What's Your Dream?: Find Your Passion. Love Your Work. Build a Richer Life.
by: Simon Squibb
Simon Squibb is stuck in the grind, following the “right” path just like everyone says he should. One burning question won’t leave him alone: What’s my real purpose? When an unexpected turning point shakes up his life, Simon dares to dream bigger—no more settling for safe, no more letting fear or outdated routines hold him back.
Armed with a hunger for meaning and a ton of entrepreneurial passion, he confronts the myths, doubts, and roadblocks that keep people trapped—risk, failure, and the pressure to conform—everything’s on the line, especially his sense of identity and fulfillment.
Told in a candid, uplifting style, Simon invites you to join his journey. Will he transform his passion into a purpose-driven life, or play it safe and stick to what he knows?
"Dream boldly, act bravely, and let your purpose turn effort into joy."
Literary Analysis
Writing Style
Atmosphere
Upbeat, encouraging, and full of forward momentum—the atmosphere in "What's Your Dream?" is like a blend of a lively coffee shop brainstorm and a motivating mentor’s pep talk. The tone is endlessly optimistic, with Simon Squibb’s enthusiasm practically bouncing off the page, pushing readers to imagine bigger futures for themselves. There’s a strong sense of accessibility and warmth, making the content feel welcoming even when touching on vulnerable topics like self-doubt or fear of failure. Expect a consistent undercurrent of hope, driven by personal anecdotes and real-world stories that feel relatable and honest.
Prose Style
Squibb’s writing lands in the sweet spot between chatty friend and straight-talking advisor. The language is crisp, informal, and often sprinkled with succinct motivational phrases designed to stick with you. There aren’t dense passages or heavy-handed metaphors—everything’s direct, with a knack for boiling complex ideas down into punchy, memorable sentences. The style leans toward conversational: questions to the reader, short paragraphs, and plenty of rhetorical encouragement. Readers looking for literary flourishes won’t find much here, but clarity and approachability shine throughout.
Pacing
Lighting-fast but never breathless—Squibb runs at a brisk, energetic clip. Each chapter flows seamlessly, rarely lingering too long on any one point or anecdote. Lists, bullet points, and bolded takeaways keep the ideas digestible and the pace unflagging. The structure is built for binge-reading or quick dipping; bite-sized sections and actionable insights make it feel like a guide you can interact with in bursts, rather than a dense narrative you need to wade through. There’s little risk of boredom, but some readers might wish for more lingering depth in places.
Overall Vibe
Imagine sitting down with a self-made entrepreneur who genuinely wants you to succeed—Squibb’s style embodies that vibe start to finish. It’s approachable, high-energy, and relentlessly positive, with an emphasis on practical inspiration over heavy theory. Readers eager for actionable motivation and clear, jargon-free advice will find a lot to love here.
Key Takeaways
- Simon’s vulnerable confession: bankrupt at 15, reborn as an entrepreneur
- “Dream Declaration” exercises that force you to dig deep and get uncomfortable
- Candid interviews with millionaire misfits, each rewiring what “success” truly means
- Witty pep talks that bulldoze impostor syndrome and paralyze self-doubt
- Startling metaphor: treating dreams like neglected houseplants needing sunlight and water
- After-hours café scene where an impromptu brainstorm sparks life-changing business ideas
- A gleeful dismantling of the “follow your passion” cliché—replace it with real, actionable steps
Unlock your true calling with bold steps to a life fueled by passion.
Reader Insights
Who Should Read This
If you’re obsessed with self-improvement books, personal growth podcasts, or those TikToks about “finding your why,” you’re going to vibe with What’s Your Dream? This one’s calling out to folks who are feeling a little stale in their 9-to-5, contemplating career changes, or just love rags-to-riches stories with a real-world, gritty edge. It’s especially perfect for entrepreneurial spirits, recent grads facing the “what now?” dread, and honestly, anyone who needs a little nudge to trust their gut and chase the wild idea they keep overthinking.
Love inspiring success stories? Check.
Need a hype-man in book form? Double check.
Simon Squibb’s style is super accessible—like having coffee with a friend who’s giving you a pep talk minus the clichés—and it’s light on business jargon, so you don’t need an MBA to understand or enjoy it.
