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20 Questions Tuesday: 475 - Impostor Syndrome

November 11, 2025 Scott Ryan-Hart
2 color image of a person in the kitchen in front of a sillhouette labelled "Impostor Syndrome"

Today’s topics is sadly near and dear to my heart. This is a phrase I put together fir a 20 Questions I am doing with someone right now and it launched the idea that maybe I should investigate this further:

“I consider myself an artist, a storyteller, a writer, a blogger, a user experience designer, a geographer. Sometimes these are isolated individually, sometimes they are in the same constellation. In many ways they are often compartmentalized and those identities are only broken out when that part of me is actuated. 

My impostor syndrome kicks in all the time. I am not that great of an artist, I "no longer" "do" geography," I'm an unemployed user experience designer, in many ways I also feel like a failure due to my laziness... and in some ways that is not untrue.”

So, today’s topic was born. Name it and shame it,  A couple prompts later and ChatGPT has gifted me with 50 Questions to sift through and create a collection of 20 Questions for the good old bloggarooney (of which I have been doing for far too long with very little actual readership).. Impostors Unite!

Here we go… onto the questions. 

1. What  is impostor syndrome, really — insecurity, humility, or mis-calibrated confidence?

Here is the simplest and best definition I could find:

The persistent inability to believe that one's success is deserved or has been legitimately achieved as a result of one's own efforts or skills.

So, it is primarily insecurity with a tinge of mis-calibrated confidence. Humility is not a lack of confidence, it is a quiet, non-hubristic understanding of one’s capabilities.

2. Does impostor syndrome fade with age?

Some of it does… some of it is worse… They are letting me make adult decisions that will affect my children and loved-ones’ lives, and I am not that competent of a person. 

3. Can competence and self-doubt coexist peacefully?

Somewhat, but they are often at odds with each other. Can light and dark coexist?

4. What’s the difference between healthy self-critique and self-sabotage?

Volume, magnitude, and specificity. Self critique can be the accurate identification of issues that should be corrected for better outcomes… everyone should have a certain level of self-critique, it is when critique becomes un-actionable and demoralizing that it shifts to a type of self sabotage. 

5. Are doppelgängers/Impostors born, conjured, or manifested from someone’s self-doubt?

So, are dopplegangers actually tulpas constructed from our manifestation of impostor syndrome?  Interesting concept.  Dopplegangers are much more fey creatures who take the place of other people. 

6. What role does comparison play in sustaining impostor syndrome?

It plays a huge role. It is difficult to feel like an impostor if you don’t have a good example to feel you are not living up to.

7. Does success cure impostor syndrome — or deepen it?

Honestly, it depends. It could go either way. 

8. Can you fake confidence until it becomes real?

Some people can, but not me… I can fake it until someone thinks I am making it.

9. When does “I don’t belong here” turn into “I earned my place”?

Hopefully after I am gainfully employed again, otherwise when I look around at my under-employed self… and I am afraid I have actually earned this.

10.  Is a D&D mimic just imposter syndrome with teeth? How long could you pretend to be a chest before you forget you’re a monster?

I think less an impostor.  I imagine that when the mimic’s reaction to being used as a chest is not to devour the person opening the “chest,” but to politely store the materials offered to be stored.

D&D Mimic

11. Does a mimic ever wish someone would open it — just to be seen for what it is?

I imagine mimics consistently fantasize about that moment. (oooh look an “em” dash… did ChatGPT write these questions? Yes, yes it did.)

12. Does your impostor whisper or narrate in full TED Talk form?

Definitely a whisperer… and insidious, quiet whisperer

13. Do AIs ever get impostor syndrome — or just “version anxiety”?

Umm… ChatGPT… You Ok, bro?

14. How many awards does it take to silence a fraud alarm?

Not sure that awards are the thing that will silence the “fraud alarm,” as you put it. I typically hit the snooze button and just push that alarm down the road.

15. Is impostor syndrome contagious, like yawns or burnout?

I don’t think so.  I think it is something that is born of anxiety or depression, not passed along like the flu or ecoli

16. What’s scarier: being exposed as a fraud or realizing no one was watching?

Oooh… different sides of the same coin.  I have been writing this blog for over 15 years… it would definitely hurt more to be outed as a “not good writer” than to realize no one is watching… I have been aware that no one is watching for years now. 

17. If everyone feels like a fraud, who’s left to be the real deal?

I guess ai’s and llm’s? At least that is what ChatrGPT wants you to think

18. If you fake it till you make it — when do you stop faking?

Ummm… when you make it.  You answered your question with your question. But that doesn't actually work… Oh GOD! I”M A FRAUD!!!!

19. Can imposter syndrome ever be useful fuel?

I think for some people, it definitely can.  It is about what motivates you to do better. Some people worried that they will be found out to be a fraud will work harder to prove people wrong… some people will just lay low and keep their heads’ down trying not to be seen.

20. If a changeling blends in too well, do they lose their true form — or finally find it?

A changeling’s true form is someone aware that they are other.

And one to grow on…

21. What if imposter syndrome isn’t in your head — but sitting quietly in the room, waiting for you to notice it has your face?

It’s right behind me, isn’t it?

  • To recap: 

  • Dude, I need a gainfully employed job

  • Badly

  • I am trying to push through the depression of under-employment and do things again

  • Need to draw more

  • Need to write more

  • Need to post 20 Questions more

  • The government shut down has not been helpful for the contract work I was working on

  • Hopefully it spins back up soon

  • I would love to get one more paycheck from it

  • I’d love to get regular paychecks from the company I am subcontracting with

  • They are a great group of people who are doing really interesting work

  • BUt I do not think my continued regular full-time employment is a thing for them

  • The market is complete crap right now as well

  • I am getting ghosted by 3rd party recruiters now

  • Maybe I should play the lottery

  • Mega MIllions would be awesome

  • I hear it is at $10.4 Million right now

  • Art commissions are open

  • Slots for 20 Questions interviews are open and ready as well

  • Do the thing with Substack

  • Or with Medium

  • Have a great week everyone

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