Day #021

A Letter from a Café in Lisbon

This isn’t a sermon – or a lecture. It’s a reckoning with myself.

Last week, when I was silent and offline for a bit – I found myself rewriting the same post five different times. Not because I was chasing perfection – if you’ve read this blog, you’d know that’s definitely not been my aim!

Rather – honestly – it’s because I wasn’t sure if I actually believed what I was writing or what I was doing anymore.

With my journey unalterably derailed, I was questioning the point of this experience entirely. With goals and objectives dashed, what was the point of going on? What was I doing – aiming to accomplish? If there isn't a larger aim - larger than simply a summer vacation - why not go home?

So I put the computer away to reflect and meditate. I focused on some side projects stared out into the ocean, and listened to inspiring podcasts interspersed with the melancholies of Radiohead.

Basically, in my sedentary state, I’ve been thinking about the journey of this summer, professional and personal efforts the last several years, relationships with family and friends, etc…

And I keep coming back to an important realization about myself: When it comes to life’s grand pursuit - unraveling life's deeper and holistic meaning - I’m not sure I can tell the difference between ambition and avoidance anymore.

What I mean by that is I’ve wandered life in many beautiful disguises – successful, busy, praised. All the right masks that I’ve been taught are the signs of a successful membership in Corporate America.

But I knew – I knew deep down that I was giving the best parts of myself to things that I didn’t agree with – things that didn’t really matter to me in the way they should. I was giving my horsepower, intellect, and effort to various professional and personal endeavors for the wrong reasons.

I was drifting.

And – now I feel a sense of emptiness about it all.

Anger, mostly directed at myself.

And shame, for time I’ll never get back.

Funnily enough though, the hard part isn’t actually acknowledging that I’ve been drifting – that’s not a difficult code to crack. Rather, it’s recognizing how much I liked it.

Drifting asked less of me.

It didn’t require any courage – there certainly wasn’t some great mystery being solved – it required compliance.

Yes, it asked for complicated problem solving, multi-disciplinary management, and complex strategic planning – but it didn’t ask for anything hard.

It didn’t ask me to invest my soul into the experience – just a lot of hours, a lot of travel, and a lot of meetings.

It asked me to sacrifice my pursuit of life’s meaning – and I willingly signed the contract. An annual salary and two weeks of vacation in exchange for my dreams of fulfillment?

Done. Give me the pen.

There’s something eerily addictive about motion without meaning.

We live in a world where it’s easy to stay busy – to answer another email, build another slide deck, post another thought. But movement is not momentum, and motion is not meaning.

As Seneca once wrote, “If a man knows not which port he sails to, no wind is favorable.”

And as I sit here – at a café I never intended to arrive at…at a time I thought I’d be somewhere else – the more I believe he is right.

It’s not that purpose has disappeared – we’ve simply made it harder to access. Beneath productivity apps, convenient diagnoses, Instagram reels, and “next quarter’s goals.” Under layers and layers of convenience.

In many ways, life has become easier. On the positive side, most of us no longer chase food or shelter or survival.

Instead, we chase preference: A better option. A faster path. A safer bet.

We’ve replaced hard, focused effort with frictionless activity. We say yes too much, and no to almost nothing. And we wonder why we feel scattered, anxious, quietly guilty – like a boat with no keel, spinning in every direction but forward. 

In my generation, there’s this myth of the single big push.

Somewhere along the way, we’ve developed the lie that a single moment of effort – a flash of brilliance, a sprint toward success – can replace the slow accumulation of discipline.

We celebrate the “overnight success,” forgetting that it took ten years to become one. We idolize the podium but forget the mornings we never saw – the ones when greatness came down to nothing more than showing up. Trying again. Failing. Not quitting.

Because the truth is: Purpose is not a revelation. It’s not an epiphany. It’s repetition. A rhythm. A refusal to stay on the ground. Time and time again.

We rarely talk about fear.

Certainly not the loud kind – panic, chaos. But we tolerate the small, subtle kind.

The kind that keeps us playing small. Thinking small. Living small.

The kind that tells us to only pick the games we know we’ll win. To stay where we’re praised, where we’re polished, where we won’t embarrass ourselves.

We have trained ourselves to believe safety is the best option. We are so afraid to get hurt, to fall, to fail - that we forget how to be free. To do hard things.

We curate instead of commit. We perform instead of pursue. We stay good at the many – instead of becoming masters of a few.

We spend our lives in open tabs – multitasking our way to our next paycheck.

Here’s what I’m appreciating now: I can’t dock at every shore – I can’t perfect every skill. I can’t live every life.

At some point, I have to choose my direction – or be lost, drifting, caught in the paths of everyone else.

It's simple: choose to be me - the man that I want to become - or choose safety.

Seneca doesn’t promise that life will make this choice easy. He simply reminds us: The winds will come. The current will shift.

And that’s what it means to live a story. To chart a course. To become something other than just happy – to become fulfilled. At peace.

The irony – of course – is that the port is not a place. It’s never just a location. It’s not a job title or a net worth or a finish line.

It’s an attitude. It’s a way of being. A story we write with conviction. It’s who we become on the journey – and what we’re willing to endure as well as leave behind.

Not everyone will understand your journey – not everyone will applaud your sail. But that’s not the point, right?

The point is simply: Name your own port. Name your own direction – your own aim.

And go. With a full heart. Conviction. Clarity.

Show up every day – even when the wind disappears – and journey on. Resilient. Gritty. And smiling.