143: Stop outsourcing your business problems: finding your own path with Daryl Seager

Meet freedom business owner Daryl

Daryl is a leadership and confidence coach who helps female leaders and entrepreneurs thrive in male-dominated industries. With 15 years in coaching and consulting, he’s gone from supporting corporate leaders to find his true calling working exclusively with women.

What makes Daryl’s story so damn compelling? After walking away from his corporate job (with zero plan!), he spent 18 brutal months trying to make his business work. The real breakthrough came when he finally connected with his personal why – growing up with a single mother who had to juggle raising kids, returning to work, and rebuilding her life after his father left.

 That deep personal connection created the clarity his business desperately needed. Now based in Estonia (where he’s lived for five years, though considering a move back to the UK), Daryl focuses on helping ambitious women build their confidence, grow their success, and lead effectively in spaces traditionally dominated by men. 

His journey shows us that sometimes the long, messy road to clarity is exactly what your business needs to finally click.

“I left with absolutely no plan of what to do, but I thought how hard can starting a business be? And then I realized it’s a little bit harder than I thought it was going to be.”

Key takeaways from our freedom chat with Daryl:

➡️ The truth about starting over: Daryl walked away from his corporate role without a plan and spent 18 months struggling to find clarity. The real breakthrough came not from outsourcing his problems but from doing the deeper work of understanding his “why.” Sometimes the hardest business lessons come from jumping without a parachute.

 ➡️ Find your clarity: The pivotal moment in Daryl’s business came when he could clearly articulate his value in one simple sentence at a networking event, leading to immediate referrals. Before that moment of clarity, nothing was working properly. When you can explain your business to your neighbor, you’ve found gold.

 ➡️ The outsourcing trap: Daryl spent months and significant money outsourcing his lead generation and messaging, only to discover it didn’t work because he himself wasn’t clear on his message. External support can’t replace the internal work of understanding your unique value. No lead generation expert can fix a foundation that’s still wobbly.

 ➡️ Simplicity creates freedom: After trying to be everywhere and do everything, Daryl found success by drastically simplifying his approach—focusing on LinkedIn, establishing a consistent outreach routine, and sticking to what aligned with his natural strengths. Freedom comes from doing less, better.

➡️ Focus on connection, not algorithms: Rather than obsessing over social media algorithms, Daryl found success through authentic connection. He prioritizes meaningful engagement over trying to game the system, focusing on building relationships, networking, and following up with real people who engage with his content. This human-first approach creates both better business results and more sustainable freedom.

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 Daryl

Visit on LinkedIn @Daryl Seager

Instagram: @coach.darylseager

Website: www.darylseager.com

141: Building conscious community in southern Italy: The freedom business journey of Liz Cirelli

Meet freedom business owner Liz

Liz Cirelli is a former internationally successful DJ and award-winning music producer who now runs La Vita Sukha, a conscious co-living community and regenerative farm in Puglia, Italy.

Born and raised in London to Italian parents, Liz moved to Italy ten years ago and inherited her parents’ property in Roseto Valfortore after they passed away.

Beyond music, Liz is also a yoga teacher, permaculture designer, and massage therapist who is passionate about creating spaces where people can connect with nature and each other while living according to permaculture ethics: earth care, people care, and future care.

“When things get overwhelming, which is often because I’m wearing lots of hats, I just remind myself to plug into the big vision.”

Key takeaways from our freedom chat with Liz:

➡️ Learn the local language & systems: Learning the language of the country where you establish your business is crucial for success. It enables you to navigate bureaucracy, build meaningful connections, and understand cultural nuances that affect your business operations.

➡️ Build a strong local support network: Find knowledgeable locals who can guide you through complex systems and regulations. The right accountant, lawyer, or mentor who understands both the local environment and your vision can save you countless hours and prevent costly mistakes.

➡️ Stay aligned with your vision: Regularly reconnect with your big-picture vision, especially when day-to-day tasks become overwhelming. An aligned business should feel energizing rather than draining. If it feels like “pulling a heavy boulder uphill” instead of “wind beneath your wings,” something needs to change.

➡️ Be willing to pivot: Don’t fear letting go of partnerships, approaches, or audience segments that aren’t working. Successful freedom business owners recognize misalignment quickly and aren’t afraid to make necessary changes, even significant ones that might initially seem scary.

➡️ Trust your intuition and capabilities: Don’t underestimate your ability to run a business independently, even without prior experience. Listen to your body’s responses to different opportunities and decisions—physical sensations of freedom or constraint can be valuable guides toward greater business alignment.

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 Liz

Visit on LinkedIn @Liz Cirelli

Instagram: @liz_cirelli

Website: www.lavitasukha.com

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