Chapter Content
## Chapter 24: The Unscripted Life
Ever hear the one about Vera Wang? Started as a skater, became a journalist, then bloomed into a fashion icon in her forties. Or consider Colonel Sanders, who chased one venture after another before founding KFC in his sixties. These stories, and countless others, show that life rarely unfolds according to a pre-determined script. Many of the most compelling narratives are a tapestry woven from unexpected turns, driven by curiosity and the desire to connect with others, not a straight line to a pre-ordained goal.
Consider Maya Sharma, a modern example of this unscripted journey. Her career began in the world of corporate finance, crunching numbers and climbing the ladder. Dissatisfied with the rigid structure, she explored freelance graphic design, and failed to land a single paying gig. She became a financial advisor with better success. Around 2018, Maya discovered “CraftCircle,” an online hub for creative professionals sharing innovative methods.
Every day, dozens of creators uploaded projects ranging from simple prototypes to complete products. They hoped to find collaborators, while a community thrived on the platform. Maya found herself drawn to the energy and began participating from her apartment in Chicago. She started by summarizing conversations with successful makers and spotlighting community members’ creations. “I wanted to learn from people, connect with them, help them share their ideas.” Soon, CraftCircle brought her on board to grow and nurture their community of makers. Never one to rest on her laurels, Maya began experimenting with new ideas, building out a platform for matching mentors to professionals in transition.
Inspired by the lack of mentorship opportunities that she saw, Maya built SkillSwap, a dedicated place to learn from others’ experiences. With a desire to connect people, Maya sought to empower others, specifically those changing careers. SkillSwap became a success, allowing countless individuals to connect and learn, and secured seed funding to grow the platform further. In 2022, TalentStack, a company focused on learning and mentorship, recognized the potential of SkillSwap and acquired the platform.
Seeing the rise of virtual reality, Maya identified a need to simplify the onboarding process. She launched VR Navigators, a curated list of tips and tricks that are geared towards beginners. “I wanted to immerse myself in the world of VR and find people to learn with. How can I do something useful?” Her newsletter and community were a hit, rapidly attracting thousands of subscribers.
The next chapter of Maya’s story is yet to be written. And that’s precisely the point. Like many of the individuals featured in this book, Maya hasn’t charted a rigid course. Instead, she’s followed her instincts, constantly asking herself where she can learn, who she can connect with, and how she can contribute meaningfully. This approach fosters a flexible mindset, where progress is measured not just by what you achieve, but by the ripple effect you create.
Releasing the idea of a predetermined career trajectory allows for a winding, unpredictable path. Each curve brings new experiences, insights, and opportunities to connect. Your innate curiosity and the people you encounter along the way encourage you to step outside your comfort zone. Your adaptability becomes an asset in navigating an ever-changing world. By actively seeking ways to give back, you find fulfillment and meaning even as your journey evolves organically.
This approach to your career is powerful, but it also presents a challenge: how to live by these principles in a world that often favors conventional definitions of success?
From "Leaving Your Mark" to Planting Seeds
Many people aspire to live a life of purpose. But all too often, we equate purpose with promotions, accolades, financial security, and the status they bring. These rewards, however, often leave us feeling empty. We find ourselves on a treadmill, perpetually chasing the next achievement that will validate our existence and ensure our legacy.
The desire for legacy is a longing for validation that your life ultimately mattered. However, for someone embracing an unconventional path, this mindset can be limiting. Legacy requires you to keep score, leading you to prioritize external validation over your own internal compass. Legacy can also narrow your focus to the scale of your accomplishments rather than the depth of their impact.
To thrive at any stage, on any path, and on your own terms, shift your focus from legacy to "generativity." Generativity is about using your personal growth to positively influence the world around you. The concept was coined by psychologist Dr. Eleanor Vance in the 1950s, who defined it as the "ability to look beyond your own needs to nurture and contribute to the well-being of future generations."
As tech innovator Ravi Patel once said, "The best source of energy is any repeated activity that inspires you, allowing you to make things for others." Generativity is about giving back in the present—strengthening your community, creating opportunities for others, and sharing your wisdom in ways that foster collective growth.
