How to Find the Right Support During a Midlife Transition
How do you find the right support during a midlife transition? Start by figuring out what you need right now, and only then choose the best match. Retreats, courses, communities, life transition coaching and therapy all work beautifully for high-achieving women when the support is designed to meet the need. But they are costly and ineffective when the need and support don’t match.
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Dear Kerry Ann,
I’m approaching my 50th birthday and feeling the weight of several big transitions happening at once: menopause, my last kid started college this fall, and I’m in a new and high visibility leadership position (I oversee operations at a large hospital system).
I’m navigating each of these transitions reasonably well and I’m not in a crisis. But it does feel like there’s something else happening that’s hard to describe. My body is changing, my family is changing, and my work is changing. But it also feels like something deeper is shifting and I don’t know what kind of support people seek out in this nebulous type of situation. Frankly, I’m a little embarrassed that I can’t figure this out.
I spent time in therapy during my mid 40’s, I’ve worked closely with my OB-GYN to navigate perimenopause, and I had an executive coach during the first year of my new role, but I feel like I need to create a different kind of support system for this new era of my life.
I remember how helpful your advice columns were when I was getting my PhD, so I thought why not ask you directly: How do I figure out what I need, where do I find it, and why is this all so unclear?
Sincerely,
Seeking Something, Not Sure What
Dear Seeking,
I love the clarity you already have about the difference between specific midlife transitions (an empty nest, perimenopause, a job change) and the deeper shift you can sense but not yet name. Most of the high-achieving women I coach arrive able to describe only the surface transitions. You’ve already sensed the deeper shift underneath them, and that’s the harder part of this work.
Why does needing support in midlife feel so hard?
I get it. You’ve spent decades solving problems and helping people and systems figure things out. You’ve run departments, raised children, led organizational change. And like many high-achieving women, you’ve been trained, rewarded, and come to identify with your expertise. In that context, not knowing can feel destabilizing, frustrating, confusing, and even a bit embarrassing.
But here’s the thing about midlife. Lots of people talk about the various concrete transitions, but few people acknowledge that there’s also a developmental shift occurring. You are experiencing a change that is qualitatively different and more profound than any of the specific transitions you’ve mentioned. Each transition can serve as a portal into this deeper shift, but there’s no pill, app, or AI prompt that can hand you the answer to what within you is asking for attention. Other people can create the conditions for the inquiry. But the answers have to emerge from you.
Let me be clear, during midlife it is completely normal to have hard-to-describe needs, to feel uncomfortable about having needs, to outgrow past roles, relationships, and versions of yourself, to realize that the ways you fixed things in the past don’t work anymore or to feel like you’re the only one struggling (because most of the struggle is inner work).
The key is to start identifying what your needs are and selecting the specific type of support that will help you do the work that is calling you.
And you already have the pattern down cold. When perimenopause symptoms required attention, you went to your doctor. When you had mental health concerns, you saw a therapist. And when you stepped into your new leadership position, you added the support of an executive coach. In each case, you were clear about your need and what type of support made the most sense. So let’s map the possibilities.
What do you need right now?
I’ve observed that high-achieving women in midlife have a wide range of needs. Some need to work through old and heavy baggage they’ve been carrying for too long. Some need structure and accountability to move through a process, because left to their own devices they will get infinitely distracted with anything but their own inner life. Some need to be in a space where they are not the most accomplished person in the room, so they can stop performing and get real about what they’re facing. Some need to be removed entirely from their daily life to connect with their deeper self. And some need an occasional exorcism to cast out the deeply ingrained voices that stop them from doing the very work they need to do.
I’m naming the variation so that you can start to pinpoint your own needs and consider the best fit for getting them met. So before you Google or ask Claude anything, ask yourself three questions:
What kind of work am I trying to do? Do I need to heal something, discern something, learn something, change something, or just stop trying to figure everything out alone?
What kind of container will help me do inner excavation? Do I need privacy and individual attention? A structured group? A community of peers going through the same thing? Or what exactly?
How much structure do I need right now? Do I need a defined process with dates, assignments and expert facilitation? Or do I just need some time and space to allow what’s emerging to come up?
The best midlife support for you depends on the work you need to do, the kind of container in which you do your best work, and how much structure you need to dig deep.
What kinds of support exist for midlife needs?
Once you know what you need, choose the type of support that provides the best fit. It really is that simple (even if that’s not easy). I’ve seen many accomplished women pick well and just as many pick poorly. It all comes down to the match.
