The ‘I’m Not Good Enough’ Trap: How to Transform Your Fears into Alignment and Purpose

The ‘I’m Not Good Enough’ Trap: How to Transform Your Fears into Alignment and Purpose

Lisa Marie Bobby, PhD, LMFT, BCC

Dr. Lisa Marie Bobby is a licensed psychologist, licensed marriage and family therapist, board-certified coach, AAMFT clinical supervisor, host of the Love, Happiness, and Success Podcast and founder of Growing Self.

Ever feel like no matter what you do, it’s not enough? Like you’re always one achievement away from reaching your personal pinnacle and finally feeling good enough… except that moment never actually comes? Maybe you’ve been underestimated your entire life and overcome exceptional odds to land where you are now, but it still isn’t hitting the mark for you.

So many smart, successful, compassionate people quietly carry the belief that they’re falling short. Even when they’re winning on paper. Even when their Instagram feed looks like a highlight reel. Even when everyone else is saying, “Wow, you’ve really made it.” Deep down, they’re still wrestling with the same fear: I’m not enough.

And if you’ve ever felt underestimated — by others or (let’s be real) by yourself — you know how much of a dream-killer that can be. It makes you overthink. Overwork. Overextend. All in a relentless effort to prove something… to someone.

I recently had the absolute delight of sitting down with bestselling author Mary Marantz on the Love, Happiness and Success podcast, and in this deeply affirming conversation, we explore how the experiences that once made us feel underestimated—and the relentless drive to overachieve—can keep us stuck in cycles of perfectionism, people-pleasing, and fear-fueled productivity. 

But what if fear isn’t your enemy? What if it’s actually pointing you toward your purpose?

Let’s unpack it together.

The ‘I’m Not Enough’ Trap

Mary calls it a “pervasive sense” — that filter many of us start from, especially if we come from what she calls “hard story people” backgrounds. Maybe you grew up with scarcity. Maybe you were constantly underestimated. Maybe the pressure to succeed came from family, culture, or your own inner critic wearing khakis and an LL Bean shirt (yes, we talked about that too).

Whatever the source, here’s the punchline: You can achieve everything… and still feel like you’re not enough.

Mary went from a single-wide trailer in rural West Virginia to Yale Law School. You’d think that would be a mic drop moment, right? Nope. Instead, she told me:

“People ask if that’s when I stopped underestimating myself. I say, ‘Try this morning.’”

Ugh. YES. Been there.

Underestimating Yourself Is Fear In Disguise.

Here’s the thing about that sneaky “not enough” voice: it doesn’t just sound like doubt. Sometimes it sounds like perfectionism. Sometimes it shows up as people-pleasing, procrastination, or endlessly prepping and planning instead of starting.

We don’t call it “fear,” because it’s not always obvious. But it is fear. Fear of failure. Fear of being visible. Fear of not being perfect and lovable and amazing on the first try.

The real kicker? It’s usually a fear you learned long ago.

Maybe you grew up hearing that achievement = worth. Or maybe you were never given permission to take up space, ask for help, or get messy with your dreams. So now your brain’s got one job: keep you safe. And the best way to do that? Convince you not to try.

Because if you don’t try to face your fears, you can’t fail, right? That’s how we keep staying small. That’s how we stay stuck. That’s how we continue underestimating ourselves.

The Lie of “When I Finally…”

So many of us — especially high-achievers — live in what I call “the land of ‘when I finally.’”

• When I finally lose the weight…
  
• When I finally get that degree…
  
• When I finally have a partner, a house, a six-figure salary…
  
• Then, and only then, will I feel like I’m enough.
  

Spoiler alert: You won’t.

Mary calls it the “Pez dispenser of success” — the sugary high of doing “just one more thing” to prove yourself. But it’s a trap. Because as soon as you get the gold star, your inner critic moves the goalpost.

That’s why so many of us keep climbing higher, working harder, pushing ourselves to the brink — and still feel hollow inside.If you’re stuck in this cycle, check out my interview with Dr. Richard Swartz for more on how to work with the inner parts of ourselves including the Inner Critic. It’s packed with insight on shifting these self-sabotaging patterns at the root.