Practicing a Life You Love

A conversation with Lonny McLoughlin

Artist, coach

How letting go of the life he had built brought Lonny McLoughlin to Porto—and opened the door to art, love, a different relationship with aging, and a new understanding of what it means to create a life.

“What does it take to love your life? What does it look like to love your life?”

Watch the Conversation

About this conversation

At 67, Lonny McLoughlin moved to Porto alone.

He had stepped away from his career as a coach and consultant, let go of many of the things that had defined his life, and arrived with a fairly simple idea: live in Portugal for a year, study art, write, paint, and see what happened.

He was also carrying a question.

Years earlier, Lonny had encountered a line in a book: What does your soul want?

He wasn’t even sure he believed in a soul. But he couldn’t stop thinking about the question.

Eventually, three answers emerged: beauty, art and legacy.

Those answers became part of what brought him to Porto.

What happened here wasn’t exactly what Lonny planned.

He discovered how deeply he had connected his value to productivity and accomplishment—and how difficult it could be to simply be when those familiar measures disappeared. He found his way back to painting, sometimes one brushstroke at a time. And he began creating structure around the things he wanted his life to contain rather than the things he thought he was supposed to achieve.

Portugal also changed the way Lonny experienced other people. He noticed the conversations that happen in grocery stores, strangers saying good morning on the street, and a culture that seemed to make more room for simply being with one another.

Then, in a coffee shop, he met a Portuguese man who invited him to lunch.

That man, João, would eventually become his husband.

Lonny had come to Portugal intending to be alone. Instead, saying yes to a relationship became one of the most consequential choices of his new life.

Today, his art explores another part of this chapter: aging. Inspired by Porto’s weathered walls—the layers, cracks and imperfections that reveal rather than conceal the passage of time—Lonny has begun exploring what it might mean to see aging itself as something alive, vibrant and beautiful.

Our conversation moves between all of these things: identity and productivity, art and creativity, relationships and belonging, aging and letting go.

But underneath them is a larger question.

What if creating a meaningful life isn’t something we figure out once?

What if it’s something we practice?

In this conversation we explore

• What brought Lonny to Porto at 67

• Letting go of the identities and accomplishments that once defined him

• Discovering how closely he had connected self-worth with productivity

• Finding his way back to painting

• Why freedom still needs structure

• The difference between retirement and creating

• What Portuguese culture taught him about relationships and connection

• The unexpected lunch that eventually led to marriage

• Being open to a life different from the one you planned

• How Porto’s weathered walls inspired Lonny’s exploration of aging

• Finding beauty in imperfection and change

• Becoming more playful and comfortable in his own skin

• Why loving your life may be something you practice

Memorable moments

“What my soul wants is beauty, and what my soul wants is art.”

“What I had to let go of was letting go of who I thought I was for the possibility of what this next chapter might be for me.”

“No amount of accomplishment and no amount of results are ever going to give me real freedom, real joy.”

“How much vacation do you need? How much retirement do you need?”

“People take the time to see each other and just say, ‘I see you.’”

“Welcome to my country.”

“Most people don’t view aging like an alive and vibrant and beautiful possibility. And it can be.”

“It’s just practicing being free, practicing being yourself fully, practicing loving your life.”

“I’m practicing being moved by life and living.”

“What does it look like to live in wonder?”

Reflection

There is a moment early in our conversation when Lonny describes what it was like to arrive in Portugal without many of the things that had previously told him who he was.

His career was behind him. No one here knew him. He didn’t even understand much of what was being said around him.

For someone who had spent much of his life measuring his value through productivity, that created an unusual amount of empty space.

Who am I when I’m no longer proving who I am?

Lonny’s answer wasn’t to fill the space with another list of accomplishments.

Instead, he began experimenting with what he wanted his life to contain.

He painted.

He went to museums.

He paid more attention to people.

He fell in love.

He began making art about aging.

And he created enough structure around those things that they could become practices rather than simply intentions.

That distinction feels important.

A life with fewer obligations doesn’t automatically become a meaningful one.

Freedom gives us space. But then we still have to decide what deserves to fill it.

Lonny talks about discovering that he is “never retiring ever.” Not because he needs another career or another set of achievements, but because he wants to keep creating.

The motivation has changed.

So has the measure.

Twenty years ago, Lonny says loving his life might have meant having the right house, the right neighborhood, the right job or the right car.

Now his questions are different.

Does my life move me?

Am I creating?

Am I connected?

Am I open to what life is presenting?

Can I find beauty in who I am becoming rather than trying to preserve who I have been?

Those questions show up vividly in Lonny’s paintings of Porto’s aging walls.

He is drawn to their layers and imperfections—to the visible evidence of everything that has happened to them over time. When one of the walls that inspired his work was covered during a renovation, Lonny found himself wanting to preserve the others before they disappeared.

Then he recognized something familiar in that impulse.

The desire to preserve the past.

To hold onto what was.

To resist what is becoming.

Perhaps that’s one of the more interesting possibilities Lonny’s story offers.

Designing the next chapter of our lives may require us to do more than decide what we want next.

It may also require loosening our grip on who we’ve already been.

Lonny describes himself today as freer, more playful and more comfortable in his own skin than he has ever been.

Not finished.

Practicing.

Practicing painting.

Practicing relationship.

Practicing being himself.

Practicing being moved by life.

And practicing something that might be the most interesting challenge of all:

loving the life he’s actually living.

A question to consider

What would it look like to practice loving your life?