Growth Beyond Obstacles

The Hidden Conversations Behind Transformation

After undergoing vertical sleeve gastrectomy (VSG) in December 2024, I entered a new chapter of my life—one that came with profound transformation, not just physically, but emotionally, mentally, and spiritually.

People see a physical change and naturally have questions. Sometimes those questions are supportive, kind, and genuinely curious. Other times, they come with assumptions, with comments that sting, or with words that miss the mark. I’ve been asked countless times about how I feel, whether I regret the surgery, how I view my appearance now, and what comes next. While I’m not offended by curiosity, I’ve come to realize how much misunderstanding exists around weight loss surgery, long-term healing, and the reality of this journey.

This post is my open letter to those questions. It’s for anyone walking through a transformation who feels unseen in the messiness behind the milestones. It’s also for anyone considering bariatric surgery and wondering what really happens beyond the operating table. I’ll walk you through the five most common questions I receive and offer the full truth behind my answers.

Question One: “Do You Realize How Far You’ve Come? You Look Amazing.”

This is usually the first thing someone says when they see me after a long time. It’s meant to be a compliment, and it’s often accompanied by surprise, admiration, or even disbelief. I do appreciate when people recognize the changes in my life. But this question also forces me to reflect on how far I’ve come—not just in appearance, but in the countless sacrifices and daily disciplines that got me here.

Yes, I absolutely realize how far I’ve come. But the weight loss is only one part of the story.

Before surgery, I was juggling multiple jobs. I woke up at 3:30 in the morning with my fiancé so we could be at the gym by 4:00 a.m. We would get in a solid hour and a half workout, then head back home, shower, and blend up a protein shake before I transitioned into my workday, which began at 9:00 a.m. By that time, I’d already completed more in a morning than most people would in an entire day.

I journaled regularly, did breath work, drank my water, took my supplements, and kept my commitments. I worked from 9:00 a.m. to 5:30 p.m., and afterward, I studied late into the evening to finish my undergraduate degree in Leadership. That was just the beginning. I’m now pursuing my MBA.

The changes didn’t happen because of one surgery. They happened because I made thousands of small, deliberate choices over time, often when no one was watching. There were days when I broke down crying while walking on my treadmill. Days when I didn’t believe I could keep going. Days I showed up anyway.

What people see now is the outcome. What they don’t see is the relentless commitment to healing in every area of my life—body, mind, and soul.

Question Two: “You Must Feel So Much Better After Losing All That Weight, Right?”

This one is tough. It’s framed like a compliment, but it touches a complicated truth. The honest answer is: not always.

I understand why people assume I feel better. From the outside, it looks like I shed a burden and now move through the world with ease. But internally, it hasn’t been that simple. There are days when my body aches more now than it did when I carried over 390 pounds.

The irony is that, even though I’ve lost more than an entire person’s worth of weight, I often experience discomfort that never existed before. My tailbone hurts from sitting too long because there’s no longer the cushioning that once protected it. My hips get stiff, my joints ache, and if I’m not moving throughout the day, I feel it—deeply.

This is why I invested in a walking pad and a standing desk. I can’t sit for hours without pain. My body needs consistent movement now in a way that it didn’t before, because the redistribution of weight has changed my posture, joint stress, and the way I carry myself.

So when people say, “You must feel amazing now,” I want to say, “There’s more to this story than you think.” Yes, I feel emotionally lighter. Yes, I have more stamina. But physically? It’s still work. Every day. I manage new pain, new sensations, and new challenges that I couldn’t have anticipated.

And sometimes, hearing that question makes me feel like all the effort I put in is still being evaluated by other people’s expectations. That I need to feel grateful all the time or never complain. But the truth is, healing isn’t linear. Feeling better is not a guarantee. And not every body responds to weight loss the same way.

Question Three: “Do You Regret Having Weight Loss Surgery?”

Absolutely not. I have zero regrets about having the surgery. If anything, my only regret is not doing it sooner.

I first looked into weight loss surgery in 2018. At the time, I was living in Virginia. I had a surgeon lined up and a plan in place, but I didn’t have a support system that could help me recover. I couldn’t ask an EMS partner or church friend to let me stay at their house for two weeks while I healed. I was working, studying, and essentially alone in that season.

Then, in late 2019, COVID began to circulate. By March 2020, the world shut down. Elective surgeries, including bariatric ones, were postponed indefinitely. I lost my chance to proceed.

