What's Your Dream?

1. Embrace Your Dream: It's a Powerful Force, Not a Folly

If you have any doubts at all, any sense that there might be something else to life, or that you might want more, then read on.

Your dream awaits. This book is for those who feel a yearning for more, a sense that their true potential remains untapped. Simon Squibb, having experienced homelessness and later immense business success, realized that true fulfillment comes not from money alone, but from pursuing a deeply personal dream. He even bought a literal staircase in London, turning it into a "dream factory" where people can pitch their aspirations, symbolizing the first step towards something bigger.

Unlocking potential. Simon's mission with HelpBnk and his #GiveWithoutTake movement is to help 10 million people start businesses and pursue their dreams for free. He found that many people, like Delon the McDonald's worker who secretly dreamed of being a Twitch streamer, already have a dream but are afraid to voice it. Giving voice to a dream can instantly transform a person, igniting confidence and inspiring others.

A powerful anchor. A dream is more than a goal; it's a power source that provides unwavering motivation and direction. It allows you to envision a better future and start working towards it immediately, regardless of your current circumstances. Like Chris Gardner's journey from homelessness to stockbroker, a dream can sustain you through the lowest points, providing an accessible destination and an invitation to begin.

2. Shatter the Myths: Hard Work, Failure, Comfort, and Possessions Don't Define Success

These myths will kill your dream unless you learn to identify, reject and overcome them.

Debunking false beliefs. Society often instills harmful myths that prevent us from pursuing our true aspirations. Simon identifies four key myths that must be dismantled to create space for your dream:

• Myth #1: The harder I work, the luckier I get. Hard work is necessary, but not the sole reason for success. Working smart on something you love is more effective than endless toil.
• Myth #2: Failure means disaster. Failure is an inevitable part of growth and a powerful teacher. Jamie Oliver's restaurant empire collapse, or Simon's $1.5 million comic book failure (DevaShard), show that setbacks provide invaluable lessons and can lead to greater success.
• Myth #3: It’s OK to avoid hard things. Modern convenience can breed laziness and a lack of ambition. Tackling difficult challenges is essential for personal growth, resilience, and achieving meaningful dreams.
• Myth #4: Possessions make you happy. Material wealth, like Simon's Porsche or homeownership, often brings anxiety and obligation rather than lasting happiness. Possessions can own you, diverting focus from your real dream.

Reframe your mindset. These myths are pervasive, often taught from childhood, and can create a self-denying view of the world. By recognizing and rejecting them, you free yourself from self-imposed limitations. True success isn't about accumulating things or avoiding discomfort, but about pursuing a purposeful life.

Embrace growth. Instead of fearing failure, embrace it as a learning opportunity. Instead of avoiding hard things, seek them out for personal development. Shift your focus from external validation to internal fulfillment, understanding that your greatest achievements will come from working on something you genuinely care about, not just working hard for its own sake.

3. Uncover Your Purpose: It's the Fuel That Turns Wants into Needs

The purpose of life is a life of purpose.

Your essential reason. Purpose is the indispensable counterpart to your dream, providing the motive and energy to keep you moving forward. It's the "why" behind your "what," deeply rooted in your life experiences, passions, and even pain. For Bradley, a former helicopter engineer, his purpose became fixing people's pain as a massage therapist, finding profound gratitude and fulfillment.

Beyond burnout. Without purpose, work can become a draining treadmill, leading to burnout. When your work aligns with a strong purpose, it recharges your "battery," making effort feel worthwhile and even enjoyable. Simon's agency, Fluid, struggled with staff retention until they rediscovered their purpose: celebrating creativity and ensuring designers were valued and fairly compensated.

Problem-solver and motivator. Purpose provides focus, negating distractions, self-doubt, and bad habits. It transforms "wants" into "needs," creating an unshakeable mission that drives relentless action. Sophie's "I Am Denim" brand, born from her post-surgery struggles, exemplifies how personal pain can become a powerful purpose, compelling her to create "tummy-friendly jeans" to help others.

