This site has limited support for your browser. We recommend switching to Edge, Chrome, Safari, or Firefox.


🔥 NEW! An Elevated, Comfy Short for Summer SHOP NOW

🧵Encircled is proudly ethically-made in Toronto, Canada LEARN MORE

👚 Ready to refresh your summer wardrobe? TAKE OUR STYLE QUIZ

Woman Crush Wednesday: Meet Kat Gaskin, Founder of the Content Planner

Woman Crush Wednesday: Meet Kat Gaskin, Founder of the Content Planner


In celebration of women, we've created a series honouring inspiring women who we have serious crushes on. From artists to entrepreneurs, all are passionate about what they do - we hope that sharing their stories will inspire you to turn your dreams into a reality.


For our sixth #WomanCrushWednesday we’re featuring Kat! Fed up with the comfortable routine of working a corporate job, Kat decided to quit. Seeking travel and adventure she worked as a freelance graphic designer while working on her personal brand, The Salty Pineapple, allowing her the freedom she craved to travel the world.

Tell us about yourself.

My name is Kat Gaskin, I am a graphic designer, entrepreneur and founder of the content planner. I have been working for myself for the past 7 years. I remember when I had that ‘ah-ha’ moment at my desk. Back in 2011, I was feeling completely unsatisfied and unfulfilled with my corporate job. When I graduated university I had that dream of working 9-5 and having a secure income, and that's what that job gave me. But at the end of the day, I was completely unfulfilled, bored and wanted to travel more. One and a half years later I started my personal brand based around following your dreams, the tropics, and everything pineapple. That lead into becoming a content creator and getting really into building my own brand on Instagram, which then led me into creating the Content Planner. The Content Planner is the first and only physical planner for your blog and social media content.

When you’re in university you’re only really given one example of making a living. You go to school, get your credits, graduate, get a 9-5 and then eventually retire. No one ever told me in university to become an entrepreneur and work for myself.


@KatGaskin Wearing The Minimalist Sleeveless Mock Neck and All Day Wide Leg


What inspired you on your journey to entrepreneurship?

The fear of being comfortable. I don't want to wake up and live the same day every day and call that a life, I don't want to be complacent. I want to be in the driver's seat and take control of my life and design it exactly how I want to live. When I first wanted to quit my job, my number one goal was to work less and travel more. Now that I have done that, the possibilities are endless because I’ve realized anything is possible! 


What were some early signs at the beginning that made you feel confident that you were onto something?

When I quit my job I was absolutely terrified. What kept me going and kept me motivated was my community. I would read messages from complete strangers telling me they loved my photos, they made them feel happy and added sunshine to their day. Most importantly being able to inspire others. I’m living that dream and when I first started that's all I ever wanted, to encourage people to follow their own dreams. I’m very grateful social media exists because without it I wouldn’t be able to make those connections with people all around the world.



What is one of the biggest obstacles you encountered in establishing your business from the ground up? What kept you going?

When I first quit my job and started this whole entrepreneur journey my biggest obstacle was finances. I was broke. Really broke. To the point where I thought opening a dog walking business was a good idea, even though I was a freelance graphic designer trying to work less and travel more. At the end of the day, I accepted client work that didn't speak to my soul. I worked from 7am-1am every day, grinding through my client work and spending time discovering who I was as a graphic designer. During the day I would work on my client graphic design work, and by night I would work on things that were Salty Pineapple related. I wasn't getting paid for anything in regards to content or Instagram at this point, but every day I created from my heart and figured out what my personal style was. Eventually, I figured out my finances. It took around 2-3 years for me to really get on my feet and earn an income that could sustain the lifestyle I wanted to live.

Knowing what you know now, is there anything you would do differently or wish you had done sooner when starting the journey of The Content Planner?

One thing I would change knowing what I know now is believe in myself. You have to be your biggest cheerleader. I think going through my own journey, I expected so much from my parents, my partner, and my friends. Really, you have to be your biggest supporter. Your friends and family won't necessarily understand why you’re doing what you’re doing, why you quit your job. They will judge you and question you, and you don't need that in your life. Now I could care less what people think of me and my journey to success because it is my own unique journey.



What place have you visited that inspires you the most? Why?

Hawaii. I could cry. It speaks to my soul. I remember visiting in 2013, it was my first time doing a solo trip. My relationship was in shambles, my life was going downhill and I just needed to reset and be at the beach. I booked my first flight on my own to Ohau. Its where I first learned to surf and owned who I was as a graphic designer. I was only 1 year into my Salty Pineapple journey so I was still figuring myself out as a creative. Being there, being surrounded by the people and the kind of environment that reflected what I wanted to be as a creative felt so synchronous.

What is the best travel advice you have ever received?

The best travel advice that I have ever received is to just book your flight. Just go. You only get one chance at life. The timing won't always be right and you might not always have all the money in the world, but if you don't take that trip now who knows if you’ll wake up tomorrow. The only thing guaranteed in life is death. It sounds negative, but it's a reminder that you have to live each day to the fullest and to stop waiting and to start living.


Did you have any important female figures in your life, or is there anyone in particular who inspires you?

I would love to tell you that I had some famous mentor that I could look up to that represented who I was and who looked like me. But growing up I didn’t. Now that I am in the position I am, I’ve learned that I need to inspire myself, and you need to inspire yourself. You are the one on your journey and if you can live up to your fullest potential and live your greatest life, you don't need anyone else to inspire you but yourself.

How would you define female empowerment?

I would define female empowerment as a lifestyle. It's all of the choices you make when you wake up every single day. You vote with your dollar. I always try to support female run, female owned, female-founded businesses. That's how you empower women. Supporting their businesses, helping them rise to the top without asking for discount codes, without asking for free products, without asking for giveaways.  You refer them to your friends, you post about them on social media. You vote with your dollar. Every single day I try to talk another female or support a female-founded business because that's who I am too. 


Thanks so much, Kat, for welcoming us into your space. Find Kat on Instagram @KatGaskin. Interested in the Content Planner? Visit their website or find them on Instagram @ContentPlanner

Loving #WomanCrushWednesday? Subscribe to our YouTube channel to never miss an episode! 





Leave a comment


Congratulations! Your order qualifies for free shipping You are $225 USD away from free shipping.
No more products available for purchase