The following is a transcript of this episode. It has been edited for clarity.
Intro (Maryann): This time of life comes with so much change. Much of it, we have no control over. But sometimes, we’re the ones initiating it. Life Coach Anne Pillsbury says change helps us grow, but it can also be scary. On this episode, she tells us how we can figure out what we really want in life, and how we can gain the courage and confidence to make those changes we’ve been dreaming about. Plus, Anne, who’s a mom of four, is going to tell us about the midlife internship she did to get the ball rolling on her own career.
Welcome to More Beautiful, the podcast for women rewriting the midlife playbook. I’m Maryann LoRusso, and I invite you to join me and a guest each week, as we strive for a life that’s more adventurous, more fulfilling, and more beautiful than ever before.
Maryann: Hi, everybody, I’m so pleased to be sitting down today with Anne Pillsbury, a life coach who specializes in helping women pivot, whether those women are leaders or they’re in career transition, or they are moms ready to return to work. She calls her clients courageous women in transition. Hi, Anne!
Anne: Hi, Maryann, I’m so excited to be here.
Maryann: We’re going to have such a juicy conversation today about how women can pump themselves up to make those changes that will lead them toward what they really want in their lives. And we’re going to offer some concrete steps that we can all take in order to move forward and get the life we’ve always dreamed of. But first, I think it’s so interesting that you yourself said you’ve had several pivots over the past decade. Can you tell us about those and how maybe the changes in your life inspired you to help other women who are trying to pivot?
Anne: Yeah, sure! I feel that over the past 10 years, I’ve had practically every midlife pivot a woman could have. [Laughs] I’m a mother of four kids. And well after my fourth was born, I stayed home for 14 years. [One day I thought], What’s next for me…and I got this calling to become a life coach. And I immediately signed up for a two-year certification process, which was really the most important step I’ve ever taken. For myself, it was the first time that I really invested in something just for me. You know, I went to college, I did all those things, but that there was a lot of external expectation around that. And at first I was like, I’m going to step into something that I want. And it absolutely shifted my whole perspective because I didn’t even know who I was outside of all my roles and responsibilities and all the shoulds. I had such a fixed mindset on things, that [taking that step to become a coach] just expanded and helped me realize that I had this essential self beyond all those things, what my gifts and skills were and how I could bring to the world…It just cracked open all this sense of possibility for me. I was super excited about coaching. Loved it. But you know, I wasn’t really in a space where I could be building a business…So I relaunched myself back into a full-time career work as a 45 year old intern at a startup…
Maryann: I love those midlife internships.
Anne: It was amazing. I didn’t even know what a meme was. [Laughs]
Maryann: I’m still not sure I know what it is. [Laughs]
Anne: This was, you know, 10 years ago. I started in marketing and absolutely loved it. I had written on a vision board that I wanted to work for this company and met a mom at school who was a founder and was willing to take me on as an intern…Anyhow, the thing about us women in midlife is that once we get the opportunities, we quickly prove ourselves because we have a lot of experience, life and education, all these things that we quickly bring. And I was able to work my way up into project and program management roles pretty quickly and was full time for four years there. Then something’s happened, a toxic work environment…and I ended up [getting] laid off. And so another pivot…I then faced the 50-year-old-woman unemployed thing…So I started coaching again, but I also still had four kids at home. I needed get back to work, so went back [into corporate] and did that for a few years. But then COVID hit, and like many of us I had that reevaluation of like, What am I doing? It’s time for me. Three kids have gone to college and so I was like, Alright, I’m leaving corporate…and then launched my coaching business two years ago. And so now I’m an entrepreneur.
Maryann: We’re so happy you are. It’s interesting, so many women have taken their experiences and are applying them toward some really amazing, fruitful work in midlife. I think it’s so exciting. What I also find exciting is that as a coach, you believe in something called the confidence trap. And you say many women fall into that trap. Can you tell us more about that?
Anne: Well, we get this idea that competence is something we have or we don’t. Every woman who comes to me frankly says, Well, I want more competence, because I can’t do the thing I want to do until I feel more confident. Well, that’s just a trap. Because you’re never going to feel confident about something that you’re new to doing. Competence comes through actual experience. That’s what keeps you stuck, right?…I call that the confidence Trump.
Maryann: Yes, when I started podcasting, I had no idea what I was doing. I was terrified each time I did an episode, but after 10 or so I got more and more confident. That happens with every single skill set, right?
