Today we’d like to introduce you to Jake Strickland.
Hi Jake, please kick things off for us with an introduction to yourself and your story.
Hello, my name is Jake Strickland, and even though I’m not from here, it only took a few months for me to fall in love with Houston. For me, it is the city of forgiveness. When Houstonians find out I’m new, they’re quick to ask, “Oh, where did you come from?” It’s a question that brings a crushing moment of anxiety followed by an internal question: “should I tell them the truth?” However, this moment quickly fades when I remember that, in this city, my answer is usually met with compassion, not judgment.
The answer is prison. As a young man, I chose the path that would lead to two decades in a city of barbed wire, steel, and concrete. While there I reencountered the God of my youth, and along with forgiveness and mercy, was given a heart of service. By the grace of God I was able to spend my last 10 years coordinating rehabilitation and religious programs alongside Wardens and Chaplains.
When I emerged back into the world in July 2025 everything seemed so, well, bright: the landscape, the people, the future. But it didn’t take long for me to realize that I wasn’t as prepared as I thought. At the end of the day, reentry is hard, and your past can be an employment barrier. But in September 2025 I attended RISE, a career readiness workshop offered at Career Gear Houston. At the end of the day I was invited to have a conversation with someone who had been quietly serving in the background – cooking, cleaning and distributing snacks and materials. As it turned out, that servant was the CEO, and today I have the honor of serving as her Executive Assistant.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
No, it definitely has not been a smooth road. Rebuilding your life from the ground up after being away for so long comes with challenges that most people never have to think about. One of the hardest parts was simply getting someone to give me a chance. Time after time, job applications were dismissed because of my past before anyone took the opportunity to see who I had become.
There was also the challenge of learning how to navigate a world that had completely changed during the twenty years I was gone. I remember being handed an iPhone and honestly thinking, “What do I even do with this?” Everything had become digital — applications, communication, transportation, schedules — and I had to learn it all from scratch while trying to survive day to day.
Transportation itself became another obstacle. When I first got my job, my commute was nearly two hours each way: bike, bus, bike — both coming and going. Some days were physically exhausting before work even began. On top of that came the mental and emotional weight of starting over, trying to rebuild confidence, stability, and identity all at once.
Then there was Houston. If you have never lived here before, it can feel massive and overwhelming. Learning a new city while simultaneously rebuilding your life added another layer of uncertainty and pressure. But every challenge taught me resilience, adaptability, and perseverance. Looking back now, those struggles became part of the foundation I stand on today.
As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
Today, I serve as the Executive Assistant here at Career Gear, where I work closely alongside leadership in several key areas of the organization. My primary focus is supporting our CEO in fund development and membership and partnership management, helping cultivate relationships that strengthen our mission and expand our impact throughout the community.
At the same time, I also assist across many of the organization’s operational areas, including client services, programming, and donations. One of the things I value most about my role is that no two days look the same. I have the opportunity to support both the strategic vision of the organization and the day-to-day work that directly impacts the men we serve.
Career Gear serves men from all walks of life, but we also intentionally support several specialized demographics, including youth, veterans, and justice-impacted individuals. Because of my own lived experience, working within the justice-impacted space is especially meaningful to me. It allows me to connect with people in an authentic way and hopefully show them that their past does not have to define their future.
What I am most proud of is being able to turn my story into service. I know firsthand what it feels like to try to rebuild your life while facing barriers, doubt, and uncertainty. That perspective gives me a level of empathy and understanding that cannot be taught in a classroom. I believe what sets me apart is my ability to bridge professional work with lived experience — not just speaking about transformation, but actively living it every day.
Do you have any memories from childhood that you can share with us?
It would have to be not one, but every Christmas. It was never just a holiday — it was an experience. Whether putting up the tree, playing on the ice, being a present private investigator, or stealing Santa’s Cookies, it was my favorite time of the year.
I especially remember sitting by the fire cracking walnuts with my Papa while he sang his corny songs that somehow became part of the soundtrack of Christmas for our family. And like a scene straight out of the song, I remember one year catching “Grammy kissing Santa Claus” and being genuinely worried Papa was going to be upset — only to later realize that Papa was Santa.
Yeah, Christmas was home.
Contact Info:
- Website: https://careergearhouston.org
- Instagram: https://instagram.com/careergearhou
- Facebook: https://facebook.com/careergeargreaterhou
- LinkedIn: https://linkedin.com/careergeargreaterhouston
- Twitter: https://twitter.com/careergearhou
- Youtube: https://www.youtube.com/@careergearhouston7525
