139: Intuition vs structure: creating an aligned freedom business that actually feels like freedom with Lavinia from The Offsite

Meet freedom business owner Lavinia

Lavinia is the founder of The Offsite, creating immersive travel experiences for people seeking community and a taste of location freedom without necessarily being digital nomads.

As a manifestor in human design with a fire for new experiences, she’s created unique travel containers where people from all walks of life connect authentically.

What started as organizing a fun trip to Lisbon with friends has evolved into a thriving business that’s hosted 25 trips across four continents – all while Lavinia navigates her own journey of delegation, energy management, and designing a business that honors her natural flow.

“I’ve never had a business plan. For so many years, I felt like a fraud. I go where it feels good to go.”

Key takeaways from our freedom chat with Lavinia:

➡️ Honor your energy type: Lavinia (a manifestor) and Nienke Nina (a projector) both discovered they needed to stop trying to work like generators with constant energy. Find your own rhythm – whether that’s tracking your productivity patterns or riding waves of inspiration.

➡️ Delegation doesn’t mean dilution: When you build a business on your unique energy, delegating can feel impossible. Reframe it through the lens of impact – if your mission is helping more people, delegation becomes essential rather than optional.

➡️ Alignment feels different for everyone: What feels like alignment varies person to person. For Lavinia, it’s an excited fire and obsessive thinking about a new idea. For Nienke Nina, it’s calm groundedness. Discover your own alignment cues rather than copying others’.

➡️ Create from service, not survival: When you approach your business decisions from a place of serving your mission rather than survival, it takes the pressure off and helps you make better choices about growth and delegation.

➡️ Freedom requires breaks: True freedom isn’t about constant movement but knowing when to pause. After pushing through burnout, Lavinia recognized the importance of planning rest and bringing in support.

Connect with Nienke Nina

More digital nomad tips and life advice via instagram @digitalnomadsdaily

Connect with Nienke Nina on LinkedIn @Nienke Nina Keizer

Find Nienke Nina on Instagram @growwithnienkenina

Connect with Lavinia

Visit on LinkedIn @Lavinia Giarre

Instagram: @thelavinia

Website: www.theoffsite.uk

Episode 137: Freedom business reality: from agency life to freedom freelancing with Jake Madoff

Meet freedom business owner Jake

Jake Madoff is a full stack growth marketer specializing in paid media, SEO, and funnel optimization. What began as self-teaching web design for his own e-commerce business in 2014 evolved through co-founding a trade and barter app startup, to spending five years scaling a company’s ad spend from $300K to $2 million monthly.

During COVID, Jake transitioned to full-time freelancing, where he now helps businesses across diverse industries—from e-commerce to legal to B2B SaaS—grow through strategic digital marketing.

Based in Manhattan, he represents a new generation of marketing professionals who’ve learned their craft not through traditional education but through hands-on experimentation, adaptation, and saying “yes” to new opportunities before they felt fully ready.

“Some people just aren’t really wired to be managed. I find myself so much more productive if I am telling myself what to do versus other people telling me what to do.”

Key takeaways from our freedom chat with Jake:

➡️ The psychological freedom effect: Even though entrepreneurs often work more hours than employees, having control over when and how you work creates a profound psychological freedom that transforms your relationship with work.

➡️ Say Yes, then learn to say No: Early in your entrepreneurial journey, saying yes to opportunities—even ones you’re not fully prepared for—forces rapid growth and skill development. As you mature, learning when to say no becomes equally critical.

➡️ The hidden economics of freelancing: Agency marketers managing six clients while making $60-80K could potentially earn $15K monthly by taking those same clients freelance—a dramatic shift in income potential that’s rarely discussed in traditional career paths.

➡️ Sustainable vs. unsustainable business models: Some business models (like dropshipping) have shorter shelf lives due to easy replication, while others (like growth marketing) offer medium-term sustainability before potential AI disruption—choose wisely based on your timeline.

➡️ The self-development accelerator: Entrepreneurship functions as “a self-fulfilling journey on steroids,” forcing rapid personal growth in areas like boundary-setting, communication, and self-discipline that transform far more than just your income.

