Black Sheep

The Journey Begins: Embracing Minimalism, Digital Nomadism, and the Stoic Path

As I sit here in a café, Macbook open, sipping my Matcha Frappachino, I reflect on a simple truth that has guided me through life: less is more. This philosophy, grounded in minimalism, stoicism, and a relentless drive for freedom, has shaped not only my lifestyle but my mindset. I want to welcome you to a journey of discovery — not just across borders but within yourself.

The Call of the Digital Nomad

In a world that constantly screams for more, the life of a digital nomad is a silent rebellion. I’ve roamed the cities of Europe, trekked through jungles, and found peace in the mountains. Each place I visited offered lessons, but one thing remained constant: my laptop and the internet were my keys to freedom. I wasn’t tied to a desk, a country, or even a fixed identity. I could reinvent myself wherever I went, carrying only what was essential.

The digital nomad lifestyle is more than an escape from the 9-to-5 grind; it’s a mindset shift. It’s about rejecting the conventional path of working for others and instead building something for yourself, on your own terms. But to succeed in this journey, you must learn to carry less. Which brings me to minimalism.

Minimalism: Owning Less, Living More

We’ve been conditioned to believe that happiness lies in material wealth — the bigger house, the faster car, the latest gadget. But when I started travelling, I learned a profound truth: happiness comes not from accumulating, but from stripping away.

When all you own fits into a backpack, you become acutely aware of what truly matters. You begin to ask yourself: what is essential? What brings value to my life? Minimalism isn’t just about decluttering your possessions; it’s about decluttering your mind. It’s about creating space — for experiences, for relationships, for self-growth.

In my journey, I found that once I let go of what wasn’t necessary, I could focus on the things that were. And this led me to Stoicism.

The Stoic’s Path: Control What You Can, Let Go of What You Cannot

Stoicism teaches us to control our reactions, not the world. It’s the ultimate philosophy for anyone living an unpredictable life, whether you’re navigating a foreign country or dealing with the chaos of modern living. As a digital nomad, you will face challenges — some external, others internal. Delayed flights, lost luggage, unreliable Wi-Fi are minor in the grand scheme of things, but the real battle is with your mind.

Embrace discomfort. Learn to thrive in uncertainty. Understand that the only thing you can truly control is how you respond to life’s challenges. Stoicism arms you with this mindset. It helps you build resilience, not just in travel but in life itself.

The Adventure Awaits

As I set out to document this journey, I invite you to join me. Whether you’re looking to simplify your life, become location-independent, or develop a mindset that thrives in adversity, this blog will serve as a guide. I’ll be sharing insights from my travels, lessons from the minimalist lifestyle, and the philosophical wisdom that has helped me stay grounded in an ever-changing world.

The road ahead is uncertain, but that’s what makes it exciting. Together, we’ll explore the world of self-development, travel, and everything in between. Are you ready?

Welcome to the journey.

Harry Holland

The Writing Journey

From The Side Hustle Blueprint to The Nomad Entrepreneur, and even The Bandit Bachelor, one theme remains consistent: self-reliance.

Whether you’re looking to escape the corporate grind or find freedom in an unconventional path, success begins by embracing discomfort and understanding that the road to independence is a mental game. Each of my books is a toolkit — a guide for those who want to take control of their lives, master productivity, or harness their mindset.

In books like How to Reprogram Your Brain or The Maverick’s Manifesto, I explore how to break free from societal norms and embrace the full potential of self-determined living. For the modern digital nomad, titles like Digital Nomad: The Complete Guide or Digital Nomads: Lessons from the Past offer actionable insights on navigating this evolving lifestyle.

Whether it’s through stoic wisdom, practical side hustles, or lessons in entrepreneurship, my journey as an author reflects the pursuit of freedom, adaptability, and resilience. Each title is a chapter in the story of modern self-development, where success is no longer defined by traditional standards but by our ability to thrive in an ever-changing world.

I hope you find inspiration and actionable advice within my work, no matter where you are on your path.

Harry Holland

Be the Sheepdog not the Sheep

In today’s ever-changing world, it’s easy to feel lost or disconnected. Every generation faces its challenges, longing for the “good old days,” but the truth is, human behaviour has not fundamentally changed in millions of years. The real obstacle isn’t society or trends; it’s how we choose to react.

As I mentioned in Wanderlust Wisdom, success, particularly in relationships, comes from understanding and accepting these truths. You can either be a sheep, blindly following the herd, or you can be the sheepdog, awake and aware. Now more than ever, there’s an opportunity to break free from conventional thinking.

To truly live freely, you must take back control of your emotions and decisions. These truths might sting at first, but once you accept them, they’ll set you free.

The choice is simple: be the sheepdog, not the sheep. Wake up to the vast possibilities around you and live a life defined by your terms, not societal expectations. This path might be unconventional, but it’s the one that leads to personal growth, fulfilment, and real freedom.

90% Action, 10% Theory: The Key to Real Progress

If you’re waiting for the perfect plan or more information before taking action, you’re missing the point. In life, 90% of success comes from just doing. Planning, reading, and theorising are useful, but they’re only 10% of the game. The rest is action.

Stop thinking you need every detail worked out before you begin. Start small, start messy, but start now. The path to success is paved with imperfect steps. Action builds momentum, and momentum brings results.

