A few days ago, I was flying from Tampa to Dallas. The executive sitting next to me glanced over and noticed I was editing our weekly newsletter titled “Accountability, Failure, and the Joy of Starting Over.”
He asked what I did. I told him I help people prepare for federal prison—emotionally, practically.
He paused. Then he asked a question I’ve heard thousands of times:
“Did you go to prison with kids?”
I said no.
He replied, “It must’ve been easier then.”
He’s right. It was.
Same thing came up that morning on my podcast with Matthew Cox. His words were almost identical. And again, he was right.
Let’s talk about what that actually means.
The Part I Didn’t Live—But See Every Day
I don’t have the experience of hugging a five-year-old goodbye in a courthouse hallway.
I didn’t have to call a daughter from the prison and pretend like I wasn’t crying after the call.
I didn’t miss birthdays, school plays, or the first time my kid hit a baseball.
So yes—my time in prison was easier.
That doesn’t mean it was easy. But it does mean I didn’t carry the guilt that so many parents carry behind bars.
I Paid to Get Home Earlier
That same night on the flight, I paid extra to get on an earlier connection home.
Why?
Because I hadn’t seen my kids in four days, and I wanted to be there when they went to bed.
That was just four days.
Now imagine four years. Or even four months.
That longing doesn’t go away. It gets heavier. I talk to men and women every day who are crushed under the weight of missing their children grow up. Some try to distract themselves with routines. Others write daily. Some just isolate.
None of it really fills the gap.
“Well, They Should’ve Thought of That Before They Broke the Law”
People love saying that. You’ve probably heard it—or thought it yourself when you saw someone get sentenced.
Here’s the thing: it doesn’t change the reality.
Yes, mistakes were made. Choices had consequences. I get it.
But moral judgment doesn’t reduce the pain of separation. It doesn’t help someone sleep at night knowing they won’t be home for their daughter’s graduation.
And if you’re facing time and have young children at home, you don’t need a lecture. You need a plan.
So What Do You Do With That Pain?
If you’re a parent preparing for prison, there are a few things you can do. They won’t erase the pain—but they might give it structure, so it doesn’t crush you:
1. Communicate Early and Often
Don’t wait until you’re in prison to think about how to stay connected. Talk now. Set expectations. Reassure your kids the best you can.
2. Create a Routine for Staying Present
That might mean weekly letters, shared journals—anything that keeps a thread going between you and your kids.
3. Don’t Use Guilt as a Wall
Your kids may be angry, confused, or withdrawn. Accept that. Your job isn’t to force a connection—it’s to stay consistent, so they know you’re still their parent.
4. Be Honest—Age Appropriately
Kids pick up on BS. Don’t sugarcoat. But you don’t need to unload adult details either. Let them know you’re working every day to come home better.
I Can Sympathize—But I Can’t Pretend to Understand
I didn’t go to prison as a father. That’s a gap in my experience.
But our team has worked with hundreds of parents who did. We have seen the pain and regret. Yet, we have also been inspired by their willingness to prepare regardless.
So if you’re someone staring down the reality of missing a year—or five—of your child’s life, don’t waste time pretending it won’t hurt and do not delay preparing.
Start now.
Build the structure that gives your family the best shot at thriving without you.
They can’t visit if you don’t tell them how.
They can’t write if you never send the first letter.
They can’t forgive if you never apologize.
You don’t have control over everything. But you do have control over how you show up—even from federal prison.
If this resonates, join our team this Monday at 1 p.m. Pacific, 4 p.m. Eastern. We host a free webinar to answer questions, share lessons from real cases, and help you avoid the most costly mistakes people make during a government investigation. Bring questions. Come ready to learn.
