Winter Henderson is not a woman who can be put into a box.
Throughout her life, she’s always recognized this power about herself that couldn’t be contained, so she put it to use. You may recognize Winter from Love & Marriage: DC, her transformational speeches at conferences, or through one of her books.
No matter where you’ve crossed paths with Winter, there is no doubt you’ve likely walked away inspired to pursue your purpose with boldness.
Winter Henderson is a marketing professional by trade and gained crucial experience as a Mortgage Marketing Manager. She is a published author of nine books and a 2-part devotional series in the YouVersion Bible App titled “Purpose Over Panic.” She is well-known for being a cast member on Love & Marriage: DC and recently said ‘I do’ to her now husband Edward Henderson. On the horizon, Winter is excited to expand her personal consulting for professional entrepreneurs, focusing on leadership development. She shared that she will pour into women who want to grow as writers, speakers, and coaches.
Her Agenda had the opportunity to catch up with Winter as she embraces a new season in her life, discusses her commitment to empowering women through her Esther Academy program, and the power of pivoting.
Her Agenda: I know the first time we chatted, you mentioned the word “pivot” a couple of times. I’d love to dive a little deeper into your perspective when it comes to pivoting.
Winter Henderson: I feel like a lot of people are going through this right now, so it’s actually really timely. It might sound like, ‘Oh gosh, that’s all she talks about,’ but it’s just been a recent theme. So many people are losing their jobs, contracts are ending, there’s a lot of uncertainty about what comes next. It’s one of those moments where you can either wallow in it or try to see it as an opportunity. It’s definitely a much-needed conversation.
Her Agenda: I know you’re familiar with pivoting. It seems as though it comes naturally to you whereas most people may hesitate.
Winter Henderson: It’s definitely been an abnormal journey. I’ve lived an unusual life, and the older I get, the more I’ve just learned to accept that. For a long time, I used to hide parts of myself. I was actually talking about this today, how I didn’t always want to share everything. Not because it was bad, but because certain things make you stand out, and that can feel uncomfortable. It reminds me of that quote: ‘Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure.’ That’s real. I’ve battled with that: this fear of owning how powerful I might actually be. Because if I do own it, if I step into it fully, will that make me so different that I become unrelatable? Will people pull away? But I’ve realized that comes with the territory. And at some point, you have to learn to be comfortably uncomfortable.
Her Agenda: I want to focus on something you said, because for me, the words ‘if’ and ‘when’ are really powerful. You mentioned, ‘What if I step into that version of myself?’ So how do you shift your mindset from ‘What if’ to ‘Okay, when?’
Winter Henderson: So that’s it. I really feel like it’s an identity journey. The word ‘if’ often comes from not fully understanding the ‘why’ behind the ‘when.’ I can live in ‘if’ all day long. I can ‘if’ myself into complacency. I can ‘if’ myself into staying in spaces where people are comfortable with me. I can ‘if’ myself out of doing, out of achieving, out of being. But when I make the decision to let go of ‘if,’ something shifts. And there is a kind of safety in ‘if,’ right? It keeps you from fully leaping. But when I release that, when I step into ‘when,’ the ‘if’ becomes irrelevant. When you let go of the safety of ‘what if’ and the safety of who you’ve always been, you start existing as you were meant to be. And you realize that ‘if’ was never real, it was only imagined. That’s the mindset shift: ‘if’ is imagined, ‘when’ is reality. For those of us who have the desire to become, to truly be, one of the greatest outcomes we seek is impact and influence.
Her Agenda: Let’s talk more about impact and influence: how you see that showing up in your own life, and how you’re leveraging the influence and impact you have within your community.
Winter Henderson: Funny enough, I was actually talking about this today on my Instagram Live. I had a really transformative spiritual experience back in 2019. I was a speaker at a women’s retreat, and I had just gone through a really painful breakup. I was there by myself, and something about being in that room, something shifted. Before that moment, every time I walked into a space to speak, I felt like I had to shrink. Almost timid and apologetic. I’d make excuses for who I was. But that weekend, I had an epiphany. I told myself, ‘No. I’m going to own all that I am. I’m going to own every part of my story, every experience I’ve lived through. And I’m going to use that to impact other women, especially the ones who are living in the shadows of who they really are.’ That moment sparked something in me. After the retreat, I went on a 16-week fast, it was intense and long, but it was part of me stepping fully into my purpose.
Her Agenda: What happened after your 16-week fast?
Winter Henderson: During that time, I felt like I was shedding so much dead weight, emotionally and spiritually. And once I made the decision, ‘Okay, I’m going to do this. I’m going to own being a speaker. I want to change lives. I want to impact women,’ something shifted. I started showing up every day on Live, even if it was just one person watching. Two people, three people, it didn’t matter. I was going to speak my truth. I was writing like crazy, doing these daily Facebook diary posts. Any thought I had, any lesson or reflection, I was putting it out there.
Her Agenda: How did your friends, family and audience receive that?
Winter Henderson: By May of that same year, I had built a six-figure masterclass and consulting brand. I’m not exaggerating. I tell people all the time: have your receipts. I’m not just saying this, I went back and looked at my records, especially during moments when I felt stuck or unsure. I had to remind myself, ‘You’ve done this before. You can do it again.’ I was literally going through old invoices and receipts and realized I had closed $10K, $12K, even $15K in just an hour or two. It was wild, and it was real.
Her Agenda: That’s powerful. You spent intentional time with yourself, incubating, and then emerging with clarity, confidence, and results.
Winter Henderson: It was crazy. I launched a mentorship program and we enrolled over 300 people in just 24 hours. To be exact, it was 327 people. The program was called The Esther Academy. Within the next two to three weeks, we had over 700 people enrolled, and we ended up closing around a quarter of a million dollars in just a matter of days. I was honestly blown away. I had never done anything like that before.
Her Agenda: I’d really love to learn more about your initiatives, your interests, and your purpose when it comes to helping women grow. Could you share a little more background on that?
Winter Henderson: I would say I’ve always been a champion of women. They’re near and dear to my heart, because we go through so many phases, experiences, and challenges that are unique to us. One of the things that’s benefited me the most throughout my life is having wise women around me. On top of that, I’ve always been surrounded by older mentors who were just rich in life experience and insight.
Her Agenda: I’d love to hear more about your reality TV experience and how you were able to pivot that into your consulting business.
Winter Henderson: Oh wow, reality TV was a very unique experience for me. I’m genuinely grateful for the opportunity because it taught me a lot about myself. I’ve said this before: reality TV can be a very toxic environment. I initially went into it thinking I needed it to grow my brand, my reach, my platform. But in the end, reality TV became a blessing, because it showed me something powerful: I never needed it in the first place.
Her Agenda: For a lot of us, including myself at times, it feels like we’ve built an identity around who we’ve been, and pivoting into something new takes time, not just for us to accept it, but for others around us, too. So what do you think that internal battle really is?
Winter Henderson: Fear. It’s fear. Nothing else prevents us from fully owning who we are, but fear. I’m of the belief system that if one person shows up and one person gets something out of anything that I’ve said or done, it was worth it. And that’s actually something to be proud of. It’s honestly not easy to change and impact a life.
Her Agenda: As you’re pivoting into this new chapter in life, what title or identity are you owning, and then how are you hoping it impacts other women? Winter Henderson: A disruptor. My goal is to disrupt how you exist so that you show up authentically yourself no matter who you are and what you’re around.
[Editor’s note: This article has been edited for length and clarity.]
