Gamble Everything, but Only if You’re Going to Win
- 6 days ago
- 8 min read
Written by Abi Hill, Entrepreneur, Mentor & Coach
Abi Hill is a UK entrepreneur, mentor & coach, and the founder of Just Starting Out. Widely recognised for championing underserved communities and cost-of-living resilience, she’s on a mission to cut first-year failure rates. “If you want to make waves, pack a swimsuit!”
From the moment we are old enough to understand the world around us, we are encouraged to dream big. We tell children they can become anything they want to be. We applaud imagination, celebrate ambition, and remind them that the sky is the limit. Yes, you be that astronaut who reaches Mars, kiddo!
Then, somewhere along the way, the narrative quietly changes. “Isn’t it better to play it safe?” “Why don’t you get a secure job?” “I wouldn’t take unnecessary risks if it were me.” My all-time favorite, “What if it doesn’t work?”
It seems we have created a society that encourages courage in theory but questions it in practice. We celebrate entrepreneurs, inventors, and athletes once they have reached the finish line, yet often doubt them while they are still standing at the starting blocks.
This contradiction has fascinated me for years, not simply because I have witnessed it firsthand, but because it raises a much bigger question. Why are we so frightened of taking risks in the first place?
The answer lies somewhere between evolutionary biology, modern psychology, and the uncomfortable way we judge success.
We tell people to dream big until they actually do
This is something that almost everybody understands, but very few people articulate. Society celebrates risks in hindsight, yet criticises them in real time. Wait! What? The hypocrisy bowls me over! Why is it that we treat failure as evidence that the risk was foolish, yet treat success as evidence that the risk was visionary?
Consider two men standing on a rock. One jumps and lands safely, while the other is frightened and decides not to. The man who jumped is hailed as a brave hero, right? Right! Until he is gobbled up by a crocodile and is then forever deemed the stupid man who jumped. However much luck is involved, we do tend to encourage people to take the leap in business as if they know exactly where they will land.
Success rewrites history
History has an amusing habit of editing itself. The entrepreneur who was once considered unrealistic becomes visionary. The inventor who was dismissed becomes a genius. The athlete who sacrificed everything suddenly becomes inspirational. But nothing about their original decision has changed. Only the ending has.
This is the contradiction that we rarely notice. Perhaps we do not admire courage quite as much as we think we do. Perhaps we actually admire successful courage. Because if the exact same decision ended differently, we would likely call it irresponsible.
5,217 prototypes
History is littered with people whose greatest achievements were almost never realised because, at one point, they looked like failures.
James Dyson famously created 5,126 prototypes before developing the vacuum cleaner that would revolutionise an entire industry. Had he stopped at prototype number 5,125, history would almost certainly have remembered him as a man with an expensive hobby rather than a visionary inventor.
Before Spanx became a billion-dollar global brand, Sara Blakely spent years selling fax machines door to door while repeatedly hearing “no.” She invested her life savings in an idea that many manufacturers initially dismissed, yet her persistence ultimately transformed an overlooked gap in the market into one of the world’s most recognisable brands.
Colonel Harland Sanders, the founder of KFC, was in his sixties when he began travelling across America, trying to persuade restaurant owners to use his fried chicken recipe. Legend has it that he was rejected more than a thousand times before somebody finally said yes. Most people would have interpreted those rejections as evidence that they should stop. Instead, he viewed them as part of the journey.
Even Walt Disney, now synonymous with imagination and creativity, was reportedly once told that he “lacked imagination” and had no good ideas. Today, his name has become one of the most influential brands in entertainment history.
Just imagine meeting any one of these people halfway through their journey. Would you have described them as courageous or verging on crazy?
Your brain wasn’t designed to build businesses
Before criticising yourself for feeling anxious, it is worth remembering one important fact. Your brain did not evolve to help you build a business. It evolved to help keep you alive.
For hundreds of thousands of years, uncertainty represented genuine danger. Exploring unfamiliar territory could expose our ancestors to predators, hostile environments, or food shortages. Playing it safe dramatically increased the chances of survival.
Although our lives have changed beyond recognition, many of the neurological systems involved in responding to danger and uncertainty remain active.
Your survival system can still sound the alarm
Today, uncertainty rarely involves wild animals, thankfully.
Instead, uncertainty looks like handing in your resignation, launching a website, making your first sales call, investing your savings, or posting that announcement. Yet your brain can respond in surprisingly similar ways.
The amygdala, often described as part of the brain’s alarm system, helps process potential threats. When uncertainty is perceived as threatening, it can contribute to a stress response involving hormones such as adrenaline and cortisol.
