Kelly O’Shea is the author of How To Fall In Sh*t And Come Out Smelling Like A Rose and this week’s Featured Interview
Kelly O’Shea is a powerhouse in the world of luxury travel, private aviation, and personal transformation. With over 20 years of experience in PR and the high-end travel sector, she has built a multifaceted career as an author, jet broker, and spiritual entrepreneur. Known for her charisma, candor, and deep industry knowledge, Kelly brings a rare blend of luxury insight and soulful leadership to everything she touches.
Her work spans high-level jet sales, brand ambassadorships, and inspirational storytelling—all rooted in authenticity and reinvention. Whether closing jet card deals with UHNW clients or mentoring individuals navigating personal reinvention, Kelly is trusted for her discretion, strategic mind, and bold honesty.
What sets Kelly apart is her ability to merge soul with strategy. Her brand is not about polished perfection—it is about real transformation. Through her first book, How to Fall in Sh*t and Come Out Smelling Like a Rose, Kelly shares her journey through grief, addiction, and healing, offering others a roadmap to rise on their own terms.
Clients and collaborators value her not only for her professional acumen, but for her lived experience and magnetic energy. Kelly makes luxury feel personal, empowerment feel attainable, and transformation feel inevitable.
If you are looking for a jet broker, thought leader, or brand collaborator who leads with both power and presence, Kelly O’Shea is your go-to.
About the Book
How to Fall in Sh*t and Come Out Smelling Like a Rose is a raw and empowering journey of resilience, healing, and self-discovery. Kelly invites readers to look inward, reconnect with their authentic selves, and realize that the greatest love story begins with self-love – the rest is just roses.
From battling eating disorders, addiction, and toxic relationships to losing her husband to alcoholism, Kelly faced it all. Revisiting old journals, she uncovers the roots of her pain and chooses to show up for the younger version of herself. She told her that all the trauma and chaos were not her fault. She told herself that she was worthy and deserving of greatness. She told herself that she loved her, and she gave herself a lot of grace and space to heal. Because hurt people hurt people, but healed people heal people, Kelly says.
Today Kelly is the happiest she’s ever been, but not from anything materialistic or something society told her should make her happy; just from within. Because as you will read, she had all of the things that society promised would make her happy, but she wasn’t. And then she realized that all humans are capable of this. And she wanted to share everything she learned.
With spiritual nods to The Celestine Prophecy, this book is a powerful reminder that no prince is coming to save us-but we can save ourselves. This princess became a Queen and wrote her own happy ending.
When I first read the manuscript that Kelly sent me just months after our book conversation, I realized that I had underestimated both the power of Kelly’s stories and the depth of her determination. What Kelly had written went far beyond candid and revealing. Reading How to Fall in Shit… felt like lying on your stomach and peering over the edge of a towering cliff and feeling that you wanted to edge out as far as you could to see all that was happening below, yet gripping the earth like your life depended on it, because how could anyone survive such a fall?
Somehow, though, Kelly did. She survived the kind of childhood that could end a kid’s life, whether emotionally or physically. She survived too many drugs and too much loveless sex. She survived betrayal and abandonment, the dashing of hopes, the bleakness of loss, and the desperate search for traction in a world where all the people who are supposed to be helping you aren’t.
This is her interview…
Why did you want to write this book?
Because I needed to go back and find the underlying cause of my issues and heal all of that if I was going to step into the best version of myself and stop repeating the cycle. Then I wanted to provide a survival guide to others in the darkness, as soon as I got out.
What was the most difficult part about writing the book?
Going back to where my heart was broken in my early 20’s by a man named Cliff in San Diego, California. Particularly because he came back into my life during the writing of this book last year, but only via text and email, and they were just words with no action, leaving me disappointed again.
But this is when I started to learn about narcissism, and started to see red flags I missed 25 years ago. So I was able to go back into that abandonment wound he created and heal it myself. I told myself that none of that was my fault, and it absolutely did not mean that I was unworthy.
We choose a familiar hell over an unfamiliar heaven until we heal, that’s why a lot of us sabotage anything good that comes into our lives, that is rooted in a feeling of unworthiness that only the human themselves can fix, frustrating as that may be to those that love them and see their potential. We are often in love with the potential, not the reality; we miss red flags and we stay too long thinking we will be the one to save them when only they can save themselves.
The most rewarding?
Through processing all of this sh*t and rising above it, I have shown up for myself and become my own advocate. I no longer depend on anyone or anything outside of myself for my own happiness, nor do I take the actions or inactions of others personally. I take less sh*t and give less f*cks. I worked on things that no one can ever take away from me. I have grounded myself.
What do you hope other people will take away from reading your book?
I want to be a ray of light for humans in the darkness. I want them to see me and think, wow – if she made it through all of this shit and came out on the other side as the very best version of herself, truly living her best life, there’s hope for me, too. I can rise above this.
How long did it take to write your book?
Only one year! I put pen to paper on April 1, 2024.
Can you walk us through the process?
I’ve been close with the Publisher of Social Life magazine, Justin Mitchell, for 18 years and the former Editor of Worth magazine, Richard Bradley, for 12 years. For spring break 2024, I took my son, Dylan, to NYC and went to a Social Life magazine party where Justin introduced me to fashion designer, Shani Grosz. She invited me to her showroom the next day and I told her that I was planning to write a book in my 50’s, once Dylan is grown. She looked at my Instagram and told me that the time for this was now. The next day, I met Richard for coffee and he further encouraged me to write the book now, and he said that he would help. When a multiple best-selling author says that to you, I suggest you do it, quickly.
