To adequately tell this story, we have to go back to 1991. My algebra teacher, Mrs. Patterson, made us do a report on what we wanted to be when we grew up and how math might be used in that profession. Unlike a lot of 14-year-olds, I knew exactly what I wanted to be. I’d wanted to be a copywriter before I even knew what a copywriter was. I was the kid glued to the TV after school and all weekend, not getting up when the commercials came on. When other kids dreamed of being astronauts, I dreamed of writing the next “Where’s the Beef?” commercial.
I found an ad agency in the Yellow Pages, called them up, and asked to speak with someone who writes commercials. I talked to him briefly, then asked the all-important question: “How do you use math in your job?” He paused for a long while, then said flatly, “I don’t.” That was it—I was sold. I made a poster board masterpiece covered in clippings from Seventeen magazine and proudly announced my career choice.
Fast forward a few decades, and I was deep in advertising—as an Account person. Turns out, there’s some math.
The Work I Loved and What Wore Me Down
While not a copywriter (portfolio school is expensive), I loved advertising as much as I thought I would. I loved the rush. I loved working with creative people, solving messy problems, and watching ideas turn into something real. But there were trade-offs. Late nights. Coming in on snow days for meetings. The heartbreak of losing a pitch you’d poured your soul into. Somewhere along the way, I started to wonder whether “fast paced” was just another way to say, “perpetually exhausted.”
I tried to leave the agency world more than once, but marketing departments saw “agency” on my résumé like it was a warning label. Apparently, they thought we lived in some alternate business reality with no rules.
The Nudge Toward Freedom
The real turning point came from a media freelancer who worked in our office. She floated in, did great work, and floated out. No drama. No politics. No 10 p.m. emails. Watching her, I didn’t just want her schedule. I wanted her calm.
So, in January 2018, I made a plan: save up, line up a side client or two, then leap. Three months later, I had no savings, no clients, and one sticky note on my monitor that read:
“What if the fear of what could happen made nothing happen?” -Doe Zantamata
I quit anyway. With zero cushion and two kids. My husband and I braced for chaos, and it came—financially, emotionally—but so did the freedom. I freelanced for my former agency to stay afloat, then projects started finding me. Colleagues, friends of friends, and random referrals. It snowballed faster than I expected. I know not everyone can take that kind of leap; I had support, privilege, and a healthy dose of luck. But I also had the growing conviction that work didn’t have to cost me everything else I valued.
What Freelance Gave Me
I worked from home on my own schedule. I saw my kids off the bus every day. I said “yes” to projects that felt good and “no” to the ones that didn’t. I also worked plenty of late nights and the occasional “vacation.” But it was all on my terms.
Here’s what helped me get started (and might help you if you’re considering the same):
- Name your fears, then reframe them.
“I’ll end up taking bad projects out of desperation.” → “Some projects won’t be a good fit, but that’s how I learn what is.”
- Tell everyone.
Let your network know you’re available as soon as you can. They can’t help if they don’t know.
- Leave on good terms.
My agency became my first client. It helped them through a transition, and it gave me a soft landing. Win-win.
- Don’t overthink the website.
If you’re a creative, yes have a clean, current portfolio site that reflects your best work. But don’t let perfection delay your start. For most freelancers, relationships drive the first projects more than a flawless website ever will.
- Find your people.
Other freelancers will save your sanity. They share advice, projects, and commiseration. All vital currencies. I grabbed coffee every few weeks with people I barely knew, and it was surprisingly great. You can also check out groups like CreativeMornings and Meetup.
- Stay present.
Freelancing can spin you into constant future planning. The best thing I did was focus on the project in front of me and do it well.
- Use marketplaces wisely.
Platforms like Wripple helped me fill in gaps between projects and get work with clients I wouldn’t have found otherwise. They’re great for stability, just make sure you balance that with your own outreach and relationships.
Where It Landed
Freelancing made me whole. It reminded me that stability isn’t the same as security, and sometimes the safest move is the risky one. I know I had a lot working in my favor—a supportive partner, a strong network, no catastrophic debt—and I don’t take that lightly. But stepping off the treadmill let me design a version of work that fit my life, not the other way around.
And yes, Mrs. Patterson, I still do math.
Angie Vaughn is Wripple’s Director of Marketing and a former freelancer who’s thrilled to stay close to the freelance world, without the QuickBooks subscription.
