Episode 137: Freedom business reality: from agency life to freedom freelancing with Jake Madoff
👇 Or listen in your fav podcast apps👇
What you’ll learn from Jake:
➡️ How to find true work freedom
➡️ How to develop as a freelancer
➡️ How to accelerate personal growth in entrepreneurship
➡️ How to multiply your income
Learn everything about creating more freedom and live your dream life
Start a side hustle or build a freedom business – creating multiple revenue streams is the way to your freedom life. We show you how others do it successful too.
Get freedom business growth tips in your inbox 💌 Join 4000+ digital nomads and freedom seekers!
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.
Review the podcast to get instant access to our FREEDOM BOOSTER Framework Training
For busy business owners who want to experience MORE Freedom
1️⃣ Leave a review on Apple or Spotify ❤️ 2️⃣ Take a screenshot & upload it here 3️⃣ We’ll send Nienke Nina’s free training right away to your inbox!
Learn everything about creating more freedom and live your dream life
Start a side hustle or build a freedom business – creating multiple revenue streams is the way to your freedom life. We show you how others do it successful too.
Get freedom business growth tips in your inbox 💌 Join 4000+ digital nomads and freedom seekers!
Fresh Freedom Business Episodes
Learn with Nienke Nina from successful business owners
🎙 The Freedom Lifestyle Podcast 🎙Episode 137: Freedom business reality: from agency life to freedom freelancing with Jake Madoff👇 Or listen in your fav podcast apps👇What you'll learn from Jake: ➡️ How to find true work freedom ➡️ How to develop as a freelancer ➡️ How to accelerate...
🎙 The Freedom Lifestyle Podcast 🎙136: When your Freedom Lifestyle no longer feels free with Nienke Nina👇 Or listen in your fav podcast apps👇What you'll learn from Nienke Nina: ➡️ How to continue feeling free in your freedom lifestyle ➡️ The new modern of digital nomad in 2025 ➡️ How to...
🎙 The Freedom Lifestyle Podcast 🎙Episode 135: Creating a Powerful Personal Brand for Digital Nomad with Marina👇 Or listen in your fav podcast apps👇What you'll learn from Marina: ➡️ Strategies to kick-start your personal branding➡️ The reality of digital nomad solopreneurship➡️ Why you...
136: When your Freedom Lifestyle no longer feels free with Nienke Nina
👇 Or listen in your fav podcast apps👇
What you’ll learn from Nienke Nina:
➡️ How to continue feeling free in your freedom lifestyle
➡️ The new modern of digital nomad in 2025
➡️ How to navigate when you’re shifting lifestyles
➡️ How to create more freedom in your aligned freedom business
Learn everything about creating more freedom and live your dream life
Start a side hustle or build a freedom business – creating multiple revenue streams is the way to your freedom life. We show you how others do it successful too.
Get freedom business growth tips in your inbox 💌 Join 4000+ digital nomads and freedom seekers!
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.
Review the podcast to get instant access to our FREEDOM BOOSTER Framework Training
For busy business owners who want to experience MORE Freedom
1️⃣ Leave a review on Apple or Spotify ❤️ 2️⃣ Take a screenshot & upload it here 3️⃣ We’ll send Nienke Nina’s free training right away to your inbox!
Learn everything about creating more freedom and live your dream life
Start a side hustle or build a freedom business – creating multiple revenue streams is the way to your freedom life. We show you how others do it successful too.
Get freedom business growth tips in your inbox 💌 Join 4000+ digital nomads and freedom seekers!
Fresh Freedom Business Episodes
Learn with Nienke Nina from successful business owners
🎙 The Freedom Lifestyle Podcast 🎙Episode 137: Freedom business reality: from agency life to freedom freelancing with Jake Madoff👇 Or listen in your fav podcast apps👇What you'll learn from Jake: ➡️ How to find true work freedom ➡️ How to develop as a freelancer ➡️ How to accelerate...
🎙 The Freedom Lifestyle Podcast 🎙136: When your Freedom Lifestyle no longer feels free with Nienke Nina👇 Or listen in your fav podcast apps👇What you'll learn from Nienke Nina: ➡️ How to continue feeling free in your freedom lifestyle ➡️ The new modern of digital nomad in 2025 ➡️ How to...
🎙 The Freedom Lifestyle Podcast 🎙Episode 135: Creating a Powerful Personal Brand for Digital Nomad with Marina👇 Or listen in your fav podcast apps👇What you'll learn from Marina: ➡️ Strategies to kick-start your personal branding➡️ The reality of digital nomad solopreneurship➡️ Why you...
124: Celebrating 20 years of working remotely with Liam
👇 Or listen in your fav podcast apps👇
Listen to our interview with digital nomad Liam:
🔥 The future of work and digital nomadism
🔥 The power of remote work to transform lives
🔥 Why mastering the art of asynchronous management
🔥 Expert predictions and data-driven insights about the future of work
🔥 The biggest conference about remote work Running remote in 2024
🔥🔥🔥 And so much more must-know digital nomad lifestyle tips for (aspiring) digital nomads!
“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.
Remote Work Isn’t Just For Digital Nomads With Lorraine
👇 Or listen in your fav podcast apps👇
Listen to our interview with digital nomad Lorraine:
🔥 What are refugees?
