Chapter Content
Okay, so, you know, I was thinking the other day about, um, careers, and how we kind of, like, expect them to be this straight line, right? But, uh, it's really not always the case. Like, did you ever hear about Giorgio Armani? Started out in freakin’ medicine! And then, boom, world-famous fashion designer. Or Harrison Ford? Like, the guy was a carpenter for fifteen years before Star Wars happened! And, get this, Pope Francis, uh, apparently, he was a bouncer at a nightclub before… becoming the Pope. I mean, come on!
It’s, like, we *love* those stories that make sense, that have a clear narrative, but honestly, a lot of really cool success stories, they're just… all over the place. It’s not a straight line. It's more about curiosity and community, you know? Not just sticking to one path. Every twist and turn gives you, like, unique insights that you can use later.
Take Ben Tossell, for instance. This guy is a perfect example of how just being curious and helping other people can lead to a really fulfilling life, even if it's… unexpected. He was pitching a mobile app to pubs in London, didn’t sell a single one, did some social media ads, even helped out at his dad’s law firm. Then, around 2015, he found this website called Product Hunt, which is, like, this online hub for tech nerds to share their projects.
And every day, there were, like, tons of products launching, from little prototypes to full-on platforms, all trying to get their first users. And there was this whole community growing there. Tossell was super into it. So, from his home in Cardiff, he started, uh, transcribing interviews with startup founders and, like, promoting other people’s projects. He said he just wanted to talk about ideas and connect with others who were building stuff. And, eventually, Product Hunt hired him to work with their European audience.
So, he's an employee now, but he didn’t stop being creative. Instead, he started messing around with side projects, like a chatbot and an AI art generator. And then, he got into the whole no-code thing, you know, building stuff without needing to code. He realized how powerful these tools could be, and he created Makerpad, which is a platform teaching people how to build digital products without code.
His goal was to empower, like, a new generation of makers. Makerpad took off, letting thousands of people bring their ideas to life. It all came from his curiosity and wanting to help others, and it just kept growing. He even got funding to make the platform bigger. And in 2021, Zapier, that’s a huge company worth like five billion, they acquired Makerpad.
Then, with the rise of ChatGPT, the AI boom, Tossell saw another opportunity to contribute, you know? He started writing Ben’s Bites, which is an AI newsletter. He wanted to help people navigate this crazy, fast-moving world. He was like, "How do I learn from everybody? How do I get in the room with these people? How can I play a small part here in doing something that could be helpful to people?" So he started curating AI news.
And again, his curiosity was contagious. The newsletter got over a hundred thousand subscribers in its first year! And who knows what he’ll do next? Even *he* doesn't know, and that's kind of the point, right? He doesn’t have a set plan. He just moves towards what he's curious about, where he can grow, who he wants to grow with, and how he can help others. That's how progress is defined, not just by what you learn and earn, but by the impact you create.
If you let go of the idea of a fixed career, you might end up on a really winding road. But each bend brings new experiences, lessons, and chances to connect with the world. Your curiosity and the people you meet push you outside your comfort zone. And your willingness to adapt becomes, like, a superpower for navigating the uncertainties of life. By looking for ways to contribute, you get satisfaction *now*, not just when you retire or something.
It's a great way to live your life, but it can be tough. How do you do this in a world that wants everyone to have a nice, neat little label?
Okay, so, we often look for meaning in our job titles, promotions, degrees, or possessions. But that never really fills the void. It keeps us chasing the next thing, always looking for that one accomplishment that will secure our "legacy," right?
But thinking about legacy can actually hold you back, especially if you're on an unpredictable path. Legacy is, like, the ultimate "end game," and it makes you prioritize what *other* people think is important, not what *you* think is important. It also makes you focus on scale. Not what you built, but *how big* you built it.
So, instead of focusing on legacy, focus on generativity. It's about using your personal growth to make a positive impact *now*. It’s about contributing to your community, creating opportunities for others, and sharing your experiences.
Generativity isn’t about scale, it's about the *depth* of connection in the here and now. The conversations you have, the work you produce, the lives you touch. It's about the mentorship you offer, the knowledge you share, the support you give. These small actions make a real difference in people's lives.
That's how you find meaning: by focusing on what you do *every day*, not on your future eulogy. When generativity is your focus, the immediate impact of your actions is all the motivation you need. Every choice becomes a chance to inspire and elevate others. Your career isn't a ladder, it's a journey of shared discovery.
As someone said, maybe the best thing we can leave behind isn’t ambition, but a sense of privilege, of finding a path and being allowed to walk it, with all its ups and downs, and being a full participant in the conversation.
Deep down, we want to have an impact, to be able to say, "I was here." But you *are* here *right now*. So, contribute good ideas, nurture good relationships. That’s ambitious, too. By using a few simple keys, you can turn your twists and turns into adventures, helping you grow with others, right here, right now.