Anne: Yes. And one thing I realized—because I held that belief about confidence for so long—is that even the most remarkable people, like Michelle Obama, feel a lack of confidence [sometimes]. We build competency through action—that’s the way we build that inner trust that we can pull upon to propel us forward.
Maryann: And the ability to problem-solve, right? To be able to say to yourself, I can handle this. I am resourceful. I will come up with a solution. I think that really does come with age, don’t you?
Anne: I do. I do. But I also think there are some situations that are special that arrive in midlife that can keep us stuck.
Maryann: Oh, yes, they do. That goes into my next question. Because I think even if we’re the most confident person in the world, with all these great skills, there are cultural [forces that can keep us stuck]. Because our generation was fed this idea that women over “a certain age” are not relevant anymore, that our time is up and we must sit on the sidelines. Does our [youth-obsessed] culture feed our self-doubt, when we reach 40, or 50, or beyond?
Anne: I think we’ve heard these messages for so long that we’ve internalized the patriarchy within ourselves. And we have all sorts of micro-aggressions toward ourselves that we don’t even realize…We talk about fighting aging or [say that] we’re having a “senior moment,” or we refer to ourselves as “old” or “you can’t teach and old dog new tricks.” All these things are running through our minds and make us feel a little increased insecurity and fear. I think there are actually three things going on. So there’s that. Then there’s the whole menopause thing, right?
Maryann: Yes, that’s a whole other episode!
Anne: Yes, that’s a whole other topic. I’m not an expert in [menopause], but I think it affects us all in so many different ways. And we’re just starting to have those important conversations to demystify menopause so that we are clear on what’s happening and how that might be affecting us. And then third, I think in midlife, we start to be called upon to show up in a different way. We’ve achieved the external validation, we’ve done the shoulds. And we’re kind of left feeling burnt out and unfulfilled. And all of a sudden, this calling comes in. Most of the women who come to me say, “I want to do something with more meaning or purpose,” or “I want to serve in some way.” That doesn’t mean you need to sell all your assets and move…but just in little ways [this life stage ushers in] a whole new way of being. It calls us to go internally and figure out who we are now and what we want. And we may feel an urgency to follow our passion or share ideas or answer a calling or use our unique skills and gifts differently. And that [can make us feel] really vulnerable, because we’re putting our whole selves on the line. It’s a whole different way of being and that feels super, super scary.
Maryann: Yeah, it really is hard to be vulnerable sometimes. And this idea of purpose is coming up a lot because when you reach a certain age, you tend to be focused on your purpose. You’re like, “I can do all the things, but what does it all mean and what do I want to contribute to the world and what’s my legacy going to be?” I think those are important questions that all the women I know are contemplating right now.
Anne: Yes, it’s part of that second part of life when…you want to be more intentional with your time and energy. And so what comes up kind of that that feeling of purpose? And I think actually some women get really overwhelmed because they’re like, “I can’t figure out my purpose.”
Maryann: Right. So, don’t put too much pressure on yourself to find your purpose! It’ll [eventually] come to you, right? But I want to backtrack to something you mentioned earlier, the physical changes that are happening with menopause and stuff. Midlife brings so much physical change, but does it alter the way we view ourselves? I was talking to a friend the other day…about menopause. And I was saying to her, “Do you remember when you were 12 and 13? And you were starting to develop and your hormones were changing? I remember feeling like, ‘Oh, what is this body? What are these hips? And why do I have boobs?’ ” It was kind of it was really disconcerting, right? It was a confusing time. So I don’t think we’re being too hard on ourselves as women when we say that [menopause] is kind of throwing us for a loop. Because our bodies are changing, and those changes might be altering the perceptions that we’ve had of ourselves for so many years. How can we handle those changes?
Anne: I wish I had a great answer for this, because I really struggled with it. I wish I could say that I had it all figured out. I just think it’s a process. It’s a process of self acceptance and compassion…and loving ourselves. All those ideas of what my body should look like, and what clothes I should fit into….[what] unrealistic expectations. And I’ve always struggled with that, so it’s not a new thing. But it is a crazy feeling of being out of control. Sometimes I feel like I have lost control of my body and that all the things that used to work don’t work. And I look at myself in the mirror, and I’m like, “Who is this?” And that is very much how I felt puberty—and I went through puberty really young, so it was very uncomfortable. So yes, I do feel that way again. And you know, the one big thing is community and talking about it, like being here and talking to you about it. Actually saying these things out loud makes them less shameful. And then you hear that other women are feeling the same way. Because yeah, I can bring me to tears.