Connect with Nienke Nina

More digital nomad tips and life advice via instagram @digitalnomadsdaily

Connect with Nienke Nina on LinkedIn @Nienke Nina Keizer

Find Nienke Nina on Instagram @growwithnienkenina

Connect with Jake

Visit on LinkedIn @Jake Madoff

Website: www.jakemadoff.io

136: When your Freedom Lifestyle no longer feels free with Nienke Nina

Ever feel like the freedom lifestyle you chased so hard suddenly doesn’t feel freeing anymore?

Nienke Nina talks about her personal journey through an identity crisis after five years as a digital nomad, falling in love, settling down, and questioning everything she built her brand on. She dives deep into what freedom really means beyond the Instagram-perfect shots of laptops on beaches, and why creating true freedom in your life is both painful and beautiful.

If you’ve ever felt out of alignment with your business, lifestyle, or identity, this raw conversation will help you reconnect with what freedom truly means for YOU.

“I focus more on alignment. I say ‘aligned freedom business’ because I see so many people copying someone else’s freedom business because they think that’s freedom.”

Key takeaways from our freedom life & business episode:

➡️ Freedom is about Aligned Expressions: True freedom comes from creating expressions of your life (business, relationships, location) that are in alignment with who you are. When these expressions aren’t aligned, you’ll feel friction, self-doubt, and may fall out of love with things you used to enjoy.

➡️ Freedom isn’t static: Your freedom goals will evolve over time. What feels freeing now may not feel the same next year. Freedom requires constant exploration and curiosity about what works for you in each season of life.

➡️ How the Digital Nomad identity can be limiting: The stereotype of a digital nomad (constant travel with a laptop) is just one expression of freedom. There are countless ways to create freedom sensations in your life without fitting this narrow definition.

➡️ Creating freedom takes intentional ongoing work: Building a freedom lifestyle requires deep self-reflection, strategy, and implementation. It’s not a quick fix but a continuous process of alignment and realignment as you grow.

➡️ Business Alignment requires regular check-ins: When your business no longer feels enjoyable, a thorough alignment audit can help you understand what’s working, what’s not, and how to create a strategy that brings back those freedom sensations.

Connect with Nienke Nina

More digital nomad tips and life advice via instagram @digitalnomadsdaily

Connect with Nienke Nina on LinkedIn @Nienke Nina Keizer

Find Nienke Nina on Instagram @growwithnienkenina

124: Celebrating 20 years of working remotely with Liam

“Remote work isn’t just a way to do your job; it’s a way to reclaim your life, giving you the freedom to choose how, where, and when you work. It’s the gateway drug to a life of autonomy and purpose.”

Meet Remote Work expert and digital nomad Liam

In this week’s gripping episode, Nienke Nina sits down with the intrepid Liam, a seasoned digital nomad who’s been riding the waves of remote work for over a decade. Liam, with a background as eclectic as his passport stamps, has carved out a niche for himself by blending his passion for travel with his knack for web development and online marketing. Yet, it’s not all beachside co-working spaces and exotic locales; Liam opens up about the tightrope walk of maintaining a reliable internet connection in remote corners of the world—a challenge that can turn paradise into a professional purgatory in no time.

Meet Remote Work expert and digital nomad Liam

In this week’s gripping episode, Nienke Nina sits down with the intrepid Liam, a seasoned digital nomad who’s been riding the waves of remote work for over a decade. Liam, with a background as eclectic as his passport stamps, has carved out a niche for himself by blending his passion for travel with his knack for web development and online marketing. Yet, it’s not all beachside co-working spaces and exotic locales; Liam opens up about the tightrope walk of maintaining a reliable internet connection in remote corners of the world—a challenge that can turn paradise into a professional purgatory in no time.

Key takeaways from Liam about 20+ years of working remotely

Dive deep with us as we explore the unfiltered realities of nomadic life. From the logistics of juggling time zones to ensure seamless collaboration with clients across the globe, to the personal hurdles of building and sustaining meaningful relationships on the move. Liam doesn’t hold back on the highs and lows, sharing his insights on staying productive in the most unconventional of offices, and the mental fortitude required to thrive in constant change. This episode is a treasure trove of wisdom for anyone curious about ditching the conventional 9-to-5 for a life of adventure, underscored by the raw truths and resilience it demands.

