your fault, but it absolutely feels like failure. In the ad agency world, when they lose accounts, copywriters are often the first to go. So there I went. I’ve been through a dot com bust and a recession and have lost jobs I dearly loved. It’s always a gut punch, even when you see it coming. Every time I’ve been laid off, I’ve staggered around for a while, usually taking the first job I could find, which was never a job I wanted. But I always found my way back—usually by a completely different route than the one I was taking before the layoff.

Hot tip: When they start taking the plants and free food away, you best start battening down the hatches.

I could never have planned the career I have—it’s been meandering and unexpected. But all those wrong turns and detours and dead ends have made me a lot more zen about work. And they’ve opened my eyes to truths about myself and about life in general that I may have never seen otherwise.

[Read more: Your UX job title ultimately doesn’t matter—but this does]

Her work setup:

This is my desk at work. Desktop backgrounds are both by Camille Rose Garcia.

LaDonna’s desk from above.

No matter how small the workspace (they keep shrinking, the further I go in my career, which is… backwards, somehow), I’ve always gotta have some tchotchkes to spice things up. And photos. And stickers.

LaDonna’s personal details on her desk.

On the importance of a good thesaurus:

The thesaurus was my first-ever work-related purchase, bought for my very first copywriting job at an agency in Chicago, umpteen years ago.

I was a brand new copywriter, I needed to name some paint colors, and I was scraping my brain looking for fresh words. I decided to go to a nearby bookstore for help and bought myself the fattest thesaurus I could find. It was trying to be fancy, calling itself a “Synonym Finder,” but I knew what was up. I lugged that thing back to my desk, submitted my $17.99 expense report, and named the heck out of those paint colors!

LaDonna’s book collection. The stuff of legend.

A thesaurus, digital or printed, has always been my friend. Especially when I’m staring at a blank page and a blinking cursor.

[Read more: 5 interviewing tips you need for 2020, according to design leaders]

On making time for passions:

I just finished NaNoWriMo (National Novel Writing Month). You sign up to write 50,000 words in 30 days during the month of November, and I made it to 51,575 words. I’m pretty proud of myself for doing that! Today someone asked me how I made the time and I said, “I didn’t. I stole it.” Five minutes here, an hour there. I wrote in waiting rooms and airplanes, on my lunch break and on Thanksgiving. I just made writing a priority every day, in whatever way I could manage. I was constantly doing calculations in my head like, if I don’t check Instagram right now, I bet I could spend 15 minutes writing and get 200 or so words in.

On failing up:

Failure is not the end. It’s nowhere near the end. It’s life/the universe/your brain saying, “Well, that didn’t work, so how ‘bout you flip this situation on its side/head/top corner and look at it from a whole new perspective. And then try again, but differently. And then try again, but differently, again. And then, try again.

On what she really wants you to ask her:

I wish someone would ask me to read them a poem.* People just don’t go around asking people to read poems enough, you know?

*Of course I want to read you one of MY poems! 

The table of contents of LaDonna’s book, New Hymns.

What she wishes someone had told her…

  • Before starting her first job. Writers are designers too—we design with words! It’s taken me 22 years and a whole luggage set full of imposter syndrome to finally realize that.
  • About becoming a mentor. It’s not about having bucketsful of helpful answers, because what worked for me isn’t necessarily going to work for anyone else. Mentoring is about lifting someone else up and giving them what they need to trust themselves enough to figure out their own answers.
  • About life. Follow the questions and embrace the mystery. The older you get, the more you’re going to realize that you don’t know much at all. And that not-knowing is a beautiful, free-ing thing.
LaDonna embracing the mystery in Jordan, en route to Petra.

[Read more: Why Google UX Director Chloe Gottlieb wants her team members to be more successful than she is]

Three designers we should be keeping an eye on:

    • Michelle Morrison. Michelle is just ridiculously wonderful. She’s the Design Program Manager at Dropbox, and she’s been at Facebook, Intercom, Square, and IDEO. For 5 years or so she ran Designers + Geeks, which was San Francisco’s largest design community and lecture series. But I especially love her because she has a strict policy of working on fun projects only. It’s a truly excellent policy, I can tell you from personal experience.
Cover of The Secrets of Falling, designed by Kathy Azada.
    • Kathy Azada. Kathy was my design partner way back in the day and we became the best of friends—she’s now my daughter’s godmother! She is a creative director and visual designer who does a lot of brilliant work for nonprofit organizations, including The Goldman Environmental Prize, Women Donors Network, and The Redford Center. Kathy also designed my second poetry book, The Secrets of Falling.
Cover of New Hymns, designed by Lexi Visco
  • Lexi Visco. Lexi designed my third book of poetry, New Hymns, and is doing some fun new work as co-founder of Companion Platform.
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