Jackie Rupp

Words with Women: Jackie Rupp, Copywriter & Blogger


Having been a writer for over 20 years, Jackie Rupp’s career has spanned working as a freelance writer, newspaper reporter, and editor-in-chief, before moving into marketing, and becoming VP of Marketing for a publishing company. Although she had a secure position, a few years ago she decided she wanted more control of her work life and to put  her time and efforts into something that was hers. 

“Something was missing for me. And I didn’t exactly know what that was, but it felt like the thing that was missing was having my own brand and owning my own product. So sort of on a whim, actually, I had been toying with the idea for several months, but wasn’t feeling like it was the right time. And then there was a rough time for the company outside of my department, but I was on a conference call. And I decided to give my resignation on that call. I hung up the phone and I was like, ‘well, I guess it’s time to do this.’”

After launching a series of print magazines and creating a publishing company based in the wedding industry, she closed her business when COVID hit. Jackie found herself just this year starting completely from scratch again. “One of my big messages is that there’s never just one chance, as long as we’re breathing, there’s always another chance. And I think, for me, it’s been a lesson in learning that idea of, it’s okay to end things when they’re not working. Giving something its time and giving it its place in your life and then not feeling satisfied or fulfilled by it, that’s not necessarily a bad thing, that can lead to the next thing. And I think we can only get to that place that feels right for us, where we’re in that zone of doing what we’re meant to do, by trying new things” 

Through the pandemic, Jackie built up her new business, a marketing company that helps businesses and individuals brand and market themselves better through copywriting, websites, and social media marketing. She found a love for helping individuals hone in on their passions and build out their personal brand and blogs by defining their focus and messaging better. 

She decided to fudge the rules a bit and go back 10 years to a time that was a major transition point for her for her five pieces of advice she’d give to her younger self. It was a time of living on her own for the first time after the break-up of a long relationship, re-entering the world of dating, and trying to build a career as a single mother of two. 

1. Situations don’t change just because you deserve them to.

“I think for a while, I felt like if things didn’t feel right, maybe with a relationship or a job or a boss, it took me some time to maybe figure out what the problem was. And once I identified the issue, I thought, ‘well, the problem is going to solve it. I did the hard work, I’ve identified it.’ And what I’m coming to learn is that it takes a lot more than that, and multiple steps and actionable steps to actually correct things. Just identifying things isn’t usually enough. We may deserve better, but we’re stuck with what we have sometimes and it’s up to us to sort of make those changes for our own good because oftentimes, we can’t convince or make someone else change.

2. Don’t force things to happen.

“I tend to think of myself as like Miss Proactivity and probably a lot of us women do because we’re used to getting stuff done ourselves. And for me doing the most is a way I’ve felt comfortable expressing love. So if you mentioned you like picnics, well, I’m going to make the picnic basket, I’m going to grow the vegetables myself and make you a lunch from scratch, I’m just going to go all out. And there’s this idea of the more effort I put into something, the more love I’ll get out of someone. And I’d be disappointed and often heartbroken when that wasn’t the case. What I’ve found is that the right things are actually the easiest things; that there’s sort of this beauty in simplicity. When things are right, they just are right. And they just work.”

“I can’t tell you the amount of hours and probably days and weeks I’ve spent ruminating on situations because I so desperately wanted them to be right. Because I thought I had some power to control those outcomes, when I really don’t. At the end of the day, there’s very little control over how others see us or feel about us. Not everyone will fall in love with us, not everyone will even like us. And the less time I think we invest in trying to win people over, the more that it can actually happen naturally.” 

3. Don’t feel guilty for the feelings that you’re having.

“For me, it’s been a struggle to recognize my feelings and not just kind of push them down and think I have to power through them. A lot of situations we don’t have to power through if something feels uncomfortable; maybe it is uncomfortable, and maybe we need to honor that feeling in ourselves. I think I’ve had the issue of apologizing for my feelings. A lot of times it causes more stress when we don’t just acknowledge our feelings. That’s still a learning process for me.”

“I used to think that my empathy was a weakness. I cry over a sentimental commercial on TV. Never ever saw that as a strength or even a good thing. But now, I’m actually being hired by people because of that ability to connect with people’s feelings and their pain points and I can help businesses better connect with those. Empathy is an amazing strength that especially women possess, that we can put ourselves into someone else’s shoes. Particularly now, these days, it’s become a challenge, especially with things like social media and how virtual we all are and disconnected. But empathy is such a powerful and underrated quality.”

4. Don’t let imagination replace reality.

“Especially with things like online dating and chatting virtually, it’s so easy for our brains, I think without us even realizing it, our brains automatically want to fill in the gaps. And with virtual interactions, there are a lot of gaps! Of course our brains can tend to go to the best case scenario and focus on this fantasy aspect of things. Even sometimes with regular in-person relationships, it can be very easy to give meaning to things where it doesn’t exist. We can save ourselves a lot of heartache when we remind ourselves what actually is concrete and stay grounded in the reality of things.”

5. You are enough.

“I’ve been in therapy for over a year now and I always try to sprinkle that into any of my talks, because I feel like it’s important to normalize it and make it not something that has a stigma. I thought it would be this painful, arduous thing that wouldn’t actually be of any benefit. But it’s been very worthwhile from an everyday perspective, not just involving our big issues, but the little daily things. And this is a mantra that I’ve learned.”

“The idea of ‘you are enough’ has really been driven home for me through the  pandemic because I felt like I was on this loop of doing things and not being conscious of them. I was confusing self-care with self-maintenance. I found myself cut off from the world, so I wasn’t getting my hair done, or my nails done, no pedicure or manicure or eyebrows done. It felt like I was doing all those things for me and it’s not that I don’t love getting my nails done occasionally. But, when it became such a habit and reinforced this idea that I needed to do all this, it was coming more from an idea that I was lacking and wasn’t enough. My eyes aren’t enough, my body isn’t enough, my nails aren’t enough.” 

“And so it’s this subtle kind of reinforcing that I’m not enough from head to toe. The pandemic gave me that break of realizing nothing changed when I let it all go. My roots grew out, my nails grew out, and no one stopped loving me, no one changed how they acted towards me. That was a great liberation. Those things are nice, but that’s the way they should stay, as nice and extra, rather than a necessity of life.”

You can read more from Jackie in Here Is What I Know’s Style department, where she’s a regular contributor. 


Leave a Reply

You May Also Like