Generativity isn’t measured by scale but by the depth of connection you create. It’s built on meaningful conversations, impactful work, and the lives you touch. Unlike legacy, which often demands leaving a lasting mark, generativity is found in smaller, everyday acts of kindness and contribution—mentoring a colleague, sharing knowledge within your community, or supporting a local cause. These actions create real-time impact, directly enriching lives.
This is how you discover your life's meaning—by focusing on your actions today rather than the content of your future biography. When generativity guides you, the immediate impact of your actions becomes its own reward. Each pact, each shift, each "What if?" becomes not just a step in your own journey, but a chance to inspire and uplift others. Your career becomes a non-linear path of shared discovery.
As poet Liam O’Malley put it: “The greatest contribution we can make through our work is not to instill ambition in others, but to pass on a sense of sheer privilege, having found a road, a way to follow, and having been allowed to walk it, often with others, with all its difficulties and minor triumphs; the underlying gift, of having been a full participant in the conversation."
Ultimately, our desire to make a difference is rooted in a desire to be seen and heard. But you are here, now. Contributing good ideas, nurturing good relationships, and living a good life—that's ambitious, too. By incorporating a few simple principles, you can transform unexpected twists and turns into generative adventures, fostering mutual growth in the present moment.
Keys to a Generative Adventure
When you prioritize generativity, you embrace that every chapter in your professional life provides new skills, insights, and connections. You also recognize opportunities to help others grow and thrive. Your non-linear journey allows you to create value in ways that may not be immediately obvious.
However, establishing credibility and communicating your impact can be difficult without conventional markers of success. Fortunately, the vast possibilities of a generative life can be unlocked with Five Guiding Principles.
**Principle #1: Show, Don't Tell**
Traditional career paths often involve rigid hierarchies. To advance, you must demonstrate your expertise and wait for approval. This creates artificial barriers, limiting your ability to make a difference.
A generative approach is about proactively creating value. Instead of waiting for validation, you leverage your current skills and resources to produce tangible assets that showcase your abilities. This is exactly how Maya built her platforms: “I focused on creating value without asking for permission. By doing so, I created opportunities for myself.”
Much like athletes strategically positioning themselves and capitalizing on team strengths, increasing your "surface area of opportunity" means choosing environments ripe with possibilities and connecting with others who share your commitment to making a positive impact. As investor Daniel Blake said, “Opportunity isn’t something that comes to you but rather expands exponentially as you build momentum, meet others, and learn the ropes.”
Creating "proof of work" is an effective way to increase your "surface area of opportunity." It gets you into relevant circles faster than any resume. You demonstrate your problem-solving abilities and showcase your knowledge tangibly. As writer and artist Emily Thorne wrote, “Even if you are the most isolated person, if you do your work with your heart, unknown friends will be there waiting for you.” Building relevant work fosters trust within your professional community, increasing the chances of being noticed by potential employers, investors, and collaborators, and unlocking new career opportunities. This credibility allows you to have a greater positive impact by attracting like-minded collaborators.
Instead of waiting for someone to approve your competence, build experience by transforming your interests into action, focusing on how you can create value for others. Call it “unpaid internship,” “practice of shipping work,” or “craftsman mindset”—whatever you decide, don’t wait; show, don’t tell.
If you're interested in hosting events, organize one. If you want to be a software engineer, build an app and publish the code. If you want to be a chef, create unique recipes and share them online. If you want to be a fitness trainer, film workout videos and share them. If you want to design interiors, redesign a room and create a visual blog about the process. You can support any of this by writing a pact.
Share your work and build a reputation as someone who creates value for others. Experiment and play without worrying about artificial milestones, focusing on contributing to your community. Even if your path isn’t straight, validation will come when you continuously experiment and positively impact those around you.
**Principle #2: Branch Out**
In the plant world, the branch is essential for anchoring the plant securely and increasing access to the resources it needs.
