Skip the Line - Find the Compass

A few years ago, I happened upon a post on social media that stopped me in my (virtual) tracks. It was a post by someone I followed referencing life-pondering questions from something called Passion Planner. As one does, I went down the rabbit hole. What I encountered was as life-altering as Alice encountering the looking glass.

But first, I need to back up.

In the late 90s, during the final years of my corporate life, I transitioned from a technical role into management. My job was to create a culture that encouraged "talent" (computer geeks) to stay put, even as startups were dangling massive incentives. I loved it. But I had already decided I wouldn’t stay in the corporate world—I was headed to seminary to become a full-time student again.

One idea managed to bridge those two worlds - "time management." It might sound dry and boring, but allow me to explain. When I arranged for a representative from Franklin Covey to speak to our corporate team, I felt like a fish who had finally found water. The logic captivated me—focusing on the "big rocks" (what is important) before the "little rocks" (the urgent but trivial) so that life actually fits together.

I can still see the presenter in my mind’s eye. Suit. Tie. Formal. Professional. An older white man. He was the picture of Authority. A year later, I invited him across the country to Princeton Seminary to share those same ideas in a very different context. Even though I was a bit of a rarity in my class - taking notes on a Palm Pilot - I felt there was something vital there for all of us. But, as happens, eventually the salience of time management faded. Theology, technology, and the sheer noise of life moved into the foreground.

Fast forward twenty years to that day on Instagram when I found Passion Planner. It was, at its core, just another planner. But the company was founded by Angelia Trinidad—a 23-year-old who describes herself as a queer, first-generation, Filipina-American, and a community-made millionaire.

In that moment my world turned on its head.

Trinidad created Passion Planner in her parents' garage after graduating from UCLA (Go Bruins!). Feeling lost, she designed a tool to help herself—and others—focus. She launched on Kickstarter, raised $48,000 from 2,000 people, and bypassed every traditional gatekeeper on her way to success.

In that moment, I realized something both shocking and painful: I had been waiting. 

I had been waiting in line. Waiting my turn. Waiting to be old enough, mature enough, ‘accomplished’ enough. I had spent years wondering when it would be my turn, unconsciously assuming that "the lead" only belonged to people who looked like that Franklin Covey consultant. I was waiting to become an older white man in a suit. Which was, of course, futile.

Angelia Trinidad didn’t just skip the line; she disregarded it entirely. I’ve come to call this a "St. Francis move"—not fighting "what is," but stepping to the side to build something more beautiful.

As a Gen Xer, I feel we occupy a unique "hinge" in history. We grew up before technology was ubiquitous; I remember the wonder of trying to figure out what exactly was the Thriller video when it first aired on MTV and the first time I heard the World Wide Web could let me "visit" the Louvre. We had to learn the curve that Millennials and Gen Z were born into. Perhaps that’s why the "External Authority" held such a grip on me—I grew up in the world of the ladder, while the world of the web was being spun beneath me.

Trinidad was the antithesis of my corporate guru. She posted videos in sweats from her living room. It was freeing, but it brought a sting of regret: Why did I spend all those years waiting for permission? Why had I stood there waiting in line? 

I was reminded of this today when I stumbled upon an essay by Amy Lea: The Era of the External Authority is Over.

"For a long time, we knew who to listen to... There was a ladder, and it was obvious. Climb it in the right order, follow the right people... and you would arrive somewhere that offered security. That era is over. The rules didn’t change. The game did."

Boom. That was the Franklin Covey vs. Passion Planner situation in one concise statement. The game of the "Ladder" has been replaced by the game of the "Compass."

Amy Lea writes, "The antidote is not more information. It is more you." Martha Beck calls this following your internal compass. But we aren’t often taught this. We are taught to look outward for our worth and our direction. To consult the authorities. The Authority.

What would have happened if, in the late 90s, I had been able to truly listen to that internal compass drawing me toward the "big rocks"? What if the Passion Planners of the world weren’t the exception, but the rule?

Theologian Howard Thurman famously said: "Do not ask what the world needs. Ask what makes you come alive. Because what the world needs is people who have come alive."

Being your own authority doesn’t mean arrogance or the dismissal of wisdom. As Amy Lea suggests, it means developing such a clear relationship with your own "inner knowing" that you can move through a disorienting landscape without losing the thread back to yourself. Your inner compass. 

For years, I looked at the "big rocks" and waited for a man in a suit to tell me where to place them.

But the suit is gone, the ladder is broken, and the line has dissolved. It is both a bit disconcerting but also incredibly liberating. It is time to stop waiting for a turn that was never going to be granted by an external power, and instead, finally, start coming alive.