How We Afford to Travel So Much: Insider Secrets from a Self-Employed Duo

The question “How are you able to travel so much?” is one Jared and I get asked all the time. Let me clarify right from the start: I am definitely not a trust fund baby. In fact, we’re quite the opposite! Our journey to frequent travel is built on strategic planning, hard work, and smart financial decisions, not inherited wealth.

I also want to be upfront – traveling frequently, especially while running a business, often means I’m frequently tired and sometimes as grumpy as a troll! Having just returned from an almost three-week Scandinavian adventure, it felt like the perfect time to pull back the curtain and reveal how we manage our trips. My main goal is to reiterate that consistent travel is a priority for us, despite the very real, often unglamorous sacrifices it entails. It’s a labor of love, allowing us to explore new cultures, gather fresh inspiration for content, and continually discover new DIY ideas.

The nature of my work, which involves creating DIY content, means I can’t effectively produce new projects from a cruise ship or a hotel room in a foreign country. This necessitates a demanding pre-production schedule. We often have to shoot double, sometimes even triple, the amount of content before we leave the studio to ensure everything runs smoothly while we’re away. The intensity doesn’t stop there; upon our return, we typically shoot just as much to catch up on projects and brand collaborations that came in during our absence. It’s a relentless cycle, but one we’ve refined over time.

Mastering Pre-Production: The Foundation of Frequent Travel

Our approach to frequent travel begins long before we ever pack a suitcase. It hinges on rigorous pre-production and a meticulously managed editorial calendar. While we generally schedule projects for Sugar & Cloth a few weeks in advance, I’m particular about ensuring our published content always feels fresh and relevant. This means we have a pipeline of ideas and content, but usually not on a rigid, day-to-day schedule.

However, when we’re planning to be out of town, a set editorial calendar becomes our absolute lifeline. We dedicate several consecutive days to shooting a large volume of content in the studio. This batch of pre-shot material is then scheduled to publish over the entire duration of our trip and for a few weeks after our return, giving us a crucial buffer to catch up and produce new content without immense pressure immediately upon getting back. This system allows us to maintain a consistent online presence even when we’re thousands of miles away.

The same principle applies to social media. I strive to schedule everything so it’s evenly distributed, preventing gaps or an overwhelming flood of posts. I’m certainly no expert at this, but as long as a significant portion of our social content is locked down before we depart, we’re in good shape. One crucial lesson I learned early on is that I simply cannot rely on my 9 PM self to write a detailed blog post after a full day of exploring a new destination. It’s just not realistic for me. My mind needs rest more than we need to pump out pretty pictures. If I leave myself with unwritten posts for our travel period, I make it a strict rule to complete those first thing in the morning before I allow myself to head out and explore. It’s a form of self-discipline that ensures productivity without sacrificing the travel experience entirely.

Of course, this description might make it sound like I always have my ducks perfectly in a row. But I must confess, every single time we’re about to leave town, I inevitably have a minor mental breakdown, convinced it’s “the worst time ever to be leaving.” Yet, without fail, once we arrive at our destination, everything falls into place, and I’m perfectly fine. Ah, the human mind – a beautiful and sometimes miserable thing, isn’t it?

The week leading up to a trip is a whirlwind. Ensuring all work tasks are tidy and our beloved fur babies are well cared for consumes approximately 99% of my time. This means my own packing often turns into a frantic scramble the night before, and I almost always regret what I packed or didn’t pack! It’s a journey of baby steps, and I’m confident I’ll become a better packer eventually.

A typical week before flying out usually involves working six, twelve-hour days, interspersed with general errands. The day before departure is spent writing posts and tackling laundry from home. By the time travel day arrives, we’re usually utterly exhausted, but there’s also an overwhelming sense of relief. The first day of the trip often feels a bit hazy as we decompress, but then, finally, we get to fully immerse ourselves and enjoy the adventure. It’s by no means a perfect process, and certainly not something I’d recommend to everyone, but it’s our system, and it works for us.

Unlocking Global Adventures: Maximizing Credit Card Rewards for Travel

Can I get an amen for credit cards that earn points?! This is a cornerstone of our travel strategy. Jared and I literally never use debit cards. Every single expense, both for Sugar & Cloth and our personal finances, goes onto its respective credit card. The crucial part? We pay them off in full every month. Don’t be too impressed; this wasn’t always my financial habit. This discipline is a newfound goal, sparked after accumulating some intimidating credit card balances in the past and the feeling of being judged by my accountant. Definitely not my shining moment, but it taught me invaluable lessons!

When used responsibly and paid off, credit cards essentially become our source of free travel money. We fly on points a lot, cutting down significantly on airfare costs. Beyond flights, we leverage points for booking rental cars, hotels, and practically anything travel-related, dramatically reducing our overall expenditure. This strategic use of rewards allows us to stretch our travel budget considerably further.

Our Go-To Cards: Southwest Airlines & American Express Platinum

Our favorite credit cards for maximizing travel rewards are the Southwest Airlines credit card and the American Express Platinum card. To accelerate point accumulation, we’ve found it incredibly helpful to designate one primary name and rewards member to receive the points on our shared cards. This consolidation helps us earn rewards faster, unlocking perks like companion passes, free seat upgrades, or expedited airport lines.

For those interested in the Southwest card, you can very quickly earn a Companion Pass, especially if you can find a sign-up invitation offering 40,000 points (if you need one, I can refer you! Just send me a quick note, and yes, I shamelessly earn points for referrals, haha). This offer is particularly advantageous for business cardholders.

A Southwest Companion Pass is a game-changer: it allows you to designate one person to fly with you for free on any Southwest flight you book (you just pay taxes and fees, which are minimal). The real kicker is that you receive the Companion Pass not only for the remainder of the year in which you earn it but also for the entire following calendar year! The annual fee for the Southwest card is typically under $100, which is an incredible value considering how quickly you can earn points and the significant savings from the Companion Pass.

