I started small and sentimental a few months ago. I tattooed little sun/moon/star symbols where the boys’ fingers hit when they hold my hand. I love it so much - subtle, meaningful, and uncommon. And when I left the appointment last time, I already knew what I wanted to do next.

My new one is the view between the ears of my heart horse, Indy, my dream German-bred Hanoverian gelding who died suddenly and tragically right in front of me.

If you were a little girl that loved horses (or an adult that has found your love for them later in life) you already know the exact image I mean. Two ears and the horizon in front of them. I’ve tried to explain it to non-horse people, but they hear something sweet and simple and move on. What’s hard to convey is the feeling a “between the ears” image evokes in your body. The memory of the horse underneath you, and what it was carrying you toward. Horse people feel that without anyone explaining it. And when you lose a horse, it is the image that does the most work to remind you of what is gone.

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I bought him when I was 28 and working a demanding corporate job that had me traveling all over the world. He was barely a year old, rapidly growing, and a handful. It was a totally unhinged purchase for a reasonable adult and a totally obvious one for little Lindsay the horse girl that dreamed of owning a warmblood for dressage since she was ten years old riding old, grade quarter horses in 4H shows. So, when he came along and I could afford him because he wasn’t yet ridable or proven, I said yes. The first enormous want I had ever sprung for without asking permission from anybody.

So much love and soul work went into his upbringing that when he died almost twelve years ago in late 2014, it sent me into a tailspin. I can still barely talk about it.

I had quit my corporate job in January of that year, and moved into consulting. I finally had the freedom to work AND do the life things I wanted to do…no boss or structure telling me where to be or when. It felt exhilarating and empowering and also so wildly uncomfortable.

I was one of those kids that rode the 90’s girl achievement escalator - high GPA, tons of AP classes, and a million extracurriculars in high school so that I could get into an elite college (got accepted to several, chose to go to Cal Berkeley). Then good grades, NCAA Division 1 athlete, 25 credits a semester and a part-time job so I could graduate in 3 years and save myself a year of student loans (young adult Lindsay had stamina baby!). Then the great corporate job, then the MBA, then the ladder climbing and on and on and on. I loved it all, it all felt…easy. Do something with excellence, identify the next thing, and repeat. But once I got a few years out in the real world and the ladder rungs were less distinct, I could never reconcile the emerging feeling I had that I didn’t really belong there. I struggled with the slow pace of change in a corporate environment, the very obvious glass ceilings, and that effort was not directly correlated with reward. I loved to work, but I didn’t love the work. It made me a difficult employee to manage (long overdue apologies to my former bosses lol), but it planted the seeds of entrepreneurship…a much better fit for those of us wanting to get off the escalator.

When I quit in early 2014 I was so certain about it. But within a year, I was deep in the grief of Indy dying, and all the collateral damage of a life lived on a moving walkway that I was just waking up to.

2015 was a broke, floaty, structureless year where I did very little work and made almost no money and could not have told you what I wanted to do next if you had paid me for the answer. It was also the most present I have ever been in my life. I took up trail running. I spent long lazy days on my friend’s boat at the lake. I spent an embarrassing amount of time at the local speakeasy learning about whiskey. I was adrift.

To the little overachiever angel on my shoulder (and my parents lol), it looked like a breakdown. But deep in my soul, it felt like the first real space I’d had since high school. I was completely paralyzed without a concrete next thing to aim for, but I was also finally starting to ask myself what I really wanted.

I think that year was the closest I have ever gotten to answering that question without an external achievement or someone else’s opinion as the anchor. One single year of my life with no parent, no school, no boss, no partner, and no kids to consider.

And what feels the most interesting and the most confronting now is that so much of that presence in 2015 came as a result of being in deep grief.

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By early 2016 I met RT and that fall I got pregnant. And then in the blink of an eye, I’m sitting here 10 years later realizing I’m back in a season of grief and the presence it demands. Tending to a fresh tattoo that reminds me of a version of myself who was also navigating loss.

Everyone says grief is love with nowhere to go, and it is that. But I also think it’s deeper than that - it’s love across the past, present, and future crashing over you at the same time, constantly. It is the love and yearning you feel for the past version of you before the loss, it is the love in this present moment that you ache to express to a person, an animal, a life that is no longer there to receive it, and it is the love for the future version of you for whom this loss will be the wound that scars over but never disappears. That is an enormous amount to hold in one nervous system.

