Perspectives: Rising from the fire
A dumpster fire of jobs and an actual fire in Hawaii led to a career pivot
This week’s Perspectives comes from Gail Marie. Gail and I worked together at a marketing agency, but our roles didn’t interact much. We began chatting after we both left the agency and found that we had a lot in common.
Gail lives on the island of Maui, which was ravaged by wildfires earlier this year. Between that and several dumpster fire work experiences, she has decided to pivot her career. She plans to freelance and focus on art. You can check out her art on Instagram.
Gail shared her story with me via interview. Her story has been edited for length and clarity.
Three things happened all at once.
The first was that I quit a job I’d been at for about seven months because I didn’t trust the CEO. He owes me, freelancers, and former clients hundreds of thousands of dollars. I felt very taken advantage of. But I’m more about the money he owest to people whose contracts I signed. I talked them into coming to work with me. It was so crappy.
About two weeks later, the Lahaina fires happened. We’re about seven miles from the edge of the burn zone. But the wind that day was blowing away from us. So we didn’t even know the town was burning down. We couldn’t smell or see smoke. We had no idea that so many people just down the road were dying and fleeing for their lives. It was terrible and is still terrible, because so many people are having a hard time finding places to live.
And I’ll turn 50 in about six months. I’m tired of working for other people. I'm a little jaded. The job before my last, I was fired for no reason, out of the blue, with no warning. The job before that was a shitshow.
You’re just an employee, if you don’t own the company. And they can talk about how they’re people-first or their DEI policies or work-life balance, whatever. Ultimately, you represent a cost. The end, right? That’s it. That’s all you are. And yet, we invest so much of ourselves in the work we do for them.
I’m looking at the back nine of my career thinking, “I don’t need to keep doing the same thing over and over and expecting a different result.” Maybe the universe is saying something to me.
I’m still interviewing for full-time positions with companies whose leadership I admire. I’ve interviewed for some really interesting positions. And I could get pretty far in the interview process for VP, Director, or Head of Content roles. And I couldn’t get a job. Part of me was relieved… it was a weird feeling.
I started applying for copyeditor positions, account director positions, non-managerial, and individual contributor roles. I was way overqualified, but I would explain everything in my cover letter: “I want to pivot, I’m here for you.” I wanted to dial it down. But I couldn’t get those jobs either.
I started picking up my watercolor paints again because I had time since I wasn’t working. And when I paint and when I’m learning how to draw, I think, “This is how I want to feel. This is how I want to spend my time.” And I’m a marketer. I know how to market myself if I were to try this. And part of what I want to do through my art is educate people to appreciate Maui.
I have some short-term freelancing gigs lined up. I didn’t look for any of them — they all came to me. And I would make enough in one month that I could take the next two months off. I’m excited about the challenge of the work and the people I’ll be working with. But my new focus is art. That’s where I want to put my time and energy.
If my freelance work is project-based and I’m in charge of a particular deliverable, I can be done and walk away. I’m a pretty focused person and I’m pretty good at managing my time.
A pivot like this almost had to be forced. I don’t actually feel like I’m that resilient or strong enough to make this pivot without being forced to, to be honest. Because I really did enjoy my work and the teams I was working with, building teams and hiring people. I like setting a goal and working with people to reach the goal. And I played “office” as a kid at a card table. My dad had old briefcases and we had a phone on the table and I’d have meetings.
But I’m increasingly disillusioned with it. This is a better way to honor myself. I’m going to try pivoting and freelancing. I’ve freelanced before and it was fine. I worked for some really great companies and it was fun.
I went into this with a lot of money in my bank account. I want to make that clear. I’m saver, and that’s allowing me to do this. My wife has health insurance through her job, so I don’t have to worry about that. The risk I’m taking isn’t that risky. Even if I don’t get freelance work, I’m ok for a while. I’ve lived very purposefully and that has given me some financial freedom now at 49. Which also feels so late to be making this pivot! So late.
I’m excited and oddly confident. I’ve started posting about my art on LinkedIn. And I’m so surprised at the number of views, comments, and likes I get on those posts. Even people reaching out to me saying, “I’d love to see what you’re creating.” I already have people saying they want to support me.
I’ve been working for a long time and my network is strong. I feel more in control of things than I’ve ever felt. Even when it comes to art. I have a vision for what I want to do. I’m taking an online course and learning how to draw. And I know I need to be on YouTube and Instagram and eventually I’ll need a website.
For years, people have been telling me, “The thing you light up about is not work.” For a while, I had a podcast about reading. This was back in 2014. It was called The Spine. The show was about the ways reading can shape how we think, love, and live. I would interview writers about their reading lives. And I loved The Spine and everything about it. With art, I have the same energy.
I don’t want to look back and wonder why I didn’t stick with it, like I do when I look back at 2014. So with this freelance work coming to me, maybe it’s a sign. I don’t really believe in signs, but it’s making the pivot easier.
With Lahaina burned down, I lost my vet clinic, my favorite coffee shops, the place I used to buy clothes, my bookstore where I volunteered, and my library. And every conversation you have here is about the fire. You go into the grocery store, you fill up your car with gas, you go to the coffee shop, wherever. It’s all we think about. There are the people who experienced the fire. And the people who didn’t experience the fire. So the island feels really, really small.
I need to get off the island on a regular basis. Just because it’s a really hard place to be right now. I can take my art with me and I can take my work with me and spend more time off the island, with real people as opposed to virtual. I hope to create a community through my art and connect with people.
Art has really ignited my desire to write. I’ve always been known as a writer because that’s just where I landed. I have a Master’s in English Literature. But I haven’t really felt like writing in years. Suddenly, I want to write about the stuff I’m learning about art and how it’s making me think differently.
My wife thinks I'm crazy. She's like, “What are you even doing? What do you mean, you're gonna be an artist? What’s going to happen?” And I'm like, “I don't know. It's just what I'm doing.” I’ve got freelance jobs. It's okay. I'll make it work.
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