Lisa Callahan of DTLA on Life, Lessons & Legacy

Lisa Callahan shared their story and experiences with us recently and you can find our conversation below.

Lisa, so good to connect and we’re excited to share your story and insights with our audience. There’s a ton to learn from your story, but let’s start with a warm up before we get into the heart of the interview. What do the first 90 minutes of your day look like?
Water, supplement and exercise. It gets my mind, body and emotions set for the day. Unless I am sick this routine is a non-negotiable for me.

Can you briefly introduce yourself and share what makes you or your brand unique?
I am the co-host of “The Things We Know,” a popular podcast in the top 10% globally, a Transformational Coach and public speaker. I have helped thousands of women identify what they truly want and then go after it. I guide dynamic, high-achieving, professional women with my signature Transformation for Real™ system, taking them from chaos to clarity so they can live a life they are fully in love with.

Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. Who saw you clearly before you could see yourself?
I began working for Weight Watchers in 2003 as what was then called a Receptionist—the person behind the desk, checking members in, quietly supporting from the background. Every now and then someone would ask if I wanted to become a Leader, the one who stood at the front of the room and guided the meetings. My answer was always a gentle no. I simply couldn’t imagine standing in front of people and speaking.

Then, in 2010, everything shifted. My manager at the time, Ed, was preparing to leave the company, and before he did, he called to tell me I was being placed in the next Leader training—starting in a week. I didn’t have time to decline or overthink it. It was happening. He saw something in me long before I saw it in myself. He believed I could do it, and eventually, I did too.

And now? I’ve stood on stages far bigger than a Weight Watchers meeting, and I co-host a successful weekly podcast. Two things I never would have imagined for myself back then—yet here I am.

If you could say one kind thing to your younger self, what would it be?
If I had one piece of advice, it would be this: just do the thing. So many women wait until every duck is perfectly lined up before they take a chance on themselves. The truth? Those ducks rarely, if ever, cooperate. And while we wait for the perfect moment, we risk missing the very experiences that could carry us into our next, most extraordinary chapter.

We fear failure so deeply that we forget the real failure is staying stuck—never pursuing what lights us up, never choosing the life that makes us happy.

That’s why I co-host Best Chapter Yet, our twice-yearly retreat designed for women of every age who are ready to remember that their best is still ahead of them. Surrounded by a community that lifts and reflects possibility, women discover they can create whatever they desire—bravely, boldly, and without waiting for perfect.

I think our readers would appreciate hearing more about your values and what you think matters in life and career, etc. So our next question is along those lines. What would your closest friends say really matters to you?
My friends would say my heart is rooted in human rights and justice—standing up for what’s right, speaking out when something is wrong, and working toward a world where everyone has a seat at the table. They would tell you I value joy, courage, and possibility. I believe in taking leaps even when things aren’t perfect, choosing happiness over fear, and building a life that feels alive—not just one that looks good on paper.

Okay, so let’s keep going with one more question that means a lot to us: Are you tap dancing to work? Have you been that level of excited at any point in your career? If so, please tell us about those days. 
Since launching Transformation for Real in 2017, I’ve said many times that the Sunday Scaries no longer exist for me. I never wake up dreading work. I love what I do, and there’s nothing more fulfilling than watching my clients experience growth—both personally and professionally. Even on the hard days, the ones where another job might make me call in sick, I know that time with a client will lift me. Their breakthroughs bring me joy, energy, and the perspective that pulls me right out of my own head.

Contact Info:

• Website: https://transformationforreal.com
• Instagram: https://www.instagram.com/thethingsweknowpod
• Linkedin: https://www.linkedin.com/in/lisa-callahan-transformational-life-coach
• Youtube: https://www.youtube.com/@thethingsweknowpodcast

Image Credits
Diana Lundin and Robyn Richardson