🔥 What are some of the misconceptions that we have about refugees
🔥 Here is an insight into the future of remote work for refugees with Na’amal
🔥🔥🔥 And so much more must-know digital nomad lifestyle tips for (aspiring) digital nomads!
“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.
Alone together | How to combat loneliness as a digital nomad couple
How wonderful it is to travel with your partner! Never being alone and always having someone to talk to whenever you feel lonely. Well, not exactly. Many couples discover that being together 24/7 doesn’t fill their need for human interaction and it can even be unhealthy for their relationship. As a result, they might want to interact with other people, but their go-to ways of socializing with friends from back home and family members are not accessible to them as digital nomads. When they try to meet new people locally, they discover that organically mingling with others is harder to do as a couple than for solo travelers.
Despite all these challenges, socializing with others is still a basic human need. So it’s important to know how to combat loneliness as a digital nomad couple. And with all the love and respect for our partners, they are not enough for human interaction. So here are a few tips on how to socialize with others as a digital nomad couple:
Get yourself out there
The first way to combat loneliness as a digital nomad couple is by putting yourself out there. This is the most important thing to keep in mind when it comes to socializing. You need to put yourself out there and do the horribly awkward thing of reaching out. Usually, in life, we have structures that help us socialize with others and potentially make friends: Our studies, our job, our hobbies and so on. When you become a digital nomad many of these structures are gone or do not work in the same way. You want to replace those structures with ones you build yourself. No matter what kind of structures you want to build, remember the most important part is taking the action that will allow you to socialize. If you are not sure what that action can look like, here are a few of the things that work for us while we travel.
Social media is your friend to combat the loneliness as a digital nomad couple
The least awkward action you can take is posting to social media. We met digital nomads that met new people through tinder, Instagram, Reddit, and Twitter. As a couple, the platform we usually use is facebook’s groups\communities. Find local groups of digital nomads or expats in your area and write a general post that you would like to meet people. Usually, people will respond. Sometimes those connections happened even when we were asking general questions in those groups, like asking about good places to find accommodation or fun activities to do on the weekend. The downside to this method is that it is essentially like a blind date with a stranger. If the thought of meeting someone you don’t know at all is uncomfortable for you, you might want to try the following actions:
Weekend adventures and joined activities
Do something fun over the weekend that will make socializing easy. As digital nomads, we usually use the weekends to enjoy the place we are staying at. A fantastic way to answer your socializing needs is using that time segment to choose activities or places that will help you socialize with new people. Here are two examples:
When we stayed in Albania, we used the weekends to explore places around the country. When we went on our weekend adventures, we would try to book a hostel instead of a hotel. Hostels are places where people naturally speak to each other and hang out, and it is so much easier to find new friends when the atmosphere encourages it. When we stayed at a hostel in Berat, we met new people and decided to grab lunch together during check-in! We later spent the whole day with them when we went on a canyon trip that the hostel offered and we became really good friends. We even met them again in Tirana before they flew to their next destination.
When we stayed in Koh Phangan, we dedicated one of our weekends to a well-being retreat. During that time, we were in classes and workshops that introduced us to new people each time, as well as during our free time hanging out in the pool or eating in the dining hall with other people. We met a couple of friends we stayed in contact with until today while eating one of our meals in the dining hall. See, it’s easy to combat the loneliness as a digital nomad couple when you know how.
Go to where the people are
Weekend adventures are lovely, but you don’t have to limit yourself to meeting new people just over the weekend. Assuming you don’t speak the native language, another method you can try is finding where many digital nomads, expats, or even tourists hang out and come visit. You can go there for something you already supposed to do, like work or eat, and get to know people along the way.
Co-working and co-living spaces are obvious examples to combat loneliness as a digital nomad couple. We had one of our best social periods when living in a co-living space with other digital nomads in Sri Lanka. But co-working\living places are not your only option. Many times, there are specific bars, cafes, or restaurants favored by the people you want to meet. In Krabi, for example, there was a family garden where many locals and expats would go to and it was a wonderful place to meet people. Sometimes there is even a hanging spot of digital nomads from your home country, which makes making friends much easier. We went to a Shabat’s dinner in such a place when we stayed in Koh Phangan, and we made some great connections there.
Follow your interests
Another excellent option is using your passions and hobbies as a way to meet people and deliberately channel them for that goal. For example, I practice yoga independently, but when we settle for a few months, I like to find a studio where I can practice with others. By deliberately doing my yoga practice in an environment where I can have a community, I extend my social circle and the possibilities of meeting people and making new friends. This is how I met friends both in Krabi and Bangkok, and we know of other digital nomads that used hobbies like water polo, Muay Thai, singing, and surfing with similar results.
Friendship is a never-ending quest for the digital nomad
Unfortunately, making friends as a digital nomad is a never-ending quest; whenever we come to a new place, the quest for friends begins anew. You will make amazing friends along the way, but at some point, your paths will probably separate, and you won’t be able to stay together all the time. But don’t discourage! Keep on putting yourself out there with confidence, and you will make more friends with whom you truly connect. As time goes on, you will have amazing friends scattered all over the globe, and the quest for meaningful social connections will become easier.
Do you want to learn more about the digital nomad lifestyle? Tune in on The Digital Nomads Daily Podcast to discover more tips about how to combat loneliness as a digital nomad couple and a solo traveler. The episode with digital nomad Marcel is a great way to start as he shares how he makes friends around the world as an introvert.
