The Happiness of Pursuit

Quests bring meaning to life and help us become better versions of ourselves—a purpose-filled journey is the path to true happiness.

1: Everyone has a desire to embark on a meaningful journey

Many of us dream of stepping outside the predictable routines of life. Whether it’s sailing around the world, traveling across the country, or even living in a tree, these dreams represent a quest—a pursuit that tests our limits and brings deeper fulfillment.

Quests often stem from an internal calling combined with an external push. Tom Allen, for instance, turned down a dream job to bike around the globe, despite lacking experience. His challenges, which included navigating a Sudanese desert without a map and facing malaria, transformed him into a more resilient person. Others embark on quests in response to life changes, like Sandi Wheaton traveling Route 66 after losing her job. Such quests not only test physical endurance but also affirm our sense of identity.

For many, quests reflect a higher purpose. Laura Dekker’s goal to become the youngest sailor to circumnavigate the globe wasn’t just about adventure—it was her way of proving her love for the sea and following what she felt destined to do. Similarly, Miranda Gibson lived in a Tasmanian tree for over a year to protest deforestation, demonstrating how quests can be deeply personal yet aimed at creating global awareness.

Examples

• Tom Allen’s transformation during his global bike journey
• Sandi Wheaton exploring Route 66 after losing her job
• Laura Dekker’s record-setting solo sail around the world

2: Passion comes alive when combined with the right trigger

While everyone has a calling, it often takes external factors to reveal it. Your passion might simmer quietly until dissatisfaction or a major life event acts as fuel for action.

For example, dissatisfaction pushed Juno Kim to quit her engineering career to solo backpack around the world, challenging the stereotype of Western travelers. Similarly, thinking about mortality can push people toward life-altering quests. Phoebe Snetsinger, upon receiving a terminal cancer diagnosis, dedicated herself to seeing as many bird species as possible—and set the world record before her passing. These moments remind us that heightened self-awareness often leads to bold decisions.

Passions also emerge when reality challenges idealized dreams. As Bob Dylan reflected, everyone has a unique passion, but recognizing it often requires us to actively seek and combine these inner urges with opportunities for exploration.

Examples

• Juno Kim transitioning from engineer to solo traveler
• Phoebe Snetsinger’s birdwatching quest inspired by her cancer diagnosis
• Bob Dylan’s belief in the power of personal calling

3: Self-belief and embracing rejection are key to achieving goals

The road to fulfilling a quest is filled with obstacles, but believing in yourself can turn those challenges into stepping stones. When passion is your fuel, persistence becomes your vehicle.

Gary Thorpe’s lifelong aspiration to perform the Gothic Symphony, the longest symphony ever composed, faced skepticism for 28 years. Despite this, his perseverance culminated in a triumphant performance. Dividing tasks into manageable portions also helps with daunting journeys. Steve Kamb turned his journey into a video game where each milestone earned him “level-ups,” motivating him to accomplish diverse feats like piloting a stunt plane. Finally, Jia Jiang turned rejection into empowerment, spending 100 days intentionally seeking rejection to build resilience, a philosophy that can help anyone facing criticism or failure.

Examples

• Gary Thorpe refusing to abandon his symphony performance dream
• Steve Kamb gamifying his goals to stay on track
• Jia Jiang learning through 100 days of deliberate rejection

4: Quests aren't constrained by money or circumstances

Personal quests don’t have to involve extravagant journeys or extensive funds. Even small, structured steps toward a dream can lead to fulfillment and change.

Sasha Martin, for example, couldn’t afford international travel but found adventure by cooking meals from every country—a culinary quest that brought the world into her kitchen. Similarly, Allan Bacon’s experiments, such as visiting museums during lunch breaks or learning new skills like photography, proved that even tiny changes can spark transformation. Sometimes, rethinking goals around available time and budget is necessary, as evidenced by the author’s strategy to visit all 197 countries over a span of several affordable years.

