Five Portraits, Two Years of Growth

Two years ago I met a woman at the morning market who would become one of my best clients. She saw my prints of Hunter S. Thompson and Audrey Hepburn and immediately recognized something special in what I was trying to do.

A few days later she called and told me about a project she had in mind.

She had five grandchildren who had each come into her life through different circumstances. She wanted to write a love letter to each of them and have me render their portraits inside those letters.

What she described gave me chills.

It was the perfect project for me.

She understood that my word portraits weren’t just about likenesses. They were about trying to capture a more complete version of a person. Their history. Their relationships. Their hopes. Their fears. The things that make them who they are.

The first portrait was about kindness and belonging.

Her letter described a shy little boy who simply needed time, space, and love to become himself.

I realized immediately that these weren’t going to be portraits.

They were going to be stories.

When I delivered that first painting, the whole family came to pick it up. It was humbling to be trusted with something so personal.

A few months later came the second portrait.

This one revolved around basketball, but the letter wasn’t really about basketball.

It was about determination.

I found myself letting the environment become part of the story. Clouds became obstacles. Atmosphere became emotion. The painting wasn’t just describing what he looked like. It was describing what it felt like to cheer him on.

Looking back, I think I was also trying to outdo myself.

This was the first client who kept coming back every few months, and with every portrait I had changed a little as an artist.

The expectations weren’t just hers anymore.

They were mine.

Then came the granddaughter.

Her letter could be summarized in one word.

Joy.

Everything about her felt bright and full of life.

Instead of the muted earth tones I’d been using, I took a leap into saturated yellows, purples, and pinks.

It was one of the biggest risks I’d taken with color.

I was nervous.

It felt like a huge departure from the previous portraits.

My client cried when she saw it.

Moments like that become rarer as your career goes on.

It wasn’t just validation that the painting had worked.

It changed the way I thought about my own work.

I became bolder with color.

I stopped chasing realism quite so hard.

I started chasing mood instead.

Loose enough to capture energy.

Careful enough to capture the details that mattered.

That painting quietly changed everything.

The fourth portrait arrived during a difficult period in my own life.

My wife and I were preparing to move. Work had slowed dramatically and I had started wondering whether my work had simply stopped connecting with people.

Social media has become a strange place for artists.

The silence can make you question everything.

Had my work gotten worse?

Had I lost the plot?

Eventually I realized I wasn’t making work for myself anymore.

I was performing.

Trying to predict what people wanted instead of listening to what interested me.

So I stopped.

I spent the beginning of the year giving myself permission to wander.

I made abstract paintings.

Experimented with color.

Mixed oils into my acrylic word portraits.

Played without worrying where any of it would lead.

Ironically, walking away from portraits made me fall in love with portraits again.

When the fifth and final portrait arrived, I was no longer trying to protect a style.

I was simply trying to make the best painting I could.

The youngest grandchild’s letter was full of warmth and openness.

A child who wasn’t afraid to tell people he loved them.

For this portrait I began experimenting with transparent layers of text, giving myself much finer control over color than I’d ever had before.

The gradients became softer.

The transitions became richer.

My client told me it was my best portrait yet.

When I looked at all five paintings together, I realized they weren’t just a record of five grandchildren.

They had become a record of my own journey as an artist.

I could see myself growing from one painting to the next.

Not just technically.

Emotionally.

Conceptually.

Each one had asked a new question, and each answer had quietly changed the next painting.

I don’t think they’ve brought me closer to mastery.

I think they’ve given me momentum.

There’s an important difference.

Mastery sounds like the end of something.

Momentum feels like the beginning.

Looking at those five portraits together, I don’t see someone settling into a style.

I see someone becoming more curious.

More willing to take risks.

More willing to trust the work.

Every new discovery feels like another door opening.

And instead of worrying about which direction to take, I’m finally starting to believe they’ll all lead somewhere worth going.