Mitch Hedberg, Job Interviews, and Celebration

Some thoughts about jokes and some jokes about thoughts!

Jul 07, 2025

Dear friends,

I am grateful that you are here!
Thank you for making the choice to be here.
And now for another edition of my project where I share jokes that I love and the reasons for that.

The project began with a piece about one Mitch Hedberg joke, where I assessed Hedberg thusly:

”His jokes are songs, infinitely relistenable. Whereas so much comedy requires surprise to have its desired effect, Hedberg's has somehow transcended that.”

I now revisit another Hedberg beaut that delights me. I hope you enjoy!

"I had a job interview at an insurance company once and the lady said ‘Where do you see yourself in five years?’ I said ‘Celebrating the fifth year anniversary of you asking me this question.’"
— Mitch Hedberg

Where do I see myself in five years?
Celebrating the 30th-ish-year anniversary of loving this joke.

I love Mitch’s answer to "Where do you see yourself in five years?" for a lot of reasons.

One, I like that he says he's CELEBRATING.
I'm a big fan of celebrating.
I celebrate celebrating!

In this case, it’s about gratitude and optimism!
Looking forward to looking back!

Next, job interviews are like games sometimes.
Sure, there are questions they can ask you that will help you share with them what your skills are in a way that might let them know how good you might be at doing the job in question.

But THIS question?
Basically, can you predict your own future?
Man, he doesn’t even work at the company yet.

Where might one see oneself in five years?
Well, what's the best thing that can happen at this job?
I get promoted?
I take over YOUR job?
I'm your boss?
I own the company?
I win the lottery but keep working here because I love this job so much, specifically because of you, the person hiring me, and then I give you half of my lottery winnings so you can quit if you want?

It's a “normal” interview question and also it's weird.

So I love that his silly answer is basically highlighting the arguably even more ridiculous question, in addition to being celebratory.

I love that he's basically holding a mirror up to what the interviewer says, being completely present and in the moment with it, even though it's about the unknown Future.

Being present discussing the future. A tricky move to pull off!

Because no one knows the future, as much as job interviewers would like job interviewees to be able to.

So, because the question is weird and Mitch is being weird back, he ironically turns out to be very reasonable, which I also like.

Now, I don’t know if Mitch got that job, because I don't know how much insurance companies prioritize senses of humor in their hiring processes, but if I were in charge, I either would have given him the job OR refused him the job and encouraged him to go out on the road and become an iconic genius comedian.

Either way, I think Mitch showed that he understands the spirit of insurance, because insurance is about insuring that we have what we need in our lives, so that we can feel good and secure, so that we can experience joy.

And I believe Mitch's answer brought joy to the people at that interview.
I imagine it brought joy to himself.
And even if the interview never happened, this all certainly brought joy to me.
Joy that I celebrate now, joy that I look back on celebrating joyfully, and joy that I look forward to celebrating in the future.

Mitch took a serious question and made something silly out of it.
And now here, I take his silliness and make something sincere out of it.
And the circle of joke continues.

And I can see that continuing for at LEAST the next five years, which I think is, will be, and has been something to celebrate.

And now, because I also enjoy sharing my own jokes, I now will share a few of my own jokes:

A) is for A joke about a job interview:

"Where do you see yourself in five years?"
"President of Psychics Incorporated."
"You're hired."
"I know."

B) is for But wait, here’s another joke about a job interview:

*Achilles at a job interview*

"What's your greatest strength?"
"My whole body minus my heel."
"And your greatest weakness?"
"I'd rather not say."

C) is for Clark Kent at a job interview:

*Clark Kent at a job interview*

”What’s your greatest weakness?”
”Kryptonite… I mean perfectionism!”

And that’s about it for me. But what about from YOU?
Here are some questions you can answer!
Respond in the comments, email me back, or just think about it real hard!

1) How are you doing? What is new and good? How is your heart?
2) Do you have any fun job interview stories?
3) Have you ever predicted the future?
4) What is your greatest strength?
5) How are you doing NOW?

Arty Har-Hars

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