How to Engineer 'Overnight' Success
A Portfolio Careerist's Guide to Creating Luck (Not Waiting for It)
We all know that person—the one who gracefully exits their corporate career and seems to hit the ground running with their solo business venture. While the rest of us are carefully building our websites and agonising over our service offerings, they're already landing premium clients, speaking at industry events, and building an enviable personal brand. Their LinkedIn posts attract hundreds of comments, and their calendars fill with high-ticket projects. Their transition from corporate executive to successful business owner appears seamless, almost magical.
It's hard not to feel a complex mix of admiration and, let's be honest, a touch of envy. After all, we all draw from similar corporate experiences. We all left with solid expertise, strong track records, and well-maintained networks. So what makes their journey seem so charming while others of us navigate a bumpier path?
Is it really just luck? This question led me down an unexpected path of discovery, beginning with a story about my father's name.
In my family, my father's name carries a profound story. In Italian, his name is Fortunato, the literal translation is "Fortune" or "Lucky" – a name that would take on deep complexity throughout his life. At age 39, he survived a near-fatal workplace accident that left him an amputee, an event that seemed to confirm what he had always believed: that his name was just a cruel irony. Despite carrying the meaning of good fortune in his very name, he became convinced that luck was something that happened to other people, never to him.
Though the accident tested his spirit, my father showed remarkable resilience in rebuilding his life. Yet the experience shaped how he viewed possibility itself. Over the years, I watched as his belief that he was inherently unlucky led him to draw smaller and smaller circles around his dreams. He built a good life, but always within careful boundaries as if to protect himself from hoping for too much. When new opportunities arose that might have led to bigger adventures or grander dreams, he'd pull back, convinced they were meant for "luckier" people.
This personal history became the lens through which I began to understand success in my business journey. As independent business owners who've transitioned from corporate careers, we know that luck isn't just something that happens to us—it's something we actively create or block through our beliefs and actions.
Whenever I find myself hitting that wall of belief that good things can't happen to me, I become my own detective. I go searching for research and data to challenge what I'm telling myself – to discover whether these beliefs are truly fixed or if they can be transformed. This investigative spirit led me to research showing that there are four distinct types of luck, and three of them are within our power to influence. This insight was powerfully demonstrated in groundbreaking research by Dr. Richard Wiseman1. In his study of 400 participants – half who considered themselves exceptionally lucky, and half who described themselves as perpetually unlucky – Wiseman revealed remarkable patterns in how people create their own luck.
Consider one of his most interesting experiments: Wiseman gave both "lucky" and "unlucky" participants a newspaper and asked them to count the photographs inside. The "unlucky" people took about two minutes to complete the task. The "lucky" people? Mere seconds. The difference? On page two, in bold text, was a message saying "Stop counting, there are 43 photographs in this newspaper." The "lucky" people spotted it immediately. The "unlucky" people missed it entirely [1].
As professionals, we're trained to be thorough, to check every detail - qualities that have served us well in corporate careers. But sometimes this perfectionism can blind us to quick wins and unexpected opportunities. The very traits that made us successful in traditional roles might need recalibrating for solo business success.
This uncovers something curious about luck: it's not just about what opportunities exist – it's about our ability to spot them and our willingness to embrace them. Think of it as your "luck surface area" – the space in your life where good fortune can land. Every action you take, every connection you make, every skill you develop either expands or contracts this surface area.
Let's break down the four types of luck and explore how you can expand your luck surface area in each dimension.
Type 1: Blind Luck - Embracing the Unexpected
Yes, sometimes pure chance plays a role – that random LinkedIn message that leads to a dream project, or bumping into an old colleague who becomes a key client. While we can't control blind luck, we can learn to be open to it. Instead of dismissing unexpected opportunities because they don't fit our rigid plans, we can cultivate the flexibility to recognise and embrace them when they appear.
Type 2: Luck from Hard Work - Creating Your Own Opportunities
In the corporate world, opportunities often come through established channels - performance reviews, internal job postings, and structured networking events. But when you step out on your own, you need to create your own opportunity ecosystem. As engineer and inventor Charles Kettering once observed, "Keep on going and the chances are you will stumble on something, perhaps when you are least expecting it. I have never heard of anyone stumbling on something sitting down."2 This doesn't mean frantically chasing every potential lead. Sometimes, it means sharing your journey and letting opportunities find you.
My own journey illustrates this perfectly. Before leaving corporate life, I began writing a free newsletter about consciously uncoupling from my traditional corporate career. In the beginning, I wasn't necessarily trying to build a business—I was simply documenting my journey and sharing insights. Then like magic, Executive women began reaching out, resonating with my experience and seeking guidance for their career revolutions. This organic response to my writing revealed a clear need in the market, leading to the birth of the Portfolio Career Club—which has become one of my most profitable income streams.
As independent business owners, we can create this type of luck by:
Sharing your story openly - your challenges, insights, and wins can become powerful content that attracts like-minded professionals
Creating valuable content consistently, even before you know exactly how it will pay off (my newsletter started with zero strategic intent, but became my biggest business asset)
Building in public - document your journey from corporate to independent success, letting others learn from your experiences
Saying yes to unexpected conversations - those "coffee chats" with curious corporate connections might evolve into your next business opportunity
Turning your corporate expertise into teachable insights - what seems obvious to you might be exactly what others are seeking (all that stakeholder management seemed useless but is so valuable in small business!)