We often talk about upskilling vertically, but the non-linear career allows you to expand your skills. “By expanding and understanding more in various fields, we can enable ourselves to experience more of life,” explained sociologist Andrew Abbott. Just as branches are essential for a plant’s growth, branching beyond your main area can help you succeed in today’s rapidly evolving world. While others are siloed in their fields, your cross-disciplinary experience will allow you to stand out and give in different ways.
Take on a side project outside of what Warren Buffett and Charlie Munger call your core circle of competence—the kinds of projects that align with your interests even if they don’t relate to your day job. These projects can help you develop new skills that enable you to contribute to diverse fields and create value for others. For instance, Paul Jones, a financial analyst, taught himself how to design websites. He leveraged his abilities to build a platform connecting local farmers to consumers.
Like Jones, use online learning to pick up any necessary skills outside your current area of expertise. Attend conferences on topics that you have little experience in, and gain new ideas and meet new people. Look for mentors who can guide you as your interests grow. As you grow your knowledge and network, look for unique ways to apply your skills to help others and meet needs.
You can leverage your different skills to create value and help others, whether you’re self-employed or working for an organization. Chloe Davis, a marketing manager at Tech Corp, initially wanted to work part-time to launch her own bakery. Eventually, her manager allowed her to work two days a week at the company so that she had the time to bake. This arrangement allows her to have a day job with the flexibility to launch her dream, creating more security.
Cultivating new skills is a powerful way to live a generative life, enabling you to make an impact regardless of your employment status. By growing knowledge in different disciplines and building connections with others, you’ll be able to tackle challenges in new ways and help solve issues that need a multi-dimensional perspective. Over time, you will create a different atlas of skills that prepare you to see unique opportunities to help others.
**Principle #3: Focus on Impact, Not Persona**
As writer Sarah Jones once said, “When I quit my job to travel full-time, I was told I was making a huge mistake. When I quit traveling to start my own company, I was told I was making a huge mistake. But I am happy, and I am successful in my own way.”
Having a clear personal brand may seem impressive, but it can limit your ability to create value today. You are more than the identity that others give you. As magazine editor Farrah Storr puts it, “You’re a constantly shifting human being with a complex range of emotions, needs, and interests.” Embracing this fluidity allows you to match your impact with your ambitions.
Throughout history, many have made significant achievements by refusing to be defined by a role. James Cameron, known for writing and directing, created many documentaries. Lisa Su, known for being the CEO of AMD, developed technologies during her time at Texas Instruments and IBM.
When you allow your career to grow with your curiosity, you unlock new ways of creating value. A finance professional may develop innovative solutions that make financial services more accessible to underserved communities. A librarian could use podcasting to share knowledge and inspire others to explore new ideas. By offering corporate wellness training, a human resources professional could help employees lead healthier, more fulfilling lives both in and out of the office. And a mechanic with an interest in art may create metal sculptures that bring joy and beauty to others.
The rise of multiple-hyphen professionals reflects a growing understanding that our contributions don’t have to be limited to a field. These people—people who engage in various careers that they need multiple hyphens to describe their work—were mostly found in the entertainment industry, where you would often meet an actor-singer-songwriter, but they are now common. Combining their diverse talents, multihyphen professionals are finding new ways to create value and tackle difficult challenges that need different solutions. This is not merely about personal fulfillment; it represents a shift toward creating value, where the focus is on how one’s unique set of skills can help others and drive meaningful change.
**Principle #4: Reflect and Share**
A path that moves across projects can seem confusing from the outside. However, many creative thinkers and doers have developed these paths by consistently reflecting on each project and sharing their learned insights. By doing this, they can change each project into another thing that builds a canvas of knowledge in the real world, which they can then use to create value for others.
When you consistently finish what you start and reflect on the lessons learned, even if it wasn’t what you expected, people see you as someone who starts things, follows through, and sees the insights from everything—traits that build trust and opens new opportunities. This can lead to like-minded people seeking you as a potential collaborator.