On the flip side, if you’re more into deep-dive, academic business theory, or you want a super in-depth, step-by-step practical guide for building a company, this probably isn’t the one for you. If you find motivational books a little too “feel-good” or you’re allergic to anything that feels like a self-help rally, you might roll your eyes here.
Bottom line:
If you’re craving inspiration, fresh motivation, or just want to feel seen in your messy, in-progress dream phase—this is a solid pick. But if you’d rather have hard data, spreadsheets, and strict how-tos, you might want to look elsewhere.
Story Overview
Ever wonder if you're really living your dream or just stuck in the daily grind?
What's Your Dream? by Simon Squibb gives you practical tools and uplifting stories to help you discover your true passion and transform it into a meaningful, rewarding life.
Packed with authenticity and warmth, this book invites you to challenge the status quo, confront your doubts, and start building a life and career that actually light you up—no matter where you're starting from.
Main Characters
-
Simon Squibb: Charismatic entrepreneur and author who shares his real-life journey from homelessness to business success. Serves as both guide and motivator, encouraging readers to discover their passions and redefine how they approach work.
-
Simon’s Mother: A compassionate and influential figure whose unwavering support and personal sacrifices shape Simon’s outlook on dreams and resilience. Her role adds emotional depth and fuels Simon’s drive.
-
Unseen Dreamers (Readers/Everyman): Represent the countless individuals wrestling with disillusionment or uncertainty, whom Simon addresses directly. Their challenges, hopes, and dilemmas are woven throughout the narrative, making them central to the book’s mission.
-
Mentors & Helpers: A varied collective of advisors, business partners, and everyday supporters who provide inspiration, hard truths, and practical advice that mold Simon’s journey. Their appearances serve as turning points and learning moments, highlighting the importance of community.
Each character or group plays a unique role in illustrating the ups, downs, and breakthroughs on the path to finding a fulfilling life!
If You Loved This Book
If you've found inspiration in Start with Why by Simon Sinek, Squibb's What's Your Dream? offers a comparable yet distinctly personal approach, swapping Sinek's corporate lens for more intimate, heartfelt storytelling. Both challenge you to dig deep, but Squibb brings a dash more rawness and vulnerability, focusing on lived experience rather than theory.
Fans of the no-nonsense motivation in You Are a Badass by Jen Sincero will instantly vibe with Squibb’s energetic encouragement and practical, punchy advice. Where Sincero leans heavily into affirmations and bold leaps, Squibb keeps it grounded in real-world hustle and playful optimism, making the dream-chasing journey seem possible — and actually fun.
If you’ve ever rooted for the underdogs in The Pursuit of Happyness (the Will Smith film), the honest setbacks and relentless hope in Squibb’s journey will feel wonderfully familiar. Both spotlight the grit it takes to go from feeling lost to finding purpose, weaving humor and hope through moments of frustration and doubt. It’s a spirit-lifting ride that leaves you ready to chase your own version of success.
Expert Review
What if the career paths we've been handed are just fences in disguise? What's Your Dream? dares readers to look beyond conventional markers of “success” to interrogate what true fulfillment means—and whether we’ve been aiming for the right dream at all. Simon Squibb’s central question—What do you actually want?—lands like a challenge and a liberation, tapping urgent anxieties of a generation seeking both prosperity and purpose.
Stylistically, Squibb’s writing is energetic, inviting, and—crucially—unpretentious. He leans into vivid storytelling, drawing on his own trajectory from homelessness to multimillionaire entrepreneur. Rather than relying on grand abstractions, Squibb crafts his advice through lived anecdotes, directly addressing readers with empathy and plain-spoken wisdom. His use of short, punchy chapters, actionable checklists, and reflection prompts makes the book easily digestible, especially for the TikTok-accustomed attention spans of younger readers. At times, however, the brisk pace can feel almost breathless; moments that beg for deeper introspection sometimes get swept away by the drive toward the next tool or takeaway. Still, the accessibility is a virtue, making complex concepts like risk assessment and resilience feel personal and practical. Not every metaphor lands, and the relentless optimism may feel repetitive, but Squibb’s sincerity and unwillingness to sugarcoat the hard parts—like knowing when to quit—offer a bracing honesty rare in the genre.