Rather than holding a personal American Express Platinum card, we opt for the business version. While its yearly fee is quite steep, it’s a tax-deductible write-off for business owners, making it a viable investment. The card comes loaded with an impressive array of travel benefits that we utilize constantly. These include a free Global Entry application (essential for speedy international customs), a complimentary Priority Pass lounge membership (we absolutely live for the American Express Centurion and Priority Pass lounges during layovers!), numerous hotel perks and upgrades, and a free Boingo Wi-Fi membership. Furthermore, it offers an astounding five times the points when you book travel through American Express, making it a powerhouse for accumulating rewards quickly.

You can often snag a significant 100,000-point sign-up bonus offer from Amex Platinum as well (and again, I can shamelessly refer you if you’re interested!). The beauty of Amex points is their versatility; you can use them to book airfare on virtually any airline, as well as hotels, cruises, or complete vacation packages. Having both a dedicated airline card like Southwest and a flexible points card like Amex allows us to optimize our travel for both domestic and international adventures.

Strategic Stays: Finding Accommodations That Fuel Our Wanderlust

Beyond flights, securing accommodations smartly is another key element in our frequent travel strategy. We employ a mix of last-minute booking apps and strategic brand partnerships.

Last-Minute Deals with HotelTonight

I am an avid HotelTonight addict. This app is our go-to for almost all of our short, spontaneous, or last-minute trips, allowing us to snag fantastic hotel discounts. It’s not ideal for the meticulously organized planner, but if you’re comfortable not knowing your exact lodging until a few nights before your stay, it’s an absolute gem. HotelTonight also has a helpful rating system, categorizing hotels so you know the standard you’re getting. We typically stick to the ‘Hip,’ ‘Luxe,’ or ‘Solid’ categories, making our choice based on the hotel’s location and price point. A crucial tip: always vet the hotels with Google reviews before finalizing your booking!

The pros of HotelTonight are numerous: ease of booking, the ability to earn status points for frequent bookings (which translates to bigger discounts and free room upgrades), and a referral program that benefits both you and your friends (use my code “SUGAR25” for $25 off your first booking, and I get $25 off my next one – #shamelesspromotion!). The app also covers almost every major city imaginable. The primary con is that once you book, you generally can’t cancel. We’ve had a few instances where we changed our minds about a chosen hotel. However, we once called HotelTonight and asked if we could switch our reservation to another hotel, and they surprisingly allowed it, so there might be some hope there if you make a mistake!

Collaborating with Brands for Complimentary Stays

Another significant way we secure accommodations is by working directly with brands. This involves brands offering us either a media rate or a complimentary stay in exchange for our content creation and promotion on the blog and/or social media. When we engage in these types of partnerships, our vetting process is incredibly thorough. We conduct extensive research, ensuring the chosen brands align with our values and aesthetics, and that both we and our audience will genuinely appreciate the experience. Once a suitable partner is identified, we plan the collaboration well in advance.

I’d estimate that we utilize this brand collaboration route about 70% of the time. The major upside is that we gain access to incredible locations and experiences, resulting in cool, aspirational content. Furthermore, our audience benefits from our first-hand recommendations, covering the do’s, don’ts, and essential planning tips. The downside, however, is that these trips often involve even more work than our usual travel. The adage “nothing is ever free” rings especially true here. If a brand offers us something, they invariably expect something substantial in return. We commit only when we are 110% confident we can fulfill their requests.

This commitment translates into immediate work upon arrival: the first hour we walk into a hotel room is dedicated to taking photos before anything is touched or moved, ensuring we capture perfect, pristine room shots. Our trip itinerary is meticulously planned around weather forecasts to guarantee the best possible outdoor amenity shots. We wake up early to photograph spaces before they become bustling with people and edit on the spot to ensure real-time social media updates. While this is still undeniably work and not what most would consider a relaxing vacation, once you develop an efficient system, it absolutely becomes an amazing job perk!

Beyond the Postcard: The Reality of Running a Business While Traveling

Even when we’re not specifically traveling for a work project or collaborating with a brand while on location, we’re still very much on the job. That’s the inherent reality of being self-employed: you are never truly, fully off-duty. Questions from clients or team members will still arise, deadlines will persist, and bills will always need to be paid. The dream of completely unplugging is often just that – a dream.

I’ve essentially become a professional, on-the-go iPhone worker. Thankfully, modern tools like G-Suite and Dropbox have been absolute lifesavers, allowing us to manage documents, communicate, and collaborate seamlessly from anywhere in the world. It has also been an enormous help having Kayla working with us. Her ability to manage many of the day-to-day operations and inquiries takes a significant load off my plate while we are away, allowing me to focus on creating content and experiencing the journey.

The Ultimate Verdict: Is the Travel Lifestyle Worth the Hustle?

All things considered, is all this effort, strategic planning, and behind-the-scenes hustle worth it for us to maintain our travel-rich lifestyle? Absolutely, unequivocally yes! While it’s clear it’s not as simple and magical as it often appears on social media – but then again, nothing online ever truly is, right?! – the rewards far outweigh the challenges.

Travel invigorates our creativity, fuels our passion for discovery, and provides an endless wellspring of inspiration for our content and DIY projects. It allows us to immerse ourselves in diverse cultures, broaden our perspectives, and create unforgettable memories. The journey to frequent travel is a demanding one, requiring discipline, financial acumen, and a willingness to work hard, but the joy and enrichment it brings to our lives and our business make every bit of effort worthwhile.

If you have any other questions about our travel strategies or anything else you’d like to see covered in a future FAQ post, please let us know right here!