6 Legit Paths to Work From Anywhere & Build a Location-Independent Life
Six smart, doable paths to help you ditch the 9-5, stay financially stable, and build a life you love, all while you work from anywhere.
Craving community on your path to working from anywhere? Join our free Work From Anywhere ✈️ group and connect with like-minded midlife nomads!
You don’t need to be a 22-year-old tech genius or a trust-fund traveler to live and work from anywhere. Whether you’re mid-career or midlife, the remote revolution is real, and there’s a seat at the table for you.
Landing a fully remote job with a fancy job description and generous employee benefits might be just the ticket for you... but those jobs are difficult to come by.
There's also less freedom in this sort of arrangement, as you're just trading one 9-5 desk for another (although lunch breaks and weekends can be pretty fantastic, I will admit).
On the other hand, building an all-remote company could be a great option, too. But the uncertainty and demands of entrepreneurship aren't for everyone, either.
In this guide, you’ll find six realistic and rewarding ways to build a work-from-anywhere lifestyle, with real talk about the trade-offs and encouragement for wherever you are on your journey.
1. Fully Remote Job
What It Is
A traditional employee role with a company that supports remote work—either hybrid, flexible, or fully distributed.
Pros
Steady income and healthcare benefits
Access to personal development budget and mentorship
Clear career path and structure
Cons
You're still on someone else's clock
Asynchronous communication can lead to misalignment
You may still be expected to work U.S. hours… even if you're in Thailand
Considerations
When you're evaluating remote roles, don’t stop at the job description. Dig deep into how the company supports its remote workers. Are they truly remote-first, or are they reluctantly remote for now? There's a big difference. Ask:
Do they provide a monthly allowance for home office expenses?
How do remote teams communicate—Slack? Loom? Endless Zoom calls?
What does a typical day look like in terms of meetings? Will you be expected to align with U.S. time zones regardless of your location?
Is the interview process reflective of remote work values, or does it feel like a rehash of their in-office days?
Will you have access to a personal development budget or structured mentorship?
And don’t skip that final chat with your future manager. You’re interviewing them, too. Their approach to leadership in a distributed setting matters just as much as your resume.
2. Freelance & Contracting
What It Is
You work project-to-project as an independent contractor—often with multiple clients, offering services like writing, web development, or coaching.
Pros
Total control over your schedule
Work with clients globally
Potential to out-earn a salaried role
Cons
Inconsistent income
You wear all the hats (sales, admin, taxes) although AI and business support services are helping to lighten the load
Client churn is real
Considerations
This path offers the most immediate freedom, but it also comes with the steepest learning curve in self-management. You’ll need to build systems for everything from invoicing to client onboarding to your daily schedule.
Choose one core service and specialize. Clients are often looking for very specific skill sets—content strategy, not just "writing"; conversion optimization, not just "web design."
Embrace tools that help you automate and scale: Notion, Dubsado, ChatGPT, and niche-specific platforms.
Protect your income. Set boundaries around scope, ask for deposits, and diversify your client base to avoid dependence on a single contract.
Be ready for rounds of interviews just like a regular job. More agencies and clients now screen independent contractors like employees.
Financially, expect ebbs and flows. Build a buffer and treat quiet months as an opportunity to market, refine your offers, and rest.
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3. Online Business Owner
What It Is
You sell a digital or physical product, offer online courses, or build a membership community.
Pros
Highly scalable
Time and location freedom
Full creative control
Cons
Steep learning curve
Income builds slowly
Requires marketing and tech skills
Considerations
This is the most empowering—and demanding—path. It often starts as a side hustle and grows into a full-time venture. Success here depends on your ability to stay consistent through the slow months.
Start with one product or offer. Too many new entrepreneurs try to build an entire product suite on day one.
Focus on marketing early. You can’t sell what people don’t know exists.
Understand the tech stack: email marketing tools, course platforms, e-commerce systems, and SEO strategies.
Get support. Hire a VA or join a mastermind group. Don’t isolate yourself.
Handle the unglamorous parts early—register your business, set up accounting systems, and research your tax obligations depending on where you're based.