Type 3: Luck from Awareness - Developing Your Expert Eye
Your corporate experience is a fine-tuned radar for opportunity. As I wrote about my emerging portfolio career, patterns emerged in readers' responses. Corporate women weren't just seeking practical advice—they were looking for permission to reimagine their careers.
Years in corporate culture had taught me to recognise the unspoken: that hesitation, that need for validation from someone who'd walked the path. This insight led directly to the structure of what I offered in the Portfolio Career Club. I could spot what readers needed before they could articulate it—a skill honed through years of reading between the lines in corporate settings.
To cultivate this type of luck:
Invest in continuous learning in your core areas of expertise
Stay updated with industry trends and emerging opportunities
Develop a strong understanding of your target market's needs
Trust your instincts when they're backed by experience and knowledge
Lean into your natural gifts - what is obvious to you isn’t necessarily obvious to others (this is where Human Design can be used as an excellent tool)
Type 4: Luck from Uniqueness - Becoming Magnificently You
As a former corporate professional, you might have initially worried that leaving your corporate identity behind would diminish your value proposition. But here's what you've likely discovered: your corporate experience combined with your entrepreneurial agility is precisely what makes you valuable to clients. You speak both languages. You understand both worlds. This isn't just unique - it's a superpower.
I discovered this firsthand when I found my unique edge in bringing unconventional tools like Human Design into conventional corporate spaces. By acting as a translator between these two worlds—understanding both the pragmatic needs of corporate environments and the transformative potential of alternative frameworks—I created a distinctive offering that neither pure corporate consultants nor traditional Human Design practitioners were offering.
Consider these ways to build your unique advantage:
Identify and utilise the unusual combinations in your background
Develop signature approaches to organising and solving problems in your field
Build a personal brand that authentically reflects your unique perspective
Create content and offerings that only you could create
Expanding Your Luck Surface Area
Your transition from corporate to solo business owner isn't just a career change—it's a masterclass in creating luck. Every corporate relationship you've transformed into a client connection, every big-company process you've adapted for solo efficiency, and every institutional insight you've translated into client value, represents a deliberate expansion of your luck surface area. But here's where many stop, satisfied with these initial transformations. The real magic happens when you systematically amplify these advantages.
Think of your luck surface area as a garden. It's not enough to simply plant the seeds of opportunity—you need to actively cultivate the conditions that allow luck to flourish. This means simultaneously removing the weeds that choke potential growth (those self-limiting beliefs, toxic relationships, and rigid mindsets) while nurturing the elements that help opportunities bloom.
The process of expanding your luck surface area requires both elimination and addition. First, you must methodically remove what I call "luck blockers"—those insidious beliefs and behaviours that block opportunity. This means challenging the voice that whispers "that's not for people like me," distancing yourself from those who consistently dampen your ambitions, and breaking free from the rigid routines that keep you in familiar but limited territories.
Simultaneously, you need to actively cultivate "luck accelerators." This means strategically positioning yourself at the intersection of corporate decision-makers and independent innovators. It means sharing your unique perspectives on bridging these worlds, maintaining relationships across both spheres and engaging authentically with your network. Most importantly, it means surrounding yourself with people who push you to think bigger—who see possibilities where others see limitations.
The Luck Razor
The transition from passive luck-waiting to active luck-creation requires a systematic approach. Think of it as building your own luck machine, one that continuously generates opportunities. This machine has four essential gears that must turn in sequence:
First, audit your current luck surface area—
Step 1: Audit Your Luck Surface Area
Map your network, catalog your unique insights, and analyse how opportunities currently find you.
Step 2: Remove Friction Points
Clear away limiting beliefs, low-return activities, and relationships that block potential opportunities.
Step 3: Activate Luck Accelerators
Share insights regularly, rekindle valuable connections, and position yourself where corporate and independent worlds intersect.
Step 4: Build Sustainable Systems
Create routines for opportunity scanning, success story collection, and relationship nurturing that keep your luck machine running automatically.
This isn't just theory—it's a practical framework for expanding your possibility space. When you approach each business decision, apply what others refer to as the "Luck Razor": Which path has the larger luck surface area? Which choice will expose you to more potential opportunities, connections, and discoveries?
That's your north star.
Remember my father's story – his name meant "Lucky," yet his belief that luck was for others became a self-fulfilling prophecy. The truth is, the most successful ex-corporate solo business owners aren't just waiting for luck to strike. They're methodically engineering it, using their unique blend of corporate wisdom and entrepreneurial spirit.
Your corporate experience taught you how to execute with precision. Your leap into solo business proved your courage. Now it's time to combine both to create your own luck machine.
Success isn't about waiting for luck to find you—it's about deliberately creating it. Your future is waiting to be engineered.
The time to begin is now.
Wiseman, R. (2003). The Luck Factor: The Scientific Study of the Lucky Mind. Miramax Books.
Austin, J.H. (1978). Chase, Chance, and Creativity: The Lucky Art of Novelty. MIT Press.
And if you are looking for support to kickstart your portfolio career in 2025, here are some ways to work together:
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Love this article! I have just one tattoo and it is the work “lucky” on my wrist to remind me that “being lucky” is a mindset 💫🫶