How to Overcome Your Past When Life Is Hard, with Jacqueline Cooley

Somewhere along the way, life handed you something hard. Maybe it was a home that never felt steady. Maybe it was a season that broke you, or a chapter you still do not bring up. And if you have ever wondered how to overcome your past when life is hard, I want you to hear this first: what happened to you is not a measure of your value, and it does not get to write your future.

Here is what I have watched an old chapter do to brilliant women. It whispers that they are behind. It tells them to wait until they are more ready, more polished, more perfect. And without realizing it, they let a story that ended years ago decide how big the next one gets to be.

My guest Jacqueline Cooley is living proof that it does not have to go that way. Jacqueline is the Leader of Learning and Development at JBM Packaging, and I found her through the Women in Manufacturing community, where she had just given a presentation. She grew up watching addiction pull her father in and out of her life. Today she leads a program that has impacted more than 300 people coming out of incarceration and recovery. She did not just move past her story. She turned it into her purpose.

Her Past Could Have Written the Whole Script

Jacqueline grew up primarily with her mother in a single parent home. Her father was in and out of her life, and through all of it, he was addicted to drugs. She could not predict when he would show up or when he would disappear. She could not count on him for much of anything, because the addiction had him so tightly tied into it.

And in her family, it was the thing everyone could see and no one talked about.

We always talk about the people who are addicted to drugs, but we don't talk about the kids or the wives or the husbands who are right there in the mix of the addiction and how that affects them.

Jacqueline Cooley

Her mother did the best she could, and Jacqueline calls her a great mother and her very best friend. But it was not until Jacqueline raised her own children that she looked back and understood just how hard that situation really was.

Now watch what she built from it. She became a deeply structured person, because structure was the thing her childhood never had. Her kids grew up with routine, and the family moved as a unit. If one child had a cheerleading tournament, all five of them were at the cheerleading tournament. She chose a husband who is intentional about his family, the complete opposite of the inconsistency she grew up with. Every hard thing became a blueprint for what she would do differently.

I wish things had been different. But despite that, I believe that they made me the person that I am today.

Jacqueline Cooley

You Do Not Overcome Your Past Alone

Ask Jacqueline how she got from that childhood to a leadership seat, and she does not start with a strategy. She starts with names.

The first was Teresa, her supervisor at a school district in Freeport, Illinois, in her first job out of college. Teresa was a leader who, in Jacqueline's words, really had herself together, and she was the kind of example Jacqueline had rarely seen in a leadership role. They worked with families and young people in genuinely difficult situations, and Teresa's counsel was simple and unshakable.

Just don't stop. Don't quit. Keep going. Sometimes you're going to run into difficult people, but that's okay. Keep going.

Jacqueline Cooley, on her first mentor's advice

Years later, a mentor at Cliffs in Ohio, one of the HR leaders there, showed her that HR did not have to fit in a box, that there were so many directions she could take her career, and taught her the timing that makes candor work: when to say something, when to hold back, and when to press a point.

Nobody succeeds alone in a vacuum. Every strong career has someone in its corner.

That is the pattern I want you to see. The woman who is now the mentor, the advocate, the builder of second chances, got there because somebody stood in her corner first. If no one is standing in yours right now, finding that person is not a luxury. It is the next step.

What a Second Chance Actually Looks Like

Here is where Jacqueline's story stopped me in my tracks. At JBM Packaging, she leads the Better Lives program, which hires people coming out of incarceration and people in recovery, and then surrounds them with real support. Not a pamphlet. Support.

Every new Better Lives team member meets with a life coach once a week for the first six months, tapering to biweekly and monthly meetings, all the way to a graduation. The point of those meetings is growth, both personal and professional. There is financial coaching. There is support with transportation, parenting, and furniture. JBM has even given out cars when someone needed one to keep moving forward. And every one of those services is open to any employee in the company, not just Better Lives team members.

Those are the numbers Jacqueline shared on the episode, and that last one should make every executive sit up. Support is not charity. It is a retention strategy.

The tone came from the top. When JBM's CEO, Marcus Sheanshang, introduced the idea, he told the company plainly that this was the direction JBM was going, and everyone could get on board or choose to leave. Because leadership never treated it as optional, it simply became a way of life.