Your heart beats faster. Your breathing changes. Your palms become sweaty, and your thoughts accelerate. To your nervous system, uncertainty can still resemble danger.
The chemistry of courage
One of the most fascinating aspects of human psychology is that fear and excitement can sometimes feel almost identical. Think about the last time you experienced either emotion. Your heart probably raced, your stomach probably churned, and you may even have felt slightly sick.
Fear and excitement can involve similar forms of physiological arousal. The difference often lies in the story we tell ourselves about the experience.
“I can’t do this” versus “This matters.” That subtle shift in interpretation can change everything.
In business, it’s who you don’t know
For a long time, I believed one of the oldest clichés in business, “It’s all about who you know.”
Then I started mapping out Just Starting Out, try saying that fast five times, and found that some of the people closest to me at the time doubted the vision. They were not convinced that the platform would succeed and, more than that, slated it in front of other people, making a mockery of it, yet interestingly, never saying it to my face.
Initially, that was difficult to hear. After all, we naturally assume that the people who know us best will become our biggest supporters, but life does not always work that way.
My old neighbour built my future
Whether you have heard the story of how my cofounder Richard and I began Just Starting Out or not, it is a wholesome tale, so I will briefly tell it again.
At a time when I had an epic idea, a limited budget, and a severe lack of confidence because of family reactions of “What is she doing?”, I bumped into my old neighbour. After the pleasantries, I asked him how his work was going, knowing it was something to do with computers, and I famously, and thankfully, spat out what would become five words that shaped my life: “What do you do again?”
Richard replied, “I’m a backend software developer,” and, as you can imagine, my ears pricked up. I spent the best part of half an hour convincing him to listen to the idea I had, which he did, and after a lot of thought, we decided to go into partnership.
One of my earliest memories of our journey was thinking, “I hope I’ve made the right decision, as I barely know Richard and this is a biggie.” Within 15 minutes of having that niggling thought, Richard sent me an invitation to Jira, a system we have used since the very beginning to log the thousands of tasks that need to be completed. It was at that point that I had an overwhelming feeling of confidence in both Richard and Just Starting Out.
Had I not bumped into Richard, where would Just Starting Out be today? Would it even exist?
Complete strangers may become some of your closest advocates
Almost every significant milestone in Just Starting Out has come through people I had never met before, and this is exactly what can happen with your business too. You will have LinkedIn connections who believe in the vision, form partnerships with people who want to be involved, and meet customers and other professionals who offer advice, introductions, and encouragement.
Your perspective will completely shift as you realise that success is not about who you know. It is about who you have not met yet.
The hidden cost of playing it safe
I recently came across a quote that has stuck in my brain. It appeared alongside an image of a man beside a ledge and said, “The problem wasn’t that you aimed too high and missed. It was that you aimed too low and hit it.” This got me thinking. Are we measuring success incorrectly?
How many careers have been built around goals that felt achievable rather than meaningful? How many businesses never started because certainty felt more comfortable than possibility? Perhaps the greatest tragedy is actually never knowing what we are capable of.
Anxiety isn’t weakness
At Just Starting Out, we have surveyed more than 1,800 aspiring and new business owners across the UK, and the findings were both revealing and reassuring. In short, the findings spoke volumes, as around one in four respondents reported feeling anxious about starting their business. Many also admitted that there had been moments when they questioned whether they should continue.
Those statistics do not suggest weakness. They remind us that every significant achievement begins before confidence arrives. So perhaps, after all of this, we have misunderstood courage.
The greatest gamble of all
Life rarely provides guarantees before asking us to make important decisions, and I appreciate that there are many ways to look at this. I would certainly agree, however, that one of the greatest gambles could be constructing an entire life around decisions that attracted the least criticism rather than the greatest fulfilment. The decisions were logical and safe, but were they really yours?
If we were guaranteed to win, we would all go for it. Likewise, if we were guaranteed to lose, nobody would bother. Entrepreneurs are the perfect example of people who do not know but try anyway.
If you are ready to roll the dice but could use a little advice and encouragement along the way, we would love to hear from you. At Just Starting Out, we are passionate about helping new business owners take those first steps with confidence. Whether you have a question about starting your business, need pointing in the right direction, or simply want a little reassurance, there really is no such thing as a silly question. Drop us an email, and we will do our very best to help.
Read more from Abi Hill
Abi Hill, Entrepreneur, Mentor & Coach
Drawing from a Senior Management background and 20+ years working alongside minority and underserved communities, Abi is best known for advocating within the start-up community, her mission being to reduce the 20% of small businesses that don’t make it through year one by giving them the tools, training, and trust they deserve. Because why should starting out mean forking out?
