How one influencer gained a massive following and quit her job to start a full-time blog
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When you think of an influencer, you might imagine a privileged young person trotting the globe and taking superficial selfies. As one of the first fashion influencers in the industry, I’m not going to lie and say that this stereotype doesn’t exist.
But there’s much more to the role of influencer than many people realize.
A little more than a decade ago, I was on my honeymoon when I found myself at a turning point in my career. Fresh off of my last role in corporate entertainment after working for The Oprah Winfrey Show, E! News, and Imagine Entertainment, I wanted to do something more hands-on creative, but I also wanted the security of a steady paycheck. Not an easy balance to strike.
I am so grateful that fate handed me an opportunity when WordPress, the hosting site for the blog I had started just as a hobby, featured one of my photos. Suddenly, I had an incredibly valuable asset—followers—and the chance to turn my blog into my own business.
Still, as you’ll read in the following excerpt of my new book, Liking Myself Back, it was a difficult decision to pursue blogging (the term “influencer” didn’t really exist yet) as a full-time job. I had no safety net; I didn’t want to ever take advantage of my followers by aggressively selling to them; and I knew even then how much posting pictures of myself online could affect my mental health and my self-esteem. It was not an easy path from blogging to sitting front row at fashion week shows to running my own successful businesses (and, yes, trotting the globe and posting selfies).
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Influencers are entrepreneurs and experience the same highs and lows as any small business owner. But if I could go back to my honeymoon, I wouldn’t change a thing. I’m so grateful for the life and career that I have now and the work that I’ve done to heal and create balance so I can enjoy it all even more. I would only tell myself to buckle up for an incredibly exciting but somewhat bumpy ride.
Below is an excerpt from my new book, Liking Myself Back: An Influencer’s Journey from Self-Doubt to Self-Acceptance.
“I’m just sick of working for other people,” I told Grant now with my eyes closed as I angled my face toward the sun. “But what else can I do? I’m not going to start my own company. I’m not going back to Texas to farm alongside my dad.” I laughed out loud at the thought.
“Can you imagine?”
We both smiled as Grant floated on his back in the pool just a few feet away from me. He looked thoughtful.
“You’ve been really into your blog,” he said. “Do you think you could keep doing that? Maybe design sites for other people to make some cash?”
I looked at Grant. What he was saying sounded amazing, but I had never considered anything like that as an actual career option.
“I didn’t go to school for that,” I reminded him. “I’m not a graphic designer or a coder; I’ve just been learning as I go. Why would anyone hire me?”
I was getting worked up, but Grant remained impassive, practical.
“I could name ten people I know in LA who probably need a new website right now,” he said. “Start with them. Build a portfolio. Take some classes. I can float us for a bit financially if this is something you want to do.”
I sat up on the lounger and started tapping both of my feet as I looked at Grant, a smile forming on my lips. Until then, I had never allowed myself to imagine how it would feel to devote myself to something creative full-time, something that belonged to no one else but me. I had been so busy trying to build a resume that would look impressive to other people. But as I’d gotten to know myself, I’d realized that those jobs that looked so good on paper weren’t fulfilling for me. Maybe being true to myself didn’t just mean a quirky wedding or an atypical honeymoon. It had to extend to all corners of my life, including the very center of what I did for work each day.
When we got home from the honeymoon, I didn’t dip a toe in or get my feet wet or any other metaphor for starting something slowly. I dove in headfirst and devoted every ounce of my energy to the blog. For the first time, I was using my ADHD to my benefit. I was hyper-focused on something I felt passionate about, and it all just clicked. I realized that I didn’t have to let my ADHD hold me back. Instead, could use it to thrust myself forward.
The first thing I did was respond to every single comment I’d gotten on my honeymoon pics. The mostly women who’d visited the blog wanted to know more about what hotels we’d stayed at and other sites we’d visited. Some were even asking about my life back home.
I started emailing with many of these women, wanting to learn more about their own lives and the type of content they wanted. I learned that while they were super interested in travel, they had tons of questions about fashion. They wanted to know what I’d worn on my honeymoon and asked me what they should wear to various events and outings. It was amazing to me that these women looked at me as some sort of expert, when I had started the blog just for fun. But this was an opportunity to use my own passion for clothes to turn it into something these women might find truly valuable.
I started posting more frequently and putting together content to meet my new followers’ needs. One woman asked me what to wear on an upcoming fly-fishing trip, so I posted an entire outfit with links to buy each item. Another reader asked me for links to everything I was purchasing that month for my closet, and another wrote in asking for advice on what to wear to her engagement shoot.
