How to Tell an Employer that You're Going to Jail


Thinking about going to jail can be so stressful that you will find it impossible to focus on something else. Imprisonment is one of the few things society looks down upon. Prisoners are considered outcasts who don’t belong anywhere else but jail. Is it scary? Yes it is. So, you have just been handed a sentence and wondering how to break the news to your professional associates, including your employer. How do you go about it?

In many cases, finding the right words to break such news can be difficult due to the stigma associated with going to jail. You want to pass the message clearly and still afford to wear a smile, albeit subtle. Here are tips on telling the boss that your time in the office has been cut short and jail is your next stop.

Get the environment right

As you may have little control over your manager’s environment, it is necessary to ensure they are alone in the office before going in. You could ask the secretary to keep other visitors waiting until you are finished explaining the news. If it’s a busy office, it’s preferable to meet your employer in the evening when there is less work. However, should your boss agree to meet you outside the office, choose a friendly setting that is away from people. This environment will give you the confidence to break the news and allow him to console you. In times of difficulty, we all need that warm and reassuring hug.

Have someone around

Have a close friend or workmate you trust who already knows your situation to join you. Telling someone that you are going to jail tends to go differently from what you actually had in mind. Some people will understand why you are going to jail. Others will instantly judge you, yet they have no idea why you did what you did. Others will just be plainly confused. Having someone else with you makes the whole experience friendlier and helps you control the emotional shock associated with breaking such news to your boss.

Be straight up

Be straight up with your employer. Having to tell him you are going to jail means you trust him and share a close, professional relationship. Therefore, don’t need to beat around the bush. If you have been handed a two-month sentence for driving under the influence, tell him. If it’s a case of hit and run, say so. They deserve to know. Telling the truth will help you embrace the fact that you are jail-bound.

Give the specifics

Give your boss the specifics. By now, you should have observed their facial reactions and judged whether he or she is supportive. Narrate to their how you found yourself in your current situation. This is especially important if you are innocent. Your boss can be in a position to defend you if you choose to appeal your sentence. Besides, they can decide to retain you as an employee of the company thus showing support, even while you are away.

Lighten up

Make the whole experience as lively as possible. Don’t create a somber mood as people often make mistakes. Some are forgiven and others are fined or jailed. You could be away for a month or two years, but there is still light at the end of the dark tunnel you are in. Make it a matter that you can both laugh about while having a beer or mojito on the beach after completing your jail time. Yes, you can laugh about it someday!

Remember, the fact that you have the time to tell your employer that you are going to jail means your crime is light. Otherwise, if you robbed a bank, you could already be locked up. Let this cheer you up as you prepare to inform the boss. Take it step by step. Let him hear from you. Good luck!