Hindsight is 20/20: 10 Years of Failures and Victories


For the young, the days go fast and the years go slow; for the old, the days go slow and the years go fast. – Anna Quindlen, author

Who knew how accurate that quote is for adults, especially those fortunate enough to have children. I don’t look back much. Recently, I realized a few weeks ago that my “big girl move” anniversary was approaching. It’s been ten years, a whole decade since I packed up my old Toyota Camry with all my belongings and moved three states away from family, friends, and everyone I knew to become a Florida resident.

I blinked, and July 18, 2010, turned into July 18, 2020.

I blinked again, and it’s mid-August and my son is only a few days away from starting *gulps* high school. That significant amount of time and a significant milestone in my son’s life embody that quote perfectly.

It seems the older I get, the faster time passes and the faster he grows.

Standout Mistake Number One

He was a four-year-old, full of energy and playful as can be when we got our first apartment in Florida. I was a college-educated, 24-year-old single mother and news journalist. I was ready to dive into my career and had no qualms about it. I also was not fiscally competent and foolishly commuted one hour and a 40 minutes (one way) from St. Pete to Highlands County for 10-hour workdays Tuesday-Saturday. That was a standout mistake number one in Florida.

Why did I feel the need to live on the beach and drive that far to work every day? Naive and energetic are the words that come to my head now about that mistake. Since then, I’ve never lived further than 20 minutes from my job — lesson learned.

I also quickly learned that rural communities in Florida were not for a young girl who happens to be an extrovert. So I told myself country life is not for me and moved here to the Suncoast. 

Another Lesson Learned

Sarasota has been the epitome of a roller coaster since we relocated here in 2015, and I have never been a fan of roller coasters. I have always preferred a more linear experience, but these ten years have taught me my second big lesson: the best experiences are born from unexpected routes.

I learned humility through rejection.

I was fired from what on the outside looked like a dream job. I stood up for myself after a toxic environment at work became too much to tolerate anymore, and I was fired for complaining about it. I failed at providing a paycheck for myself and my son, but I learned that being fired can sometimes be an opportunity for growth disguised as a social shortcoming.

And I have legit won at life when it comes to friendship.

Friendships have grown right along with J— slowly at first but strong and beautiful now after pouring energy and love into them over the past five years. I’ve been mentored and pushed in the right direction by the right people, especially these past three years. Some amazing people have provided shelter, food, and comfort for my son and me. Those people are etched in my heart forever. Through them, the handful of beautiful souls I’ve been fortunate to know these past ten years, I’ve come to know and experience true kindness in a sometimes bitter world.

But I still stumble(d) in motherhood.

Planning my life was my safety net. It gave me a sense of control. It was what kept me from running home to Mississippi, tail between my legs, in the fall off 2011 when I was going on week seven of not eating a full meal because I couldn’t afford to buy enough food for both me and J.

Standout Mistake Number Two

Standout mistake number two was being too prideful to ask for help when I was barely keeping our heads above water.

These first eight months of this year have been — for lack of better terms — a hot mess.

All the plans have been thrown out the window.

Our wedding plans have been decimated twice, our life-changing trip to South Africa for J’s birthday won’t happen for at least another 18 months now (if ever). My would-have-been first summer with J has been three months of boredom complaints, demands for extra helpings of pasta at dinner, and a natural need for him to shut his door for half the day and pretend I don’t exist.

And now, I’ve added acceptance and perspective to the list of things I’ve learned over these years. Especially when it comes to letting go of the things you can not change. I can’t change the fact that my son is not a baby anymore, he’s not the same little boy I moved to Florida with alone ten years ago. He doesn’t need the same things from me anymore and I don’t need to take that personally.

It’s just a part of the journey we are on and the journey I have to take alone as he grows into a man, and I continue to grow into much more than just J’s mother.

I’ve found so much peace amid some difficult times.

I’ve given all that I have to my son— every ounce of being. I’ve driven 16 straight hours so that he can see his father for half a day.

I’ve given up press passes to the Super Bowl to take him to see his favorite animal tv show stars. I’ve yelled and cheered him along as he attempts to conquer things that terrify him (and overcome a few of those myself along the way). I’ve given up every summer with him since he was born so that he and our family can spend time together even though the distance and time away continually broke my heart.

Standout Mistake Number Three

Putting what my family wants before what I need and not enforcing my boundaries much earlier.

The beauty of those sacrifices is that they have all made way for so many pivotal opportunities to grow and heal in my life and progress as a mother.

The lessons along the way have become invaluable and will steer me, along with a little discernment, in the right direction through the next ten years, maybe even longer. Ten years to reflect on at a time when our world is at a near standstill.

What I would have told myself ten years ago.

Now, as I look back to the young woman I was when I packed up and left New Orleans with only an open-mind, a new job, I would tell that girl to brace herself. I’d say to her that she will feel immense betrayal, she will work with some complete jerks, she will find the love of her life, she will watch her son eat while her belly grumbles from emptiness, she will own her own companies, she’ll survive an abusive relationship, she’ll never back down from a challenge or fold under pressure, and she will fail and win and fail again.

Above everything else, she will truly love the woman that she transforms into. More than she ever thought she could.

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Samantha Gholar
Samantha is an award-winning former news journalist, mother, and soon-to-be wife. After working as a reporter for 12 years, she stepped out of the newsroom in 2015 and launched a couple of local businesses and organizations from the ground up. A southern belle through and through she has lived all over the Southeast but has called Sarasota home for six years. Samantha is a local philanthropist who spends much of her time highlighting and shining a light on the growing minority and women-owned businesses in the region; lending a hand to those women who need it most. She and her son Jaden have grown up together through the years-- from a 20-year-old young mother and newborn, to a seasoned, confident local leader and budding student-athlete. In addition to her philanthropy, Samantha is most passionate about health and wellness, after a private battle with postpartum depression all while finishing up her first bachelor's degree, and education.


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