I enrolled in coding classes so I could learn how to code HTML better. But I was mostly self-taught, googling and watching YouTube videos to learn how to do things as I was doing them. I was excited by Grant’s idea of creating websites for other people and knew that I needed an example of my work to attract clients. So, I offered to create a site for his sister, an aspiring singer, for free. She came over to our condo, and we drank wine while messing around with templates and various designs for hours. It didn’t feel like work at all, even after I started charging other friends and neighbors $500 per site and set up my own company, Jolly Bulldog, in honor of William and Polly. I put so much work into each site that if you broke that rate down hourly, it would have been hilariously low. But it still felt like stealing to get paid to do something I truly enjoyed.
When I wasn’t designing sites for other people, I was working on my own blog, emailing with my followers, and researching other fashion and travel blogs so I could learn more. Blogs had been around for a long time, but the idea of anyone making their living from a blog was brand new. There were very few people who had a blog as a career, and it sounded like a fantasy to me.
At this point, I was less concerned about making money from my own blog. I wanted to continue doing it as a creative passion and make ends meet by earning money off Jolly Bulldog. But I needed to level up.
We were still skating by and mostly living off of Grant’s income, and I hated it. I wanted to contribute more financially, and the idea of being able to do that while doing something I loved that didn’t involve going to an office and working for someone else seemed too good to be true. But I was determined to figure out how to make it happen.
Everything I was doing felt right in a way it never had before, and I would’ve done anything to hold onto that feeling. For the first time in my life, I didn’t need external validation because I was truly fulfilled by my work. Working in our living room wearing jeans and a tank with my bare feet on the coffee table, I felt more powerful than I ever had in my Theory suit.
Through my research, I discovered that there were blogging conferences where I could learn more about the industry. The Alt (short for Altitude) Summit in Utah seemed like the most important one, and I saved up over several months to buy a ticket. This was the first real investment I made in my blog, and it was more than worth it.
Over the weekend-long conference, I learned about web design, posting cadence, editorial calendars, and branding. I felt completely naïve—this was all new to me—and yet I was a total sponge, soaking so much in that it felt like it was bursting out of my skin. And hanging out with the other bloggers over coffee and drinks before and after the panels and talks was just as educational. I learned about all the hard work they were doing behind the scenes to create content, design their blogs, and brand themselves. All of these confident, successful, put together women were basically stylish computer programmers. They motivated me to put in any amount of work necessary to achieve success and that same level of confidence.
When I got home, I couldn’t wait to tell Grant all about the conference. I had barely wheeled my suitcase past the front door before I was filling him in on every detail of who I’d met and what I’d learned.
“Babe, I need a name!” I shouted to him as he went into the kitchen to pour us some wine. He poked his head back into the living room with a quizzical expression on his face. “For the blog,” I laughed. I was still just calling it Jacey Lenae. “All the other girls have cute names like the The Blonde Salad or Cupcakes and Cashmere. I need something witty like that.”
“Hmmm…” Grant ran a hand through my hair and took a sip of his wine. “The blonde burrito?”
“Grant! No!” I giggled, feeling like a bottle of champagne that someone had shaken up.
“Well, what do you want it to be like?” he asked me. “When they hear the blog’s name, how do you want people to feel?”
I took a deep breath to settle myself and thought about it.
“The women who read my blog are cool. I want them to feel like…” I stared out the window, trying to find the right words. “Like they’re in control of their lives. Like they can dress however they want and be whoever they want. Basically, the opposite of that lost little girl I used to be who always felt like a damsel in distress.”
“So, instead of a damsel in distress, how about… Damsel in Dior?”
I looked at Grant. “I love that,” I said quietly, leaning in for a kiss. “And I love you!”
My bags went unpacked (a huge deal for me) as I immediately dug into rebranding my blog as Damsel in Dior, using everything I’d learned at Alt Summit. The first thing I did was to create an editorial calendar and commit to sticking with it for two months to see how my following grew in that time. My schedule was: Corporate Mondays (featuring a work-appropriate outfit), Beauty Tuesdays (hair and/or makeup), What I Want Wednesdays (a shopping post), Champagne Thursdays (hosting tips, inspired by my Chicago days), and Fun Night Friday (with a fun outfit for going out).
In between, I experimented. I never sought out to be just a fashion blog or a travel blog. Life is all-encompassing, and the blog was, too. But my readers were naturally more interested in some things than others, and I continually tweaked my content to meet their needs.
It was fascinating to me to see what my readers responded to and what they didn’t. One week, I posted about a great fish taco recipe I’d tried, and it was met with crickets on the blog. But just a week later, I posted a margarita recipe and it got a huge response. It wasn’t random. I found that certain content received more clicks and comments on specific days of the week. For example, drink recipes got more clicks on Thursdays while fitness posts were more popular on Mondays.
After two months, my stats were more consistent and growing steadily, so I decided to stick with the editorial calendar I had created. The whole time, I was engaging with readers very intimately, one on one. They told me about their upcoming vacations, and I put together entire packing lists for them and posted them on the blog. I showed them how to style the same items from those lists in different ways, because this was real life and of course they would wear the same clothing multiple times.