To learn more about any or all of these solutions, contact your Wripple Client Lead, or
request a demo.To adequately tell this story, we have to go back to 1991. My algebra teacher, Mrs. Patterson, made us do a report on what we wanted to be when we grew up and how math might be used in that profession. Unlike a lot of 14-year-olds, I knew exactly what I wanted to be. I’d wanted to be a copywriter before I even knew what a copywriter was. I was the kid glued to the TV after school and all weekend, not getting up when the commercials came on. When other kids dreamed of being astronauts, I dreamed of writing the next “Where’s the Beef?” commercial.
I found an ad agency in the Yellow Pages, called them up, and asked to speak with someone who writes commercials. I talked to him briefly, then asked the all-important question: “How do you use math in your job?” He paused for a long while, then said flatly, “I don’t.” That was it—I was sold. I made a poster board masterpiece covered in clippings from Seventeen magazine and proudly announced my career choice.
Fast forward a few decades, and I was deep in advertising—as an Account person. Turns out, there’s some math.
The Work I Loved and What Wore Me Down
While not a copywriter (portfolio school is expensive), I loved advertising as much as I thought I would. I loved the rush. I loved working with creative people, solving messy problems, and watching ideas turn into something real. But there were trade-offs. Late nights. Coming in on snow days for meetings. The heartbreak of losing a pitch you’d poured your soul into. Somewhere along the way, I started to wonder whether “fast paced” was just another way to say, “perpetually exhausted.”
I tried to leave the agency world more than once, but marketing departments saw “agency” on my résumé like it was a warning label. Apparently, they thought we lived in some alternate business reality with no rules.
The Nudge Toward Freedom
The real turning point came from a media freelancer who worked in our office. She floated in, did great work, and floated out. No drama. No politics. No 10 p.m. emails. Watching her, I didn’t just want her schedule. I wanted her calm.
So, in January 2018, I made a plan: save up, line up a side client or two, then leap. Three months later, I had no savings, no clients, and one sticky note on my monitor that read:
“What if the fear of what could happen made nothing happen?” -Doe Zantamata
I quit anyway. With zero cushion and two kids. My husband and I braced for chaos, and it came—financially, emotionally—but so did the freedom. I freelanced for my former agency to stay afloat, then projects started finding me. Colleagues, friends of friends, and random referrals. It snowballed faster than I expected. I know not everyone can take that kind of leap; I had support, privilege, and a healthy dose of luck. But I also had the growing conviction that work didn’t have to cost me everything else I valued.
What Freelance Gave Me
I worked from home on my own schedule. I saw my kids off the bus every day. I said “yes” to projects that felt good and “no” to the ones that didn’t. I also worked plenty of late nights and the occasional “vacation.” But it was all on my terms.
Here’s what helped me get started (and might help you if you’re considering the same):
- Name your fears, then reframe them.
“I’ll end up taking bad projects out of desperation.” → “Some projects won’t be a good fit, but that’s how I learn what is.”
- Tell everyone.
Let your network know you’re available as soon as you can. They can’t help if they don’t know.
- Leave on good terms.
My agency became my first client. It helped them through a transition, and it gave me a soft landing. Win-win.
- Don’t overthink the website.
If you’re a creative, yes have a clean, current portfolio site that reflects your best work. But don’t let perfection delay your start. For most freelancers, relationships drive the first projects more than a flawless website ever will.
- Find your people.
Other freelancers will save your sanity. They share advice, projects, and commiseration. All vital currencies. I grabbed coffee every few weeks with people I barely knew, and it was surprisingly great. You can also check out groups like CreativeMornings and Meetup.
- Stay present.
Freelancing can spin you into constant future planning. The best thing I did was focus on the project in front of me and do it well.
- Use marketplaces wisely.
Platforms like Wripple helped me fill in gaps between projects and get work with clients I wouldn’t have found otherwise. They’re great for stability, just make sure you balance that with your own outreach and relationships.
Where It Landed
Freelancing made me whole. It reminded me that stability isn’t the same as security, and sometimes the safest move is the risky one. I know I had a lot working in my favor—a supportive partner, a strong network, no catastrophic debt—and I don’t take that lightly. But stepping off the treadmill let me design a version of work that fit my life, not the other way around.
And yes, Mrs. Patterson, I still do math.
Angie Vaughn is Wripple’s Director of Marketing and a former freelancer who’s thrilled to stay close to the freelance world, without the QuickBooks subscription.
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