How to Begin
A Proven Plan to Start Something That Matters
Book Edition Details
Summary
"How to Begin (2022) argues that you unlock your greatness by working on the hard things. The things that matter. Not to your partner, friends, or family – but to you. The hardest part isn’t the work itself, though. It’s identifying the kinds of projects that are worth investing your time in. Projects which give your life meaning. And that’s what this book is really about: helping you discover worthy goals."
Introduction
There comes a moment in everyone's life when the familiar feels too small and the safe feels suffocating. Maybe you're scrolling through social media, watching others chase their dreams while you remain stuck in routines that once felt comfortable but now feel like cages. Perhaps you're lying awake at night, knowing deep down that you have more to offer the world than what you're currently giving. The stirring of ambition isn't just personal restlessness—it's your soul recognizing that your current path, while perhaps successful by conventional measures, isn't leading you toward the impact you're meant to make. This disconnect between who you are and who you could become is both uncomfortable and necessary. It signals that you're ready to step beyond the boundaries of your comfort zone and into the territory where real growth happens. The journey toward meaningful change begins with a single, crucial decision: to pursue something that matters deeply to both you and the world around you.
Set a Worthy Goal That's Thrilling, Important and Daunting
A Worthy Goal isn't just any goal—it's a carefully crafted ambition that possesses three essential qualities. It must be Thrilling, igniting genuine excitement and aligning with your deepest values. It must be Important, contributing something meaningful to the world beyond your personal satisfaction. And it must be Daunting, pushing you to the edges of your current capabilities and comfort zone. Consider Michael's own journey with Box of Crayons, the learning company he founded almost twenty years ago. When he first conceived the idea, it wasn't merely about starting another business. The goal was thrilling because it combined his passion for helping people unlock their potential through better conversations. It was important because it addressed a genuine need in workplaces where advice-giving had become a substitute for genuine curiosity and coaching. Most importantly, it was daunting—he had no formal business training and was essentially making it up as he went along. What started as a leap into the unknown gradually transformed into a successful company with twenty employees and clients like Microsoft and Salesforce. The daunting nature of the goal forced Michael to grow beyond his comfort zone, developing skills he never knew he possessed while creating something that genuinely improved how people interact in professional settings. To craft your own Worthy Goal, begin by exploring three dimensions: Work versus Not Work, scale from intimate to broad, and focus on Projects, People, or Patterns. Don't worry about perfection in your first draft—the goal is to capture something that makes you both excited and slightly nervous. Test your draft against the three criteria, refining it until it scores at least 18 out of 21 points when rated across all three dimensions. The key is starting with a verb, transforming your aspiration into an active commitment. Instead of "having a successful podcast," commit to "launching a podcast that reaches the top 3 percent within twelve months." This shift from passive wish to active declaration changes everything about how you approach the challenge ahead.
Commit by Weighing the Status Quo Against Your Journey
True commitment requires honest accounting of what you're leaving behind and what you're stepping toward. Most people underestimate how deeply invested they are in maintaining their current situation, even when that situation feels unsatisfying. The status quo offers predictable rewards: comfort, familiar identity, established relationships, and freedom from the vulnerability that comes with attempting something new. Michael discovered this when contemplating his transition from CEO of Box of Crayons. On the surface, the decision seemed obvious—stepping away would allow the company to scale beyond his limitations while freeing him to pursue new projects. Yet when he honestly examined what he'd be giving up, the list was substantial: the status and recognition of being a founder, the daily interaction with a team he loved, the sense of control over decisions large and small, and perhaps most significantly, twenty years of identity wrapped up in the company's success. The breakthrough came through rigorous examination of both sides of the equation. The punishments of staying—watching the company plateau under his leadership, missing opportunities for both personal and organizational growth, failing to model the gracious transfer of power he advocated—ultimately outweighed the comfortable prizes of remaining in place. This wasn't merely intellectual analysis but emotional reckoning with the full cost of both action and inaction. Create your own balance sheet by first acknowledging your false starts—previous attempts at similar goals that fizzled out or never properly launched. Then identify your "mosquitoes"—the countless small actions and inactions that currently undermine your stated ambitions. Finally, weigh the genuine comfort of your current situation against the price you and others pay when you don't pursue meaningful change. The goal isn't to eliminate doubt but to ensure that your commitment is stronger than your resistance. When the punishments of maintaining status quo clearly outweigh its prizes, you're ready to move forward with confidence.
Cross the Threshold with Small Steps and Strong Support
The moment of commitment must be followed by intelligent action. Rather than attempting dramatic leaps that often lead to spectacular failures, success comes through strategic small steps that generate learning while minimizing risk. This approach transforms daunting challenges into manageable experiments that build momentum and confidence. Consider how Michael approached launching a top-tier podcast. Instead of immediately investing in expensive equipment and extensive production, he began with a simple experiment: creating a pitch document that experts could review. This small step revealed crucial insights about market demand, production requirements, and his own level of genuine interest without risking significant time or money. The feedback became the foundation for more substantial experiments, each building on lessons learned from the previous iteration. The three types of small steps each serve different purposes. A History involves mining your past for evidence that you've successfully navigated similar challenges before, providing both confidence and calibration of actual versus imagined risks. An Experiment tests specific hypotheses about your Worthy Goal through controlled, low-risk trials that generate useful data regardless of outcome. A Practice establishes ongoing routines that build capability while maintaining conscious learning and adaptation. Equally important is assembling the right support network. Drawing from indigenous wisdom traditions, surround yourself with archetypal energies: a Warrior who has your back and helps you maintain boundaries, a Healer who offers encouragement and sanctuary, a Teacher who provides insight and challenges your assumptions, a Visionary who stretches your ambition and models courage, and perhaps a Trickster who keeps you humble and prevents you from taking yourself too seriously. Remember that crossing the threshold isn't a one-time event but an ongoing choice. Your Best Self—the version of you that emerges when you're operating at peak effectiveness—will show up inconsistently at first. Create a "This/Not That" framework to help recognize and choose your optimal state: "Calm anticipation not jiggling legs," "Stepping forward not stepping back," or whatever distinctions help you navigate challenging moments with grace and effectiveness.
Summary
The path to unlocking your greatness isn't found in comfortable routines or safe choices, but in the deliberate pursuit of challenges that matter. As the poet Rilke reminds us, true growth comes from being "deeply defeated by ever greater things"—not because we seek failure, but because we choose endeavors worthy of our full engagement. Your Worthy Goal serves as both destination and vehicle for transformation, simultaneously calling forth your best qualities while contributing something meaningful to the world around you. The process isn't about achieving perfection but about becoming the person capable of wrestling with angels, knowing that the struggle itself changes us in fundamental ways. Start today by identifying one small step you can take toward a goal that genuinely excites and challenges you. The world needs what you have to offer, and your greatness is unlocked not through comfort but through the courageous choice to work on hard things that matter.
By Michael Bungay Stanier