I grieve for 2015 Lindsay with no money and no plan who was more free than I have been at any point since. I love her, and I am so proud of her because she got so much of what she wanted, and I am so sad for her because most of those things came in ways that were different than she imagined, that required her to self sacrifice in so many ways, and brought so much pain along the way.

I grieve for future Lindsay, who I am fairly certain is going to be happier than I have ever been, but who will forever feel the loss of the family structure she wanted. Who will flinch when she remembers the vow she made to herself as a teenager after her parents divorce never to end up divorced herself. Who will look at her children every day hoping they’re ok and that they understand why all this happened and don’t hate me (or their dad) for it.

And of course I grieve for myself now, today. Even amidst the confidence in my decisions and the excitement I feel for what is to come. I grieve for the boring daily routines that suddenly feel jarringly different. I grieve for my mama heart that now spends time alone in this big house because my kids are with dad. I grieve for RT being on the turbulent journey of self-discovery without me as his scaffolding. Hell, I grieve for my freaking brain trying to add “redecorate master bedroom” to my mental load (hence why I’m currently sleeping on the floor).

Grief is so layered and individual. I’m not an expert and of course what I’m grieving now is not a death or a tragedy, so the enormity of its implications are at a very different scale. But, the grief of a major life change is something I think we tend to gloss over for exactly this reason. And I think it explains why so many of us are living inside lives that feel further and further away from the truth.

Death is finite, we implicitly understand in our primal body what it means, and we never choose to have to deal with it. Death forces a relationship with grief. Whereas life changes, especially those we choose, get filed under “survivable” or “long time coming” or “I’ll figure it out”, making it easy to deny the need for grieving in favor of moving forward.

All of this of course comes on top of my general belief that modern life has made us bad at grief.

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It’s too easy to observe it from afar, via strangers on the internet, devoid of the resonance of being in proximity to the emotions in real life. It’s too easy to focus on ourselves vs our role in a village; we can justify not showing up for others because “we’re all going through it”. It’s too easy to soothe our collective depletion with comfort and distraction, all the while becoming less and less sensitized to how much of being a human in the natural world is about dealing with loss.

And even when we do get close to it, it’s too easy to default to “fixing”. We are not conditioned for discomfort, so we lean on competence. The dreaded “let me know how I can help” that forces the grief back into the shadows while our fellow human assures us they’re ok. We assume they’re “handling it beautifully”; the truth is they’re navigating everything I’ve articulated above…mostly alone.

Inwardly too - I don’t think we’re bad at our own grief because we’re afraid or in denial. I think we’re bad at it because there is no timeline inside it. There is no defined pathway to follow through it. Nothing to speed it up, nothing to make it easier, nothing to win. Grief just sits there and asks you to join it in the quiet discomfort of presence, and if your entire operating system is built on motion (and most of us millennials are) then being asked to simply be still and feel it is close to unbearable. When we can’t control the pace or set our sights on a certain outcome, we’d rather disengage and put our focus elsewhere. And we live in a world that lets us.

I’m guilty of this too. The proof is literally tattooed on my arm now.

Again, I’m not claiming to be an expert, I’m not sure there is such a thing when we talk about grief. But I do feel strongly that one of the biggest opportunities we have as humans right now is to get better at grief - with each other and within ourselves. AI can write the condolence note or the supportive Facebook comment, but it can’t sit in the room and hold space for the love with nowhere to go. The more I notice how much we’re being denatured by technology and optimization and polarization and comfort, the more certain I am that we have to practice these really human skills.

I’m the number one fan of a clearly defined path, with a strong fall back on “I’ll figure it out” if an obstacle arises. But in this midlife reckoning season now, I’m working on becoming the person that willingly walks into the void and faces the undefined nature of my grief. And anytime I need a reminder of why it matters, I just have to hold up my arm.

Today I want to open this honestly, which means telling you not only what happened, but what I was doing the whole time it was happening.

Because there was a little girl in my house in the 80’s who worked out early that if she was funny enough and smart enough and charming enough, she could get out in front of whatever was building between the adults and bring the temperature down before it broke. Nobody asked her to do that, she just noticed she was good at it. And I have been running that little girl’s playbook ever since. In every company I’ve built, every crisis I’ve walked into, every family dinner, every relationship. She is the undercurrent of every explanation I’m about to offer you for how I ended up here.

