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What happens when the life you built—personally or professionally—no longer fits who you’re becoming?
If you’ve ever looked at your business, your brand, even your personal relationships, and thought, “This used to feel right… but now I’m not so sure,” you are not alone, and you are not broken.
Today’s guest, Jen Hatmaker, is no stranger to the hard and holy work of reinvention. She’s a bestselling author of 14 books (including four New York Times bestsellers), the host of the award-winning For the Love podcast, and a beloved leader to a community of over 1.6 million.
But Jen’s newest book, AWAKE, isn’t about business strategy.
It’s about what happens when your identity, your roles, and your life fall apart… and how to rebuild from a more honest, more aligned place.
Jen walks us through what she calls a Midlife Renaissance, not a crisis. It’s a powerful season of reassessing everything you’ve been told about womanhood, worth, work, and success… and reimagining a life and business that truly feels like you.
If you’re an entrepreneur navigating change, if you’re pivoting your purpose, or if you’re wondering what stays and what goes in this next chapter, this one’s for you.
Learning to Trust the Whisper of Change
When Jen and I started this conversation, we dove into the tension so many of us feel: how to know when it’s time to walk away from something we’ve outgrown.
Jen shared that her own business and brand began in a space that was aligned with who she was at the time. But over the years, as she evolved, so did her beliefs, her values, and her definition of success.
And that evolution created tension. She no longer fit the mold she helped shape. Instead of forcing herself to stay in a box that no longer felt like home, she made the brave decision to listen to the internal whisper nudging her to move in a new direction.
She talked about how your body knows. Your intuition knows. The part of you that feels tired, disconnected, or like you’re performing more than you’re living—that’s the part you can trust.
It might feel scary to make changes, especially when your current life is seen as successful by everyone around you. But success without alignment isn’t sustainable.
Remember: you don’t have to stay just because it worked once. You can shift. You can evolve. And you can trust yourself to know when it’s time.
The Midlife Renaissance, Not a Crisis
One of my favorite reframes Jen offered in this conversation is the idea that midlife isn’t a crisis… It’s a renaissance. A rebirth. A reclaiming.
For her, this awakening didn’t happen in a neat and tidy way. It came after everything fell apart. A divorce after a decades-long marriage. A massive shake-up of her personal and professional life. The roles she had worn for so long: wife, daughter-in-law, sister-in-law, were stripped away, and she was left with the question: Who am I now?
In that question, she didn’t find an identity crisis. She found possibility. Instead of mourning who she was no longer allowed to be, she began asking herself what she actually wanted to become.
She shared openly about the grief of losing relationships that once felt foundational and the unexpected relief of shedding roles she no longer had to perform.
For anyone who’s experiencing change that feels disorienting or disruptive, this part of the episode will resonate deeply. Jen reminds us that it’s okay if you can’t yet separate the parts of yourself that are still true from the parts that were just performance.
Sometimes you don’t know until the dust settles. And that’s okay. The clarity comes, but only after the burning.
Letting Go of the Polished Version of You
Jen talked candidly about what it was like to be a public figure in the middle of personal collapse. When your life is tied to your brand and your brand is based on being relatable, there’s a pressure to keep it all polished.
But when things fall apart publicly, you no longer have the option to perform. And what’s left is the realest version of you.
She said something that stuck with me: the shine is off the penny. In other words, the polished, palatable version of herself that once felt necessary in order to lead or be seen?
She doesn’t care about maintaining that anymore. That part of her is gone. What she’s more interested in now is truth, even when it’s messy, even when it makes other people uncomfortable.
This was such an important reminder for me, and maybe for you too. As entrepreneurs, it’s easy to start by being relatable and then accidentally box ourselves in by staying only in the lanes that feel “on brand.”
But people can feel when something’s off. And more importantly, you can feel it. And no amount of polish can replace the freedom that comes with being honest.
Aging, Irrelevance, and Why We Get Better With Time
At one point in the conversation, I asked Jen what she would say to the woman who feels like she’s aging out. The one who wonders if she’s still relevant in a world that seems to celebrate youth and “fresh” voices.
Her answer? We only become irrelevant if we remove ourselves from the table.
She talked about the myth we’ve been sold that women get less powerful as we age. But what she’s discovered is the opposite.
With age comes wisdom, confidence, and a deeper connection to our values. We stop people-pleasing. We stop trying to keep up. And we start leading from a place of rootedness.
The truth is, we get better with time. And instead of competing with the next generation, we get to collaborate with them. There’s room for all of us. And we’re not done building.
If you’ve ever felt like you’re running out of time or like your moment has passed, let Jen’s words be a reminder that you’re just getting started.
The Cost of Telling the Truth
Jen’s new book, AWAKE, is different from anything she’s written before. It’s raw, it’s vulnerable, and it’s not prescriptive.
She’s not offering a tidy list of lessons. Instead, she’s sharing her memories and letting the reader take what they need from them. That kind of writing takes courage. It’s risky. It asks the reader to do their own work.
She shared how, for the first time, she didn’t tie everything up with a bow. Instead, she let it be messy. And before she published it, she asked herself a powerful question: Will I be proud of this in five years?
That question guided what she kept, what she cut, and how she framed every part of her story. Not for shock value. Not for drama. But with compassion for the real people involved, including herself.
As someone who also shares my story publicly, that hit me hard. There’s a fine line between vulnerability and oversharing. And Jen reminded me that truth-telling isn’t about spilling everything. It’s about telling the truth in a way that honors both your healing and your humanity.
When Work Becomes the Escape
Finally, we talked about what happens when we use work as a distraction. When Jen’s life fell apart, she threw herself into productivity. It was the one area where she still felt in control.
But that overwork eventually led to a full physical breakdown: emergency room visits, panic attacks, and a body that refused to keep pushing.
She was honest about how that season taught her a hard but beautiful lesson. Hustling is not healing. Sometimes the reason we keep saying yes isn’t ambition—it’s avoidance. And eventually, if we don’t listen to the whispers, our body will scream.
Her life now is slower, more spacious, and more sustainable. She’s not doing everything anymore. But what she is doing, she’s doing from a place of wholeness. That’s the kind of success we should be chasing.
Get Your Copy of AWAKE Now!
This conversation with Jen was tender, honest, and full of truth that so many of us need to hear.
Whether you’re standing in the rubble of something that used to feel right or you’re just quietly questioning if you’re still aligned with what you’ve built, this episode is your reminder that it’s okay to start over.
Goal Digger, you don’t have to justify your evolution. You don’t need permission from anyone else. The life you want next is waiting for you to trust yourself enough to claim it!
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