5 things you learn in this episode with Liam

➡️ Escape the Cold, Embrace Freedom: Liam shares how swapping snow for sand doesn’t just change your climate; it revolutionizes your work-life balance. Learn the secrets to mastering seasonal nomadding.

➡️ The Genesis of Running Remote: Discover how a void in the remote work community led to the birth of the world’s largest remote work conference. It’s the push you need to chase your dreams.

➡️ The Magic of Asynchronous Work: Liam explains why ditching the 9-5 for asynchronous work is the key to boosting productivity and happiness. A game-changer for anyone feeling chained to their desk.

➡️ Networking Gold at Running Remote: Nienke Nina’s experience at Running Remote transformed her career. Uncover how genuine connections can lead to unexpected opportunities in the digital nomad world.

➡️ Predicting the Remote Work Surge: Dive into Liam’s insights on the future of work and how embracing remote work now could put you ahead of the curve. It’s the blueprint for modern success.

Connect with our Nienke Nina and our guests

Your host Nienke Nina

More digital nomad tips and life advice via instagram @digitalnomadsdaily

Connect with Nienke Nina on LinkedIn @Nienke Nina Keizer

Find Nienke Nina on Instagram @nienkeninatravels

Meet digital nomad Liam

Find him on LinkedIn here

Instagram: @liamremote

Other episodes you might like:

🎧  Episode #01: How to Thrive in your Digital Nomad Relationship with Anat & Orr

🎧  Episode #05: Dealing with High Anxiety While Building a Successful Online Business with The Remote Yogi

🎧  Episode #07: Overcoming Fears and Building Community with Digital Nomad Magali

🎧 Episode #21: 10 Years Of Traveling The World With Daisy

Remote Work Isn’t Just For Digital Nomads With Lorraine

“What’s the point of education if you can’t earn money to sustain your life. So I wanted to understand what the situation was for refugees in this context.”

Lorraine and her journey to remote work

Lorraine started working remotely way back in 2011 and at the time, she didn’t realize it because she was just doing her thing. Since her co-worker was based in Venezuela, they collaborated virtually via video calls and using shared documents in dropbox.

She continued her remote journey and works in many different things nowadays. She is a Digital Solutions Specialist for Finn Church Aid focused on refugees, doing research at Cambridge University and consulting.

During her research about refugees, she saw a massive gap and with that an opportunity to help refugees. Lorraine is a real go-getter and co-founded Na’amal, which is an initiative supporting refugees to work remotely.

In this episode, we learned that their a strong misconception about who refugees are. In fact, Lorraine shares that everyone could become a refugee. For example, due to the impact of climate change where people have been forced to flee their homes.

So it’s really hard to stereotype refugees. Interestingly, many refugees in today’s world have a degree and speak a second language like English. Digital media on platforms like YouTube and Netflix also contribute to the English language levels.

Na’mal prepared refugees for remote work by offering training and guidance in the remote job process. They also support their students with practicalities like documents and bank accounts so they can actually be hired once a job opportunity lands on their path.

The training is focused on soft skills in remote work environments and advanced digital skills like coding and UX/UI design. The training process typically takes around six months so they can enter the job market with confidence.

We are really excited about the future of Namal and its students. If you are a business owner or are looking for talent, we highly recommend getting in touch with Lorraine and her team. It’s initiatives like these that make a difference and at Digital Nomads Daily we love this way of giving back to other communities.

Connect with our Nienke Nina and our guests

Your host Nienke Nina

More digital nomad tips and life advice via instagram @digitalnomadsdaily

Connect with Nienke Nina on LinkedIn @Nienke Nina Keizer

Find Nienke Nina on Instagram @nienkeninatravels

Meet digital nomad Lorraine

Find her on

LinkedIn: Lorraine Charles

Twitter: @na’amal

Instagram: @naamal 

www.naamal.org

Other episodes you might like:

🎧 Episode #54: What Makes a Remote-First Company Culture with Chase

🎧 Episode #40: Understanding Digital Nomad Visas In 2022 With Tim 

🎧  Episode #38: How Leaders Can Strengthen Remote Company Culture with Jürgen