4. Confront Your Blockers: The Seven Steps to Unlocking Your Dream

You need to clear these barriers out of the way to give yourself the best chance at success.

Overcoming self-sabotage. Many people, like Sam with her catering dream "Chez Sam," are stuck with a brilliant idea but lack the confidence or impetus to start. Simon identifies seven common "steps" or blockers that prevent people from pursuing their dreams:

• Step 1: I don’t have time. This is survival mode. Acknowledge your dream, and your mindset shifts, making time for small, consistent steps.
• Step 2: I’m trapped. Unresolved problems, like Davide's hidden debts, will derail your dream. Confront issues with honesty and seek help.
• Step 3: I don’t need it. This often masks financial obligations that control you. Renounce possessions as an end goal to gain financial freedom.
• Step 4: I don’t know what. Your dream is often closer than you think, related to your likes or a lingering dissatisfaction. Explore your passions and dislikes.
• Step 5: I don’t know how. Fear and overthinking create artificial barriers. Break down the dream into achievable actions and start doing them.
• Step 6: I’m worried what they’ll think. Don't let others' fears or doubts, even from loved ones, derail your conviction. Trust your belief in your dream.
• Step 7: I’ve tried before. Past failures are lessons, not proof of incapability. Learn from them, forgive yourself, and use them as fuel for future attempts.

Action over inaction. These blockers are often self-made prisons. By identifying which step you're on, you can actively work to dismantle these limiting beliefs. Inaction is the enemy; taking even tiny steps forward builds momentum and transforms doubt into possibility.

The power of belief. Simon's encounter with Sam, who launched her catering business within days of being challenged, illustrates how quickly these barriers can fall when belief and opportunity align. Your dream doesn't stay fresh forever; it needs to be pursued before it withers.

5. Discover Your Dream: Answer Three Questions to Find Your True North

The path to the future – towards the dream – begins by looking back.

Introspection is key. To articulate your dream, you must first understand yourself. Simon proposes three fundamental questions that delve into your life history and motivations:

• Question #1: What are my likes and dislikes? Identify what genuinely energizes you and what drains you. Your dream should stem from your passions and strengths, not just market gaps. Simon's podcast, born from his love of talking to people, eventually led to HelpBnk.
• Question #2: What is my pain? Harnessing personal pain—whether from abandonment, dyslexia, or the struggle of starting a business alone—can be a powerful source of purpose. Simon's childhood experiences fueled his desire to help others avoid similar struggles.
• Question #3: How can I help others? Your dream, while personal, must ultimately serve others. Whether it's Delon's streaming to make people smile, or Sophie's "tummy-friendly jeans," connecting your passion to solving a problem for others creates a meaningful and sustainable venture.

The bonus question. To confirm your dream's authenticity, ask yourself: "How can I be sure?" Let the idea sit for a few days. If it relentlessly occupies your thoughts, driving you to research and plan, then it's a genuine dream. This "acid test" reveals if your subconscious is truly invested, making it "easier done than said."

Durable dreams. These three questions, answered honestly, provide the raw material for a durable dream. They connect your inner self to the external world, ensuring your dream is rooted in genuine passion, propelled by deep purpose, and designed to make a positive impact.

6. Liberate Yourself: Free Your Finances, Mind, and Idea to Make Space for Your Dream

The freedom you need comes in several forms: you need to gain financial freedom, to free your mind from unhelpful preconceptions and self-sabotaging thoughts, and finally to free your idea so that people will know about it and can start to help you with it.

Breaking free. Once your dream is defined, the next crucial step is to create the necessary space for it to flourish. This involves a three-pronged approach to liberation:

• 1. Free your finances: Stop "selling time" (trading hours for salary) and start "buying time" (building systems and teams that generate profit without constant personal effort). Cut unnecessary costs and debt, as possessions can become financial traps.
• 2. Free your mind: Challenge the belief that your dream is "too hard" or "impossible." Cultivate a mindset that blends optimism with realism, patience with ambition, and a bias towards action. Embrace learning from mistakes and replace "I will" with "I am" to bring your future into the present.
• 3. Free your idea: Get your dream out of your head and into the world. Share it with friends, family, and your network. Asking for help, even when your idea is "new and vulnerable," is crucial for gaining feedback, support, and connections.