It was never about how many followers I did or didn’t have. There was no Instagram or social media or temptation to keep score. It was just me and my readers, and I appreciated and valued every single one of them. They sent me photos of themselves wearing the outfits we had put together, videos of their engagements, and long form stories about how they, too, always felt misunderstood or like a damsel in distress. By focusing on this, I continued to make the blog about my readers instead of about me and my personal life.
This all changed a few months after Grant and I got back from our honeymoon. I had submitted our wedding photos to Style Me Pretty, a wedding site that I had been obsessed with when we were planning our wedding. After they chose our photos to be highlighted, it brought a huge number of new readers to my blog. It was so exciting, but these readers wanted to know all about me and even Grant. They asked for more details about the wedding, the honeymoon, and our lives in LA.
I was determined to create the content that my followers wanted, and what they wanted could not have been clearer. When I posted a picture of myself and what I was wearing, I got triple the views and triple the comments of any other post. This gave me pause. Since meeting Grant and then devoting myself to the blog, I had been feeling more authentically like myself than I had, well, ever. For once, my life wasn’t about pleasing other people, either through impressive titles and accomplishments or picture-perfect looks. I was getting a taste of what it was like to be respected for my other talents, not just for what I looked like or what I wore, and I wanted to keep going in this direction.
I was worried that posting pictures of myself and what I was wearing would awaken the people pleasing beast and put too much of an emphasis on the Jacey that loved fashion and dressing up. As I finally began to feel complete, I was determined not to let farm girl Jacey slip away while making her fashionable counterpart look perfect on the blog. The real me was somewhere in between the farm girl and the fashionista.
Putting myself out there for the world to see was terrifying, not least of all because I worried about what my family back home would think. So, yeah, I guess that whole people pleasing thing was still in effect. My family obviously didn’t understand what I was doing. The blogging industry was so new that few people did. But as much as I wanted to be true to myself, every time I posted about getting drunk over the weekend or laughing so hard that I peed my pants, I cringed internally, wondering what my mother and Meme would think.
I was having a blast writing and creating, but I wasn’t making money from the blog until a company called rewardStyle reached out to me about six months after the honeymoon. They were a brand-new affiliate network that said they would provide me with links to the items I was already posting about. When my readers clicked on those links and purchased items, I would receive a small percentage of the sale. The idea that this would actually lead to anything seemed like a long shot, but I just thought, why not?
I was honestly shocked to see that once I got into the flow of it, those small commissions really started to add up. It was fascinating to see what was selling and what wasn’t and to try and figure out how to adjust my content to increase sales. If someone bought a blazer through my link, I’d buy the same blazer, post about different ways of styling it, and watch sales of that blazer triple. It was the same type of work I had enjoyed doing at Celeste’s, but in a different format and on a larger scale.
After Grant was in bed and the stars were out, I spent hours tracking the activity of my readers on the site through Google Analytics and editing my content based on their behavior. If they were clicking out of the site from a certain page, I’d add new content to keep them there or a link to another page on the site so they wouldn’t exit out. It was like solving an endless puzzle, and it was so satisfying to watch readers’ behavior change in real time based on these tweaks.
No one told me what to do or how to do it. I was very much making it up as I went along, drawing inspiration from my readers and fellow bloggers. I simply woke up and geeked out every day, experimenting and obsessing over the results.
The whole time, I was designing sites for other people through Jolly Bulldog. I saw web development as my main job and the blog as a side hustle. But after about a year of working from seven every morning until late at night on both, I had designed about thirty websites, but the balance had shifted. Now, I was earning more money from the blog than I was as a web designer.
I was just beginning to see the blog’s full potential and wanted to devote more time and energy to it, but I also had clients depending on me. And the truth is, I was scared to let go of the legitimate-sounding title of web developer and become a full-time blogger. It felt like a huge risk. “Full-time blogger” was not a title I had ever seen on an aptitude test or a list of viable career options. Would everyone think I was being silly and irresponsible? On top of that, what if I couldn’t make it work? What if all my hard work amounted to nothing and I was left with a giant hole in my resume? What if I failed?
I was scared, but I also couldn’t deny where my heart and energy and passion were, and those rewardStyle checks didn’t lie, either. I knew that if I took all the time, effort, and energy that I was still pouring into Jolly Bulldog and redirected it toward my blog, I would make double the amount from commissions. Looking at that number, I could justify taking the leap of faith. It was a tough decision, but I finally stopped taking on clients, shut down Jolly Bulldog, and devoted myself completely to Damsel in Dior.
Excerpted from Liking Myself Back: An Influencer’s Journey from Self-Doubt to Self-Acceptance by Jacey Duprie. Copyright © 2022 by Jacey Duprie. Reprinted with permission of Park Row Books. All rights reserved.