How to Begin

Picture this: you're scrolling through social media at 11 PM, watching others launch businesses, write books, or make meaningful changes in their communities. A familiar ache settles in your chest—that feeling of having so much more to offer the world, yet somehow remaining stuck in comfortable routines that no longer serve you. You're not alone in this restlessness. Millions of young professionals today find themselves caught between the safety of the status quo and the magnetic pull of something greater.

This internal tension isn't a flaw—it's a compass pointing toward your unrealized potential. The path forward isn't about waiting for the perfect moment or having all the answers. Instead, it's about learning to begin with intention, courage, and a framework that transforms overwhelming dreams into achievable realities. The journey toward your most meaningful work starts not with a massive leap, but with understanding how to set goals that truly matter and taking the first courageous step across the threshold of possibility.

Your goal must pass three essential tests: it should thrill you, matter beyond yourself, and stretch you beyond your comfort zone. Too many of us settle for goals that check only one or two of these boxes, leaving us either bored, selfish, or complacent. A truly worthy goal creates a dynamic tension that propels you forward.

Consider Michael's transformation from reluctant CEO to purposeful leader. For nearly twenty years, he founded and ran Box of Crayons, a successful learning company with prestigious clients like Microsoft and Salesforce. Yet he reached a crucial realization: his continued presence as CEO was actually limiting the company's potential. His worthy goal emerged: "Role-model a gracious, generous, and trusting transfer of power." This goal thrilled him because it represented uncharted territory, mattered because it would benefit his team and clients, and daunted him because it meant releasing twenty years of identity and control.

To craft your own worthy goal, start by examining three dimensions: your work sphere versus personal sphere, the scale from intimate to broad impact, and whether you're focusing on projects, people, or personal patterns. Write a deliberately imperfect first draft—remember, all first drafts are terrible, and that's exactly as it should be. Then test your goal against the "Spouse-ish Test" by sharing it with someone who knows you well and gauging their genuine reaction. Apply the "FOSO Test" by completing the phrase "for the sake of" to ensure your goal serves something bigger than yourself.

Your worthy goal should score at least 18 out of 21 points when you rate it on thrilling, important, and daunting. If it doesn't reach this threshold, refine it by adding one powerful word or phrase that increases its intensity and specificity. The goal isn't perfection—it's creating something compelling enough to sustain you through the inevitable challenges ahead.

Before you can fully commit to change, you must honestly examine what you're already committed to maintaining. Your resistance isn't a character flaw—it's valuable information about the hidden benefits you receive from staying exactly where you are.

Michael discovered this truth when analyzing his podcast ambitions. Despite repeatedly declaring he wanted to launch a top-tier podcast, he kept sabotaging his own efforts. His "mosquitoes"—small actions contrary to his goal—included buying expensive equipment then refusing to learn how to use it, hiring a consultant then ignoring her recommendations, and setting ambitious standards then immediately downgrading them. These weren't random acts of self-sabotage but protective mechanisms preserving his comfortable identity as a "high-performing amateur" rather than risking failure as a serious professional.

Begin by acknowledging your false starts—previous attempts at similar goals that fizzled out. Then catalog your current "mosquitoes," those daily actions and inactions that undermine your stated ambitions. This uncomfortable inventory reveals the prizes of your status quo: the comfort, control, and certainty you'd lose by pursuing your worthy goal. Weigh these prizes against the punishments of inaction—what you and others lose if you don't pursue this path.

The commitment equation becomes clear when the punishments of staying put outweigh the prizes of comfort. This isn't about guilt or shame but about honest accounting. When you see the true cost of inaction—to your growth, your impact, and those you could serve—the path forward illuminates itself with crystalline clarity.

Once committed, resist the temptation to take giant leaps. Instead, embrace the power of small steps through three proven approaches: learning from your history, conducting experiments, and building sustainable practices.

Jorge Giraldo exemplified this wisdom when pursuing his worthy goal of writing a book on overwhelm. Rather than attempting to write 20,000 words immediately, he committed to just ten minutes of daily writing—approximately 2,000 words per week. He also designed experiments, publishing two overwhelm-related articles monthly to test his concepts with real audiences. This approach allowed him to gather feedback, refine his ideas, and build momentum without risking catastrophic failure.