When I moved home to Ohio in 2021, I began seeing a specialist at the Cleveland Clinic. To qualify for surgery, I had to lose over 100 pounds. That was a brutal, uphill battle. I didn’t hit that benchmark until 2023 because I was struggling emotionally, battling hormonal imbalances, and trying to survive in a body that no longer responded to exercise or healthy eating alone.

What changed everything for me was joining Desire to Inspire in 2023. Freddy and Dylan didn’t just hand me a meal plan—they helped me change my lifestyle. They coached me hard. They didn’t sugarcoat anything. Their support gave me the courage and accountability to push through what felt impossible.

That same year, I experienced a serious medical scare—a medication overdose caused by a dangerous cocktail of diabetic drugs that my body couldn’t handle anymore. It was a wake-up call that I couldn’t ignore.

I committed, for real, and on December 19, 2024, I had VSG surgery. It was one of the best decisions I have ever made.

Question Four: “Do You Feel Prettier Now?”

This question used to catch me off guard. Now, it just frustrates me.

I understand that people often mean well when they ask this. But the question implies that I wasn’t attractive before. That my worth is somehow validated now that I fit a smaller frame. That beauty is measured by how much space I take up—or don’t.

Let me be clear: I have always been beautiful.

What I didn’t always have was confidence. My weight gain was tied to serious medical conditions—PCOS and endometriosis. My hormones were working against me. I was active, I ate clean, I exercised, I showed up—but my body resisted every attempt to lose weight.

And eventually, after years of failed efforts and being dismissed by doctors, I gave up. Depression took over. Not because I didn’t think I was pretty, but because I felt invisible in a world that only seemed to see my size.

Even worse were the comments from people—often family—who would say, “You’re too pretty to be that big,” or “You’d be gorgeous if you just lost the weight.” These are the kinds of comments that stick with you, that chip away at your self-worth, even when you try to ignore them.

So no, I don’t feel “prettier” now. I feel more confident. I feel stronger. I feel like I’m finally showing up for myself without shrinking to fit someone else’s expectations.

And that is the kind of beauty that cannot be measured by size, weight, or approval.

Question Five: “What’s Next for You?”

This is my favorite question. Because now—for the first time in a long time—I have a clear, exciting, and fulfilling answer.

What’s next is reclaiming my strength and achieving personal goals that once felt impossible.

First, I want to run a full 5K without stopping. I don’t care about pace. I don’t care about placement. I want to cross the finish line knowing I didn’t quit on myself.

Second, I want to build my physical strength. I’m working on resistance training and gradually increasing my muscle tone, not just for appearance, but for bone health, posture, and longevity.

Third, I’m writing a book. A full-length book about healing, identity, and transformation. It’s raw, it’s personal, and it’s needed. My hope is that it will encourage others who feel stuck in their bodies, minds, or pasts.

Fourth, I’m focused on growing my social media presence—not for fame, but to build community. I want to continue sharing content that’s honest, vulnerable, and educational. If my story can help someone else find their strength, then it’s worth every post, every reel, and every word.

Fifth, I’m finishing my MBA and exploring leadership opportunities in my career. I want to continue developing the skills that will help me serve others, lead teams, and make a real impact in whatever organization I’m a part of.

And lastly, I’m aiming to partner with brands that align with my journey—particularly Barilife, whose vitamins I use daily post-op. Their products have made a meaningful difference in my recovery, and I would be honored to work with them or similar companies that support the bariatric community with integrity.

Final Reflection: Behind Every Question Is a Journey You Don’t See

Transformation stories are often oversimplified. People see a before-and-after photo and assume they know the whole truth. But they don’t see the mornings filled with pain, the nights of doubt, the small wins that no one claps for, or the moments when giving up felt easier than going on.

So yes, ask questions—but ask them with care. With humility. With the understanding that behind every change is a human being who has weathered more than you’ll ever know.

To those walking their own journey—keep going. Your pace doesn’t have to match anyone else’s. Your transformation is valid, no matter how messy it looks.

To those watching from the sidelines—don’t just comment on someone’s weight loss. Ask about their joy. Their healing. Their strength.

Because we are more than the pounds we’ve shed. We are stories in motion.

And my story is still being written.

Until Next Time,

Kaylee Ann