And the leaders themselves changed. They have been trained in psychological safety, emotional intelligence, and engagement. They have learned that when a team member shuts down, it is often not rudeness. It is someone who spent five or ten years locked away and never got to practice handling frustration. Patience became a leadership skill at JBM, not a personality trait.

Actually, they're no different than you and I. And to be quite frank, a lot of times we are one mistake away sometimes from being that person.

Jacqueline Cooley

Sit with that one. The distance between us and the person who needs the second chance is one hard season, one wrong turn, one mistake. Lead with that grace, at work and everywhere else.

Speak Your Mind, and Make Sure It Lands

Jacqueline has always been someone who says what she sees. When she was younger, it would come out and land however it landed. The intention was sincere, but the delivery was not always well received. So she refined it, and what she learned is a masterclass for every woman who has been told she is too direct.

People do not like to be caught on the spot in front of a room. So she moved the hard conversations into private. She learned to read who can take the message straight and who cannot.

I hate to say fluff, but sometimes you gotta wrap it in a bow a little bit when you give it to people.

Jacqueline Cooley

Notice what she did not do. She did not go quiet. She kept the candor and changed the packaging, which matters even more in a male-dominated industry like manufacturing, where she has had to find the medium that keeps her voice in the room.

This is exactly where her world and mine meet. I told Jacqueline about a former podcast guest who was doing excellent work and got an average performance review anyway. When she finally asked, her boss told her that most of that work simply did not matter to him. She was working hard. She was not working in the language her leadership valued.

That is the Articulation Gap, the distance between the impact you create and the impact leadership recognizes and rewards. Your results do not speak for themselves. They get interpreted.

It is not about doing more work. It is about playing the notes leadership actually hears.

Bold Beats Perfect

Near the end of our conversation, I asked Jacqueline what men do for their careers that women could borrow. She did not hesitate.

Men take the risk. If they want to do something, they do not feel like they have to check off every box first. They just do it. Women, meanwhile, aim for perfection. We want everything checked, verified, and done correctly before we raise our hand. And in a fast-paced environment where everyone is learning on the fly, that habit has a price.

If you wait until you check off all the boxes until everything is perfect, you'll just get left behind.

Jacqueline Cooley

Some of what you try will be wrong. Some of it will be right. That is not a reason to wait. That is how everyone around you is already operating. The next role, the big project, the conversation you keep postponing: the version of you who moves before she feels ready is the one who gets there.

What I Want You to Take From This

When I asked Jacqueline what she wanted to leave with every woman listening, she gave me the sentence that holds this whole episode together.

Be bold and don't let your past define you.

Jacqueline Cooley

Do not settle, she added. Do not get comfortable where you are. Continue to build, and continue to strive for the best.

One more thing, because it is the part I care about most. Overcoming your past gets you into the room. Being recognized once you are in it is a second skill, and it is the one I teach. You take the bold step, and then you translate the work you are already doing into the language leadership recognizes and rewards. That is the whole game.

So name one thing you have been waiting to feel ready for. Then take one visible step toward it this week. Not reckless. Just bold.

About Jacqueline Cooley

Jacqueline Cooley is the Leader of Learning and Development at JBM Packaging, where she leads strategic workforce initiatives that strengthen retention, leadership, and long-term employee stability. With extensive experience across social services, government, and manufacturing, she brings a unique blend of operational insight and human centered leadership to her work.

She oversees JBM's Better Lives program, a holistic coaching and workforce development initiative designed to support fair chance employees through stability, readiness, advancement, and leadership. Under her leadership, the program has become a nationally recognized model for combining business performance with life changing impact. She holds a Bachelor's degree in Political Science and a Master's degree in Public Administration, is SHRM-CP certified, and is a national speaker and advocate for inclusive hiring, second chance employment, and workforce development reform.

Beyond her professional work, Jacqueline is deeply committed to family, fitness, and encouraging others to pursue bold growth. As a leader, mentor, and grandmother, she believes no woman should shrink her vision, own less than her full voice, or lead with anything short of strength and compassion.

Connect with Jacqueline on LinkedIn