Lesson 3: Ready Already

Readiness isn’t a feeling. It’s a decision.

We talk about being “ready” as if it’s something that happens to us, like a wave that finally reaches us and sweeps us into action. But readiness is just a choice. It’s the courage to say, I’m going to move forward. Or, more often than not, I’m going to move forward even though... [insert all the reasons you think you shouldn’t].

There will always be reasons to stall. Always. At any given moment along the trajectory of our careers, we can make a list of all the reasons we’re not ready for the next step. Sometimes those reasons hold truth and can help us troubleshoot for growth. Usually though, they’re excuses.

Worse, those lists of reasons are like mythic hydras; when we finally feel good enough to cross off a reason and give ourselves permission to move forward, another reason (or a few) jump to take its place. You’ll feel too young one day, too old the next. Too inexperienced, then later, your extensive experience might feel irrelevant. Too busy to start now, too idle to have momentum later. Too visible, too invisible. Too early in the process to be taken seriously, too late in the game to begin.

Twenty years ago I could’ve made quite the list of reasons I had no business launching a start-up. Actually, others made the list for me (literally). In a 2007 blog post, Guy Kawasaki, chief evangelist at Canva, bestselling author, and much else, made one of all the jobs I’d never had pre-Kiva:

“What would the ideal background be of the founder of Kiva? Investment banker from Goldman Sachs? Vice president of the World Bank? Vice president of the Peace Corps? Vice president of the Rockefeller Foundation? Partner at McKinsey? How about temporary administrative assistant at the Stanford Business School? Because that’s how Jessica started her quest.”

Ouch? In the end, Guy celebrated Kiva and my path, urging others to “bank on unproven people.” We joked about this entry last year at Masters of Scale, and I told him I’d forgiven him by now - and thanked him for seeing potential in a story that didn’t fit the mold.

I’ve come to see that list as a kind of compliment and proof that readiness was never about having someone else’s idea of the “right” background. It was about saying yes before the evidence suggested I should.

You rarely have to wait to move forward until after you have a long list of accomplishments or a perfect plan. Ready means setting the list aside and taking a step anyway. You don’t prepare your way into purpose; you act your way into it.

And if you insist on trying to tap into that readiness feeling - catching that wave - my best advice is to redefine it. Teach yourself to associate feeling ready with movement, not with standing still in preparation. Think about the thousands of tiny choices you’re making every day, nudging progress again and again.

You’re ready and already in motion. Maybe the motion is invisible, as your thinking evolves, as the next right question settles in your mind, as observations that once seemed random start to connect and become insights. Maybe the motion is small but meaningful: sending the email, making the phone call, sketching an idea that felt like it didn’t matter, but now that it’s on paper, stares back at you and tells you that it does.

You don’t have to have it all figured out to feel ready, and certainly not to be ready. You just have to keep choosing action: one half step, one brave act, one moment of motion at a time.

You’re ready already. You’re ready now.

Lesson 2: Start With Who

With apologies to my friend Simon Sinek, well-known for helping people tap into their inspiration and purpose by reminding us to “Start With Why,” I’d like to suggest a different starting point. 

Simon argues that all organizations can explain what they do; some can explain how they do it; but very few can clearly articulate why they do what they do. When organizations (and individuals) can articulate this, he believes they will tap into an abundant source of inspiration. (Of course I think Simon’s a genius, and agree generally that a company’s Why is more meaningful than the What or How.)

But I start with Who.

Growing up, as I learned about poverty near and far, it broke my heart. Over time, that heartbreak became a passion to understand the lives of people living with severe economic disadvantage. Specifically, I became fascinated by entrepreneurs working in these conditions - goat herders, fishermen, seamstresses, farmers, brick makers, rickshaw drivers. 

I fell in love with those individuals, one after another, and their awe-inspiring stories: how proactive and full of hope they were, how creative, hard-working, resilient they continued to be, even in the face of so much hardship. 

My language of “falling in love” here is extremely intentional. And while I haven’t seen many love stories on LinkedIn, I think lots of us fall in love, in a way, with the people we serve and the work we do for them. This is a very good thing. Because love is a real advantage if you want to be an innovator.

Love changes how we see the object of our fascination - the Who. We see the best in them. We see strengths, ingenuity, dignity. We look more closely at their rhythms and constraints, notice tiny details that reveal real needs, listen to every word and the quiet between the words. We linger with them, matching their pace, showing up when it matters, letting them set agendas and timelines. Love anticipates on others’ behalf: we look to remove friction before it hurts, prepare what will help next, design for agency, and safety. And love makes us brave! We advocate, defend, and boldly challenge rules for those we love. We protect their time, privacy, and power. 

The more time I spent with people I wanted to serve, the more I came to love them, and the more I could begin to understand what they wanted and needed. The more I understood, the better I got at being helpful. And eventually, I was ready to build something real, something that expressed all of that love.

