What's Your Dream?
Find Your Passion. Love Your Work. Build a Richer Life.
by Simon Squibb
Buy on AmazonEveryone has a dream buried under layers of fear, myths, and societal conditioning — this book is a practical guide to digging it out, fueling it with purpose, and turning it into a business that gives your life meaning.
The Problem: We're Taught to Kill Our Dreams
Simon Squibb — homeless at 15 after his father died in front of him, now a serial entrepreneur who sold his agency Fluid to PricewaterhouseCoopers — has spent years asking strangers one question: "What's your dream?" The response is almost always the same: surprise, then vulnerability, then a flood of suppressed ambition.
Squibb argues we're running on a broken operating system. From school age, we're told: work hard, get a safe job, buy a house, avoid failure. This programming is so deep that most people never pause to ask what they actually want. The book is structured as a staircase (literally — Squibb bought a derelict staircase for £25,500 and turned it into HelpBnk's headquarters) that takes you from myth-busting to dream discovery to execution.
The Four Myths That Kill Dreams
Before you can dream, you need to deprogram yourself from these beliefs:
1. "The harder I work, the luckier I get" — Hard work is necessary but not sufficient. Squibb's best business ideas came while on holiday. Fluid made the most money when he stepped back and hired someone else to run it. We succeed when we work smart on things we care about, not when we grind mindlessly.
2. "Failure means disaster" — Jamie Oliver lost £25 million and closed 22 restaurants in 2019. By 2023, his businesses were back to multi-million profits. Squibb himself lost $1.5 million on DevaShard, a comic book venture. His takeaway: "Does the mission justify the risk?" If yes, the failure was worth it.
3. "It's OK to avoid hard things" — A woman told Squibb her dream was to be rich. He challenged her to sell a pen to a stranger in 60 seconds. She did it in 27. Those 27 seconds changed her life — she later said she now felt confident to tackle what she'd feared.
4. "Possessions make you happy" — After selling his company, Squibb bought the Porsche he'd dreamed of since being homeless. The euphoria lasted a week. By week three, he was anxious driving it. He sold it and felt freer. "A possession should never be your dream."
Dreams vs. Goals: Why the Word Matters
Dream
- Long-term power source
- Resilient — survives bad months and bad years
- Allows course corrections and pivots
- Provides belief, motivation, and identity
- Democratic: needs no money, qualifications, or roof
Goal / Target / Resolution
- Short-to-medium term
- Binary — pass or fail
- Brittle: one miss and you quit
- 50/50 chance of failure by design
- "Almost as if they were designed for us to give up on them"
Historical proof: Martin Luther King said "I have a dream" — not "I have a plan." The American Dream — not the American Goal. Malala Yousafzai, shot by the Taliban at 14, said: "They cannot shoot my dreams." Sylvester Stallone turned down $300,000+ for the Rocky script because they wouldn't let him star in it. His reasoning: "I just believe in it."
Purpose: The Fuel That Powers Everything
If the dream is the brain, purpose is the heart — pumping blood and maintaining the beat. You can have many purposes feeding a single dream. Squibb learned this the hard way: Fluid, his creative agency in Hong Kong, was losing staff constantly until he rediscovered their original purpose (paying creatives what they're worth and giving them enough time to do great work). After recommitting to it, they never had a major staff turnover problem again.
The research backs it up. A study of 13,000+ Americans over 50 found those with the strongest sense of purpose had the lowest risk of mortality. Studies of Polish firefighters and Italian priests found purpose-driven individuals were less likely to burn out. US Bureau of Labor Statistics data shows the three most meaningful industries are agriculture, health/social assistance, and education — not the easiest or best-paid, but the most purposeful.
Three Questions to Discover Your Dream
1 What Are My Likes and Dislikes?
At 42, after selling Fluid, Squibb was miserable and directionless. He made a simple list: likes (meeting people, helping entrepreneurs, selling) vs. dislikes (sitting in meetings, poring over numbers). That list led to a podcast on a £99 microphone, which led to TikTok, which led to everything he does today. "It's never the idea that makes a business succeed — it's the people and the motivation behind it."
2 What Is My Pain?
Pain is what turns "wants" into "needs." Sara Blakely was selling fax machines door-to-door when frustration with visible underwear lines led her to create Spanx — becoming the youngest female billionaire in America. Squibb's own pain anchors: abandoned at 8, humiliated for dyslexia at school, homeless at 15 after his father's death. "The imprint of that pain has never left me."
3 How Can I Help Others?
The substance of any durable dream will ultimately be about service. A two-time cancer survivor paints to fund cancer research. A former homeless man creates a dog grooming mobile salon. Businesses without a mission to help others are "on borrowed time." The three questions work in sequence: likes give direction, pain gives compulsion, helping others ties the knot.
The acid test: Sit with the idea for a few days. If it slips from your mind, it wasn't the right dream. If you can't stop thinking about it — waking up with it, making notes at 2 a.m. — then it's real.
The Seven Steps (Dream Blockers)
Squibb frames the most common excuses as a staircase you must climb:
"I don't have time" — Start with one minute a day thinking about it. "At the start, distance doesn't matter, only direction."
"I'm trapped" — Confront your problems first. Davide dreamed of a restaurant, raised £10,000, then vanished — he had debts he'd never disclosed.
"I don't need it" — "All the things you thought you wanted end up owning you." Kids don't do what you say, they do what you do.
"I don't know what" — You probably do. Dreams are usually a better version of what you're already doing. Ban "not sure" and "don't know."
"I don't know how" — Shrink the problem: "What's the business called? When can you demo? How much to get started?" Sam catered 150 people three days after being asked.
"I'm worried what they'll think" — "Only take advice from people if you want a life like theirs."