When I returned home, I found journals from ages 19-22, which became the foundation for the book, the meat in the middle. Then I did The Emotion Code at Hippocrates Wellness, which is an energy healing technique designed to identify and release trapped emotions that can cause physical and emotional distress. It’s a method developed by Dr. Bradley Nelson. The core principle is that unresolved emotions can manifest as physical pain, emotional blocks, and even interfere with overall well-being. After my treatment, I was able to remember some repressed childhood memories, exactly when and where those emotions came to me. That provided the basis for the beginning of the book. And the end was the metamorphosis that’s occurred in the past 4 years since I stopped drinking.
I edited it myself first, and went through it 4 times. Then Richard Bradley edited it, and then Game Changer Publishing edited and took it to formatting and production.
When was the lowest point for you, and what did that feel like?
When I separated from my husband and my son’s father, Charles, in 2019.
In the spring of 2019, a few things happened to make me realize that he was never going to accept his alcoholism and that it would never improve. We volunteered at Futures Recovery Day, and he was not interested in connecting with other alcoholics or admitting he was one, although Dylan and I made our support clear.
We watched A Star Is Born, and a strange feeling came over me when Bradley Cooper hanged himself. I thought: “I can’t let Dylan find his father dead. It will ruin his life. We have to get out of here.”
On May 10, 2019, Charles wanted to drink at Dylan’s preschool event at Lighthouse Cove Mini Golf, but they didn’t have hard liquor, so he got red wine and Diet Coke. Gross. Why couldn’t he just order a beer like the rest of the guys? He was so weird, and I was so embarrassed.
On May 18, we went to Margaritaville to have a pool day with another couple from the preschool and their daughters. On the way, I begged Charles to just stick with the bucket of beer we would share with the other couple throughout the day. He couldn’t keep that promise and frequently went to the bar for shots.
My reactions to his actions were still very weak back then, and I ended up drinking too much, too. The other couple had to take us home. Charles would have to go back to Fort Lauderdale a couple of times that week before actually returning home with the car.
On May 25, 2019, Charles was drinking in the morning, and I thought it would be good to get out of the house and take Dylan mini-golfing. But this is Florida—they serve booze on mini-golf courses. He took a picture of us in our new Vineyard Vines as he smirked and said, “Picture perfect.” What a dick.
I took Dylan to the bathroom, and when we arrived at our lunch table, Charles’s head was buried in his hands, and he was crying. I was embarrassed. He said, “I took out another life insurance policy. You and Dylan are going to be fine. Please let me go.”
I replied, “That’s not okay. Dylan needs a father.”
Sadly, I never saw the benefits of that policy because he lied about his drinking on that application. But at that point, I realized that he was not going to get any better. He didn’t want to, and I had to do what was best for both me and our son.
I believe, at that moment, my soul accepted that he wanted to go, even though my mind and his would continue to fight it a bit longer. I know now, and I can share this with people who are going through something similar—whether it’s someone who’s young, which is tragic, or someone who is closer to the natural end of life—when they are ready to go, the best thing for everyone is to just let them go.
He was dead within a year.
That Memorial Day weekend, I began the tedious process of leaving home, separating from him, and getting him into rehab one last time before filing for divorce. I wasn’t even ready to file for divorce; I wanted a legal separation, but Florida doesn’t recognize that… and you have to have $10,000 to pay an attorney. Since I was planning to divorce an attorney, I definitely needed one.
His Aunt Charlotte flew out to Florida to assist and had to cancel her flight home because Charles came home drunk on the morning of Dylan’s first day of camp, set off the alarm and had Dylan wondering what was the matter with his daddy.
I visited Charles at detox on Father’s Day. I gave him a card from Dylan, and he confirmed that he would transfer to rehab the next day. I lied and told everyone that I would hold off on divorce proceedings until he got out. I hugged and kissed him, and we walked from the conference room to the front door, hand in hand for the last time. God, I wanted it to work. I wanted him cured of this terrible disease forever.
I went by our marital home in Paseos again to take down more pictures of us. This was the hardest day of my life. I was just sprawled out on the tiles between the front door and the kitchen, ugly crying, kicking, and screaming that my life was falling apart at 38 years old.
Driving home from the attorney’s office the next day, I was so upset that I could hardly see through the tears. I came home to my parents, and all I wanted was a hug from my mother. She lightly tapped me and said that I was acting like I was the first woman in the world to get a divorce.
Now, I had to accept the reality that I would not be having a daughter and I actually won’t even be a part of a “normal” family at all. I didn’t know if I would find love again, if I ever actually had it, if I was even lovable, if I could make it financially on my own, if I could raise Dylan on my own. I never liked to be alone, because “wherever you go, there you are.”
But I knew that I deserved to live better than I was with Charles drinking on a brain injury. I put a decade into him, he was not going to get better for me or his job, he could only get better for himself and he didn’t want to. I was 38 years old, and I knew that if I wanted a chance at a better life, I better go out and get it now.
What do you do when you are not writing?
I’m a private jet broker for Fly Alliance, booking private jet charters and selling private jet cards increments of 25 hours. I love to golf, surf and spend time with my son, who is now 9 years old.
What’s next for you?
I’m launching a podcast called Shit, Rose! In the fall. It will be 16 episodes to match the themes in each chapter, with relevant guests appearing for each. For example, my husband was a lawyer and we have an incredible legal team supporting us now. Many of them have asked to come on and share their tips for navigating through those specific life challenges, or sh*t, as I like to say! Then I will launch a Mastermind group in the new year, followed by an Audible version of my book next spring.
How can our readers get a copy of your book? https://www.shitrose.com
What is the best way for our readers to connect with you? (website url, social media links – we do not publish emails)
www.kellyopr.com
https://www.linkedin.com/in/
https://www.instagram.com/
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https://www.youtube.com/