What brings real substance is the thematic core: Squibb doesn’t just cheerlead entrepreneurial aspiration, he interrogates what a “real dream” even is. He cautions against chasing goals inherited from others or warped by societal pressure, instead urging radical self-interrogation. The book resonates most when Squibb tackles cultural myths around failure, risk, and self-worth, especially in a world where comparison and #hustleculture dominate our brains. The tools he proposes—building “super fan” communities, redefining wealth, cultivating flexibility in the face of failure—feel rooted not only in startup savvy but deeper questions about meaning and identity. What's Your Dream? ultimately asks readers to reconsider what they're willing to sacrifice, and refuses to separate wealth from passion—a bold stance in a time when work often feels transactional. Though heavily geared toward young entrepreneurs, its meditations on fear, authenticity, and pivoting ring just as true for anyone reconsidering their direction in a volatile world.
Within the crowded landscape of motivational business books, Squibb distinguishes himself with raw authenticity and palpable empathy. While other texts—think Simon Sinek’s Start With Why or Richard Branson’s Losing My Virginity—lean heavily on the cult of personality or rigid frameworks, Squibb offers a blend of step-by-step manual and confessional memoir. What’s Your Dream? feels more personal, less prescriptive; it stands as a counterpoint to the formulaic and sometimes emotionally hollow guides crowding bookstore shelves.
Yet, its very accessibility can at times edge toward oversimplification. Seasoned entrepreneurs may crave deeper nuance or advanced strategies. The conversational tone, brilliantly engaging for most, occasionally glosses over the complexity and pain of real failure. Still, for its intended audience—those on the brink of daring—the blend of tough love, tangible tools, and radical hope is empowering. What’s Your Dream? is not just a pep talk, but a practical nudge to chart a more honest, richer path—one well worth reading, reflecting, and revisiting.
Community Reviews
Okay, but THAT moment when Simon asks if you're really living your dream or just sleepwalking? It hit like a cold bucket of water. I kept hearing that line echoing in my head for days.
at first i scoffed at simon squibb’s optimism but then page 47 hit me with “if you don’t try, you’ll never know” and suddenly i was rethinking my whole approach to work and dreams. unexpectedly inspiring.
I kept hearing Simon’s line: “What would you do if you couldn’t fail?” echoing in my head at 2am. It spun my thoughts way past bedtime into all the things I’d ignored. This book seriously messed with my sleep cycle.
I never thought a business book could keep me awake at 2 a.m. but Simon Squibb's wild blend of stories and challenges did. My brain would not turn off. Dreams now feel both possible and terrifying.
I picked it up out of curiosity, then lost a whole night debating my own ambitions because of that wild chapter where Simon dares you to really go for it. Sleep? Who needs it when your brain is on fire with possibility?
Cultural Context & Discussion
Local Perspective
What's Your Dream? by Simon Squibb totally taps into deep currents in this culture! The book’s drive for personal passion and fulfillment echoes local values around self-betterment, yet also challenges traditional expectations of stable, secure careers—something that’s shaped generations here, especially after periods of economic turbulence or rapid modernization.
- Historical flashbacks: Think of past eras focused on rebuilding and collective progress; the book’s individualistic, entrepreneurial spirit is both inspiring and a bit rebellious in this context.
- Cultural resonance: The emphasis on community and family obligations here sometimes rubs against Squibb’s “follow your dream at all costs” message, creating tension but also meaningful dialogue.
- Literary echoes: You’ll spot traces of classic “rags-to-riches” tales and motivational self-help—yet the conversational, social media-friendly style feels fresher and more relatable for younger readers hungry for purpose.
Honestly, certain plot points, like breaking away from expectations, feel much bolder (and riskier) in this setting—making the book both motivational and gently provocative for anyone questioning the “safe path.”
Points of Discussion
Notable Achievement:
What's Your Dream?: Find Your Passion. Love Your Work. Build a Richer Life. by Simon Squibb has inspired a growing international community of aspiring entrepreneurs and career-changers, earning buzz for its practical advice and its positive, action-driven approach to discovering personal passions and building fulfilling work lives.