When it works, it’s because you’ve said my primary need is ______________. The best way for me to explore that need is ______________. And when it works poorly it’s often because a person doesn’t know what they need, hears about something that worked great for someone else (who has a different set of needs from their own), or they jumped into the first thing that turned up on a Google search, showed up repeatedly in their Instagram feed, or was suggested by AI.
So let me describe a few support systems and what needs they best fit.
Retreats are a great fit for when your primary need is enough uninterrupted space to connect with yourself. For some women, that means physically leaving home. For others, a structured online retreat creates enough space without travel. If you cannot hear your own inner voice amid day-to-day activities, are overwhelmed by other people’s needs, and/or want someone else to structure the quiet and the questions, a retreat can be a wise choice. It works when it removes you from the machinery of your life long enough to notice what is being drowned out by the noise. A well-facilitated and well-designed retreat will allow you to both rest and generate insights that wouldn’t be possible otherwise. Some examples of in-person retreats are the Modern Elder Academy, the Nostos Retreat, and you can find many options at Kripalu. I’ve attended the first, am a member of Sharon Blackie’s Nostos Institute (which runs the retreat), and the third is highly recommended by our community. If you’re looking for an online retreat, our Clarity Retreat is designed for those who already have a reflective practice or want to do this kind of inner work at home. That said, a retreat won’t meet your needs if it’s primarily an escape, if you’re unable to carry insights home, or if you return with fond memories but no ability to enact change in your life.
Cohort courses are a great fit for women who want structure, assignments, and a supportive process for their own inquiry. Instead of figuring it out on your own, courses provide a time-limited container for change and a community of other women in the midst of their own midlife awakenings. Courses provide the context for you to be a learner instead of a client or patient. You show up on the dates, you work alongside others doing the same work, and the assignments are intentionally designed to move your inquiry forward. And in course communities, other people's questions often surface things you would never unearth on your own. Great examples for midlife are the Red School’s Menopause: The Great Awakener, our own Your Next Chapter course, and the Jung Platform’s courses with global experts (some live, some recorded). While the best courses provide structure for self-inquiry, they don’t work as support systems for people who can’t fully commit to a schedule, don’t do the work, or don’t want to learn from the experience of others.
Midlife communities are a good fit for people who want a more organic, less structured, and peer-driven space to explore their own midlife shifts. Communities come in different flavors, sizes, platform types, and approaches so finding the right fit is particularly important. You can join enormous communities like Noon (which reaches tens of thousands of midlife women), small local Meetup Groups or online options (like the CMS Community). Communities are strongest when you don't need someone to lead you through a process; you need people alongside you while you live through one. And it’s important that you know how to get in, connect well, and get what you need from it. They fail (as a support mechanism) when you join a community that isn’t the right fit for your needs. For example, if you desire face-to-face conversations with a curated group of high-achievers, you’ll likely be disappointed with a free 10,000-member Facebook group. Communities can also suffer from poor moderation, one-size-fits-all models, or reductionist framing, so do your due diligence.
Private coaching can be amazing when you want targeted, forward-moving individual work on a consistent basis. It’s ideal if you’re working through a specific life transition (divorce, empty nest, menopause, etc.) and you’ve already worked through your core challenges in therapy. That’s because the primary strength of coaching is that it provides individualized attention: someone who can listen closely, notice patterns, challenge assumptions, and stay with your specific and unique questions over time. You can find an excellent life transition coach who focuses on whatever you’re working through and some even focus entirely on midlife awakenings. That said, coaching is a sub-optimal choice for people who want a quick fix, actually need therapy, or want the coach to become the authority and tell them what to do to fix their life.
I would be remiss not to name therapy as an excellent support in midlife if you have material that still needs to be metabolized in order for you to move forward. It’s best for unresolved grief, unprocessed trauma, debilitating burnout, devastating loss, or when your past patterns are running your present life on autopilot in a way that’s making you miserable. To be transparent, I refer women I work with to therapy regularly (sometimes mid-course) because I consider it a success when they uncover something that requires it. Like every form of support I’ve mentioned, it’s not the right fit for every need. But it is the appropriate choice if your primary work involves trauma, grief, mental-health symptoms, or patterns that require clinical expertise. Coaching, courses, retreats, and community can coexist with therapy, but they shouldn't be used to avoid therapeutic work.
Do you have to pick just one form of midlife support?
No, and you probably shouldn’t go looking for the perfect community, coach, or course. Instead, let’s acknowledge that it’s normal to have a wide range of needs during midlife transitions, if for no other reason than they tend to last for years, not days or weeks.
