Ask a stupid question, get a stupid answer

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I hate the notion that if you arent working, its bad... Fuck off... if i can afford it, maybe i dont want to work...

I did that for nearly a year in my mid 20's after getting off a 5 year job that managed to save me a whopping $3k... So I squatted on my cheap ass house with a roomie and just got drunk, played games, and got really into reddit.

Was it worth it then? Yeah, was it worth it now? Eh. Passive income would've been nice but eh. I did enjoy my time. And I found I could 100% be one of those people that never worked a day in their life and would have no issue.
- I wish i could do this for a month each year.
I suspect it's the implication you were doing illegal things to survive. And they don't want to be listed as your employer if those things catch up with you later.

Also, if you can say you were living on savings you'd be fine, I assume.
- If you tell a job you have savings, they're going to think you'll just leave the job whenever you want. They don't want that. They want dependable workers, as in, the workers depend on the job to live.

Can you explain this gap in your resume?
Yes. I can.
...
...
So?
So what?
Why don't you explain it?
Because you didn't asked me to explain it, you asked me if I could explain it.

"What's your greatest weakness?"

"Interpreting the semantics of a question but ignoring the pragmatics."

"Could you give me an example?"

"Yes, I could."
- A lawyer's dream client. Only answer the exact question asked.
  
  "Do you have the time?"
  
  "Yes."
  
  "....."
Found the teacher
- Person with ASD, more likely.
- More like Sensei/Guru/matrix mind master/ found the AI
  
  :p

I just say “it’s personal, and I won’t be discussing it.” If they don’t want to hire me because of it, I don’t want to work there anyway.

It’s absolutely none of their business what I was doing, especially that I went into a deep depression after my mom died and my live-in ex cheated on me while I was caring for her, and then spent a couple years selling her non-sentimental possessions to live off. And I’m not willing to make up some bullshit to hide it either, it happened and I’m not ashamed of it, but I’m not sharing it with interviewers. Meh meh.

Wow, tough situation. Glad you got through it.

I tried to found a startup with a buddy. He had a great idea, but it turned out that he didn't have the technical chops to fulfill his end. Bummed around after that on money and stocks from my previous gig. When I finally tried to get a job again, I couldn't get a callback to save my life.

I kept moving down the food chain all the way to regular physical labor. I couldn't even get a job at a vet or grocery store. Having major tech employment on my resume meant they knew I'd bounce the second I had the opportunity. It was a toxic dilemma resume: too high of a former position to qualify for something like retail, too long without a job to qualify for other office jobs.

I got back on top through a temp gig. Having recent employment got other tech employers to actually consider me again, and I've been ok since. I never would have imagined what that gap could do to make me impossible to hire.
- Unfortunately this all happened in my early 20s, I went to college after, but there’s still a big gap that can’t be explained by school alone (and it’s a gap because I had military service prior to that which I always list)
  
  I got stuck on the tempy-go-round (only able to find contracts due to gaps, and too many contracts to land a permanent job - several employers asked why I prefer contracts… I don’t, it’s all I could get.. but that answer is it’s own can of worms..). I finally found a permanent job and realized I spent so much time on contracts that I can’t do the same thing day in day out for more than a year without driving myself bonkers. Ultimate catch-22.
  
  So I’m going back to contracts. However, not entry level desperation contracts, ones actually using my degree. Covid remote work was an absolute silver lining for my field - used to be impossible to find positions, now they are there and pay super well (6 mths to make what I make in a year now), but mostly contract.
Good on you man. It's critical to work somewhere that respects people for their skills and work ethic. Not arbitrary expectations.

Similar situation myself.

Some places will understand. Many don't. I'll be either brutally honest in a interview or I'll set those boundaries.

"I signed an NDA and cannot say more."

"Where do you see yourself in 5 years?"

"I signed an NDA and cannot say more."
- If you are the hiring manager you are LEGALLY REQUIRED to tell me

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Can you explain this 20 year gap in your resume?

Well it all began when big smoke came to my house and told me to sell his weed on the streets.

....

After a while I was organzing the whole drug distribution of the town.

....

Because I always thought working in the porn industry is fun I used my contacts to get a job there too.

It was a bit difficult to get the whole drug job and beeing a porn actor done, but I managed.

....

So after breaking out of prison and changing my name I came here to this job Interview.

Tell them you did something unverifiable but technical.

"I started a game studio with a buddy from college. No, sorry, I don't have a TIN (tax identification number [IRS])"

Give them a number to a burner phone and fake an accent.

"Tom? Yeah we worked together at ___ I felt like he was a great guy to work with."

Tell them you were deathly sick.

"Yeah I had skin cancer. Nothing major but I had to take it easy and after beating it we all went on vacation to celebrate"

Tell them you lived the software engineer dream life

"After leaving my last job I wanted a change of pace so I went to become a bartender in Melbourne. It was all under the table"

Tell them you were deathly sick.

"Yeah I had skin cancer. Nothing major but I had to take it easy and after beating it we all went on vacation to celebrate"

It may depend on where you live, but it may be illegal for an employer to ask about anything medical in an interview. I have a two plus year gap and if I get asked about it, I just say, "illness." They can't ask any follow up questions.

I have occasionally expounded on it, saying, "I'm fully recovered now." Just to reassure them that I don't expect to miss work due to illness in the future.

Nobody ever asks about gaps on my CV. They always turn me down, list some bullshit reasons, like not enough experience and end with "and then there are some gaps on your cv so yeah"

That's how you know it was the excuse and not the cause.
Lie. Make them do the legwork necessary to catch you. Often they won't because that costs money.

If you want to improve it, with some work, take online or community classes.

Join a local mutual aid or similar org. and volunteer in your city.

Then you spice up your resume with those options.

That would help with the questions.

edit: word

Thx mate, but this is a meme, my actual CV is perfect! 🤡
- Great to hear.
  
  Many do not know of such options, I did not that far back.

I'll explain the gap in my resume when you'll explain the gap in your hairline

What's your greatest weakness?

Being straightforward and honest

Huh, well!… we don't think that's a weakness..

I don't give a shit about your opinion

“That’s classified”

those were the daaaays

Best way to deal with this question is to say, "No I cannot. I signed an NDA"