So, when you live a life of generativity, you realize that every bend in the road gives you new skills, knowledge, and relationships, plus new chances to help others grow. You can create value in ways that others might not see at first.
But, it can be hard to show your value without the usual markers of success. That's where the "Five Keys" come in, they can help unlock the possibilities of a generative life.
Key number one: Do the work *first*.
In a typical career, you need to prove you're ready for the next step before someone will let you take it. That creates artificial roadblocks and limits your impact. Generativity is about *proactively* creating value. Instead of waiting for permission, use what you have to show what you can do.
That’s what Tossell did. He said he was doing "proof of work" because he didn’t have any credibility in the startup world. By doing that, he got more opportunities.
Think of it like athletes who position themselves strategically, anticipate the game, and use their team's strengths to make game-changing plays. Increasing your "surface area of luck" means choosing places full of opportunity and connecting with people who want to make a difference. One investor said that luck grows faster when you meet more people, make more connections, and learn patterns.
So, show your problem-solving skills and your knowledge. If you do your work well, people will come find you. Consistently doing good work builds trust in your community, which increases your chances of being noticed and unlocks new opportunities. It also helps you attract collaborators who share your values.
Instead of waiting for approval, turn your interests into action and focus on how you can help others. One designer calls it a "permissionless apprenticeship." Others call it "shipping" work or having a "craftsman mindset." Whatever you call it, don't wait, just do it.
If you like event planning, organize an event. Want to be a software engineer? Build an app. Want to be a chef? Share your recipes online. Want to be a trainer? Film workout videos. For interior design? Redesign a room and create a visual blog.
Share your work and build a reputation for creating value. Play and experiment, don't worry about hitting milestones, and focus on how your work can help your community. Even if your path isn't straight, people will recognize your value when you put your work out there and make a positive impact.
Key number two: Grow lateral roots.
Like plants use lateral roots to get more water and nutrients, a generative approach helps you expand your skills sideways. Someone explained it like this: By bringing more experiences into our understanding and expanding our understanding to embrace more things in complex ways, we allow ourselves to experience more of life. Branching out beyond your main area of expertise helps you thrive in today’s fast-changing world. While others stay stuck in their field, your interdisciplinary experience will help you stand out.
Take on a side project outside your "circle of competence," something that aligns with your interests even if it's not directly related to your job. These projects can help you develop new skills that help you contribute to different fields. A software developer taught himself how to 3D print concrete sculptures. He sells mini replicas of famous monuments and busts of influential people and makes art and history more accessible.
Use online learning to pick up new skills outside your field. Go to conferences on topics you don't know much about to learn new things and meet new people. Find mentors who can guide you as your interests change. As you learn and connect, look for ways to use your skills to help others and address unmet needs.
You can use your skills to create value whether you're self-employed or working for someone else. A VP at a music company wanted to pursue coaching but was offered a hybrid role. She spends half a day each week coaching her colleagues, helping them grow while still keeping her job. She said, "I thought, surely there's no way I can explore coaching while keeping my day job?" We rarely have those conversations because we don't think this model is available to us."
Cultivating lateral skills is a powerful way to live a generative life, allowing you to make an impact no matter your employment status. By expanding your knowledge and connecting with different thinkers, you can approach challenges in new ways and help solve complex problems that need different perspectives. Over time, you'll create a unique set of skills that helps you spot opportunities to improve the lives of others.
Key number three: Prioritize impact over image.
One author said that when she quit her job to be a mother, people thought she was crazy. When she quit it again to be a novelist, they said it again. But she said, "I am not nuts. I am happy. I am successful on my own terms. Because if your success is not on your own terms, if it looks good to the world but does not feel good in your heart, it is not success at all."
While a clear personal brand might seem good in the short term, it can limit your potential to create value now. Success comes from following a path that allows you to help the world around you, even if it doesn't fit society's expectations. Someone said that you're not a product, you're a constantly changing human being with many emotions, needs, and interests. Embracing that fluidity helps you adapt and align your impact with your true ambitions.
Many people have made important contributions to society by refusing to be defined by one role. An actress explored her interest in technology and co-invented an early version of wireless communication. A figure skater and journalist became a fashion designer in her forties and brought a unique perspective to the industry. Someone who began in data storage has used his experiences in entrepreneurship, writing, and investing to share advice for personal growth with millions.
When you let your career evolve with your curiosity, you find new ways to create value for others. A finance professional could develop solutions to make financial services more accessible to underserved communities. A librarian could use podcasting to share knowledge and inspire others. A human resources professional could offer wellness training to help employees live healthier lives. And a mechanic with an interest in art could create metal sculptures that bring joy to others.
People who have multiple talents and interests are finding new ways to create value and address complex challenges that need different perspectives. Having multiple jobs isn't just about personal fulfillment, it's about a more generative approach to work, where the focus is on using your skills to help others and drive meaningful change.
Key number four: Close the loop to open doors.
