Ashley Derrington: Journey of a Digital Nomad and Solopreneur

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Welcome to another edition of our BizStack Solopreneur Spotlight series, where we delve into the lives of those who’ve taken the brave leap into solopreneurship. Today, we’re talking with Ashley Derrington, a seasoned digital nomad and marketing maven who’s turned her passion for travel and marketing into a business, Ashley Derrington, LLC.

Let’s discover how she seamlessly blends work and play, crafts strategies for growth, and maintains productivity and balance.

Meet Ashley Derrington

Ashley embarked on my digital nomad journey over seven years ago, swapping entertainment marketing’s fast-paced world for the freedom to explore and work remotely. Starting with no plan but to travel, she gradually built a network and carved a niche in marketing and advertising, offering services from content creation to brand strategy. She says she’s perpetually looking to evolve and learn new skills in this dynamic space.

Ashley Derrington, Digital Nomad & Solopreneur
Ashley Derrington, Digital Nomad & Solopreneur

A Week in the Life

Ashley’s weeks are anything but typical, oscillating between busy schedules and flexible timeframes. Whether it’s playing soccer by day and working by night or sticking to a traditional 9-5, she balances her time between consistent client work and personal projects, devoting attention to each aspect every day. This fluidity is central to her solopreneur lifestyle.

Essential Tools and Technologies

At the heart of her business operations is communication. Maintaining an open and consistent line of communication via email, Slack, and texts with clients and colleagues is crucial for collaboration, especially when working remotely.

Growth Strategies

Ashley says she has been able to grow her business through word of mouth.

“I think being good at what you do and having a willingness to grow and learn goes a long way! Others will feed off of that and will want to share your talents with the world.”

Ashley Derrington

Productivity Hacks

Ashley says she’s all for the tangibility of a good notebook. Physically crossing off tasks brings a sense of accomplishment.

Organizing tasks by client and priority and learning the art of saying “no” or delegating tasks has been a game-changer for her.

Overcoming Challenges

As a solopreneur, learning to say “no” to potential clients was a significant hurdle for her, given the variable nature of my workload and income.

“I discovered that focusing on work I enjoy and collaborating with people I respect, even if it means earning less at times, has enhanced my happiness and productivity.”

Ashley Derrington

Significant Achievements

Becoming a solopreneur enabled Ashley to venture into other businesses without the steep learning curve of starting from scratch. Successfully launching three additional ventures stands as a testament to the invaluable experience gained through her solopreneur journey.

Advice for Aspiring Solopreneurs

Embrace the solopreneurship journey with its highs and lows. Remember that you’re not alone. The solopreneur community is vibrant and supportive, ready to share knowledge and experiences.

Ashley Derrington’s Lightning Round

In this lightning round, I asked Ashley Derrington to answer 12 rapid-fire questions:

What’s something that’s in your pocket right now, besides your phone?


Artificial intelligence: hope or dread?

Switzerland on this, some cases good, some cases not so good

Your favorite place to think big?

Driving on an open road

If you were out of business tomorrow, what job would you pursue?

Something in marketing or brand strategy in sports or at a smaller agency

One object from your childhood you could never throw away?

N/A, not super materialistic when it comes to things but maybe some pictures?

One feature you wish your phone had?

To remove itself from my hands when I’ve been on it too long

Your favorite mobile app?

Been – helps me track all the places I’ve traveled or want to travel to

The book that most influenced you?

A bit cliche but I’ll say “The Alchemist

Messy desk or clean desk?


One thing you always have in your fridge?

Sparkling water

Your favorite time-saving hack?

Time Blocking for certain tasks so I don’t get fixated on one thing for too long

Best movie ever?

As someone who previously worked in film and TV, this is impossible to answer. “Good Will Hunting” is always a favorite that comes to mind.

Connect With Ashley

You can reach out and connect with Ashley on Instagram, LinkedIn, or via email.

You can also visit Ashley Derrington, LLC to dive deeper into Ashley’s world of marketing innovations and digital nomad adventures.

We hope Ashley’s journey inspires you to pursue your dreams with courage and curiosity. Her story is a testament to the beauty of blending professionalism with personal passions, proving that you can design a life and career you truly love with resilience and flexibility. Stay tuned for more insights from remarkable solopreneurs in our BizStack Solopreneur Spotlight series.

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