Words & Banter

Have You Ever Wanted A Second Chance? Or A "Do Over"?

Design by Sawyer Pennington, Underlying photo by Ye Jinghan on Unsplash

Has there ever been a time when you wished you had a chance for a “do-over”? We’ve all made bad decisions at times. Sometimes it’s something small. Other times it can be life-changing. Second chances are opportunities to show we’ve learned from our mistakes. So, who wouldn’t want a second chance?

For many people who have found themselves on the wrong side of the law, a second chance might be all that’s needed to truly turn their lives around, which is why April was first proclaimed Second Chance Month in 2017. But five years before that, when we detoured into the criminal justice world, Red’s perspective on second chances changed dramatically …



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I had no idea that April was “Second Chance Month” until you sent me the official proclamation. I find it interesting that in the midst of juggling our usual million and one Red & Black things, your interest in criminal justice, which I know you consider a “passion project”, is as strong as ever, maybe even stronger.


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It is not intentional, sometimes “ passion projects” find you. And, when you least expect it.


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Or where you least expect it! Only you would take a “field trip” to a men’s prison.


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I will not get on my soapbox about how our education system contributes to the criminal justice problem. I will never forget a friend of mine who was formerly incarcerated telling me, “Rehabilitating people makes the assumption they were habilitated in the first place.”


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When you stop and think about that statement, it’s pretty powerful! But I have to smile as once upon a time you, and I, used words like “offenders” and “prisoners” until we learned how our choice of words could be dehumanizing .


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Says the woman who once believed in the idea of “lock ’em up and throw away the key”.

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That was before! I know you told me that just because someone made a bad decision, it didn’t make them a bad person, but it sounded like a cliche. Now, my opinion is based on our experience and the impact we’ve seen . The feedback has been eye-opening. Unfortunately, life doesn’t come with “do-overs.”

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Exactly. None of us are perfect. We have all made bad decisions. Second chances are about opportunities to show we have learned from our mistakes.

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Well, I know I have. Obviously, not anything illegal. But it made me determined to teach my daughters what I had learned. Probably one of the most heartwarming parts of the feedback we’ve received is that so many people on the inside want better – not only for themselves, but for their children and grandchildren.

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Yes, which is why having a second chance is so critical. And, helping set people up for success, not failure, because it is about more than changing the lives of the formerly incarcerated -- it can change the lives of their families and, in turn, our communities and our country.

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A ripple effect that could mean more people may get it right the first time and not need a second chance.

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True. Maybe we should look at it as giving society a second chance …
Photograph Courtesy of KIPP Houston Art School

Every time we see the photo above of our "guinea pigs", it brings back such fond memories. You may be thinking, "What? Are they calling those students guinea pigs?!" Well, actually, yes. And before you think ill of us, please know that we use the term with great affection, deep gratitude, and utmost respect. And these eight amazing seniors from the Class of 2010 know that's our nickname for them because ...

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Red loves to stop and reminisce. Black prefers to look forward.

But even Black will admit that sometimes there’s value in looking back — it reminds us where we came from, the detours and roadblocks we have managed to navigate, and that we may be stronger and more capable than we give ourselves credit for. Sometimes, it’s a lesson learned. Sometimes, it’s a memory that reminds us what’s truly important.

But Black has one caveat (and it's one of her favorite car analogies) …

If you decide to look back, keep it in perspective. There's a reason why windshields are so much larger than rearview mirrors.


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The last few days have been beautiful fall weather, and I can't help but wonder — do you ever miss having your Ferrari convertible?


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Although some days are perfect convertible weather, given that I barely drove it the last few years I owned it, averaging less than 50 miles a year, I can honestly say, "No." In fact, I cannot even remember the last time I drove it.


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I can't help you with that, but I'll never forget the last day we taught at KIPP Houston High School, and you drove it there. You should have seen the students' faces as you were lowering the top on it.
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