Building a Better Life with Jennifer Warren Medwin

If you’re in a season of transition or challenge, here’s the good news: There is a light at the end of the tunnel. And, no, it is not a train.

“Whenever I meet with a new client, I look at them and say, ‘Congratulations, you have made it through 100% of your challenges,’” Jennifer Warren Medwin—a Miami-based Empowerment Strategist, Certified Divorce Coach, Family and Marital Mediator, Family Transition Facilitator, and Somatic Trauma-Informed Practitioner—says. 

“How do I know that? Because that person is there with me in that moment. They may have scars. They may have things to work out. We all do—that’s part of being a human being. But if you’re still here, the potential is limitless. Because I truly believe there are messages in every mess.”

A Chaotic Start 

And when Medwin speaks of scars and doing the work, she is speaking from first-hand knowledge. A little over a decade ago, Medwin found herself adrift after the loss of her parents and a divorce. A tumultuous season of life and parenthood had forced her into contemplation of some of life’s bigger questions—as the teetering tower of personal development books on her bedside would attest to. Yet she held a core belief that, as she puts it, “setbacks are opportunities for comebacks.” Could her comeback be one of more direct service? Though Medwin had run her own nanny placement agency for 15 years, she began to think about where alternate personal and professional pathways might lead. “I wasn’t sure what the next chapter of my life would look like,” she says, “but I was definitely looking ahead.”

A chance encounter between Medwin’s sister and an old mutual friend brought things into focus. The friend had become a certified divorce coach. “I had no idea what that was,” she says. But the occupation seemed to weave together many strands of her own life and interests: She was in therapy. She had graduated top of her class while pursuing her Master of Science at Nova Southeastern University. She was in the process of navigating her own divorce and the ripples it sent through the rest of her life and dreams. “The more I looked into this coaching program, the more it was like this increasingly powerful magnetic force was drawing me towards it,” Medwin says. “That was the beginning of my trajectory.”

The signs that she was on the right path were not subtle: “I remember walking outside after the first time I had a session with my own client,” Medwin says. “The rays of sunlight hit me just so, and the world felt aligned and, in that moment, I just knew that I was on the path that would inherently fill my soul.” Slowly, she expanded her practice to include family and marital mediation, co-parenting, and family dynamics. She wrote the 2021 book Strategies and Tips from a Divorce Coach: A Roadmap to Move Forward and began moving into the empowerment coaching space, further grounding her work in both two major systems that imbue practice action with philosophical power: First, her “five steppingstones:” Intentional Awareness, Mindset, Personal Power, Adaptability, and Community that leads to Transformation. And, second, the Brave Bites Method, which explores how “resilience is built on one intentional choice at a time.” (A new book on the latter is forthcoming.) 

“You know, sometimes we’re so busy being human doers we forget to be human beings,” Medwin says. “If we stop long enough to focus on intentional living and mindfulness, we can grow and evolve into much happier individuals who can stand on our own convictions and have real self-compassion. It’s about reconnecting with your inner wisdom and creating a life that feels aligned and sustainable for you.”

Flipping the Script 

So where is a bite-sized place to begin? Medwin suggests taking stock of your “private huddle,” which encompasses our inner conversation. “How we talk to ourselves is so important,” she says. “It either empowers or disempowers us. It’s about taking a pause to ask ourselves: ‘Is what I’m saying helpful or hurtful.’”

Medwin, for example, had a client who said to her, “I just can’t get out of bed.” Medwin wasn’t having it. “The word can’t is very disempowering. In no small part because in her case it’s not true. She has a choice. How do we flip the script? We say, ‘I won’t get out of bed.’ That’s the choice you’re making. And people are not aware of how their own dialogue can’t recognize the role they’re playing in their own issues.”

That’s the first two of the traditional “three As of change”—Awareness and Acceptance—and those are a prerequisite for perhaps to most essential step: Action. “Awareness is, like, ‘What’s really going on?’” Medwin says. “Acceptance is taking accountability—acknowledging everybody has a part in whatever happens in their lives, whether it’s 1% or 99%. But then we have to ask, ‘What would I like to work on? What’s the Brave Bite I need to take the real momentum necessary to move forward?’ Confidence and clarity stem from action.” 

One fun, innovative way Medwin has begun getting people to action is through interactive workshops, corporate coaching, and coaching in casual, non-tradition groups. “When people—particularly women—want to get together but not necessarily do another dinner, book club, or Mahjong tournament, they can pick a topic, invite me, and over brunch or cocktails we have an intimate 60- or 90-minute workshop tailored to their interests,” Medwin says. “So, it might be love languages or conflict management or work burnout or emotional intelligence—whatever. And we have a conversation.”

The best part for Medwin? It helps her further her mission of creating a true community of learners.

“Knowledge is power, and it should be shared,” she says. “It’s amazing how whenever I do one of these workshops, people are calling me to say, ‘That was so invigorating! I learned so much! I taught this part of your method to my husband. I taught it to my children. I taught it to my coworkers.’ It’s eye-opening. You realize, together, that life is full of change. And, also, that it’s not necessarily about fixing this or that aspect of life, but learning to communicate and adapt in better, more productive ways.” 

Looking Forward

It’s as much an ongoing process for Medwin as it is for her clients. “I like to say I’m in the seventh paragraph of the fifty-sixth chapter of my life,” she explains. “Which is to say, I’m 56 years old and I’ve been that old for seven months. I get to write the pages day, every month, every year. And I can slip in a plot twist whenever I like. I’m the sum of everything I’ve been through, every story that has led to this point. I just try to be as honest and true to myself as I can be in everything I write.” Her own trials, in a weirdly serendipitous way, have allowed her to deliver that message more effectively. “I think people can really want help from you, but it’s a natural inclination to be skeptical and judge unless they know you have walked the walk and had your own challenges. 

“Life is difficult, life is beautiful,” she continues. “And no matter what situation we’re in—whether it’s bankruptcy, disease, a conflict, divorce—we will find ourselves at what is called the choice point where you either become the victim or creator of a situation. Now, when I arrive at my own crossroads, I make a concerted effort to be a creator—to make messages from the mess. Transformation is possible for all of us. We just need to understand and believe that there is a framework that we can use to help us move forward. And that is my path and it’s the one I am working very hard to help others walk every day. Which is more rewarding than I can even say.”

For coaching or to book workshop, visit jwmcoaching.com.