Still Fighting the “Not Enough” Feeling

Reflections on imposter syndrome, self-worth, and the drive to keep going

Sometimes, I let myself get behind. I take on too much. I overdo it.And then, I crash for a few hours — just a few — before that little voice in my head starts whispering again: you should be doing more.

It’s that familiar ache many women know all too well — imposter syndrome. The nagging feeling that we’re not enough.

For women my age, it’s almost generational. We were told we could be anything, do anything — but when we tried, we were met with the quiet chorus of you don’t need to go to college, you’re not smart enough, you’re not pretty enough, or you’re just not enough.

And for some of us, that message stuck.

Growing Up with Mixed Messages

I really did believe I could do anything I wanted — I just didn’t believe anyone else thought that. My parents didn’t really. My friends and I just didn’t talk about it. And the workforce in the late ’70s and early ’80s certainly didn’t encourage it.

So, I floated along for a while, thinking nothing was too serious. Until one day, it was.

Sometime in the mid-1980s, I wanted more. I started taking classes again. I discovered I loved learning — and I really loved computers. I wrote programs, built ideas, and realized I was good at it. But there was always someone, somewhere, who made me question myself.

It’s funny the little things that stay with us.

In college (1986–1989), I was told not to go into business — it wouldn’t pay enough for a woman. I was also told to skip marketing — no future there. This advice came from a career counselor at Sinclair Community College.

Even in the 1980s, women were still being nudged toward teaching, childcare, or caregiving. All honorable paths — but not mine.

Doing My Own Thing

So, I did what I’ve always done — my own thing.

Since about 1980, I’ve run small businesses. I’ve managed restaurants, worked in grocery sales, partnered with big corporations, and helped mom-and-pop shops grow. I’ve hustled for decades. And I still do.

I take on too much. I cram 26 hours into a 24-hour day. I tumble down rabbit holes learning new things. I write. I create videos. I run our businesses.

Because this — this work — has to make it. It has to grow. It has to pay the bills.

Because even now, at 60+, that “not enough” voice still lingers. Not young enough. Not educated enough. Not something enough.

But I’m strong. I’ll fight. I’ll keep going.

A Small Ask, From the Heart

If you’ve made it this far, thank you. Truly.

If this post resonated with you — if you’ve ever wrestled with that quiet “not enough” voice — I hope you know you’re not alone.

And if you feel like it, I’d love for you to visit my shop. Maybe you’ll find something that makes you smile, sparks a memory, or feels a little like home. Supporting this work helps me keep going, creating, and sharing these stories.

As a thank you, you can use KABLOG20 for 20% off at backroadpicking.com.

No pressure — just gratitude for being here.