We caught up with the brilliant and insightful Theresa Sullivan a few weeks ago and have shared our conversation below.

Theresa, looking forward to hearing all of your stories today. Almost all entrepreneurs have had to decide whether to start now or later? There are always pros and cons for waiting and so we’d love to hear what you think about your decision in retrospect. If you could go back in time, would you have started your business sooner, later or at the exact time you started?

“What if you built a rope bridge?” my friend asked, and that’s what I tried to do.

I’m so not a “leap and the net will appear” kind of person – as an introvert and a fairly cautious person, I always assumed that something like entrepreneurship would feel way too risky and overwhelming to me. But there I was, trying to build a rope bridge – something a little more sure than leaping into a net – to transition from being traditionally employed to striking out on my own.

Now, I’m the brand strategist and copywriter behind Little Flame Creative, and I’ve been working full-time in my business since 2021. I started as a side hustle in my late 20s, after I’d been working professionally since college and was surprised to find myself curious about a different way to work and live.

I’d never really had examples that an independent creative career could be plausible or even possible, as the paths that I saw modeled looked like going to the office every day and working your way up. So that’s what I did, and it worked, for a while.

I was a thoughtful employee, made contributions, and followed all the unspoken rules. The rigidity of the traditional path got harder for me to accept as time went on, though. When my niece was born, I used precious time off to go meet her – and then had to fly right back while my husband (who worked remotely) got to stay there and help. I’ll never forget staring out the plane window knowing that I was missing out on something I couldn’t get back, that the balance was all wrong.

For a while, I didn’t really know what to do with that feeling, because I assumed that I didn’t have what it would take to create my own path. The worries about finances and health insurance were real, and I never thought of myself as someone who would voluntarily choose to face all the unknowns that are part of entrepreneurship.

But the thought kept nagging at me, and thankfully, I decided to try. I joined a business launch program and did client work on nights and weekends. My mantra was simple: “keep going.” I repeated it to myself over and over through the fear, excitement, and exhaustion. I was changing my life. I was deciding to bet on myself. And eventually, my “rope bridge” was solid enough that I left to dedicate myself to Little Flame full time.

When I first thought about this question, I figured I’d say I wish I’d started my business sooner – but actually, I think I was right on time.

The professional experience I had in my 20s was important, and I’m grateful for it. I got to do meaningful nonprofit work and live out the pros and cons of traditional employment. I don’t think I’d be as skilled a writer or a business owner without those years behind me.

I do wish, though, that I’d seen entrepreneurship as a possibility sooner. I can’t believe how much of my life I spent assuming that I’d never be able to do exactly what I’m doing now. What if I’d believed that forever?

The reality is, there are so many ways to make a living these days, and the “climb the ladder” way is just one way – not the only way. If I’d seen more examples of self-employment sooner (not talking about the “I quit with no plan and now make six figures” clickbait), I could have started challenging all those assumptions earlier. Building my own business would have seemed more normal, and I could have met more self-employed mentors along the way.

Now that my business is more established, I try to be one of those examples for other people like me. You don’t have to leap and hope the net will appear. You don’t have to be an extrovert who feels at home shaking hands at a cocktail party, or a guy who went and got his MBA, in order to succeed. It is totally possible to be a sensitive, creative person and still make it happen.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I’m Theresa Sullivan, and I’m the copywriter behind Little Flame Creative. I specialize in brand messaging and website copy for creative and purpose-full businesses because I believe that every entrepreneur deserves thoughtful copy that truly fits – not words they have to fit into.

Writing and working with big ideas has always been my thing, but the spark for the business grew over time. Over the years, I’d been lucky to work personally with many entrepreneurs who had truly changed my life or had made it more fun – everyone from wedding vendors and fitness instructors to wellness pros and coaches.

I experienced firsthand how meaningful and needed their work was. I saw how they were led by their values and their own mission to serve others. And I saw how, for many of them, talking and writing about their businesses was… not exactly their strength. The website copy that made them cringe dragged down their confidence and stood between them and their right-fit clients, which held them back from being able to fully do their thing.

And that just didn’t seem right to me, you know? Why should they have to struggle with words that were selling them short when they had SO much brilliance and purpose to share? I knew I could help, so I put my poetry degree (yup, I went to poetry school), years of communications creds, and ethical marketing know-how into a blender, and Little Flame emerged.

Being a copywriter is really special, because my clients really are inviting me into their inner world and pulling back the curtain. They’re trusting me with their big ideas, their “I don’t knows,” and their vision for what they really want, and I don’t take that for granted!

I’m always proud when I help a client have a successful launch, sell out a service, or rank higher on Google, but I’m most proud when they say “that’s exactly what I’ve always wanted to say! How on earth did you get that to sound exactly like me?!” Good copywriting isn’t magic, but sometimes it feels that way, which is really fun and satisfying.

What do you think is the goal or mission that drives your creative journey?

I talk a lot about how copywriting is a tool for both sales and self-expression, and the self-expression part is absolutely at the core of my mission, too.

It lights me up to help people find the words to say what they really mean, to show others what they believe in, and to finally own who they really are. In life (and especially in business!) it’s so easy to feel like there are parts of yourself you should hide. Like all of the “successful people” sound a certain way, and you should be like that too. Like you’re not free, or worthy enough, to show up just as you are.

But the world of online biz doesn’t need more of the same, and none of us need to spend any more time playing small. When I finish brand messaging and website copy for a client, it’s like holding up a mirror to the trustest, most confident, most fully alive version of themselves and their business, and that feeling is electric.

Most of us started our businesses because we wanted a sense of freedom and control over our lives, but it’s hard to feel that way if our words are holding us back. When our words unlock everything that’s in our head and heart, though? That’s powerful as hell, and that’s what I’m all about.

What’s a lesson you had to unlearn and what’s the backstory?

Building my business has been a major unlearning in so many ways. So much traditional entrepreneurship advice says things like “work harder, push yourself farther, take big risks, be louder, say yes to everything.” Ideas like this taught me to look outside of myself for answers, to take in anyone and everyone’s opinion, and override my own gut instinct – and that’s what I’ve had to unlearn.

Strengthening my own sense of self-trust and learning to work in ways that actually align with who I am, instead of working against myself, has been complicated but so, so worthwhile. A business that suits me doesn’t involve hustling towards burnout, pretending to be extroverted, or saying yes to an opportunity just because to someone else it looks like a no-brainer.

I’ve had to get more clear about what I want from my business, and then figure out how to create those conditions for myself. I love getting to have thoughtful 1:1 relationships with my clients, plenty of time and breathing room for creativity, and a daily schedule that doesn’t feel depleting. Bringing all of this to life has required making changes to my packages and pricing, creating clearer messaging around good-fit projects, and building boundaries around my workflow.

But most of all, it’s required actually embracing who I am. Especially when it’s easier than ever to compare yourself to other business owners online, it’s a vulnerable thing to accept your natural rhythms and stay connected to what you really want. But why build a business (or a life) that you have to struggle against? The unlearning is worth it, and I wouldn’t trade this experience of getting to know and trust myself for anything.

Contact Info:

• Website: www.littleflamecreative.com
• Instagram: www.instagram.com/littleflamecreative

Image Credits
Elizabeth Joy Sanders