Maryann: I thank you for being so vulnerable with that answer. And I agree, I remember my mom used to say in her 50s, as she was aging, “Every time I pass a window or mirror I don’t recognize that woman anymore.” And I used to be like, “Oh, don’t be vain.” But it’s not about vanity. It’s just that this picture you had of yourself for decades is changing.
Anne: Yeah.
Maryann: And you have to just adapt. But that’s the beauty of life, right? It’s all about change. It’s about adapting to your circumstances. And that’s why I really feel like once you’ve been through this last great change—I mean, what is the next one, death? [laughs]—you emerge so much stronger, don’t you think?
Anne: I do and I’m hoping I will, and I’m sure it’s a process. You know, I’m 54 and I haven’t gone through it fully. I’m still in the perimenopause phase.
Maryann: Me too.
Anne: And I’m sure once I’m passed it, there will probably be some grieving, like with everything. It’s both excitement and grief. Like I find this with my kids. One minute, I’m so excited about the adults that are becoming and the amazing things they’re doing. And the next minute I’m in tears because they are no longer that 3-year-old baby that used to crawl over me.
Maryann: I’m glad you said that.
Anne: I think midlife is all about being in the liminal phase of where you can kind of see there’s going to be a great end, but you don’t know where it is, and you can’t quite get there and so it can be super opaque feeling.
Maryann: I think that’s a great parallel between teenagers and your period. Because you don’t want your kids to leave, you know you’re gonna miss them…then they act out so much that you’re like, OK, go. Perimenopause can be so stressful, like not knowing if and when your period is coming again, and there are all these symptoms, so finally you’re like, just good riddance, please leave. Like, now I’m counting down the days.
Anne: I’ve been out for like seven months and not spotting every day, so I’m like, OK, I’m done now…
Maryann: OK, we have pivoted ourselves in this conversation many times, but that’s OK. [Laughs] So…We’re going through these physical changes and we may no longer recognize ourselves. But society is also looking at us differently. I’ve asked many executive or career coaches this next question and some of them answer really honestly, others don’t: Is there ageism in the workplace still? What is your take on that?
Anne: I absolutely think there is. You know, it is my hope that as we build awareness around diversity and equity/inclusion, ageism might [subside]. It’s kind of the last bastion that’s being addressed. But if you’re feeling it, it’s there. You know what I mean? You can trust that. But it’s another place where I think it’s really important that we keep having these conversations, because as we expose [this ageism], it will put more pressure on companies to do the right thing to shift that. And really, there’s such amazing benefit to having multigenerational corporate cultures. That was the most fun thing for me when I went back to work. I worked with 25-year-olds and 30-year-olds, and it was so amazing, because I was so enriched, and they taught me so much. And I taught them so much in my presence, and my wisdom was such an asset to them. It was such a beautiful experience of how we all learned and supported each other and super interesting ways.
Maryann: Yeah, when I became an editor-in-chief, I was young I was was a managing editor when I 27, and an editor in chief at 31. And I had people on my staff who were much older, including a copy editor in his 70s who had just written his first book. I’ll never forget that man. I learned so much from him. We had these intergenerational exchanges of ideas. Then there was another woman [in her 70s] who was a fashion columnist, and she was such an inspiration to me, I always loved the wisdom of older people. But not everybody feels that way. I love what you just said, that we can all learn so much from one another other. That’s so valuable.
Anne: And it’s on us, too. We can be snarky about the millennials or Gen Z, so we also have to remain open. We’ve talked about this before, but even as we age, we need to continue to have a growth mindset and to continue to learn and keep ourselves relevant. I mean, there’s a lot of stereotypes around older people being irrelevant, and we aren’t, we don’t have to be. But there’s also a personal responsibility on us to keep on top of things and keep ourselves relevant as well.
Maryann: Absolutely. Yesterday, I was doing some Instagram reels, and it probably took me five hours longer than take my kids to do it. But I’m learning, I’m stretching myself.
Anne: Yeah!
Maryann: So you believe there’s a science behind self-doubt that we’re wired to experience it? How so?
Anne: Well, self-doubt is really an expression of our inner critic or that inner judge—that mean voice in your head that tells you you’re not enough. It’s a negative response that we’re biologically wired for. And that’s because a long time ago, when we were in prehistoric times, and there was a tiger, or something negative happened, we needed to be ready to fight…
Maryann: Fight or flight.
