Slippers, Sailboats & DataAnnotation: How I Found Work-Life Freedom on My Terms

Hayli Egbert
April 2, 2025
I’m the kind of person who craves both adventure and comfort. I’ll spend all winter in cozy slippers and all summer barefoot. I’ll stay up too late chatting with an old friend or sleep in just because the blankets are too good to leave. Sound familiar?
Slippers, Sailboats & DataAnnotation: How I Found Work-Life Freedom on My Terms

What doesn’t fit that lifestyle? Commuting to an office five days a week.

Luckily, DataAnnotation made it possible for me to enjoy all of that—and still earn a solid income. Here’s the short version of how it changed my life.

About a year ago, my partner and I bought a sailboat... and made it our full-time home. We’re both chronic homebodies who also want to see the world, so living on a sailboat gave us the best of both worlds: home and movement.

With this new lifestyle, I needed a job that moved with me—literally. Though I had experience in digital marketing, virtual assistance, and social media, freelance work often came in waves, and I needed consistency. That’s when I stumbled across DataAnnotation.

Like many people, I was skeptical. Was it too good to be true? Was it legit? Would I put in hours only to never get paid? But I gave it a shot—and a year later, I’m still here, thriving. It’s truly been life-changing.

Here are 5 reasons I Love working for DataAnnotation:

1. Ultimate Flexibility

This is peak flexibility. Want to take the day off, work through the night, or go hard for a week and take the next off? You can. The schedule is entirely yours to design, making true work-life balance not just possible—but effortless.

2. Total Autonomy

No micromanaging. No set hours. No awkward check-ins. I choose the projects I want, decide how long I work, and move on when I’m ready. If a task doesn’t spark interest, I pivot. Simple as that.

3. Real Skill Building

Since starting with DA, I’ve learned the basics of AI, sharpened my research abilities, and expanded my problem-solving toolkit. You get to apply what you already know and pick up new skills along the way.

4. Engaging, Varied Work

I get bored easily. But with DataAnnotation, that’s rarely an issue. While repetitive tasks exist if that’s your thing, most projects are mentally stimulating and diverse. When I need a break, I take one. When I want a change, there’s always something new.

5. Fair, Competitive Pay

From day one, I’ve been paid fairly—and as I’ve taken on more complex tasks, my pay has increased accordingly. There’s no expectation to do skilled work for peanuts, which is unfortunately all too rare in the remote work world.

One year ago, if you’d told me I could replace my primary income without leaving my house—or changing out of my slippers—I would’ve assumed it was some shady get-rich-quick pitch. But now? It’s my reality.

Today, I get to enjoy slow mornings, set my own schedule, and earn good money while sailing up and down the coast. All without ever leaving “home.”

If you’re looking for freedom, fulfillment, and flexibility—DataAnnotation might be exactly what you didn’t know you needed.

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