I’ve leaned on every single one of these support mechanisms. One advantage of having a long midlife shift is that I’ve tried most of what’s out there. I attended retreats, took courses, belonged to communities, worked with a midlife coach and a therapist. Each one served a different moment in my own process. You don’t need all of them. But do give yourself permission to identify what you need, get that need met in the best way possible, and be open to your needs changing and evolving over time.
It’s far more useful to think of midlife support as a broad web. You already have an OB-GYN, a therapist, and an executive coach and you can lean on any of them as needs arise. What I’m encouraging you to do now is expand the web, since your current needs may call for different kinds of support than you’ve tried before. You’ll likely cycle through this process of naming your needs and choosing the best type of support several more times over the next few years.
Is it normal to need help during a midlife transition?
I sense some important unspoken questions embedded in your very practical letter: are you allowed to not know? Does an expert get to be a beginner? And will anyone take you seriously if you say, out loud, “I’m at a crossroads and I don’t know how to move through it?”
Yes, yes, and yes! And the women who will take you most seriously are the ones a few steps ahead of you, who remember exactly what their own midlife awakening felt like. One need that high-achieving women routinely underestimate is good company for the journey: people who understand why a life that looks extraordinarily successful from the outside can still require deep re-examination. Having peers while you explore and rediscover the parts of you that got exiled as you climbed the ladder can accelerate the process. In fact, it’s one of the needs that’s worth taking seriously and making arrangements for.
So my dear Seeking, let’s start with one concrete step today. Grab a piece of paper and take fifteen minutes to name your needs on one page. I recommend dividing the page into three questions: What work am I being asked to do right now? What kind of container helps me do that work well? How much structure or individual attention do I need? Your answers will narrow the field of possibilities considerably. Then pick somewhere to begin knowing that you’re choosing the support that fits this moment, and that you can choose again and again as your needs evolve.
Warmly,
Kerry Ann
Ready to choose where to begin?
Your answers to those three questions above will narrow the field. If what you need is depth, structure, and the company of women working through the same questions, the Center for Midlife Success offers several ways in: the Clarity Retreat (a self-paced reflection you can do at home), the Annual Membership (a year-long community of peers), and Your Next Chapter (an eight-week course for deeper identity work). Each is designed for a different need, so you can start with the one that fits this moment.
Frequently Asked Questions About Finding Support During Midlife Transitions
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It depends on what needs attention. Therapy is the right choice for mental-health symptoms, trauma, significant grief or loss, debilitating burnout, or old patterns that keep running your present life despite your insight into them. Coaching, including work with a life transition coach, is a better fit when you're reflective, functioning well, and want individualized attention to explore questions about what comes next. The two can work alongside each other, and many women lean on both at different points in a midlife transition. A good coach will refer a client to therapy when the work calls for it.
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A life transition coach works one-on-one with someone moving between chapters of life, such as a career change, an empty nest, menopause, or a deeper shift in identity at midlife. The coach listens closely, notices patterns, challenges assumptions, and stays with the client's specific questions over time. A good coach doesn’t become the authority on the client’s life. The answers emerge from you, and the coach creates the conditions for that inquiry. Coaching differs from therapy in that it isn't clinical treatment, and from group programs in the depth of individual attention it provides.
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Start with what you need instead of what you’re seeing in your Instagram feed. Kerry Ann Rockquemore, PhD (founder of the Center for Midlife Success) recommends spending fifteen minutes answering three questions on one page: What work am I being asked to do right now? What kind of container helps me do that work well? How much structure or individual attention do I need? Only then should she evaluate existing options for a match. High-achieving women in midlife often need one of a few things: to work through old baggage, structure and accountability, a room where they aren't the most accomplished person, time away from daily life, or help quieting the inner voices that keep them from doing the work. Matching the format to the need is more reliable than choosing whatever markets best.
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High-achieving women have often spent decades being the person other people come to for answers. When a woman’s identity is built on competence, needing help can feel like a reversal of who she is, rather than an ordinary part of what Jungian analyst James Hollis calls the Middle Passage. Carl Jung saw this coming nearly a century ago: "We cannot live the afternoon of life according to the programme of life's morning." The strategies that worked in her thirties and forties often stop working at exactly this point. Needing support isn't a sign that something has gone wrong. For many accomplished women, accepting help is the first real step of the transition itself.
A Note on How This Column Is Written
The letters in Dear Kerry Ann are composites, drawn from five years of real questions that high-achieving women have brought to mentoring sessions, office hours, workshops, classes, and conversations with me. All identifying details have been changed. The answers come from my own teaching transcripts. For this column, I wrote the first draft from transcripts of my class lectures, then used AI to copy edit and help draft the FAQs. All of the ideas, frameworks, and recommendations are mine, and so is the responsibility for every claim.
