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Sunday, May 11, 2025
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WOMAN SCARED TO TELL BOSS SHE IS GOING TO JAIL, WANT TAKE LEAVE & QUIETLY GO IN SQUAT

If you had to go to jail for a month, would you tell your employer?

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Context: Female, early 20s, good family support (though not rich financially), job in tech start up, can afford therapy, already in current job for close to a year, have been going through rehabilitation and professional counseling since incident

Employer is not too stringent on background checks, I am doing okay work performance wise and relationship with bosses wise

Integrity is key but having to job hunt with a criminal record would suck more. So I am considering ‘hiding’ it and asking for unpaid sabbatical to fix personal matters if sentence is short

I’m at my wits end, I hope I can get some advice, thank you.

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It’s alot of mixed feelings and the question is really about honesty vs practicality. Do the right thing and be honest? Or keep quiet, hide a skeleton and keep my life going as per normal.

Netizens’ comments

  1. The following is just to clarify your understanding on criminal record declaration:
    – Your employer isn’t the one reporting to MOM or the world that you have a crim record. You cannot ‘hide’ your criminal record from a background check. Whatever is in the system, is open to all to check. And there are literal companies specialised in BG Checks. You won’t be able to hide anything.
    – You can choose to hide it from your current employer, sure, but this is almost guaranteed to be a breach of contract and if they ever do find out, termination is guaranteed, along with whatever other penalties they try to levy on you (clawback of benefits etc). Possibly even make another police report against you. Read your contract carefully.
    – You can lie on your application, pass the interview stages etc but ultimately you’ll never make it past the final background check (unless its a shit-run family SME) which basically every proper firm out there does as a bare minimum. Integrity is paramount, and no one hires a liar.
    To end off, imho I would come clean and if that leads to termination, then so be it. A crim record isn’t the end of your career.
  2. Check your contract. Usually you are obligated to disclose any pending or possible criminal charges.
    A few friends have gone through this before. Unless it’s something like fraud or assault or theft, employers usually won’t care.
  3. If it is a minor offence, just be upfront with your employer. Honesty leads to clear conscience. Even if you hide it and move to other jobs in future, your new employers could still do background checks and find out
  4. Have you considered what happens if your colleagues have a question and message you without a response during that 1 month?
    Do you have a lawyer? Is 1 month a certainty? When will it happen? Many times the case can take months or years to conclude.
  5. Somehow, they are going to find out. Just tell them the truth. The worst is getting fired.
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