This path is for you if you like autonomy, creativity, and long-game thinking. It’s not passive, but it is powerful.
4. Content Creator / Digital Nomad Lifestyle
What It Is
You create content (blogs, videos, podcasts) and monetize through affiliate marketing, brand sponsorships, and product sales.
Pros
Express yourself creatively
Build community
Long-term brand equity
Cons
Growth takes time
Algorithm changes = stress
Not always lucrative early on
Considerations
Monetizing your story or expertise takes more than charisma and a decent camera. The creator economy is thriving, but authenticity and consistency win over virality every time.
Start on one platform and master it before branching out.
Treat your content like a business. Define your niche, understand your audience, and post with purpose.
Experiment with multiple income streams: affiliate links, brand partnerships, product sales, and even personal development workshops or retreats.
Use tools like Ko-fi, Buy Me a Coffee, or Patreon to build early support.
Don't obsess over going viral; focus on building a loyal core community who trust your voice.
Being a successful content creator isn't just about the likes. It’s about intentional living, connection, and leveraging your story to create opportunities.
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5. Remote-Friendly Trades & Services
What It Is
Work in fields like tech support, customer service, virtual assistance, or online tutoring.
Pros
Fast entry
Minimal startup costs
Steady demand
Cons
Lower earning ceiling
Repetitive tasks
Limited growth unless you specialize
Considerations
These roles may not sound sexy, but they often offer predictability and portability, which is gold when you're building a stable nomad life.
Look for companies that treat remote staff as professionals. The hiring manager should be clear about expectations, growth paths, and employee benefits.
Ask if there are healthcare benefits, paid leave, or development cycle opportunities. Just because it's entry-level doesn’t mean you shouldn’t have support.
Specialize to stand out—online ESL tutoring? Consider teaching business English to executives. Virtual assistance? Niche down into podcast management or executive support.
Don’t overlook the potential to scale. Many successful location-independent entrepreneurs started by offering services and then productized their skills into digital products or training programs.
This category is ideal for anyone who wants a low-barrier entry into remote work—especially if you’re transitioning from a hands-on or client-facing career.
6. Blended Remote Life
What It Is
Combining two or more income streams, like a part-time remote job plus freelance work, or a content creation side hustle alongside online tutoring.
Pros
Diversified income = stability
Experiment with different paths
Greater control over your schedule
Cons
Can lead to burnout if you’re not strategic
Harder to explain on a resume
Requires solid boundaries and time management
Considerations
This is where many midlife nomads find their sweet spot. You don’t have to choose one path; you can design a mix that suits your strengths and lifestyle goals.
Start by identifying your primary income anchor (remote job, retainer client, etc.) and build around it.
Use your “extra” hours for passion projects or skill-building, not just more work. Think long-term: what do you want to build?
Be mindful of role to role fatigue—juggling too many unrelated gigs can leave you scattered and exhausted.
Plan your weeks with intentional time blocks. Keep track of hours worked, deadlines, and mental energy.
This model is sustainable when built with intention. Think of it not as juggling, but as layering.
Build a Work-From-Anywhere Life That Fits You
Don't worry about chasing a trend. Location independence is all about aligning your work with your values, your rhythm, and your ideal lifestyle. Whether you're exploring remote roles with strong employee benefits, launching your own content agency, or simply testing out your skill set in a new freelance space, the goal is the same: freedom, flexibility, and fulfillment.
Remember, every path has trade-offs. Fully remote employees may enjoy structure and product development cycles within established companies, but they’ll also navigate asynchronous communication, early-morning calls, and possibly multiple rounds of interviews.
Freelancers and contractors have more independence, but need to cultivate niche skill sets and constantly vet new projects. And creators or business owners? They’re designing a lifestyle, but also juggling uncertainty and learning curves.
Wherever you begin, you’re not behind... you’re right on time. The digital nomad lifestyle isn’t about escaping work. It’s about finding work that fits into the life you’re building, not the other way around.
Ready to take this journey with others who get it? Our Midlife Nomads – Work From Anywhere community is where real conversations happen about flexible work, slow travel, smart pivots, and creating a life you don’t need a vacation from. And it's completely free! Join us.
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