Alright – so today we’ve got the honor of introducing you to Jessica Mason. We think you’ll enjoy our conversation, we’ve shared it below.

Jessica, thanks for taking the time to share your stories with us today One of the toughest things about progressing in a creative career or as an entrepreneur is that there are almost always unexpected problems that come up – problems that you often can’t read about in advance, can’t prepare for, etc. Have you had such and experience and if so, can you tell us the story of one of those unexpected problems you’ve encountered?

One of the most unexpected challenges we faced when starting Compass to Paradise was just how much there is to learn when you’re building a brand from scratch. We knew we loved travel, storytelling, and capturing beautiful moments—but we had no idea how many layers existed behind the scenes to actually turn that passion into a business.
We thought the hard part would be shooting and editing content. And while that alone is a full-time job, we quickly realized there was so much more: staying consistent on social media (even when the algorithm seems to have a personal vendetta), learning how to pitch to brands, negotiating partnerships, building a website, writing SEO-friendly blog posts, and understanding how to make content that not only looks good but also performs.
It felt like every time we mastered one skill, five more popped up. We’d spend hours editing a Reel, then realize we needed to research hashtags, write a compelling caption, engage with our audience, schedule stories, and somehow do it all again tomorrow. And then there was the business side—contracts, invoices, copyright, licensing, media kits… it was a LOT.
There were definitely moments when we looked at each other and thought, “Are we in over our heads?” And many times we even let it paralyze us, but we keep pushing through and continue to lean into the learning curve! We took online courses, joined creator communities, asked questions (SO many questions), and divided tasks based on our strengths.
It hasn’t been easy, but it’s been worth it. That initial overwhelming season taught us resilience, resourcefulness, and how to be creative not just with our content—but with how we run our business. And now, when someone says, “It must be nice to get to travel for work,” we smile, because we know what it really took to get here.

Jessica, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

We’re Jess and Drew, the couple behind Compass to Paradise. We’re travel content creators, storytellers, and adventurers who are turning our passion for exploring the world into a brand that inspires others to travel farther, smarter, and enjoy more authentic experiences.
Our journey into this space has not been overnight—it grew from a shared love of travel and capturing memories that felt cinematic, not just Instagrammable. What started as a hobby (and a LOT of camera gear trial and error!) has evolved into a full-fledged business where we now create high-impact content for brands and hotels around the world. Think dreamy drone footage, curated itineraries, engaging Reels, hotel reviews, and travel hacks that help couples elevate their experiences—and sometimes, being able to do it all using credit card points!
Through Compass to Paradise, we offer creative services like destination marketing, short-form video storytelling, cinematic drone footage, and branded UGC (user-generated content). But what we really do is help brands tell better stories—ones that connect emotionally and visually, with content that inspires action. Whether we’re highlighting a boutique resort in Cabo, sharing hidden gems throughout Southern California, or breaking down how to fly business class on points, we’re always thinking about how to make travel feel accessible, luxurious, and unforgettable for our audience.
We solve a few problems for our clients:
* Many brands struggle to stand out in an oversaturated digital space—we help them do that through captivating, high-converting visuals and storytelling.
* Others don’t have the time or resources to produce content consistently—we fill in those gaps with professional, on-brand, and strategy-driven content that’s ready to post.
* And for our followers, we break down the “how”—how to travel on points, how to plan that bucket list trip, how to actually experience a destination, not just check it off.
What sets us apart is that we’re not just creators—we’re travelers first. Every destination we feature is one we’ve explored ourselves. We don’t promote places we wouldn’t personally return to. We’re also a husband-and-wife team, so everything we create comes with that extra layer of connection, chemistry, and realness. You’re getting both sides of the story—hers and his, luxury and adventure, strategy and soul.
What we’re most proud of? Honestly, it’s hearing from couples who’ve said they could finally afford to take that trip they’d been putting off with our education on how to best utilize their miles and points. Or that they used our itinerary and had the best vacation of their lives. That’s why we wanted do this in the first place.
If there’s one thing we want people to know, it’s that Compass to Paradise isn’t about us—it’s about helping others create their own version of paradise, whatever that looks like. Whether you’re here for travel inspo, content creation services, or just dreaming up your next adventure—we’re so glad you found us.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