Your history contains powerful evidence that you're capable of achieving your worthy goal. Chronicle past moments when a version of your future self already appeared—times you displayed the qualities this goal will require. These stories aren't just motivation; they're proof of concept. Next, design contained experiments that test your assumptions with minimal risk. What's the smallest test that would provide useful data about your goal's feasibility?

Transform successful experiments into sustainable practices—repeated actions that build upon each other while keeping you in learning mode. Unlike habits that become unconscious, practices maintain conscious engagement with growth and adaptation. Start small, gather feedback consistently, and let each step inform the next. Progress compounds when you commit to the process rather than obsessing over immediate outcomes.

Doubt isn't your enemy—it's an inevitable companion on any journey worth taking. When confusion, anxiety, and uncertainty cloud your vision, you need a reliable method to reconnect with your core strengths and values.

Michael developed his "This/Not That" framework during his product development days, originally used for brand positioning. He adapted it for personal growth by creating pairs of words describing himself at his best versus when he's slightly off his game. For his CEO transition, his list included "Calm not Reactive," "Deep Trust not Loose Reins," and "In My Corner not Fingers in Pies." These weren't abstract concepts but visceral reminders connected to specific memories and body sensations.

Create your own This/Not That list by reflecting on peak moments when you felt unstoppable and in flow. What words capture your essence in those moments? Contrast these with how you show up when performing at 85 percent—not failing dramatically, but not quite clicking either. Aim for five to seven powerful pairs that create a physical recognition when you read them.

This framework becomes your compass during challenging moments. When doubt strikes and old patterns resurface, scan your list and consciously choose the "This" version of yourself. You're not pretending to be someone you're not—you're remembering who you are at your best and making that choice available in the present moment. Your best self isn't a future aspiration; it's an existing capacity waiting to be activated.

No worthy goal is achieved in isolation. Like Dorothy gathering her companions for the journey to Oz, you need specific types of support to navigate the challenges ahead. The question isn't whether you need help, but what kind of help serves your mission best.

First, identify who doesn't belong on this journey. Some people in your life are invested in keeping you unchanged, either because change threatens their comfort or because they've built their identity around an outdated version of you. Making space for growth sometimes means creating distance from those who drain your energy or sow doubt about your aspirations.

Next, gather your essential support team based on archetypal roles: Warriors who have your back and help you channel righteous anger; Healers who offer sanctuary and unconditional encouragement; Teachers who bring insight and break you open to new perspectives; Visionaries who stretch your ambition and role-model courage; and Tricksters who keep you honest by deflating any tendency toward self-importance.

These roles don't require hiring professionals or forming formal relationships. Michael's Warriors included his wife Marcella, who fiercely defended his interests and helped him set boundaries. His Teachers included philosophers like Dr. Jason Fox, who challenged his assumptions and introduced new frameworks for thinking. Some band members might be people you've never met—authors, leaders, or creators whose examples inspire your highest aspirations.

The key is intentionality. Rather than accepting whatever support randomly appears, consciously cultivate relationships that serve your growth and your worthy goal's success.

Your greatest growth happens not in moments of comfort, but when you're wrestling with challenges worthy of your potential. As the poet Rilke wrote, "His growth is: to be the deeply defeated by ever greater things." This isn't about seeking failure, but about engaging with projects and purposes significant enough that they transform you in the process of pursuing them.

The path from aspiration to achievement requires more than good intentions—it demands a systematic approach to beginning well. By setting goals that are simultaneously thrilling, important, and daunting, you ensure your efforts serve both your development and the world's needs. When you honestly examine what you're already committed to maintaining, you can make conscious choices about what deserves your continued allegiance. Small steps, supported by the right companions and grounded in your best self, transform overwhelming dreams into achievable realities.

Start today by writing down one worthy goal that makes you slightly nervous but genuinely excited. Share it with someone who wants to see you succeed, then take the smallest possible step toward making it real. Your future self—and the world—is waiting for what you have to offer.