One of my personal heroes, Jacqueline Novogratz, launched her second book this week. As the founder and CEO of Acumen, Novogratz is extraordinary for her achievements; but what has always taken my breath away is her vibrant, honest storytelling. When I was beginning to explore a career change a few years ago, I picked up her first book, The Blue Sweater. Its dedication alone brought me to tears, and by the end I was determined to start living for the causes, communities, and meaningful work that had the power to move me like that.

I decided to support small independent bookshops with my purchase of her new book, so I’m still waiting for it to arrive in the mail. To be honest, I’m feeling a bit impatient to get my hands on her words. Initially, I thought my impatience came from years spent as an Amazon Prime customer, blissfully forgetting that there was ever anything other than free two-day delivery. But no— my impatience comes from a deeper thirst: a thirst for wisdom from relatable role models.

We’re all looking for clues

As LinkedIn has become an industry standard, it’s common for people like me— early career with a graduate degree— to “research” those we admire for clues as to how they got there. Throughout my MBA program I’ve had numerous conversations with professionals and classmates who referenced something they saw on my profile, which they reviewed prior to speaking with me. I’ve done the same; it’s just common practice now.

Sometimes we examine the paths taken by our heroes in hopes that we can model our own choices after theirs. It’s how we feel we’ve come close to getting their advice on what to do next, especially if they don’t actually know who we are. The logic is as follows: If they did this then that and accomplished XYZ, then maybe I can also accomplish XYZ by doing the same thing.

It’s perfectly fine to collect information, but it doesn’t always give us the instruction we need. Earlier this week, my elder mentor pointed this out to me, but on a much more personal level.

He said, “Daisy, if you really want to make Brio [our startup] doable in the long-run, this is a wonderful time to revisit your strategy. Particularly if you’re planning on raising a family.”

Our current model requires extensive travel at least a few times a year, which is wonderfully adventurous for two married co-founders who love exploring the world. Yet as I turn 30 in September, I know he’s right. In fact, I’ve already been reflecting on what I will have to give up, put on hold, or de-prioritize if we have children— even one child— within the next several years.

I decided to respond to my mentor by referencing Novogratz. “She’s extraordinary regardless,” I said, “but I can’t help but notice she never had children. Maybe raising a family isn’t possible if you want to build an impactful organization and lead a movement while fully shouldering parenting duties.”

“That doesn’t have to be true,” he said, “and you can’t look to our generation for models anymore. You’re going to have to model to your peers, and let them model to you, what it means to lead an enterprise and potentially raise a family in this new world.

All I wanted was someone to follow

I had wonderful spiritual mentors in high school and college. But I was less clear on my ambitions, visions, and standards back then. As that clarity has increased, I’ve not found people with similar destinies who also seem to be doing things in a manner I want to emulate.

I know this sounds supercilious, but I don’t mean it that way. There are so many people around me who are worthy of my deep admiration, but their paths and priorities are entirely different from mine. I’ll be first to applaud them for their rigor, contributions, kindness, and integrity, but I have no desire to live their lives.

Before I started business school, one of my best friends gave me a small photo frame with poetry she’d handwritten on a card.

Caminante no hay camino, se hace camino al andar
Golpe a golpe, verso a verso

– Antonio Machado

Roughly translated: Wayfarer, there is no way; you make the way as you walk. Beat by beat, verse by verse.

No words have rung truer to me in the past couple of years. And yet there’s a grief in this— we want the comfort of someone who can tell us we’re on our way to what feels like our calling, yet we realize one day that the only ones who can show us the way… is ourselves. Sure, there is wisdom, hope, and everlasting joy to be found, given freely to us, but our steps and stories are unique and the way won’t be made until we’ve made it.

Hindsight isn’t just 20/20; hindsight is actually the only way to see the path at all.

Pointing signs and something shimmering in the middle

Back in college, I went to a discussion with N.T. Wright, a famous theologian. The place was packed with individuals of all faith backgrounds, eager to hear his reflections.

One person asked about apparent contradictions in the Bible— how do we know what’s true?

It was years ago, but I remember him saying something like this: “Sometimes you have to understand the words as signs pointing toward the truth. One is pointing this way, and another is pointing that way, and the truth is something shimmering in the middle.”

The metaphor is apt, I think, for those of us looking for answers and clear steps to take us where we think we want to go. All we have are signs— opening and closing doors, moments of inspiration, and the stories of those who’ve gone before— and therefore the life we live, the way we make, is something shimmering in the middle.

I suppose this means it’s easier to feel lost, to wonder if we’ve made a wrong turn. It also means that everyone experiences this, and perhaps we can help each other remember the signs that help us find our way again.

So I’d like to know — how have you gone about finding (or making) your way? What have you done when you’ve felt lost?