Anne: Yes, fight or flight. And so we’ve internalized that [mechanism] that’s trying to keep us safe. It’s trying to keep us from risk and, but what it’s not perceiving what the real truth is. And so we have the ability, with our wisdom, to say, “I hear you, and I know that I’m OK…” To talk down that feeling of doubt, that inner critic, in order to keep taking action.
Maryann: Yes, I’ve been talking to myself, like a crazy woman, a lot lately. It’s my new thing.
Anne: It’s a sign of wisdom. It’s like, “Thank you for your feedback, but I got this.” We don’t want to fight with [that self-doubt], though. We want to have compassion for it, because it’s part of us. Maybe it’s served us in the past, maybe it hasn’t. But it’s not about being angry or fighting it; it’s just accepting it as one part of ourselves and loving it, but choosing differently,
Maryann: So if we’re looking to get our edge back and reinvigorate ourselves for our next chapter, what are some steps we can take to do that?
Anne: Well, it really all starts with turning back towards yourself. You know, we’ve spent so much time taking care of everybody else and living up to everybody else’s thoughts or expectations, that it’s important to really take some time and space to do so me self-examination and figure out who you are now and what you want. In my coaching process, we start with simple steps, like starting with just five minutes a day to just get quiet and listen to yourself and start to re-evaluate what your values are. They may be different than what they were before. And so it’s really important to get clear: What are those things that are most pivotal to my actions now? And once you have those values identified, then you have the compass on how to direct yourself. I also think it’s really important to re-examine your priorities. What are you saying yes to, and what are you saying no to? And how might you want to change that around? You know, maybe there’s certain things you’re saying no to, that you want to be saying yes to. Maybe there are some boundaries you want to put up in other areas.
Maryann: Yeah, I talked about this with somebody else recently. You almost need to write our own personal mission statement, which can guide all of that. Before you say yes to something, you can ask yourself if that thing is aligned with your mission, or is going to help get you to where you want to go.
Anne: Right. And if you have a foundation on what those values are, you can keep coming back to those. I also think it’s a mission statement or a vision statement. I like having a vision statement of where you want to be, and I always ask my clients to go big. Like, what feels kind of exciting and terrifying and impossible? Then claim it. The craziest thing is, once you start putting your actions in alignment to that vision, the miracles start coming. The crazy miracles. You go to the place and just the right person you need to talk to is there, or the book you need to read falls off the shelf. You know what I mean. The exact podcast comes along…It’s when you have the courage to actually claim it, then the universe rise up and meets you halfway.
Maryann: I believe in that, I do. And I believe you have to dream big enough to be a little scared. You know you’re dreaming big enough when you’re a little terrified.
Anne: Right, right. Because the thing about possibility is we think we know everything that’s possible. And we absolutely don’t. Our mind is limited. It limits us because it’s trying to keep us safe. So it gets to expand. And then all the cool stuff can happen.
Maryann: Don’t we also tell a lot of stories about ourselves that just aren’t true? Like you mentioned earlier, we say stuff like, “I’m not a good writer,” or “I’m not creative,” or “I’m not going to ever find somebody to share my life with.” All these things women have been telling themselves. How do they rewrite those stories into a story that they want to play out?
Anne: I think it’s just really important to first of all, identify the stories. And then think about how you could reframe the story. Like, the “I’m not creative” one speaks to me. Because when I was young, I loved art and stuff but I had decided I wasn’t a creative person.
Maryann: Did someone tell you that you weren’t creative?
Anne: I never had that experience. I just think that I was a perfectionist as a kid. The family I was raised in was a great, loving family, but there was just a lot of success and expectation within the family. And so I played it really small from a young age, and if I wasn’t really good at something, I just quit.I was too afraid that I would fail and that was not OK.
Maryann: That can also happen when you overpraise a child. You [should] praise a child not for the outcome or the achievements, but for their effort, right?
Anne: Yes, that’s where having a coach or therapist or a good mentor comes in. Getting out of your own story to have somebody else reflect the truth back to you. Because we’re just so entrenched that we can’t recognize it. That’s why I always have a coach, because I just always need somebody to help me see those things.
Maryann: Every coach I know has a coach.
Anne: I think we always need somebody.
Maryann: So…what type of midlife woman is ready for change? Describe her for us.