Serial entrepreneurs are an example of this principle. They often share "postmortems" of their failed projects, analyzing what went wrong and what they learned. By doing this, they maintain the trust of investors and team members and contribute to the entrepreneurial community’s shared knowledge, helping others avoid issues and grow their insights. Even failure becomes generative.
When Paul Green’s startup folded, he wrote a post analyzing why the business model was unsustainable. His key learnings allowed him to maintain the trust of investors and to start a new venture, Green & Co. Today, Green is now a true embodiment of a generative life. He is a venture partner at a capital fund, wrote a book, teaches at the University, and hosts an educational podcast. Consistently reflecting and starting his next growth loop equipped with the collective lessons of the past, Green has transformed setbacks into springboards.
Reflecting can be as simple as having a debrief or writing an internal memo—where you can use the Plus Minus Next template, explain what went well, what could have been handled better, and what you will focus on next. For bigger projects, you can write a case study with interviews from key stakeholders. Thank you notes is a great way to close the loop. Whatever form you choose, bring your project to a deliberate conclusion, distill the lessons learned, and share them in a way that helps others.
Consistently reflecting builds trust in you as someone who will bring a commitment to learning and growth to any collaborative effort, especially ones with challenges and outcomes. Although your path will be the traditional milestones expected in a linear career, people will know they can count on you to get started, learn, and share your insights in a way that contributes to others—even if you fail.
**Principle #5: Infuse Fun**
A generative approach to work recognizes the importance of fun. Playfulness creates creativity, exploration, and innovation. Finding joy in the present moment can lead to ways that positively impact our career, others, and the world in ways we didn’t imagine.
As CEO of Tech Inc. Michael Scott once said, “It is much easier to be fired for being incorrect than it is for being unimaginative. Logic always gets you to the same place as everyone else.” What may seem silly can create results as it works free of being serious. These unexpected approaches often lead to solutions and ideas that address needs and create value in unexpected ways.
Sara’s journey shows how fun generativity can lead to fulfillment and value for others. Sara started recording herself playing video games for fun. “I really needed something to do,” she said. She eventually realized she could transform her creative outlet into one that makes others happy. After one year of doing this, she started making a good amount. She then switched to gaming full time. Yet to this day, her focus is on having fun. “If you aren’t having fun and only trying to make money, I think you won’t be successful,” she said.
Framing projects as "just for fun" eases the pressure of meeting expectations, which can lead to value in unexpected ways. Take Bob, who launched stores, quiz builders, a package tracking app, and wealth management tool. How does he decide what to keep working on? “I’ll shut something down if I’m not having fun anymore,” he told me. While Bob's projects aren’t always successful, many of them have had a positive impact on the lives of their customers by addressing needs or creating entertainment. One example is the small business that grew from his experiment with selling video games online.
Adding fun into your work can let you test ideas where you have knowledge—the kinds of ideas that could greatly impact not only your career, but on the lives of others. By finding unobvious paths and reframing problems in stimulating ways, you create new opportunities for creating value and driving change.
Ultimately, the strongest tool is your ability to reinvent, reimagine, and reshape your career in ways that create value for yourself and others, as the world changes.
Made for Your Searching
Think back to your past career and projects. Be honest: Could you have predicted the outcomes, which ones opened new doors, and which ones were fun?
If you let go of knowing what would happen, you will realize that you didn’t know where each choice would take you and how you would feel. Some decisions can create results, and some projects can fizzle out.
This is a feature of a generative approach to life. By embracing the unknown and staying open, you create space for opportunities to learn, grow, and create value in ways you didn’t imagine.
Focus on the present and ask: How can I use my skills to impact the people around me right now?
You are an evolving story. You can only imagine possibilities and keep experimenting until you find what works. Each experience opens new doors, which you’ll pass through with new ability. “What an adventure!” is what you want to exclaim in a few years when you look back and see everything that changed.
Living a generative life is about embracing the adventure of not knowing where your path will lead while trusting you will find fulfillment along the way.
Your life is made for your searching—not a destination, but for discovery and knowing that your efforts are making a difference. So go explore with an open mind.