Caitlin's example. Caitlin, who dreamed of a photography business, initially felt trapped by financial concerns. Simon's advice to seek sponsorship, and the subsequent viral video, led to lastminute.com funding her travel photography. This demonstrated that perceived barriers are often less formidable than they appear, and that sharing your dream can unlock unexpected opportunities.

Actionable steps. This liberation isn't passive; it requires deliberate action. Whether it's saving money, challenging negative self-talk, or openly discussing your aspirations, each step clears the path. Admitting what you don't know and actively seeking advice, rather than trying to perfect everything in secret, accelerates your journey towards making your dream a reality.

7. Start Lean, Grow Smart: Build Your Business Poor to Get Rich

It’s by starting your business poor that you will give yourself the best chance of striking it rich in the end.

Bootstrapping for success. Simon advocates for starting your business with a "poor" mentality, meaning minimal upfront investment and a focus on self-sufficiency. His experience with DevaShard, a comic book venture with a wealthy partner, taught him that excessive capital can lead to complacency and a lack of discipline. Starting lean forces you to justify every expense and ensures your business model is inherently sustainable.

Defining your model. Before spending, clearly define your business model:

• What are you selling? It's not just a product; it's also your personal brand and story.
• Who is the customer? Be specific. Niche down initially, like Gymshark starting with male weightlifters, before diversifying.
• Where will sales happen? Direct to consumer, through retailers, or other channels.
• Revenue streams: Consider sponsorship, advertising, licensing, or subscription models.

Free (almost) beginnings. Leverage free digital tools and platforms to get started. Register social media handles, use free website trials, and connect with potential customers via email. The goal is to have a functioning business with minimal outlay. Simon's first podcast started with a £99 microphone.

The magic of three. Your first customer validates your idea, the second proves it wasn't a fluke, but the third customer truly makes your business real. Three customers provide enough feedback to understand market needs, adjust your offering, and build confidence for growth.

8. Cultivate Your Crew: Find Brilliant People and Build a Thriving Community

The people you do business with matter more than almost anything else.

People are paramount. The success of your business hinges on your ability to attract, retain, and manage the right people. This includes business partners, employees, and a supportive community. Bad hires or misaligned partners can be as detrimental as good ones are beneficial.

Picking partners. While some thrive solo, a good partner balances your skills and provides a crucial counterbalance to your biases. When choosing, look for:

• Complementary skills: One partner might be technical, the other focused on marketing.
• Shared moral code: Essential for navigating difficult decisions, as Simon and Helen demonstrated during the 2008 financial crisis by prioritizing staff over immediate profit.

Hiring for purpose. When hiring employees, prioritize alignment with your business's purpose. Simon uses a "commitment test" (e.g., editing a video for free) and a "moral code" test (the Bernie Madoff question) to identify truly dedicated individuals. He also emphasizes giving employees equity, as ownership fosters commitment and prevents top talent from leaving.

The "7 and 8" rule. Be decisive with underperforming employees. The "rule of seven and eight" states that if you tolerate mediocre performers (7s and 8s), your top talent (9s and 10s) will eventually leave. Firing, though difficult, is sometimes a favor to both the individual and the business.

Building community. Beyond customers, cultivate a passionate community of fans who share interest in your brand and purpose. This creates powerful word-of-mouth marketing and a supportive ecosystem. Simon actively invests in the HelpBnk community, fostering a #GiveWithoutTake ethos, understanding that a broad, engaged community is a superpower for any business.

9. Master Risk: Develop Your Muscle to Take Smart, Calculated Chances

The more risks I take, the luckier I get.

Risk is essential. Success in business is directly correlated with the ability to take calculated risks. Simon's "flyposting" stunt for HelpBnk, though technically illegal, was a calculated risk to gain attention for a free service. Risk-taking is a skill, a "muscle" that strengthens with practice.

