Paula Boggs

Knowing When to Fold 'em—and Begin Again

For years, Paula Boggs lived a full and highly accomplished life — beginning as a young woman, rising through the ranks in the US Army, then as a federal prosecutor and later serving as a right hand to the CEO of Starbucks, Howard Shultz in a General Counsel role — all while an important and quieter part of her life lay dormant, her music. But, after the tragic and sudden death of her sister in-law who was involved in a deadly car crash, everything shifted. In the depth of the grief, she returned to music, not as a career move, but as a way to survive through the paralyzing grief. What followed wasn’t a reinvention, but something much deeper, with completely unexpected paths, turning points and outcomes.

I had the great honor of meeting Paula in person when she came through the Bay Area with her wife Randee and her band, The Paula Boggs Band. The photo above was taken the night we met in person for the first time.

I first discovered Paula years earlier, almost by accident

At the time, I was building a search practice focused on placing women on corporate boards. An old high school friend had recently become CEO of Fender Guitar, which led me to research if there were any women on their board. And there was, Paula! I wanted to know more about her background, so I started digging.

That’s when I found her TED Talk. Her story was so compelling that I reached out to her directly, hoping she might be open to a conversation. She was. I felt incredibly honored that she said yes. You can listen to her inspiring talk here Paula Boggs TedTalk

Diving into her story of tragic loss and unanticipated beautiful outcomes, this is exactly why I do this work—to show what is possible after tragedy, and to offer the hope that with time and healing, a joyful life can be rebuilt.

This is Paula’s reMADE story

The Long Desert

There was a long period in Paula’s life—her early 30s through her mid-40s—where music, while still present, was no longer something she created or performed.

There was a series of life events that contributed to this pause:

First, she was deep in her corporate career. In her early 30s, she was a federal prosecutor and assistant district attorney, in an incredibly demanding role. She had been hired into the district attorney’s office with zero trial experience—the first person in its history to do so—and had to work relentlessly to prove herself as she climbed a steep learning curve.

Second, she met the love of her life, Randee, with whom she has now been with for more than 35 years.

And third, when Paula fell in love with Randee, she made the difficult decision to step away from the Catholic Church — recognizing that the life she was was building, rooted in deep love and truth, no longer aligned with an institution that could not fully embrace it. (While she was still part of the church, she had been playing folk guitar in mass and writing music, and when that chapter closed, her music quietly closed with it.)

The music didn’t fully disappear—but the part of her that created and performed, did.

The Moment Everything Broke Open

A few years into her career at Starbucks, everything changed.

In 2005, her sister-in-law, Julie, was killed in a horrific car crash. Her two-year-old niece, Jada, was also in the car—and by some incredible miracle, survived.

The grief was paralyzing. Paula couldn’t find her way out. But then, Randee encouraged Paula, over time, to pick up the guitar again—not immediately, but eventually—as a way to process what she was going through.

When she did, something shifted. It wasn’t a raging river—but a faucet turned on. Randee helped stoke that. She found Paula a guitar teacher who encouraged her to revisit and expand on the music she had written in her teens and twenties.

Then came another turning point: a year-long songwriting course at the University of Washington. Once a week, for three hours at a time, Paula immersed herself in music again—this time as part of a community of songwriters, something incredible she had not experienced before.

It was transformative. At the end of that course in 2006, one of her teachers pulled her aside and said: “It would be a shame if you didn’t keep going.” Paula didn’t really know what that meant, but… she did keep going.

One Decision That Changed the Trajectory

At the end of 2006, Paula made a simple decision: she would do one open mic a month in 2007. That one commitment changed everything. During that year, she met someone she would go on to make music with. By 2008, he advocated for her and helped her get a real shot at performing.

At the same time, she had built a strong reputation at Starbucks. She had fully established herself in her role, giving her the confidence to continue on this path. And, serendipitously, timing wise, music was becoming a huge part of the culture. When she recalls this particular time to me, it brings back great memories of when I lived in Chicago, buying DVD’s from the “See Hear” music collections at my favorite Starbucks around the corner from where I lived. I still have them all to this day!

As she pursued her path of music, her team, her peers, and even her boss were rooting for her.

The Conversation

By 2012, in her early 50s, Paula knew… It was time to move on.

She sat down with Howard Schultz and told him she was leaving. Not because of Starbucks. Not because of law. But because of something inside her that she could no longer ignore.

Around that same time, Steve Jobs had just passed away—a moment that seemed to shift how people thought about time, purpose, and legacy.

Howard understood.

She left with full support—and with absolute clarity. No doubts. Looking back, she isn’t sure she would have reached the same clarity, let alone support, working anywhere else.

Here is her beautiful speech closing her Starbucks chapter at an annual meeting, giving her an opportunity to say goodbye to her shareholders and partners Paula Boggs Farewell

She closed that chapter in a way few people ever get to—on her own terms, with a sense of completion.

A New Life—On Purpose

Paula and Randee left Seattle and moved to Santa Fe, a place they discovered years earlier and kept returning. It was warm, creative, and diverse. It felt right. Their band had already begun forming while she was still at Starbucks, and they were performing in multiple cities. Now she could fully step into her role as a musician.

At the same time, she committed to helping support Barack Obama’s election campaign, traveling the country speaking on his behalf.

And then life shifted again.

The Life She Never Expected

Just months after the election, Paula and Randee became full-time guardians to Jada. She was just ten years old. This decision was not decided lightly and it certainly reshaped everything. Looking back, Paula believes that leaving Starbucks made it possible and created the opportunity to become her guardian in a way it might not have, if she was still there. Interestingly, there were other turns of fate in her life that allowed for this guardianship to be possible as well.

The Twist That Only Makes Sense Later

Years earlier, Paula shared with me, that she and Randee had explored adoption. They researched, worked with an attorney, and moved through the process—but it didn’t work out.

At the time, it felt like a missed opportunity. Now, she sees the serendipity.
Had they adopted, they wouldn’t have been able to take in Jada. What once felt like a closed door became something else entirely.

Finding Her Way Back

After leaving the Catholic Church years earlier, Paula’s relationship with faith and the church had faded. But, over time, she found her way back—first through a deeply diverse Episcopal church in Austin that a good friend introduced her to, and later into an Anglo-Catholic Episcopal community.

It wasn’t a return to the past. It was something new, aligned with who she had become.

A Life reMADE

Today, Paula’s life spans music, leadership, service, and creativity.
She is a musician, a speaker, and a board member.
But what stands out most is how intentionally she has moved through each chapter. She describes leaving law not as risk—but as completion.

“There’s no feeling like completion... fulfilling and complete.”

What Stays With Me

I think about this often—

some of the most beautiful endings don’t come despite the darkest losses, but because of them.

This photo was taken at Sweetwater in Mill Valley when Paula Boggs came into town to perform with her band The Paula Boggs band