My life has been awash in love - the greatest of myriad privileges - and now I’m hardwired this way. More than anything else, love has helped me see and understand details that others missed.

One final note. Sometimes the Who - the people, the community, the idea you fall in love with - won’t make logical sense. They might not fit the strategic framework you built in class or the funding model investors expect. They might not be what you expected. They might not even be able to pay (gasp!) for what you build them. None of that matters. Follow the love anyway. Follow the Who. It’s an invitation to find the work that needs to belong to you. 

Lesson 1: Listen to Yourself

“The first and most important act of building anything meaningful - a company, a movement, a career, a life - is to get radically honest about who you are and what you truly care about. Not what looks impressive, not what’s trending, not what someone else thinks is good, but what actually moves you.”

Everything good I’ve ever made or been a part of started with listening to the people I wanted to serve.

Or did it?

I’ve talked a lot about how hearing the incredible stories of entrepreneurs in East Africa, and trying to understand their needs, was the start of the most important insights that would lead to Kiva. In many ways this is true. The amazing rural entrepreneurs I met across Kenya, Uganda, and Tanzania through an internship with Village Enterprise - my big break, the first time I’d really gotten to work in the field - inspired so much.

But before I boarded a plane, I had to quit my job at Stanford. Before I quit my job, I co-created my dream work assignment with Brian Lehnen (thank you Brian!), founder of Village Enterprise. Before Brian gave me that assignment, he met with me a dozen times, patiently listening to me share my ideas and dreams. Before he met with me, I had to cold-call him to ask for an informational interview. Before I cold-called him, I had to figure out what I really wanted to do most in the world, which was to learn more about microfinance from borrowers themselves. Before I knew what that was, I had to crash the lecture where I would first learn about microfinance from Dr. Muhammed Yunus, who visited Stanford one evening in the fall of 2003 and gave a last-minute talk to about 30 people (this was three years before he’d win the Nobel Peace Prize). And before I crashed that lecture, I had to know I wanted to stay late after work and go. I had to be so curious, curious enough that for years I was searching and seeking and praying and journaling and wondering and reading and trying really, really hard to know what I wanted.

Before we can listen to others, we have to listen to ourselves.

The first and most important act of building anything meaningful - a company, a movement, a career, a life - is to get radically honest about who you are and what you truly care about. Not what looks impressive, not what’s trending, not what someone else thinks is good, but what actually moves you.

I’ve tried working on things that I didn’t fully believe in, projects that looked great from the outside but felt slightly off inside. It just never works. When you’re not aligned, when you’re spending the best of yourself on something that doesn’t feel right to you, it will drain you instead of energize you. No amount of effort or cleverness, no matter how strong others’ opinions are about what you’re doing, can make up for that. In the end misalignment isn’t just uncomfortable, it’s a waste of your time and talents.

Because here’s what I’ve learned: you can set big, noble goals and even reach them - but if they don’t align with what you value most, you won’t feel like you’ve succeeded. And the opposite is also true. When your actions are in harmony with your deepest values, even if you fall short of your goals, there’s a steadiness, a peace, that feels like success because the way you’ve been living is already an expression of what matters to you.

When we first started Kiva, I thought I was motivated to help others. But what I was really doing was listening to what pulled at me. My intention wasn’t to start a global platform; it was simply to respond truthfully to the human beings I had come so far to learn about and from. Before anything official had begun, I was already doing what I cared about most. Even if Kiva had never happened, or if it had stayed a small local project, I would have felt deeply grateful for the privilege of getting to do what I loved.

When you begin from a place of authentic passion, the work itself is the reward. Anything that unfolds beyond what you can control because of that work - like when so many others fall in love with what you’ve fallen in love with too, which happened with Kiva - is the gift of a lifetime.

Twenty Years, Twenty Lessons

This month marks twenty years since we launched Kiva. As I look back, I’m realizing I’ve been collecting lessons all along - but without intending to, I’ve kept so many of them to myself.

True, I’ve given hundreds of talks, written a book (shameless plug: the second one’s out in two weeks!), and spent countless hours with students, but there are still so many ideas and insights I’ve never shared out loud.

So I’ve been thinking about those quieter revelations: digging through old journals to unearth insights I’d tucked away, revisiting advice given in private to fellow founders and friends, reflecting on those early days and everything that’s happened since. I’ve learned so much not just about entrepreneurship, but about intention, purpose, and what it means to build a life and career that truly align with what you value most.

I’ve also felt a strong pull to reconnect with writing. It’s the best way I know how to make sense of things and clarify what matters most.

Over the next twenty days, I’ll be sharing twenty short lessons from Kiva and beyond. My hope is that they spark thought, honesty, and maybe a bit of courage for anyone on their own path to doing meaningful work.

Here’s to going back to the beginning again.