Seasonal living is a lifestyle full of contrasts—freedom and uncertainty, adventure and instability, breathtaking locations and housing struggles. For those willing to trade security for flexibility, it can be an incredibly rewarding way to live, offering the chance to work in stunning places, meet like-minded travelers, and shape life on your own terms.
But it’s not all dreamy sunsets and powder days. Finding housing can be a headache, jobs vary from season to season, and maintaining friendships across distances takes effort. It’s a lifestyle that demands adaptability and resilience, but for those who embrace it, the rewards—freedom, travel, and new experiences—are worth the trade-offs.
In this article, I’ll dive into both sides of seasonal life: the challenges you’ll face and the incredible benefits that make it all worthwhile. Whether you’re considering your first seasonal job or you’re already deep in this lifestyle, this guide will help you navigate the ups and downs of living seasonally.
Challenges
Finding Temporary Housing
One of the biggest hurdles of living seasonally is securing a place to stay. Many seasonal towns experience an influx of short-term renters, vacationers, and Airbnb guests, making it more profitable for landlords to opt for short-term rentals over long-term leases. Your first year in a new location will likely be the toughest in terms of housing. However, once you establish connections and build a network of friends and locals, finding housing can become easier. Employers may also assist returning workers in securing accommodations.
Mistakes will happen in the beginning. I’ve lived in some interesting housing situations, but I made them work. Many seasonal workers avoid year-long leases since the goal is to work for a season and then travel elsewhere. Sublets can be an option, though they can be hard to secure during peak season. My advice is to be proactive: scour Facebook groups, Craigslist, Zillow, and other rental sites. Be open to roommates—I had to adjust from living alone in Philadelphia to sharing housing in Colorado, but it was a financial necessity.
Consider looking in nearby towns if you’re open to a short commute. Have references ready when you find a place you love, as competition can be fierce. Some seasonal workers even get creative—living in RVs, trailer parks, or boats at marinas. The housing struggle is real, but over time, landlords start recognizing and welcoming back seasonal workers, and the local community will often step in to support its workforce.
Finding a Job
Job availability varies greatly depending on the location. In ski towns, jobs are often abundant because the high cost of living deters many potential workers. However, while it’s easy to find a job, it’s much harder to find housing. In beach towns, summer jobs are highly competitive due to an influx of college students and teachers looking for seasonal work.
If you’re eyeing a coveted position—like bartending in a busy beach town—you may need to work your way up. When I first started looking for a bartending job, I had to take a server position and prove myself before getting a shot behind the bar. Some jobs won’t even begin hiring until the season is in full swing, so persistence is key. Be diligent, pass out resumes early, and be prepared to take a position that may not be your dream job initially. If you prove yourself, you’ll often be rewarded with better opportunities as the season progresses.
Lack of Security
Seasonal life lacks the stability of a traditional 9-to-5 job. Your housing isn’t always guaranteed, your job may not always be secure, and income fluctuates with the season. Some years are busier than others, and tipping culture plays a big role in how much you make. Economic downturns, bad weather, or unexpected circumstances can all impact your earnings.
Because of this unpredictability, it’s essential to save during the good weeks to prepare for the slower times. This lifestyle isn’t for everyone—it requires embracing uncertainty and being okay with moments of financial anxiety. But for those who can handle the unpredictability, the freedom that comes with it is worth it.
Finding the Right Fit
Not every seasonal town or job will be the right fit for you. You might fall in love with a ski town at first but later realize you prefer the beach. I spent three years in Vail, loving the mountain lifestyle, snowboarding, and après-ski bartending. But after a few years, I craved change. I preferred summers over winters and wanted to travel more. That led me to working in a beach town, which I now love.
Your priorities and passions will evolve, and that’s okay. However, transitioning to a new town means starting over—finding new housing, securing a new job, and building a new community. This can be exhausting, but it’s necessary to avoid burnout. If you’re unhappy, make the change—whether in a seasonal job or a corporate career. Nothing is worse than seeing a bartender in a beautiful location who is miserable and burnt out but too afraid to move on.
Maintaining Friendships
One of the biggest challenges of a mobile lifestyle is staying connected with friends and family. When you move frequently, it takes effort to maintain relationships. Grabbing a casual coffee with an old friend isn’t an option when you live states away. When you visit home, you often have to schedule time with multiple people, which can be exhausting.
However, keeping in touch is worth the effort. A quick phone call or message goes a long way. While you’ll make new friends in each seasonal job, your long-term friendships require maintenance. If they matter to you, you’ll find a way to keep them strong.
Benefits
Freedom
Seasonal life offers unparalleled freedom. While it comes with its challenges, it also gives you complete control over where you live, where you work, and how long you stay. You can choose to work six days a week to save money for travel, or you can take it easy and prioritize experiences over income.
Unlike a corporate job, you’re not tied to a lease or locked into a long-term contract. If a season doesn’t go as planned, you can switch things up next time. This lifestyle is ideal for those who value adventure and flexibility over stability.
Living in Amazing Places
One of the biggest perks of seasonal work is living in breathtaking locations. While some people can only dream of visiting these places, you get to live there for months at a time. Whether it’s experiencing powder days in a ski town or enjoying sunset views in a beach town, the beauty of your surroundings becomes part of your everyday life.
Locals also have access to hidden gems—secret powder stashes, lesser-known surf breaks, the best hole-in-the-wall restaurants, and local perks like free boat rides or discounted drinks. While tourists rush to squeeze in a vacation, you get to immerse yourself in the lifestyle year-round.
Meeting Like-Minded People
The seasonal workforce is full of adventurous, free-spirited individuals. While some may be college students or trust-fund kids, most are people who prioritize experiences over conventional career paths. You’ll meet fellow travelers, entrepreneurs, ski bums, and wanderers who share your passion for an unconventional life.
These friendships are different from those formed in traditional 9-to-5 jobs. The people you meet in seasonal work often have incredible stories—retired entrepreneurs, expats, people reinventing themselves, and others who, for whatever reason, chose a different path. Being surrounded by such diverse and inspiring individuals reminds you that there’s no single way to live a fulfilling life.
The Adventure of Learning Something New
In just five years of seasonal work, I’ve gained more diverse experience than I did in a decade of finance. From bartending to guiding horseback tours to working at a golf course, each job has taught me something new. Unlike a corporate job where roles can become monotonous, seasonal work allows for continuous learning and change.
While some jobs were physically demanding, others pushed me mentally. Each role came with a learning curve, requiring me to check my ego and embrace new challenges. There’s a unique sense of accomplishment in mastering new skills, and seasonal work provides endless opportunities to do just that.
Final Thoughts
Seasonal life isn’t for everyone. It requires resilience, adaptability, and a willingness to embrace uncertainty. But for those who crave adventure, freedom, and new experiences, it’s an incredibly rewarding way to live. The ability to choose where you live, what you do, and how you spend your time is a rare privilege. If you’re willing to navigate the challenges, the benefits far outweigh the struggles
