Daily Endeavor Blog

Instant flashes of insight and overnight success are often a product years of exploring and listening. The important bit is having the self-awareness that a search for what you want to do in the world is indeed underway and actively making observations about it.

Jessica Jackley Flannery’s story is an impressive illustration of someone sharp pursuing their own path, even when all the steps were not visible.

In the Stanford Social Innovation Review article “How I Became a Social Entrepreneur”, we learn Jessica co-founded Kiva, the first peer-to-peer microlending Web site, and believes that microfinance, relationships, and stories are powerful tools for change. She’s right.

Because she did a great job of looking back on her path, we can also see some of the moments that led up to her making the leap:

I remember first hearing the term “social entrepreneurship” in a lecture…I was instantly intrigued. I wanted to be a social entrepreneur!..But doing what, exactly? I had no idea. The motivation, values, and energy were all there, but the specific context was missing. This was a problem…I felt like someone who…dreamt of going to the Olympics but hadn’t chosen a sport…So my task became choosing a context, and finding my one, specific mission.

She goes on to provide some really solid advice that’s worth following:

Learn: Read, research, write, etc. Go to lectures. Absorb whatever you can on the topics that interest you. Get an idea of what the issues are. Take a class or just make up your own little reading lists and assignments if you love structure.

Listen: Reach out to a real, specific, human being who could be your “customer” (someone whose problems you want to understand, and who you’d like to serve by addressing those problems). Listen very carefully. Learn as much as you can. Then, reach out to another person, then another, then another. (Read Paul Polak’s amazing book, Out of Poverty, for much more on this concept!)

Ask: As you start to amass questions and can’t find the answers yourself, reach out to people who might. Get their opinions, their insight, their advice. Learn how their organizations work, what problems they face, what challenges and successes they’ve had. A special note: There are many ways to be entrepreneurial and create significant social change without starting your own organization. Sometimes you can be more effective at doing the specific thing you want to do in the world by joining an existing group or project, and revolutionizing from within.

Jump: At a certain point, you just need to start pursuing what resonates with you. Follow it as best you can, wherever it leads. It’s OK if you don’t know what the next five steps are. It’s enough to take one step in the direction of your interest. Sometimes you can only find the second step after you’ve taken the first one.

Keep Dreaming: Kiva represents my wildest dream of what I wanted to do in the world. And it’s happening! I couldn’t be more thankful for this. But something else is happening too: The faster Kiva goes, the more it grows, and the more I’m convinced that other great changes are possible in the world. I hope never to stop dreaming, preparing, and being ready to see what’s next.

Place Jessica Jackley Flannery in the group of people who discovered her way into doing what she loves.

How do you know if you’re on track toward doing something that you love? One of the best indicators is whether you’re looking forward to getting in there for the next day/session/read/write/etc. Looking forward to something of course doesn’t mean it will be easy or pure joy. Plenty of people have moments of anticipation for simply getting through the hard part, if only for continuing on toward their goal (taking the Bar exam, for example).

Nevertheless, there are some strides that people hit where looking forward is an expectation of doing something that truly turns you on. This is not dissimilar to Mihály Csíkszentmihályi’s work on flow.

As I was reading Daily Routines‘ posts, the one on Ernest Hemingway struck me as an illustration of exactly this feeling.

You write until you come to a place where you still have your juice and you know what will happen next and you stop and try to live through until the next day when you hit it again…nothing means anything until the next day when you do it again. It is the wait until the next day that is hard to get through.

Put Hemingway in the group of people who discovered his way into doing what he loved.

• Dream Delayed for Financial Security: A second act story (WSJ)

• The Universal Declaration of Human Rights: The society in which you live should help you develop (Youtube)

• Marissa Mayer’s Simple Advice On Who To Hire: Smart people who get things done (Techcrunch)

• Ask Annie: ‘Dilbert’ on how to save your career (Fortune)

I’m excited to share we’ve opened the first seats for the Core Course in 2009 at Endeavor Prep. The first course is January 6, followed up the second beginning February 10. It’s been a great experience so far and I’m really looking forward to what we have lined up for the new year.

If you’re graduating soon and thinking about what to do, or if you’ve been out a few years and starting to get the quarter-life itch to carve your own path, I hope you’ll join us. To get some flavor, see what others have been saying.

On September 11, 2003, I made a guest post on my friend Ross’ blog. What’s transpired since then is a long and varied tale, but in many ways centers around the very question in that post:

Tell me, what is it you plan to do with your one wild and precious life?

For me, the answer to Mary Oliver‘s venerable question can be distilled to: Don’t settle, do what you love. It’s one of the true engines that powers people’s lives and the economies and world we live in.

This blog is going to tell a story. It’s going to take a few years because, as it turns out, it’s a story that’s never been written before. It’s the story of how 100 million people sought out and did what they loved.

Here’s where the story starts. There are three parts that you need to know.

First, who? There is a tremendous force arriving on the scene, and at just about the right time. It’s the sheer creative force of people coming into their own. Maybe they’re 24, or maybe they’re 19. Maybe they’re your friend, your brother or daughter. Or maybe it’s you. This great wave of individuals goes by many names (Millennials, Gen Y, Net Gens, you name it). The labels are not so important, it’s the individuals that are at the center of the story — who they are, and what they choose to do. This generation is going to re-shape the world as we know it. It’s already begun, and it’s fantastic.

Second, have you ever wondered why is it some people truly thrive in their work life, while others do not? This is the question we set out to answer as part of a research project at Harvard over three years ago. The pattern we found isn’t a lack of talent (there is tons) or opportunity (there are more types of jobs today than ever before). We found most people never discover what they truly want to do. Too many people settle. That’s a problem — not only is there great cost to the individual (“wow, my job really sucks”), but also to their companies, colleagues and the economy.

Consider the alternative. What if more people found a career path of genuine interest, however they define it? What if more people were able to find work that lit them up — how would their lives be different?

In our experience, these people excel, and not just economically. These people have more opportunities to grow and more ways to — dare we say it — be happy. They make better colleagues, managers, entrepreneurs, and probably neighbors too. Because they’re working from abundance, not scarcity, there’s an unmistakable productivity that’s unleashed.

As a result, we set about addressing the unmet need — helping people answer the question “What do I want to do?” –  which led us to develop Endeavor Prep, the career search prep course.

Lastly, why now? Most people (96% when we asked) want to find the right job for them, yet many (too many) people wake up at 30 or 50 and say “I guess this is what I do.” Figuring out what you want to do is a crucial rite of passage that, crucially, many people are missing. It’s not something to figure out in one hour, or even in one job. It’s an iterative process that you can learn. Because it’s iterative, tremendous gains accrue to those who start early. We want those gains to accrue to  you. In fact we want them to accrue to the entire generation.

Plain and simple: We want to see 100 million people thrive.

Though we’ve been at it for a while, we’re just getting started. And we can’t do it alone. I hope you’ll come along for the ride.