Haunted by Past Mistakes


Dear Robin:

Several years ago I made a mistake.  I stole from my employer and was caught. I did not serve a prison term but I was on probation for 3 years until recently.

I am finding it very difficult to move on from this situation, both personally and professionally. I have not been in a relationship for a while, partly because I don’t want to have to explain to someone as I get to know them what I did.

Worse is that finding a job in my field has been so far impossible. Everyone does criminal background checks and I do not make it past that point in the interview process.

I am losing hope and considering changing my name and leaving the state to try to start over, but my family is begging me not to. They are still supporting me as I try to get back on my feet. I have a college degree and 5 years in my profession before this huge screw-up happened, but now I can’t get a job that pays over minimum wage.

Any ideas on how I can reinvent myself and get on with living my life? I deeply regret my actions but it seems like nobody will forgive me and let me try again. I feel totally hopeless and like my life is washed up at 28.

-Messed Up

Dear Messed Up:

Thank you for sending me one of the most important letters I have received in the year I have been writing this blog. I hope I can do you justice because I am a big believer in second chances.

After all, without second chances I would never have gotten another date with Mr. Patience and Understanding after I almost killed him in a bizarre rafting accident (true story, but in my defense, he never should have given me the oars).


I am also a firm believer that nobody should be defined by the nadir of their existence, or in my case, 1991 and 2003-2006.

Our criminal justice system isn’t well-equipped to help people come back from their mistakes to become contributing members of society, but I think there are some things you can do to help yourself recover from your past.

Changing your name and moving away isn’t one of them, unless you can figure out how to get a new social security number. I’ve tried – it isn’t easy. Besides, everywhere you go, there you are. Just ask Terri Horman.

You told me when we chatted that your family is the central reason why you haven’t given up, so my inclination is that you should remain close to them. This is not to say you should never venture outside your state, but their support is critical to you as you recover from your mistake and make a new life for yourself.

I know your probation officer gave you some resources to access and while I encourage you to explore those programs I’m going to try to go outside the box and identify a few more ideas for you.

1. Try to get your charge reduced or your record expunged.

It is possible to have a charged reduced or a record expunged.  Since this was your first criminal offense and you have completed probation and paid all your fines and restitution to your former employer, I would not be surprised if you were successful in obtaining a charge reduction or expungement.

If your felony is reduced to a misdemeanor, once you receive the reduction from the court you won’t have to divulge the felony (and many applications do not include misdemeanor charges).

If expunged, your conviction does not have to be divulged on a job application, unless that job application specifically says “including expungements” or something similar.

However, be sure to order a copy of your criminal background check to ensure the charge reduction and/or expungement has gone through before you fill out any applications.

2. Apologize.

You told me you were a real star at your company before the theft and that they were (understandably) extremely angry and disappointed in you when they discovered what happened.


Your mentor at the company was especially upset and embarrassed because she vouched for you coming into a job for which you weren’t entirely qualified.  It’s time not only to apologize, but to make amends.  There is a big difference between the two.

I was surprised you didn’t have to write a letter of apology as part of your plea bargain but that’s actually a good thing, because an apology demanded is an apology without value.  It’s time to sit down and write a heartfelt mea culpa in which you acknowledge your guilt, that the crime was hurtful to your mentor and the company, your deep regret and a list of things you learned from this experience.

While I don’t expect them to write you a glowing letter of reference (“she was, um, really creative when it came to her purchasing card”) it is possible they will forgive you and be willing to speak with potential employers about your positive impact on the company before you went off the rails and that they believe you have been rehabilitated.

Even if they do nothing to help you, it is still a positive step in the right direction.

3. Be prepared to tell your story.

In the event you cannot get your charge reduced or record expunged, you should be well-prepared with an explanation (not an excuse) for what happened and why you know it will never happen again.

Do some deep thinking on how you got yourself into this situation and what you have changed in your life to ensure you are on the right path from this point on.  Be ready to articulate that process in a sincere and thought provoking way.


Everybody loves a good comeback story, so do your damnedest to convince potential employers that they are backing Robert Downey Jr., not Lindsey Lohan.

4. Make sure your credit is good.

Are you all wondering why?  Credit problems can cause serious dings in the application process.  This is why I now work for myself.  If your credit score isn’t the best, rehabilitate it as soon as possible.

As for romantic relationships, you need to start forgiving yourself for your crime and embrace what it taught you instead of wallowing in shame and embarrassment.  No, it wasn’t the most stellar behavior you’ve exhibited in your lifetime.  But it’s part of who you are, an off-color thread woven into the fabric of your life that can still be beautiful.

Anyone who is worth your time will come to find out (as I did from talking to you) that you are truly remorseful about what happened and you are making big changes to improve your life.  The right guy will come along and understand that a profoundly bad decision is a chapter in your book, not the book itself.

I know this is a terribly difficult situation for you and I wish you all the best.  This is a time that will define you: how you manage this adversity will create ripples that echo for years.  Dig deep, forgive yourself, work hard, be prepared to start at the bottom, and open yourself up to love again.


All my best,


(record expunged)


This Post Has One Comment

  1. Serena uible

    This is a great answer to a question that is more common than most people think. Getting out of a rut after screwing up can be really tough, especially if one falls into obsessing about the past. Something that has helped me is thinking “don’t waste your screwups, learn from them and do better”. Sometimes it helps.

    Anyway, again, great answer!

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