Kelly MacPherson's Becoming Anyway

Several years ago, when I first met Kelly Ann MacPherson, she was commanding the ship at RBI. I remember her quite literally sweeping into the room. People noticed. She had energy, presence, and gravitas, and the room seemed to reorganize itself around her. Some executives need the title, the introduction, and perhaps a small brass band before everyone understands they are in charge. Kelly did not.

My first impression was simple: this was a formidable woman. She seemed decisive, accomplished, intensely capable, the kind of person who had been in difficult rooms before and knew what to do once she got there.

Then I read Becoming Anyway: The Messy Journey of Building a Life, a Career, and Yourself — All at Once, and I realized I had met the finished photograph without ever seeing the negatives.

That is one of the reasons I love this book.

Kelly could easily have written the predictable executive memoir, the one where a successful person reaches the summit, looks backward, and somehow discovers that every wrong turn was actually part of a master plan. The failures become “learning opportunities.” The disasters acquire bullet points. Given enough distance, even chaos can apparently be persuaded to wear a blazer and call itself strategy.

Kelly doesn’t do that. She leaves the uncomfortable parts in.

Becoming Anyway gives us the story behind the presence I saw that day. It traces the making of a leader through childhood, family expectations, motherhood, marriage and divorce, career changes, insecurity, conflict, regret, reinvention, and the repeated experience of walking into situations without being entirely certain she belonged there.

What I related to most wasn’t simply what Kelly accomplished. It was her willingness to show us what was happening inside the person doing the accomplishing.

It takes confidence to command a room. It takes another kind of courage to go back through your life and show people the years when you couldn’t command much of anything, including your own doubts.

Kelly lets us see the uncertainty behind the certainty and the private questions behind a very public record of accomplishment. She writes openly about body image, motherhood, relationships, career mistakes, difficult choices, insecurity, and regret. More importantly, she doesn’t seem interested in cleaning those experiences up for us.

I appreciated that enormously.

Her vulnerability never feels like theater. She isn’t confessing for applause or turning every scar into a leadership lesson with three actionable takeaways. She simply looks back at different versions of herself and allows them to exist on the page, even when the person she was then didn’t possess the understanding she has now.

That feels personal to me because I think most of us are skilled editors of our own history. Give us enough time and we can turn a mistake into a strategy, an accident into intuition, and a period when we had absolutely no idea what we were doing into a carefully considered career transition.

Kelly resists that temptation.

One example I related to was her account of insecurity about her appearance. At sixteen, believing that changing her nose might change how she felt about herself, she underwent plastic surgery. Her nose changed. The voice inside her head simply found other material to work with.

Of course it did.

The human brain is an astonishing piece of machinery capable of language, love, imagination, mathematics, and locating a completely new reason to criticize ourselves approximately fourteen seconds after we fix the previous one.

Kelly can see now what she couldn’t have understood then. An external correction wasn’t going to settle an internal argument. What I admire is that she allows that sixteen-year-old version of herself to remain on the page. She doesn’t ridicule her, excuse her, or retrofit her with wisdom she didn’t possess yet.

She lets us meet her.

And slowly, you begin to understand where the woman who eventually swept into that room came from.

Kelly’s professional stories have the same candor. She entered technology without the conventional technical pedigree and eventually led major teams and transformation efforts across hospitality.

At Burger King, she faced the decidedly unglamorous problem of gathering consistent sales information from thousands of independently operated restaurants using different systems. The theoretically perfect solution would have consumed enormous amounts of money and time, so Kelly and her colleagues found a workable solution instead, an integration layer that became known as the “Burger Bus.”

The technology is interesting. I related much more to the realization behind it.

The hardest part wasn’t the technology. It was trust.

There is a lot of leadership hiding inside that observation. Organizations love treating human problems as technical ones because computers rarely arrive with egos, histories, mortgages, grudges, ambitions, or anxiety about what the latest reorganization means for their careers.