Visualize outcomes. Before taking a big risk, imagine both the best-case and worst-case scenarios. Natasha, the Vegan Patty Lady, and her husband Adonye, risked their house savings on her business. Adonye's perspective, "It's only money. If it takes five grand for my wife to follow her dream, then that's life," showed a clear understanding of the worst-case and a commitment to the dream.

Smart risks. Don't take risks indiscriminately. Align them with your purpose and dream. Simon's Bizzies sweet brand, launched in a competitive market, was de-risked by partnering with an existing confectionery start-up. This allowed him to pursue his dream without building the entire business from scratch.

Stand your ground. Be prepared for others to try and dissuade you from risks, whether from well-meaning friends or aggressive competitors. Simon's experience with the HK Sevens URL, where he stood his ground against a legal threat, showed the importance of conviction when you believe you're in the right. Avoid "bad risks" like shortcuts or unethical schemes, which can lead to long-term problems.

10. Persist and Pivot: Keep Going, But Know When to Change Direction

Persistence is about guts but it’s also about brains – working out the route that gives you the best chance of survival and long-term success.

The power of persistence. Success often comes down to sheer determination. Michelangelo's three-year solitary effort to sculpt David from a "defective" marble slab exemplifies how persistence can achieve the seemingly impossible. Simon's early days at Fluid, contacting 50 dream clients repeatedly until all were won, highlights that persistence "hacks luck" by creating more opportunities.

Through adversity. Every business will face significant challenges. Apple and Nvidia both nearly went bankrupt before becoming trillion-dollar companies, demonstrating that persistence through adversity builds resilience. Jensen Huang of Nvidia even celebrates "pain and suffering" as essential for refining a company's character.

Adapt and evolve. Persistence is not stubbornness; it's the ability to "pivot" when necessary. Famous brands like Starbucks (originally sold coffee beans), Netflix (DVDs by mail), and YouTube (dating service) all pivoted their business models to find success. Fluid, during the SARS pandemic, pivoted from branding to e-commerce, turning a crisis into diversification.

Avoid stagnation. Businesses that fail often do so not from lack of foresight, but from a lack of persistence in adapting. Blockbuster, for example, initially fought Netflix effectively but ultimately failed due to internal issues and a lack of sustained commitment to its new strategy. True persistence means constantly evolving and being nimble in a dynamic world.

11. Know When to Quit: Sell Your Business and Start Again for a New Dream

If quitting means giving up on your dream, then you are doing it at the wrong time; but if walking away will allow you to keep on pursuing that dream in a new or better way, then it’s probably the right one.

The art of the exit. "Never quit" is often bad advice. Every business and founder's journey has a natural lifespan. Simon realized it was time to leave Fluid when his passion waned, mirroring his wife Helen's earlier decision to pursue kinesiology. Quitting at the right time can be liberating, opening doors to new, more fulfilling dreams.

Divorcing your business. Letting go of a business you created is hard, like divorcing a child. It requires recognizing signs of dwindling passion and planning a gradual exit. Simon advises a staged approach:

• Taper off gradually: Delegate responsibilities, train successors, and slowly reduce your involvement.
• Leave your ego behind: Accept a different role, or step back entirely, allowing others to steer. Simon eventually hired a CEO who ran Fluid better than he could, leading to its successful sale.

Selling smart. Don't actively try to sell your business, as this signals desperation and lowers its value. Instead, cultivate relationships with potential buyers and make your business a "prize asset" they desire. Simon was surprised when PwC, an unexpected buyer, acquired Fluid, demonstrating that the right buyer might not be who you initially envision.

The next chapter. Selling your business isn't the end of your dream, but a new beginning. It frees up capital, time, and mental space to pursue your next big idea or a new iteration of your existing dream. The journey of an entrepreneur is often a cycle of building, selling, and starting again, always driven by an evolving purpose.

Last updated: January 31, 2026