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  • Writer's pictureJenny Dempsey

A date with imposter syndrome at 3 AM

Updated: Jul 8

The Midnight Doubts


"You can't even land a regular 9-5 job. You're not good enough. No one will hire you because you're a flight risk. Your well-rounded career choices have cost you. You currently make $0 income and are living off your savings. You spend most days in the garage covered in paint and sawdust, working on furniture you found in the trash. So, I ask you again, who are you to start a podcast and think you'll be successful?"


She hits me with this at 3:03 AM. My eyes dart around my dark bedroom, searching for an answer. I don't have one.


The Nightly Interrogation


She asked me the same question yesterday at 1:21 AM. The day before that at 4:25 AM. And the day before that at 2:22 AM. I didn't have an answer then, and I still don't have one now.


No matter what I do—mantras, breathing exercises, wave or rain sounds, getting up to pee and distract myself—she still yaps away.


The Therapist's Insight


"It's trying to keep you safe. In your comfort zone. Out of harm's way," a therapist once told me.


Yes, it's all me—thankfully, no one in my life actually says these things to me. I have a loving partner, the cutest dog, and the best friends and family. It's the negative voice extraordinaire, throwing digs at me over and over.


"You're not good enough," it says.


The Optimist's Toolbox


Through my natural inclination of being overly optimistic and as a semi-retired people pleaser, I'm proud of my ability to seek help. After years of therapy, coaches, mentors, and inspiring friends, plus one too many self-improvement books, I've built up a toolbox full of healthy ways to pull myself out of dark thoughts.


Successful furniture flipper right here

The "Anything is Possible" Era


And maybe it's a sign of progression, but these days, despite the imposter syndrome rattling in my brain making me feel shame and guilt, I find myself in a delusional haze of sorts where I'm in my "anything is possible" era. In my mind, I'm already a successful podcast host, furniture flipper, global speaker, and author of multiple books, workshops, and training courses. A haze where I can simultaneously be inspired by the people I talk to on the show and also inspire the people who tune in.


Is "Delulu" Actually Helping?


It feels almost criminal sometimes. It feels almost unreal. Do I need to check myself in somewhere? Or is being "delulu" totally acceptable and maybe actually helping me?


I'm not the type to sit around and wait, even when I'm scared or don't believe in myself. If no one will hire me, I'll hire myself.


The Podcast Beginnings


And so I did. And so here we are.


I started this podcast because I felt really alone and freaked out on this path of straying from the traditional route and starting my own thing. I bite the heck out of my cuticles. I get stress stomach aches. I don't talk about my feelings because I think they're stupid, and then I lose it over something trivial. I'm learning more every day and doing better every day.


I'm not perfect, don't have all the answers, and I can't promise anyone anything, but I do know that talking to 20+ people around the world who have experienced their own career transitions has made me realize I'm not alone. I'm not the only one who is scared.


Finding Comfort in Connection


These conversations have been an incredible comfort to my anxious mind, reminding me that vulnerability and uncertainty are part of the journey. By sharing our stories, we create a community of support and understanding.


And that has been an incredible bounty of help to my anxious mind.


Join the Journey


I hope this podcast becomes a comfort to you too, offering a sense of connection and reassurance that you are not alone on this path. We’re all in this together, navigating the ups and downs, and finding our way to success, one step at a time.




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