How I Found My Passion and Purpose as an Entrepreneur

Jess Ann Kirby styles a White and Warran Cashmere Sweater with a matching scarf
Jess Ann Kirby wears a White and Warren Cashmere Sweater with a matching Travel Wrap for fall weather

Happy September everyone. This is hands down one of my absolute favorite months of the year, particularly for my wardrobe. I finally get to break out all my favorites, sweaters, skinny jeans and ankle boots. It makes me giddy just thinking about it.  The seasonal shift that comes with fall always feels like a good time to reset. It’s an opportunity to start with a blank slate, to re-focus and remind ourselves of our motivations and goals. One thing I wanted to talk about is how I discovered my passion and purpose as a blogger/influencer/entrepreneur (whatever you want to call it). It wasn’t something that happened overnight. It was a process and I’m really excited to partner with Kork-Ease on their #OriginalYou campaign to talk about my passions, personal style and finding purpose in my career. The Kork-Ease brand is all about being unapologetically you, from your style choices to your passions in life (I could not love this anymore!) and so I wanted to chat a bit about that process for me.


When I first launched my blog almost 5 years ago I had no idea where it would take me. I wanted something different and I knew I couldn’t keep doing a job that was feeling more and more meaningless by the day. There was no joy or excitement in what I was doing, I was going through the motions and it wasn’t how I wanted to go through the rest of my life. So I started a blog called Prosecco & Plaid. It was the most invigorated and excited I had felt about something in a long time. I was having fun. I decided to quit my full time job to pursue blogging. I had no idea what I was doing and at the time was barely making money off my blog but I made it work. Fast forward another few years, a re-brand, a new site launch and a bigger audience. I had more success, I was making a living off of my blog but I felt stuck. Much of the excitement had worn off and I was lacking passion and purpose. I felt like, in the blogging world, I didn’t fit in. I didn’t own designer bags or shoes, I didn’t like going to fashion week, I didn’t drink Starbucks (**gasp). I wanted to do more than outfit posts. So I started to ask myself questions: what drives me, what really matters to me, how can I be more true to myself and how can I better connect with my readers? At the same time I started listening more to my intuition and ignoring the “noise.” I sat down and wrote this blog post. To be honest it wasn’t ground breaking or anything new, but it was the first time since I launched my blog that I didn’t feel afraid to be completely true to myself. It was a turning point at which I no longer felt confined to the narrow vision of what I felt I had to be in order to be a successful blogger.

What does this even have to do with fashion? Good question. The first answer is, it’s not all about fashion, that was something I always knew deep down but didn’t know how to express. Would I turn people off talking about issues like the environment, politics, things other than clothes? Would I make some people mad? Well, yes, but I’m never going to make everyone happy, and truthfully the reward of connecting with other women on these issues far outweighs any negative response. I am a complex person (aren’t we all?) and I’m allowed to talk about fashion, social issues, personal choices that might not fit the norm, and many of the other things that make me who I am. To bring it back to fashion, it’s how I got my start as an entrepreneur, it is something I truly love, not just clothes, but the ability to express myself through them, to feel good about myself in them. I created this unnecessary pressure to be more sophisticated, more high fashion, more “fancy,” but none of those things represent who I am. I’m a girl that grew up in New England. I love walking my dogs, going to the beach, hikes, snow days, feeling COMFORTABLE. Sometimes I think that’s a dirty word in fashion, like being in pain or uncomfortable is a badge of honor. You should wear whatever you feel good in, and part of what I want to do in this space is encourage you to do so, whatever that looks like.

So today, that’s what this post is here for. It’s a reminder to be true to yourself, in your life, in your career, in your relationships and in your style. This outfit is quintessentially me. It’s not flashy or fancy, it’s comfortable, casual, simple, classic. A look that represents where I’m at in my life right now, content with just being me. A huge thank you to Kork-Ease for partnering with me to bring some substance to a style post. I honestly LOVE these ankle boots and will be wearing them on repeat. Would love to know what outfit/style makes you feel your best. Let me know in the comments. As always thanks for sharing your voices.

Jess Ann Kirby styles Paige skinny jeans with Kork-Ease booties
Jess Ann Kirby pairs the Kork-Ease suede ankle booties with Paige jeans
Jess Ann Kirby visits the docks in Newport in a striped cashmere sweater and paige jeans
Jess Ann Kirby matches her sweater and scarf for an on-trend fall look
Jess Ann Kirby wears her favorite fall booties, the Kork-Ease suede ankle
Jess Ann Kirby wears a stripe cashmere sweater for the perfect fall outfit
Jess Ann Kirby wears a White and Warren Cashmere Sweater with skinny jeans and booties
Jess Ann Kirby pairs Paige skinny jeans with Kork-Ease suede ankle booties

Thanks to Kork-Ease for sponsoring this post.

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  1. Rach wrote:

    Thank you for the reminder Jess! I’ve been following you since you started and I love seeing how you have evolved and I truly enjoyed reading all the things you’ve shared!

    9.5.18 | Reply
    • Jessica wrote:

      Thank you so much Rach, you are so kind. Really appreciate your support all these years!

      9.5.18 | Reply
  2. Diana Ackerman wrote:

    Love this post! Respect your honesty and it’s simply a very insightful post ( I’m contemplating starting a blog and or just posting on ideas on Instagram etc).

    9.5.18 | Reply
    • Jessica wrote:

      Thank you so much Diana. Really appreciate that.

      9.5.18 | Reply
  3. grace atwood wrote:

    This is one of the best sponsored posts I’ve read in a while – love it! Miss you friend. xo

    9.6.18 | Reply
    • Jessica wrote:

      Thank you Grace! Miss you too. Come visit me. xx

      9.11.18 | Reply
  4. Lisa wrote:

    Love this, Jess! Be unapologetically you – a lesson I’m learning to embrace! Love that you’re mixing fashion with other important topics of “substance” (only quote that because it depends on who you ask, what is important to them!) The stripes are adorable and look so cozy!


    9.8.18 | Reply
    • Jessica wrote:

      Thanks so much Lisa. xx

      9.11.18 | Reply

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