People do.

Kelly understood that changing a system meant understanding the people living inside it.

You see the same instinct when she writes about taking responsibility for an IT organization. Rather than arriving with all the answers, she listened. She asked people what worked, what didn’t, and what they needed. At one point, she discovered someone had proposed installing a deli-style ticket machine to manage interruptions from the business.

Take a number. Wait for IT. Perhaps enjoy a pastrami sandwich while the enterprise system collapses.

Kelly saw the larger problem. Technology could sit behind a counter and process requests, or it could sit beside the business and help solve problems. She chose proximity.

That tells us a great deal about how she came to lead.

But what makes Becoming Anyway more interesting to me than a collection of executive war stories is that Kelly eventually turns that same scrutiny on herself.

She examines perseverance, one of the qualities that helped her succeed, and recognizes that even a strength can become a problem when we don’t know when to put it down. Persistence can become staying too long. Independence can become refusing help. High standards can turn inward. Being the person capable of carrying everything can eventually train everyone, including yourself, to keep handing you things.

I related to that.

We spend enormous amounts of time trying to identify our strengths and considerably less time asking whether one of them has overstayed its welcome and is now eating crackers on the sofa.

Sometimes the trait that got you here is precisely the trait you need to renegotiate before you can go somewhere else.

That idea runs through the heart of Becoming Anyway.

Reading these stories changed the way I thought about the Kelly I first met.

The presence was real. The gravitas was real. The formidable executive was real. But now I could see some of what stood behind her: the girl who wondered whether she was enough, the young mother improvising adulthood, the woman making relationship and career decisions without access to some magical answer key, and the executive who sometimes stayed, sometimes left, sometimes got it right, sometimes didn’t, and kept learning.

That is why I love this book.

I don’t love it simply because Kelly succeeded. I love it because she refuses to pretend success made her invulnerable.

We have built a strange mythology around accomplished people. Once someone reaches a certain altitude, we assume they possess something the rest of us don’t. More confidence. Better instincts. Some secret reserve of certainty stored in an executive vault beneath the house.

Becoming Anyway dismantles that idea.

Kelly’s story suggests something far more useful: you don’t become ready and then begin. You begin, and the beginning changes you.

You make decisions without possessing every answer. You walk into rooms before you feel completely qualified to be there. You raise children while still trying to understand yourself. You take the job, leave the job, love somebody, lose somebody, make the wrong call, and occasionally make the right call for reasons you won’t understand until years later.

Somewhere inside that glorious administrative mess, a person emerges.

Still unfinished. Still learning. Still becoming.

The presence of Kelly’s daughter, Lauren, adds another dimension. Through her perspective, we see the demanding mother alongside the loving one, the absences alongside the adventures, and the expectations alongside the example Kelly was setting without necessarily knowing she was setting it.

Children are inconvenient that way. They don’t restrict themselves to the lessons we formally announce. They watch the whole show.

Lauren ultimately finding her own path into hospitality and technology makes this feel less like inheritance than influence. Kelly didn’t hand her daughter a script. She showed her what it looked like to enter unfamiliar territory, ask questions, work hard, adapt, and keep moving.

Certainly, this book belongs in the hands of women building careers in rooms where they may still be underestimated. It will speak to people in technology and hospitality, executives and emerging leaders, working mothers, entrepreneurs, and anyone trying to reconcile ambition with the other unruly obligations of being a human being.

“Work-life balance” sounds wonderfully civilized until you discover that sometimes it means everything is simultaneously on fire, but at least you remember where the extinguisher is.

But I think the audience for Becoming Anyway is much larger than that.

I would give this book to the person standing just outside the room wondering whether they are ready to walk in. I would give it to someone halfway through a career who has begun to suspect that the definition of success they inherited no longer fits. I would give it to someone rebuilding after a divorce, a professional disappointment, a mistake, a reinvention, or simply the realization that the person who got them this far may not be exactly the person required for whatever comes next.