Anne: That’s a good question. Well, I do think it’s the woman who has that drive or ambition or desire to make headway, but also has that self-awareness and compassion to shift to that new definition of self. It’s a woman who can take good care of herself, stay connected to what she wants and [knows what she has to offer]. I mean, I’ve always been very attached to achievement. So it’s not easy for me to let go of achievement and stay in the process…It’s hard. The perfectionism kills me all the time. We were just talking about doing Instagram reels…I just learned that I have to do them and trust that I will get better over time. And sometimes I’m surprised by women who maybe didn’t have that [drive for achievement] or external success, or maybe who chose to be stay-at-home moms, who [in midlife] just tap into this part of themselves that they never knew was there, and go on to do amazing things. I don’t think it’s the person. It’s being willing to go through the process and being able to show up authentically, to have the vulnerability and courage [to try]. I always say that clarity, competence and courage are the drivers of reinvention.
Maryann: Speaking of pivoting, I think it applies to every single little thing we do every day. For instance, if the reel you create doesn’t get the traction you hoped it would, instead of beating yourself up, say, “OK, how can I do this a little differently?” Because change takes time, and learning takes time. We’re not going to hit that magic formula right out of the gate.
Anne: Right. And the lovely thing about the world we’re in now, especially with [social media], is that there’s data. So you can look at the data, and you can evaluate, and try to figure out what [worked and what didn’t]. Sometimes I really can’t figure it out, though. [laughs]
Maryann: So, Anne, tell us: If a woman wants to make change—if she wants to start a new career or start a company or make some other sort of change—what are the first essential steps to take?
Anne: Well, get that vision down. Really take some time to give yourself that vision of what what you really want. Take a day off, because [the vision] doesn’t come from sitting at your computer. Get out in nature, go swimming, go do something to kind of get yourself in your body, in your creative mind, and get the thing down and listen to what that very first action is. And it can be small…You just shared recently [on Instagram] that you bought yourself that beautiful mic that I’m looking at right now. That was your first action. You know, I just think that getting really clear on the vision and then getting super curious. And then following the next right thing that comes along. It’s more of an organic process than a seven-steps type of thing.
Maryann: You mentioned vision boards [and statements] a couple of times…I think vision board are really fun to do…They’re actually very therapeutic and great for getting focused and…keeping you aligned with your goals and missions.
Anne: [I encourage women to] take the time to write a vision statement…in first person as if [all those things are already] happening. So, [for example], for me, I’d list things like, “I run a group for Gen X women trying to pivot in midlife. I’m making an impact.” Write those visions down as if those t things are already happening in real life. It’s building a habit to help support you in making that change.
Maryann: And keep in mind that change can be slow, right? It can take time. And it can I also support other women who are trying to make change, because I find I some people I’ve had on the show have reported that when they start changing, some of their friends are not so happy about it. Why is that? Why are people threatened by people who are changing?
Anne: Well, probably because it’s about them and speaks to some fear they have that feels threatening. But that’s OK. That will, for sure, happen. Your friends now are not necessarily going to be your support group in your pivot. So keep that in mind.
Maryann: Ladies, just keep that in mind.
Anne: And your family might be really scared for it. That fear probably comes out of love, but they may not understand [your pivot]…You may need boundaries [to protect yourself from these critics]. That doesn’t mean you need to give up your friends. But you can also create new community and new friendships with people who are in alignment with where you want to go.
Maryann: Speaking of family, Elizabeth Gilbert once wrote an article about change. She equated [freeing yourself and going off to do something different] to crabs in a bucket. When one crab tries to climb out of the bucket, the other sort of pull her down. That image stuck in my head. Like sometimes, families even don’t want to see one person go off and forge their own path, right?
Anne: Right. And it can cause a lot of stress in marriage too.
Maryann: Interesting. Well, any last minute tips for everybody?
Anne: Thank you so much for having me on. I’m super excited to be here talking about midlife and hoping that we’re both contributing to lots of women shifting to having more powerful and inspirational second acts.
Maryann: I agree. I think there’s so much to look forward to and so many good things ahead. So ladies, don’t give up. Just keep trying, you can accomplish anything. …Anne, please tell us how we can find you online.
Anne: I have a great resource that I’d love to share with everybody about 10 clues to clarifying your pivot on purpose, which you can find on my website, Annepillsbury.com, like the doughboy. You can also read about me and my program, the Meant For More Method, which is my one-on-one coaching program, or come on over and follow me on Instagram at @awpillsbury, where I post all sorts of exciting things to support you daily.
Maryann: I’m gonna go check out your reels. Thank you and have a great weekend!
Anne: Thank you!
Outro: Thank you so much for tuning in to More Beautiful. Please visit Morebeautifulpodcast.com for show notes and bonus content. And it would mean so much if you could subscribe, rate and leave a review on Apple Podcasts or wherever you’re listening. See you next week for another great conversation!