Theories fade, but actions create lasting change.

Harry Holland

Podcast discussing Harry Holland

2nd Podcast

Holding Your Own

Navigating the complexities of modern life requires a unique blend of resilience, self-assurance, and an understanding of one’s own values. In Vagabond Life, I explore the concept of “holding your own”—a foundational principle when interacting with strong personalities who might be used to a world of attention and admiration. For many, the question arises: how can you stay grounded and true to yourself in these dynamic encounters?

The Core of “Holding Your Own”

At its essence, “holding your own” means embodying stability and conviction. When faced with someone who may test boundaries, the ability to remain unflappable is vital. This isn’t about overpowering or diminishing anyone but rather about staying true to oneself, regardless of external pressures. Embracing this mindset reveals an inner strength that respects both your own integrity and the uniqueness of people around you.

Balancing Non-Reactivity with Assertiveness

A common approach in challenging interactions is to stay non-reactive—to let things slide and keep your emotions steady. However, authenticity sometimes calls for more than passive endurance. While it may be tempting to appease or deflect, a more impactful response often lies in expressing your honest reaction calmly and confidently. This balance between non-reactivity and assertiveness is a powerful tool, allowing you to set boundaries with respect and transparency.

Mastering Frame Control

A helpful concept here is “frame control,” an approach that applies not just in personal relationships but across all social and professional settings. At its heart, frame control is about self-respect and recognising the impact of your presence. When we talk about “holding the frame,” it’s not about manipulation but about standing firm in your values, whether that means being playfully assertive, speaking openly, or simply choosing silence. This approach, combined with clear, respectful boundaries, can often shift the dynamic in a meaningful way.

In today’s world, where interactions are often rapid and expectations high, learning to “hold your own” can bring a sense of clarity and authenticity to relationships. Embracing these principles allows for richer connections and reveals a grounded, genuine presence that others are naturally drawn to.


If Not Now, Then When?

It’s a statement that resonates with every dreamer, every person who’s looked longingly at something they wanted to do, be, or have but thought, I’ll get to it when…. When things calm down. When work isn’t so demanding. When you’ve saved enough. When, when, when. This mindset, though, is the slippery slope of procrastination, and it’s often the real danger to living the life you truly want.

The Trap of “Someday”

It’s easy to push our dreams into an imaginary future. “Someday” seems safe, but it’s a mirage. In reality, someday has no guarantee. Life has a habit of catching us off guard, filling our days with obligations, responsibilities, and unforeseen events. The perfect time to start anything rarely arrives, and waiting for that elusive “someday” can mean never beginning at all.

“I’ll travel when my career is settled,” or “I’ll write that book when I have more free time,” are phrases that ring all too familiar. But here’s the truth: the best time to start is often when it feels slightly uncomfortable. Growth doesn’t come from sitting in perfect conditions; it comes from venturing out of your comfort zone and acting despite the imperfect circumstances.

The Mindset of Action

If there’s one thing that sets the go-getters apart from the dreamers, it’s the mindset of now. It’s deciding to take that first step, even if it’s small. If you want to write a book, start by writing a page. If you want to get in shape, lace up and go for a short run. Starting is powerful. It’s where all great things begin.

The mindset of action isn’t about making massive leaps overnight. It’s about breaking down your goals into manageable steps and doing something each day. This mindset is what separates those who live a life of fulfilment from those who live a life of regret.

The Cost of Inaction

The price of waiting is high. Every time you put something off, you risk losing momentum, motivation, and time. You may not notice it at first, but inaction compounds just as action does. Dreams gather dust. You might look back years later and wonder what could have been if only you’d acted sooner.

The real danger lies in letting life pass you by. Too many people reach the end of their days with a sense of regret, not for the things they did but for the things they didn’t. The opportunities missed, the chances not taken, the adventures that never happened – these are the true costs of inaction.

How to Get Started: Moving Past Procrastination

So, how can we move past the “I’ll do it when…” mindset? Here are a few steps that can help:

1. Clarify Your Why: Know why your goal or dream matters. Is it about freedom, fulfilment, or legacy? Get specific about why this matters to you, and remind yourself often.

2. Set a Start Date: Take control of your dreams by setting a start date, even if it’s today. Mark it in your calendar and treat it as a commitment.

3. Break It Down: Large goals can feel overwhelming, so break them down into manageable steps. Start small but be consistent.

4. Embrace Imperfection: Recognise that things won’t always go perfectly, but that’s part of the journey. Learn to take imperfect action and adjust along the way.

5. Build Accountability: Tell someone about your plans or join a group with similar interests. Having accountability can give you the push you need to stay on track.

The Gift of Seizing the Moment

Acting now has a ripple effect. Every time you choose to act, you build courage, resilience, and belief in yourself. You realise that you are capable of shaping your life, of turning dreams into reality, one step at a time. Instead of watching others live the life you want, you become the one inspiring others by living authentically and unapologetically.

So, here’s a question to ask yourself: If not now, then when? This isn’t just about pushing past procrastination; it’s about honouring the one life you have. The time will never be perfect, but it doesn’t have to be. Start now, and let every moment you embrace make way for a life well-lived.