I Was Never the “Pretty One”

I thought becoming “the pretty one” would make me feel worthy. Eventually, I realized only I could define my worthiness.

Growing up, most comments about my appearance from my mom—the person who mattered most to me—were unkind. By 4th grade, I was getting “too fat” and needed to “watch what I ate.”

(By my teens, the comments were about how my weight would keep me from getting or keeping a boyfriend. She even asked my first husband if he’d still love me if I kept gaining weight.)

I was also not the “athletic one.”

I never played sports or exercised. A boy made fun of how I ran at recess in 5th grade, and that one comment kept me from running AT ALL until my 30s.

I wasn’t the “rich one.”

Raised by a single, financially struggling mom, I was lower middle class (at best) in an area where many of my friends got new cars for their 16th birthdays.

And I wasn’t the “popular one.”

I moved 7 times by age 12. Couple that with intense introversion, and I struggled to make and maintain friendships. It’s an issue that continues for me well into adulthood (I’ve now moved 25 times).

I wasn’t the “troubled one” either.

My younger brother lived with ADD, ODD, bi-polar disorder, and eventually addiction.

That put a lot of attention on him—and heavy expectations that I be the “good one” who didn’t heap more trouble onto my parents’ very full plate.


I was the “smart one.”


✅ I was put in the “gifted” program in elementary school.
✅ I never earned less than a B in school.
✅ I served as editor-in-chief of my high school and college newspapers.
✅ I was on honor roll most semesters, and graduated high school with honors.
✅ I took enough AP classes in high school to have 21 college credits at graduation.
✅ Thanks to that 👆 I finished college in 3 years.
✅ I scored a bunch of scholarships, so my 4-year degree only cost about $5k out of pocket.

At every step along the way, I received praise (from my family and teachers) for being smart.

This led to a lifetime of me chasing gold stars. It was the only way I knew how to fill my cup of worthiness.

It also led to a habit of avoiding anything that might disprove the theory that I was smart … I only attempted what I was pretty sure I could achieve, and quickly quit anything I couldn’t immediately master.

At age 25, I landed an impressive job as an editor at Better Homes & Gardens magazine. With a readership of 40+ million at the time (the largest of any publication), my name could be found in nearly every aisle of every grocery store in America.

It felt great…for a few months.

Gradually, though, I came to the stinging realization that nothing had really changed in how I felt about myself.

My cup of worthiness seemed to have a hole in the bottom. No matter how much I filled it with achievements, it didn’t stay full.

When I turned 30, I felt an overwhelming sense of “is this all there is?”

That existential dread pushed me to quit my cushy-but-unfulfilling job to be my own boss as a freelance writer. I made more money while working far fewer hours (and while wearing PJs in bed or on the couch).

I hoped becoming the “rich one” would fill my cup.

I bought designer labels. Leased a shiny new red BMW. I built a 3,500-square-foot custom home with all the fancy finishes. I took regular vacations to Europe and nearly every Caribbean island. I built up a sizable nest egg.

My life looked so good on paper, and to everyone around me.

And still my cup was empty.

By the time I turned 33, the “is this all there is?” dread had morphed into “what if it never gets better?” panic.

I accelerated my efforts to fill that damn cup by trying to be the “athletic one” and the “popular one” and the “pretty one” all at once.

By my estimation, running hundreds of miles a month (I completed a marathon, a dozen half marathons, and countless 5ks) would be the one stone that would kill all the birds.

I’d be a real athlete, I’d get thin (which I believed was a synonym for pretty), and I’d be source of much male attention (which I thought was a synonym for popular).

It worked. I became obsessed with running and exercise and went from a size 18 to a size 2 in less than 2 years.

Men definitely noticed, and I soaked up their praise. So much so that I cheated on my ex-husband in a desperate attempt to feel more desirable.

And my cup of worthiness became the driest it had ever been.

It’s incredibly lonely to feel so unhappy and so unworthy, and not have any idea why or how to fix it … especially when everyone else thinks your life looks so perfect.

By the time I turned 35, I was reaching a breaking point. I’d gone from dread to panic to despair.

I felt trapped. I’d made this bed, and I felt doomed to lie in it.


Then everything changed.


In the early morning hours of July 4, 2010—after I had stumbled home from a drunken night with a man I was now having a weeks-long affair with—I got the phone call that would forever change my life.

“I have some troubling news,” my stepdad said in the understatement of a lifetime. “Your brother is dead.”

I knew without being told that it was a heroin overdose. He was 30.

Everything changed that day. It wasn’t instantaneous. Meaningful, lasting change rarely is. But that call marked the beginning of my liberation.

My brother’s death showed me that life is too short to settle for “good enough” or, in my case, “good on paper.”

I asked for a divorce. That decision, along with depression and fallout from an economic recession, meant I nearly lost my business (I went from $100k+ income in 2009 to less than $13k in 2010). I did lose my beautiful home and my best friends.

I spent 2 years trying to outrun my grief by working as a cocktail waitress until 2 am, drinking too much, and sleeping around.

Just before my 38th birthday, I decided to stop running and face my fears.


It took a lot of hard work.


It was a privilege, albeit a humbling one, to move back into my mom’s home so I could survive on very little freelance writing income and dedicate most of my time to grieving and growing.

  • I cried. A lot.
  • I ran a lot, too, but this time my goal wasn’t about my appearance. It was about using the time to reflect and to feel.
  • I journaled about what I had learned in my 38 years, and about how I wanted my life to look moving forward (free from the shoulds).
  • I did a lot of forgiving … of others and of myself.
  • I learned about self-compassion and acceptance, and finally began to love myself—the real me, not the version who wore different masks hoping to earn gold stars.

Within a year, I felt different. Better.

For the first time in my life, my cup of worthiness felt like it was filling up instead of constantly running out.

By my 40th birthday, nothing about my life was the same as it had been 5 years before.

I was in a healthy and happy relationship. I was letting go of professional writing to become a coach. And I was trying to have a baby.

Today, I’m married to that man, we have an amazing child, and my coaching business is the most fulfilling work I can imagine.

Most important, I no longer try to fill my cup by pleasing others or playing a part.

I fill my cup every day because I finally know deep in the seat of my soul that I am inherently worthy.


My journey isn’t unique.


I’m guessing you can relate to my story.

Not all of it, of course, but there are probably bits and pieces that ring true to your own life’s story.

❤️ You also likely developed patterns based on your early experiences around self-worth.
❤️ You may have had your own “is this all there is?” moment (or may even be currently feeling it).
❤️ You probably have disappointments and regrets, too.
❤️ You may also struggle to fill your own cup of worthiness.

I want you to know that you’re not alone. You’re not broken. And there is hope.

My life is now dedicated to helping people who, like me, are ready for more. They are ready to be gutsy and go after a life that feels good (and not just settle for “good on paper”).

Learn more about my accountability coaching program.