Bill Livolsi is a Member of our White Collar Support Group that meets online on Zoom on Monday evenings.


When Is The ‘Right’ Time?

Anyone who has been involved with the criminal justice system asks these questions:

What’s the right time to tell my family?
What is the right time to tell my employer?
What’s the right time to tell my friends and colleagues? What’s the right time in a social setting?
Is there ever a right time? How do I tell anyone?

I have come to believe that these conversations need to happen, sooner rather than later. The topic needs to be broached, otherwise it’s a sack of bricks we silently carry everywhere we go. And it gets heavier and heavier with the passage of time.

Keeping secrets is corrosive, but these are hard conversations to have.

We are reluctant to have the difficult conversations surrounding our criminal justice issues. We’re afraid of rejection, we’re afraid of judgment and we’re afraid of being ostracized. All pretty normal fears.

Anyone who knows me knows that I believe in disclosing our situation to our employer, or prospective employer, sooner rather than later. I feel that keeping it a secret is in the long run counter-productive to our employment prospects. When they find out, and they will find out, having kept it hidden only reinforces the notion that we are, among other things, untrustworthy.

What about the numerous other situations we’ll encounter in our lives? Let me share a story from this past week at work.

I was paired for a day-long task with another one of my coworkers. We had never worked together before. The task at hand gave us ample opportunity to have a conversation while we were working.

As we were comparing our relative experience with our employer they told me how grateful they were to have this job because it was so difficult to find work as they were on federal probation.

BOOM, there it was!

Here I was thinking of ways I was going to broach the topic with them (at some yet to be determined ‘right time’) and they got there first. I felt good that they were comfortable sharing this part of their life with me. Then I felt a sense of relief as I shared my situation. As we continued our conversation throughout the afternoon we found that we had so much in common irrespective of the differences in our convictions. It was a really good day.

I’ve been thinking about this experience and here are some thoughts I’ve come away with.

Prior to that moment did I have any inkling they had a felony conviction? No! And the same is true for them about me, they had no idea. Did we have large F’s stamped on our foreheads? Obviously not. Yet we both were silently keeping the same secret, until we weren’t.

It felt very good to be able to talk openly about our experience free of judgment and not having to hide something so impactful in our lives.

Too often I forget that there are hundreds of thousands of men and women in our society carrying around the same guilt, shame and fear of judgement that I am. They are the checkout person at the grocery store, they cut my hair, they’re my plumber, they’re my electrician, they are the men and women I work with.

I am very mindful of the fact that not every experience that I will have, or you will have, is going to be pleasant. I have had plenty of unpleasant ones in the past. Sometimes my worst fears will be realized; I will be judged, or rejected.

So, is there ever a right time? And with whom do I share? I don’t really know for sure, but I do know this much – the more I hold it inside, the more energy I expend keeping my secret, my sense of isolation will never truly end.


Bill Livolsi is a Life Coach supporting the white collar justice community and a volunteer with Progressive Prison Ministries. He helps men and women facing prosecution for white collar and non-violent crimes navigate their journey – including rebuilding their lives after prison. He was prosecuted for a white collar crime and spent 13 months in Federal prison. Bill can be reached at