I would give it to the person who has become extraordinarily competent at carrying everyone else and has recently begun wondering who, exactly, is supposed to be carrying them.

And I would especially give it to someone who looks at accomplished people and assumes they were born with the map.

They weren’t.

Kelly wasn’t.

Most of us aren’t.

That is the generosity I found in Becoming Anyway. Kelly doesn’t hand us a map. She shows us her footprints, including the places where she wandered around for a while.

There are wrong turns, course corrections, stretches of confidence, periods of doubt, victories, bruises, and the occasional realization that something she once believed about herself was no longer true.

I began this book remembering the woman who swept into that room years ago. At the time, I remember thinking, That is what confidence looks like.

After reading Becoming Anyway, I see her differently.

What I saw wasn’t a woman who had somehow escaped uncertainty. I was looking at someone who had spent years learning how to move through it.

Knowing the vulnerability behind that presence doesn’t make Kelly seem less formidable to me. It makes her more so.

Maybe becoming isn’t the moment when we finally conquer doubt, solve ourselves, and stride magnificently into the rest of our lives with everything figured out. That sounds lovely, but so does owning a dragon, and the evidence for both remains disappointing.

Maybe becoming is what happens when we stop waiting for that day.

Kelly did.

She became anyway.

And I love this book because she was generous enough to show us what that actually looked like.

Kelly, thank you for trusting me with an early copy of your manuscript.

There is something particularly intimate about being handed someone’s story before it becomes a book in the traditional sense, before the reviews, the interviews, the podcast conversations, and all the machinery that arrives once a private manuscript becomes a public object.

You trusted me with the story first.

I don’t take that lightly.

I also know enough about you to appreciate the contradiction. Leading organizations, solving complex problems, walking into rooms filled with people expecting answers, that is familiar territory for you. Handing someone pages containing your doubts, mistakes, insecurities, relationships, regrets, and younger versions of yourself and saying, in essence, Here. This is me too, requires something different.

I appreciated that vulnerability more than I can adequately say.

I related personally to more of your story than I expected to. The uncertainty that can coexist with confidence. The instinct to carry more because you know you can. The realization that capability can become its own trap. The decisions that make perfect sense while you are living them and look entirely different when viewed through the merciless binoculars of hindsight.

And perhaps most of all, I related to the idea that we can spend years believing there is some future version of ourselves waiting just over the horizon who will finally have the whole thing figured out.

Apparently, no one is sending that version.

What you have written reminded me that strength and vulnerability aren't opposites. Sometimes the willingness to say, I didn't know. I struggled. I got this wrong. I changed. I kept going, tells us far more about someone than another victory ever could.

So thank you for the early read. Thank you for the trust. And thank you for leaving in the parts that would have been easier to edit out.

I respected the woman I met years ago.

After reading Becoming Anyway, I understand her better.

And I appreciate her even more.

Kelly Ann MacPherson is a technology executive, entrepreneur, independent board director, author, and longtime leader in hospitality and organizational transformation. Becoming Anyway: The Messy Journey of Building a Life, a Career, and Yourself — All at Once brings together the professional and personal sides of that story, including the parts that don't fit comfortably into a résumé.

Connect with Kelly on LinkedIn. Kelly shares her thinking and work around leadership, technology, hospitality, transformation, and the experiences surrounding Becoming Anyway. Her LinkedIn presence is the natural place to follow her professional work and the continuing conversation around the book.

Listen to the Becoming Anyway podcast. The conversation extends beyond the book through Kelly's podcast with her daughter, Lauren, where two generations explore careers, family, relationships, leadership, technology, AI, and what becoming looks like from opposite sides of the generational table.

Read Becoming Anyway. The book is available for readers who want to go beyond the polished biography of success and spend time with the much more interesting story underneath it.

Because that's ultimately what Kelly has given us.

Not a manual for becoming her.

Permission to keep becoming ourselves.