For When You Feel Like an Imposter
What happens when you finally look at the evidence.
I recently had a conversation with a friend and client of mine, Lester Sydney.
We were talking about that familiar feeling - being stuck. Feeling like an imposter. Like somehow you slipped through the cracks and ended up somewhere you don’t deserve to be.
You know the voice.
You’re not qualified.
You’re not good enough.
Any minute now, they’ll realize you don’t belong here.
And the worst part?
You start believing it.
So I asked Lester a simple question:
“How do you help someone who feels this way?”
His answer was simple.
You start by asking why.
Why do they feel stuck?
Why do they feel undeserving?
Why do they believe they’re not good enough?
And then - you get it out of their head.
Put pen to paper.
Because as long as those thoughts stay inside your mind, they echo. They grow. They rewrite your story without permission.
So you write it down.
Write out every reason you believe you don’t deserve where you are.
Every insecurity. Every doubt. Every failure you replay.
Get it out of your head and onto the page.
And then - this is the part most people skip - you do the opposite.
You write down your accomplishments.
What have you accomplished in the last year?
The last five years?
The last ten?
What roles did you earn?
What skills did you build?
What projects did you complete?
What risks did you take that paid off?
Most people forget.
Life moves fast. We’re always planning the next step, chasing the next goal, measuring ourselves against a future version we haven’t reached yet. In the process, we erase our own progress.
Most people remember their failures vividly, but treat their wins like background noise.
And here’s what almost always happens when people actually do this exercise:
The list of accomplishments dwarfs the list of doubts.
A promotion you chalked up to luck.
An internship you downplayed.
A skill you taught yourself.
A project you led.
A moment where you stepped up when it mattered.
You didn’t accidentally do those things.
You earned them.
Yet so many of us rewrite our story to make ourselves smaller - telling ourselves we were lucky, or it “wasn’t that big of a deal,” or that someone else could have done it better.
But if you step back and actually look at the evidence, the story changes.
You’ve made it further than you give yourself credit for.
You’ve done more than you remember.
You are more capable than the voice in your head allows.
And when you finally see it - written out in front of you - it becomes harder to keep believing the lie.
Because the truth is simple:
You are not where you are by accident.
And remembering that might be the first step to moving forward again.
Thanks for reading. I truly hope this was helpful. Happy New Year. I’m excited for what 2026 will bring. Keep pushing forward.
- Isaac




Isaac, this is such a fantastic post. So, so, so relevant.
Your friend Sydney Lester is right on with his observations. I can only speak for myself when I say ‘I cannot remember the last time I thought about my accomplishments.’ Yes, I’m serious! Sure I’ve rebuilt my resume. But that’s NOT the same as every point that you and Lester have documented. What you and he refer to is for ‘mental’ health which is critically important for our daily wellbeing and emotional stability.
growth.
I will spend this weekend examining myself (mentally) and figuring out a strategy to implement what the points you have stated.
Thanks so very much! I hope you will get over rough patch soon. I’m so happy I’m reading and digesting posts like yours on Substack.
Issac, I repeat… you’re a sage! I hope that we can stay in touch. I have followed Lester on LI.
Mohan