One of the biggest lessons we had to unlearn was the idea that success only looks a certain way—and that stepping away from a “safe,” established career path to start something completely new meant risking everything we’d worked for in our lives up until this point.
Before launching Compass to Paradise, we were both already successful in our own fields, completely outside of content creation, with stable careers, financial security, and the kind of life that made sense on paper. But we kept coming back to this feeling—this tug—that we were meant to build something of our own. Something creative, something meaningful, something that let us merge our love of travel, photography, education on how to travel more often through credit card points / perks, while inspiring others to live their lives to the fullest.
The limiting belief we had to unlearn was that making a pivot like this would mean starting from scratch… or worse, “losing” the success we’d already built. There’s a fear that comes with changing lanes—that people won’t take you seriously, that you’ll fail publicly, or that you’re being “irresponsible” by chasing a dream that doesn’t follow a traditional path and by some isn’t considered as important as the careers we were already established in.
But here’s what we’ve learned: everything we did before Compass to Paradise helped us build it. The communication skills, the work ethic, the project management, the understanding of how to show up professionally—all of that translated. We weren’t starting over. We were building on top of the lives we’d already created.
We also had to unlearn limiting beliefs around money—like the idea that creative work isn’t as valuable as traditional work. Creating content, negotiating partnerships, understanding the value of your intellectual property, and showing up consistently online is work, it’s actually A LOT of work. And it’s worth being compensated fairly for. The second we stopped treating Compass to Paradise like a side hustle and started treating it like a business, things start changing. We began charging what we were worth, showing up with confidence, and making decisions from a place of growth instead of scarcity.
So, to anyone holding back because they think it’s too late to start over or too risky to change directions—our advice is: it’s never too late. You can be grateful for your past while still building a future that looks completely different. And sometimes, the scariest pivots lead to the most fulfilling work of your life.

Are there any resources you wish you knew about earlier in your creative journey?

There are so many resources we wish we had known about earlier in our creative journey. When we first started Compass to Paradise, it felt like we were constantly swimming through an ocean of information—Googling every tiny question, watching hours of YouTube tutorials, and buying courses that didn’t always deliver what they promised. There’s a lot of noise out there, and it’s easy to get overwhelmed or led astray by creators who are more focused on selling you something than actually helping you grow.
One of the biggest lessons we’ve learned is this: yes, there are endless tools and resources—but learning how to sift through them and find what actually works for you is the real key!
We’ve spent more time than we can count on trial and error—how to shoot and edit content, how to pitch brands, how to write SEO-friendly blog posts, how to grow on Instagram, and how to monetize our work without selling our soul. And while some of that learning curve is unavoidable, we’ve found a few game-changers we wish we’d tapped into sooner.
AI tools, like ChatGPT and Perplexity, have honestly been a huge help. Not to replace creativity—but to support it. When we’re stuck trying to brainstorm a Reel hook, write a blog intro, or map out a pitch email, bouncing ideas off AI gives us a solid starting point. It’s like having a creative assistant in your back pocket. It’s not about shortcuts—it’s about streamlining workflows so we can spend more time creating, and less time second-guessing.
Another massive resource has been finding a community of like-minded creators. Surrounding ourselves with people who get it—who are also navigating algorithms, client calls, and creative burnout—has been such a lifeline. Whether it’s through online memberships, private groups, or even casual DMs, having that support system is everything. You need people you can learn with, not just from.
And speaking of burnout—let’s talk systems. Content creation is nonstop, and if you’re not careful, it can eat up all your time and energy. We use tools like Repurpose.io, which allows you to upload a piece of short-form content once and have it distributed across multiple platforms automatically. It saves us hours each week and helps keep us consistent, even when life gets busy. Other tools like vidIQ, Canva Pro, CapCut, Final Cut Pro, and TikTok Creator Insights have also been major players in keeping our business running behind the scenes.
Additionally, hiring a virtual assistant to help keep everything moving has been a game changer! Having that accountability of an employee counting on you to get your content delivered on time adds a whole new level of motivation and structure to your workflow. It shifts your mindset from “I’ll get to it eventually” to “This is a real business with deadlines.” Our VA helps with everything from scheduling posts and organizing content calendars, to finalizing blog posts and promoting them, and managing backend tasks—freeing us up to focus on what we do best: creating, connecting, and storytelling. It’s one of the best investments we’ve made, both for our sanity and for scaling Compass to Paradise sustainably.
Looking back, we wish we knew that you don’t have to do it all at once—or alone. The right resources are out there, but more importantly, the right mindset is key: stay curious, stay resourceful, and stay connected. That’s how you build something sustainable.

Contact Info:

• Website: https://www.compasstoparadise.com. (currently under construction, but basic site should be back up by 4/28)
• Instagram: https://www.instagram.com/compasstoparadise/
• Other: https://www.tiktok.com/@compasstoparadise

Image Credits

All images taken by Compass to Paradise