A career that zigzags through different experiments can seem confusing. But innovative thinkers have built non-linear careers by always closing the loop on each experiment and sharing what they learned. That way, each experiment builds up to a foundation of expertise that they can use to create value for others.
When you finish what you start and reflect on the lessons, even if it didn't go as planned, people see you as someone who takes initiative, follows through, and learns from every experience. Closing the loop shows that you're dependable and accountable, and that you can help others navigate similar challenges. This builds trust and opens doors to new opportunities. It can lead to more like-minded people seeking you out to collaborate.
Entrepreneurs often share detailed "postmortems" of their failed businesses, analyzing what went wrong and what they learned. This helps them keep the trust of their investors and team members, and it also helps others avoid similar mistakes and build on their insights. Even failure becomes generative.
One person's startup failed, but he wrote a postmortem analyzing why the business model was not good. Because he shared his key learnings, he kept the trust of investors and was able to take the company's team and what was left of their funding to start a new venture. By reflecting and starting his next project with the lessons of the past, he has turned setbacks into springboards.
Closing the loop can be as simple as hosting a debrief meeting or writing an internal memo at work, explaining what went well, what could have been better, and what you will focus on next. For bigger projects, you could write a case study including interviews with key people. Sending thank-you notes is also a great way to close the loop. Whatever you do, the goal is to bring your experiment to a clear conclusion, learn from it, and share it in a way that helps others.
Consistently closing the loop builds trust in you as someone who will bring a commitment to learning and growth to any collaborative effort, especially those with difficult challenges and unclear outcomes. Even if your path doesn't feature the milestones of a traditional career, people will know they can count on you to get started, learn as you go, and share your insights in a way that helps others, even if you fail.
Key number five: Play along the way.
A generative approach to work recognizes the importance of playfulness. Playfulness encourages creativity, exploration, and innovation. Finding joy in the present act of working can lead to discoveries that help our career, others, and the world in ways we might not have imagined.
Someone said that it's easier to be fired for being illogical than for being unimaginative. Logic always gets you to the same place as your competitors. What seems silly can lead to transformative results because it operates without the constraints of seriousness. These unconventional approaches often result in solutions and ideas that address unmet needs and create value in unexpected ways.
One person started baking cakes and filming them for fun. She needed a creative outlet. As people started asking how they could order her cakes, she realized that her hobby could become a way to create joy for others. After about a year, she started making a decent profit. After four years, she switched to baking cakes full time. Yet to this day, her focus is on having fun. She said that if you don't enjoy it and are just trying to make money, you're not going to be successful.
Framing experiments as "just for fun" takes away the pressure of meeting certain expectations, which can lead to creating value in unexpected ways. An entrepreneur has launched dozens of ventures, including an action figures store, a quiz builder, a package tracking app, an online community for pug owners, a wealth management tool, a music industry simulation game, and handmade homewares. He shuts something down if he's not having fun anymore. While not all of his ventures were huge successes, many of them have positively impacted the lives of their customers by addressing unique needs or providing entertaining experiences. One example is the small but profitable business that emerged from his experiment with laser-engraving tweets into wood.
Injecting playfulness into your work can free you to test ideas where you have limited knowledge, the exact kinds of ideas that could have an important impact not only on your career but also on the lives of others. By exploring unusual paths and reframing problems in entertaining and intellectually stimulating ways, you open up new possibilities for creating value and making a positive difference in the world.
Ultimately, the most powerful tool you have is your ability to reinvent, reimagine, and reshape your career in ways that generate value for yourself and others, as the world around you changes.
So, think back on your past decisions and projects. Be honest: could you have predicted which ones would go well, which ones would fail, which ones would open new doors, which ones would be fun, which ones would be a pain?
If you can free yourself from thinking you knew what would happen, you'll realize that you had no idea where each choice would take you and what the journey would be like. Some of our most harmless decisions can lead to surprising results; some of our most exciting projects can fizzle out.
This unpredictability isn't a bug, it's a *feature* of a generative approach to life. By embracing the unknown and staying open to serendipity, you create space for unexpected opportunities to emerge to learn, grow, and create value in ways you may not have imagined.
Focus on the present and ask yourself: How can I use my skills and experiences to positively impact the people around me *right now*?
You're an evolving painting, an unfolding story, a great work in progress. All you can do is imagine a world of possibilities and keep experimenting until you find what works. Each experience, whether successful or not, opens new doors, which you'll pass through with new skills and wisdom. A few years from now, you want to look back on your path and see all the wiggles and question marks that show you took an experimental approach to life.
Ultimately, living a generative life is about embracing the adventure of not knowing where your path will lead while trusting that you'll find fulfillment along the way. Someone wrote that though life is short and sometimes dark, the beauty to be found offers a constant source of wonder to those who seek it.
Your life is made for your *searching*, not for a set destination, but for the joy of discovery and the satisfaction of knowing that your efforts are making a positive difference in the world. So, go forth and explore with an open mind and a generous heart.