Today we’d like to introduce you to Jenny Hyland.
Jenny, we appreciate you taking the time to share your story with us today. Where does your story begin?
As a single mom, my kids were everything to me. I dedicated myself entirely to raising them, always being present for every school activity, every sporting event. The four of us were incredibly close, and I wanted to share my love for travel, adventure, and road trips with them. Whenever we had free time, we’d pile into the car and explore—choosing a new city or destination and seeing where the road would take us. We loved visiting quirky roadside attractions, hiking scenic trails, enjoying fun and unique restaurants, and diving into adventurous activities. People often asked me for ideas or what we were planning next, so I decided to start an Instagram page to help others find exciting things to do with their teens.
As my kids grew older and started leaving for college and moving out, I found myself facing the reality of becoming an empty-nester. It hit me hard, and I found myself struggling with feelings of loneliness. My adventure partners were gone, and I was left with a sense of emptiness. I craved the excitement and joy of those adventures, but with my social anxiety, I couldn’t imagine doing it alone. One evening, during a walk, I started to think about how I was spending my life. If I only had 24 hours to live, what would I do with that time? Would I feel proud of the life I had been living since the kids had moved out? At that moment, I made the decision to start living for myself and to embrace the adventures I once shared with my kids—but this time, on my own.
The first step was terrifying. I sat in my car in the parking lot for hours, too anxious to even step out. Eventually, I left without going in. But the next day, I tried again, and this time, I succeeded. I kept pushing myself to step outside my comfort zone, to visit new places and try new things on my own. It’s not always easy, but with every outing, I learn more about myself and gain confidence. Along the way, I’ve met the most amazing people, and I’ve rediscovered the joy of adventure, proving to myself that I can do this, even alone.
I have since changed my focus on my Instagram page from family fun to solo adventures and a little best friend fun thrown in there as well. I hope to inspire those that want to get out there and do things alone to actually get out there. I want to set an example and show others it is possible to not only find yourself, but have fun and love yourself as well!
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
Struggling with social anxiety has been my biggest obstacle. Walking into a place and thinking everyone is staring at you is a hard thing to overcome. Especially when going to restaurants and breweries or trying out new activities. Trying to convince yourself that no one is even paying attention to you is harder than it seems.
Alright, so let’s switch gears a bit and talk business. What should we know about your work?
I am a substitute contractor for Shipt. I shop and deliver groceries for people. I actually love what I do because it has given me the flexibility to be a major part of my kids lives as a single parent, along with giving me the opportunity to travel as often as I would like.
What were you like growing up?
Growing up I was extremely shy but craved adventure. I have always been drawn to strong, outgoing personalities because it was something I was envious of. I hated being shy.
Contact Info:
- Instagram: @mnroadtrips