"I've tried before" — Squibb has run 19 businesses. Plenty failed. The most important decision in business is choosing who to trust.
Free Yourself, Then Build a Boat
Once you know your dream, Squibb says you must achieve three freedoms before launching:
Free Your Finances
"Stop selling time, start buying time." Ask for equity. Cut costs ruthlessly. Amazon has 750,000 robots — your job is not as safe as you think.
Free Your Mind
Use present tense: "I am building" not "I will build." One-day plans over 5-year plans. Ben Francis (Gymshark) started sewing in his parents' garage at 19 — valued at £1B+ eight years later.
Free Your Idea
"It's not who you know, it's who you ask for help." Caitlin's photography dream went viral (10M+ views) and landed her a lastminute.com sponsorship — all because she shared her idea.
Then build the boat — but build it quickly. Get ready to quit (six-month rule: once you've decided, you should be working on it within six months). Find your first customer (Squibb's Tesco story: he gave a shelf-stacker £150 as a "deposit" on a bed at her future care home). Go all in: "You cannot build a company part-time." Even with 19 businesses worth of experience, Squibb says he'd fail part-time.
Start Poor, Grow Rich
Start Poor
Not having money is a strategic advantage. It forces you to justify every penny and build a business that pays for itself. WeWork raised $22 billion and went bankrupt. Squibb's most expensive failure (DevaShard) happened when he abandoned his bootstrapping discipline. Your first target: zero (break-even). He throws a party when a business hits zero.
Grow Rich
Growth = compounding small wins. Squibb's first YouTube video got 150 views; four years later, 1.5 million in ten days. The golden rules: always get 50% payment upfront, reinvest all profits (don't take money off the table), go deep with existing customers (Pareto: top 20% generate 80% of profit), and eventually step back using the Three Ts: Train, Trust, Tear yourself away.
CoasterAds: Squibb's best bootstrap story. He noticed beer coasters in Hong Kong bars were an untapped ad medium. Launched with zero investment, signed United Airlines as the first client with 50% upfront, and within a year it matched Fluid's revenue. Total investment: $0. Revenue by sale: millions.
People, Risk, and Persistence
Find Brilliant People — Partners need complementary skills but a shared moral code. During the 2008 financial crisis, competitors laid off staff. Helen told Simon: "If the company dies, we can always just do something else." They hired instead — and won. The Rule of Seven and Eight: if you keep mediocre performers (7-8/10), your stars (9-10) will leave. And always give equity: "Do you want 100% of a struggling company or 51% of a thriving one?"
Develop a Risk Muscle — Risk-taking is trainable. Visualize the worst case first — if you can stomach it, the fear dissolves. Derisk through partnerships and pilots: Squibb co-ventured his candy brand (Bizzies) with Tasty Mates instead of betting his fortune on an industry he didn't know.
Keep Going — Persistence beats talent every time. Squibb wrote a list of 50 dream clients. In the first month, zero agreed to a meeting. He kept going — seasonal greetings, relevant articles, unsolicited insights. After nine years, all 50 had hired Fluid. Nvidia had one month of cash left when they launched their make-or-break product. Jensen Huang: "People with very high expectations have very low resilience."
Sell and Start Again
There will come a time when quitting is the right decision — not quitting on the dream, but leaving a business that's run its course. Signs: pitches feel like chores, you can't write a new dream client list, the fire is flickering low.
Squibb's exit from Fluid: he replaced himself by hiring someone better (not someone he liked), staged a gradual exit, and sold to PwC — not the biggest offer, but the right one for his people and brand. His advice: never put up a "for sale" sign. Make the business so good that buyers come to you. After an exit: don't retire. "I think retirement is for people who hate what they do." Invest in yourself and pursue the most ambitious version of your dream.
8 Actionable Takeaways
Answer the three questions in order. What do I like? What is my pain? How can I help others? Direction, then compulsion, then purpose.
Say your dream out loud. Tell someone today. The act of naming it breaks the inertia. "Once you have named it, you can launch it."
Do the acid test. Sit with the idea. If you can't stop thinking about it after a few days, it's your dream. If it fades, try again.
Start at zero. Your first real milestone is break-even, not millions. Celebrate hitting zero. Then compound from there.
Only take advice from people whose life you'd want. Others' doubts come from their fears, not your reality.
Get 50% upfront, always. The first half covers costs. The second half is profit. This single rule funded Squibb's entire growth engine.
Give equity to your best people. "Do you want 100% of a struggling company or 51% of a thriving one?" Equity is the strongest retention tool.
Practice #TakeFour daily. 1 minute to learn who someone is, 1 minute to find what they need, 1 minute to help, 1 minute to pass it on.
Who Should Read This
- Anyone stuck in a comfortable job — If you have a nagging feeling there's something more, this book will make you confront it honestly.
- First-time entrepreneurs — The "start poor" philosophy and practical bootstrapping stories (CoasterAds, Gymshark) are worth the price alone.
- People who've failed before — Squibb normalizes failure with his own $1.5M loss and 19-business track record. The staircase framework for dream blockers is genuinely useful.
- Parents and mentors — "Kids don't do what you say, they do what you do." If you deny your own dream, your children will replicate the pattern.
§ Verdict
7 / 10
A genuinely motivating book with memorable stories — Squibb's personal journey from homeless teenager to serial entrepreneur gives him credibility that most "follow your dream" authors lack. The frameworks (three questions, seven steps, three freedoms) are practical and memorable. Where it loses a point: the business advice occasionally oversimplifies (not everyone can just "quit and go all in"), and some chapters repeat the same themes. Best read as a shot of entrepreneurial adrenaline paired with a surprisingly structured playbook. Skip the Acknowledgements and Notes unless you want source references.