Examples

• Sasha Martin’s journey of global cooking from her Oklahoma home
• Allan Bacon’s “life experiments” to make small, impactful changes
• The author achieving global travel by breaking it into smaller budget-friendly trips

5: The pursuit, not the destination, brings joy

The joy of pursuing a passion often outweighs the satisfaction of reaching the end goal. It’s in this ongoing effort that we find meaning and fulfillment.

Independent musician Stephen Kellogg embraced this during his struggle as an emerging artist. Though he wasn’t immediately successful, he relished being at the “bottom of a ladder” he wanted to climb. The same can be said for Jerry Seinfeld, who, despite immense success, continually practices stand-up comedy as a way to refine his craft and maintain perspective. This love for the process proves that fulfillment stems from growth and dedication, not just accolades.

Examples

• Stephen Kellogg finding motivation in his aspiration to be a musician
• Jerry Seinfeld’s endless commitment to his stand-up routine
• Guitarists practicing tirelessly to master a song

6: A quest offers purpose when life feels directionless

When life feels empty or without aim, taking on a quest can restore a sense of meaning. Stephanie Zito found this after disillusionment with her nonprofit work led her to the ##Give10 project, which rekindled her passion for philanthropy.

While some quests might fail initially, like Mark Boyle’s aborted walk to India, failure often reveals deeper truths. Boyle discovered his true calling wasn’t the walk itself but learning to live without money. Rethinking his quest led to new and fulfilling ventures like his Freeconomy Festival. A quest can help recalibrate your life toward what truly matters.

Examples

• Stephanie Zito’s ##Give10 charity project inspiring global giving
• Mark Boyle’s shift from traveling to living money-free
• New failures leading to greater clarity about life goals

7: Quests transform your life and personality

Quests often lead to remarkable personal growth by challenging behaviors and attitudes. Nate Damm, for instance, turned from a socially timid person into a self-assured individual after walking across the United States.

Beyond personal changes, quests empower individuals to think bigger about their potential. The author’s global travels boosted his confidence to take on even more significant challenges, fueling his drive for self-improvement. These personal transformations ripple outward, as seen in Sasha Martin’s culinary journey, which evolved into sharing messages of peace.

Examples

• Nate Damm overcoming shyness during his walk across America
• The author’s self-confidence after achieving his global travel quest
• Sasha Martin’s shift from personal cooking to spreading cultural harmony

8: Completing a quest is both rewarding and bittersweet

Finishing a quest may leave you proud but longing for new purpose. This bittersweet feeling can only be resolved by reflecting on lessons learned and embarking on your next adventure.

Alicia Ostarello illustrates this with her 50-date journey across America, which left her unsure of her next move. Jumping into work too soon disrupted her ability to process the experience. By contrast, figures like Scott Young naturally transitioned from one quest—intensively studying an MIT curriculum—to another, like learning languages, without skipping the reflection phase.

Examples

• Alicia Ostarello’s unfinished reflection after a cross-state dating quest
• Scott Young continuing personal growth through serial quests
• The importance of debriefing before diving into a new goal

9: Quests push personal boundaries and inspire others

In pursuing meaningful journeys, individuals not only grow but also inspire those around them. Efforts like Sasha Martin sharing her global meals extend new perspectives to diverse audiences. The reflection and sharing of quest experiences amplify their positive impact.

Successful quests often break stereotypes or change narratives around what’s possible, leaving others to wonder, “What can I achieve?” Whether it's birdwatching world records or living an entirely barter-based year, these quests redefine normalcy.

Examples

• Sasha Martin inspiring others by using food to share cultures
• Phoebe Snetsinger’s birdwatching legacy galvanizing new adventurers
• Mark Boyle proving that living without currency can be a viable choice

Takeaways

1. Start small. Pursue manageable experiments to identify passions, like visiting museums or taking short personal challenges.
2. Embrace rejection as fuel. Use failures and nos to strengthen resolve and explore further possibilities.
3. Plan your next move. When completing a quest, reflect deeply and determine how to carry your newfound purpose into the next chapter.