Be Prepared to Lose Everything.
I remember the day I lost everything.
It was a hot summer afternoon, one of the dog days, and I was sitting in my cramped studio apartment, staring at the eviction notice in my hands. My startup, the one I had poured my heart and soul into for the past two years, had finally collapsed under the weight of its own ambition.
I had no money, no prospects, and no idea what to do next. Just hours before, while drunk out of my mind and suicidal (that’s a story for another time) I had self sabotaged by burning down and deleting my blog and Medium with over 120,000 subscribers. In short — I was fucked.
As I sat there, surrounded by the remnants of my shattered dreams, I felt a sense of overwhelming despair wash over me. I had risked everything for this venture — my savings, my relationships, my health — and now I had nothing to show for it but a mountain of debt and a crushing sense of failure.
But as I wallowed in my misery, a small voice inside me began to whisper a different narrative. It reminded me of the passion and purpose that had driven me to pursue this path in the first place. It spoke of the incredible journey I had undertaken, the lessons I had learned, and the growth I had experienced along the way.
And as I listened to that voice, I began to realise that losing everything was not the end of my story. It was simply a chapter in the larger narrative of my life as a creator and entrepreneur.
When we choose to pursue our passions and bring our ideas to life, we are signing up for a journey that is fraught with risk and uncertainty. We’re stepping out of our comfort zones and into the unknown, armed with nothing but our conviction and our determination to succeed.
And while the possibility of losing everything is a terrifying prospect, it is also an essential part of the creative process. It is, frankly, the price we pay for the opportunity to make a difference, to leave our mark on the world, and to live a life that is truly our own.
As I picked myself up off the floor that day, I made a promise to myself. I would not let this setback (read: fuckup) define me. I would not let the fear of failure hold me back from pursuing my dreams. I would embrace the risk, embrace the journey, and be ready to lose everything all over again if that’s what it took to bring my vision to life.
And that’s the message I want to share with you today. As creators and entrepreneurs, we must be willing to face the possibility of losing everything head-on. We must be ready to put it all on the line, to bet on ourselves and our ideas, even in the face of overwhelming odds.
That’s what it takes, to be creators. It’s what it means.
We’re driven by an insatiable desire to bring our ideas to life, to make a difference in the world, and to make our own paths to success. As creators, as founders — that’s who we are.
We pour our hearts, souls, and resources into our ideas, fuelled by a shaking, frequently fucking terrified but always determined belief in our abilities and the potential of our ideas.
In all the exhilaration and the hope, there’s a sobering reality that we face head-on every single day: the possibility of losing everything.
It’s a thought that keeps us up at night, gnawing at the edges of our consciousness. We try to push it aside, to focus on the positives, on the potential for greatness. But the truth is, we can’t ignore the inherent risks that come with the territory of entrepreneurship. Every decision we make, every strategy we implement, and every investment carries with it the potential for failure. Abject, total, fuck-up-failure.
The statistics are staggering. The vast majority of startups and creative endeavours fail. The odds are stacked against us, and the path to success is littered with obstacles and setbacks. It’s a reality that anyone would find difficult to swallow — not least because we’ve poured our hearts and souls into our work.
Embracing this reality is not a sign of pessimism or weakness. It’s a badge of resilience. It’s a marker for our determination, and our willingness to take on the challenges that come with the pursuit of our dreams.
When we accept the possibility of losing everything, we free ourselves from the paralysing fear of failure. We recognise that setbacks and obstacles are not the end of the road. Even our greatest falls from grace are opportunities to get better at what we do, to grow, learn and evolve our craft.
Think about it. How many stories have we heard of successful entrepreneurs and creators who have faced crushing defeats, only to rise from the ashes stronger, wiser, and more determined than ever?
But their success didn’t come without sacrifice. They had to be willing to put everything on the line, to bet on themselves and their ideas, even in the face of overwhelming uncertainty.
And that’s the key.
As creators and entrepreneurs, we will never reach our potential without being willing to embrace the uncertainty, to take the risks, and to accept the possibility of failure. Because it’s in those moments of adversity that we discover our true strength, our resilience, and our ability to adapt and overcome.
Embracing the risk of losing everything means learning that our self-worth and identity are not solely tied to the success or failure of our ventures.
Too often, we become emotionally attached to our ideas and our work. We pour our hearts and souls into our creations, and they become an extension of ourselves. But when we tie our self-worth to the outcomes, we set ourselves up for disappointment and heartbreak.
Instead, creators who last learn to cultivate a sense of detachment. They keep their passion and their commitment, but they get that their value as individuals is not dependent on the success or failure of their work. Their value is inherent, innate. The work is just an extension.
Creators who last focus on the process, on the joy of creation, and on the impact they make along the way. Success is not measured solely by financial metrics or external validation, it’s measured by the lives they touch, the problems they solve, and the legacy they leave behind.
And when they do face setbacks and failures, they remember that this shit is not the end of the story. It’s a short chapter in the longer narrative of their lives and their careers.
Every failure, every setback, every obstacle is an opportunity. That’s the takeaway. Fuck ups are a wonderful thing. They teach us invaluable lessons that no amount of success can impart. They force us to confront our weaknesses, challenge our assumptions, and adapt to changing circumstances.
And it’s through these challenges that we develop the resilience, creativity, and adaptability necessary to navigate the unpredictable landscape of entrepreneurship.
But perhaps most importantly, being prepared to lose everything allows us to live life on our own terms. When we are no longer shackled by the fear of failure, we become more daring, more innovative, and more willing to take the risks necessary to bring our visions to life.
We understand that the journey is the reward, and that every step along the way is an opportunity for growth, learning, and self-discovery.
This isn’t to say that we should recklessly pursue our dreams without consideration for the consequences. That’s not courage, it’s abject stupidity. We owe it to ourselves to be strategic, calculated, and mindful of the risks we take.
But at the same time, we can’t let the fear of failure paralyze us into inaction. We must be willing to step out of our comfort zones, to take bold action, and to embrace the uncertainty that comes with the pursuit of our passions.
And when we do face setbacks and failures, remember that they are not a reflection of our worth as individuals. They are simply a part of the journey, a necessary step on the path to success.
That’s the mindset we must adopt as creators and entrepreneurs. The mindset that views failure not as a dead end. Instead, a learning opportunity, a chance to iterate and improve.
Take risks, to experiment, and to try new things, even if they don’t always work out as planned. Because it’s through this process of trial and error that we discover what does work, and what has the potential to change the world.
Being a creator or entrepreneur isn’t about achieving fame, fortune, or external validation. It’s about making a difference, about solving problems, and about leaving the world a better place than we found it.
And that’s a journey worth taking, even if it means risking everything along the way.
Embrace the risk. Embrace the possibility of losing everything. Because it’s in those moments of uncertainty and adversity that we discover our true potential.
Be willing to bet on yourself, on your ideas, and on your dreams. Be willing to put everything on the line, knowing that the journey itself is the ultimate reward.
I’m 5 years sober now. I’m working harder than I ever thought I would or could. I’m doing more. And I’m risking more. And I can tell you — it gets better. It never gets less terrifying. But it’s always worth it.