If you’re a millennial woman, you’ll recognize yourself. The competence that is your entire identity and also the loneliest thing about you. The capacity that seems infinitely expandable while the load drains your life force out of a hole you can’t plug. The confidence that lets you believe “I’ll figure it out” is just a strength, rather than the thing that keeps you in the relationship three years past when you knew, in the family role nobody has revisited since 1997, in the version of motherhood where you’re the only one who knows the pediatrician’s name, managing and absorbing and cleaning up chaos (usually somebody else’s) with nothing but a long exhale and a what the fuck muttered under your breath at the kitchen sink.

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For me it culminated a couple weeks ago, in a quiet conversation with RT, my partner of ten years. Nobody yelled. Nobody blamed. I said I didn’t see how we get back to feeling good, and he said he’d been thinking the same thing, and then we sat there and worked out what we both actually wanted, which turned out to be almost everything except the marriage. Co-parents, obviously. Family, always. Friends, business partners, the people who show up. Just not this.

A little over a year ago he had a massive stroke that nearly killed him. His recovery has been miraculous, and it has been happening in parallel with the slow unraveling of my willingness to keep holding everything together for us. This last year was the end of a five year repair arc after his two affairs in 2020, which happened during a pandemic that killed two of my businesses, six months after I had our second baby. So: after many years of life doing its thing inside our relationship and me mopping up the aftermath, we have mutually agreed to separate, permanently, and to do it kindly and peacefully.

I would love to tell you it was a hard decision.

But the sentence that keeps coming out of my mouth when I tell people close to me is it’s been a long time coming, and every single person nods. Not one person has asked me a follow-up question. Which is its own kind of information, and also a very convenient place to stop talking.

So here’s the part I haven’t shared previously:

We started dating in the spring of 2016 and a few months later I was pregnant with our oldest son Sawyer (surprise!). At the time I thought it felt “meant to be”, but as time has gone on I’ve realized the shadow of that belief. Karmically, dharmically, spiritually, Universally - Sawyer is definitely meant to be. He’s my greatest gift, he made me a mother, he is a cosmic starseed here on soul contract with me and his dad, and he will definitely do big things with his life. RT and I both deeply love him, and absolutely do not regret choosing to have him, but in that moment we both decided to set aside a very hard conversation we should have had that ultimately led to this outcome 10 years later.

RT’s side of the story is his own, but from my vantage point, he was a 25 year old man thrust into a life structure that he didn’t “choose” with a version of me that wasn’t gonna slow down long enough for us to be honest about that, so he just “went along with it” (the yin to my “I’ll figure it out” yang). As a result, he has spent a good part of the last 10 years subconsciously angry at the world (and me) without the tools to articulate, process, or heal it, while I’ve swallowed my own feelings of betrayal and resentment in an effort to hold it all together. His affairs in 2020 came on the heels of his mom dying of cancer and the world shutting down, and I became the dumping ground for the externalization of his grief. Hard things kept happening to him that he couldn’t control, so he blamed me, took the reins, and found someone else to tell him he was right to do so (2 of them actually, both friends of mine at the time…story for another essay).

And here’s my half of it, which took me considerably longer to see. By 2016 I’d spent a decade with unavailable men who were never going to pick me, and I’d built my entire operating system around it: stop waiting, chart the course yourself, and go. Then I met RT. Eight years younger, already a successful entrepreneur, and he did choose me…he said it out loud, early, which nobody had done in a very long time. What made it feel safe wasn’t only that he loved me, it was that I never had to make a case for anything. He was 25 and in love and he said yes, and I was 33 with a plan and a lot of momentum…and then four months later I was pregnant. He chose me. He never once got asked about the rest of it. And I didn’t ask, because I already knew what I wanted and I wasn’t willing to find out that he didn’t. That’s the dichotomy we then ran for ten years…I figured it out, he went along with it…and it worked until it didn’t.

For the last several years, I thought the hard conversation that would help was the one I kept having with him. Over and over I asked him what was true for him, what he really wanted, how he planned to figure it out, and how I could support that. I thought that if he knew the answers to those questions, the energy would shift, and I’d feel the polarity in the relationship I was so hungry for. I’d get to share some of the immense burden of holding everything together because he’d be more present and aligned and sturdy (read: masculine energy). But, I was mostly met with a version of “I don’t know what you mean” or “I can’t focus on that right now because I have so much else on my plate”.

It turns out the conversation I needed to have was never with him. It was with myself, about what was already true. And I avoided that one with more skill and more stamina than I have applied to anything in my life, and I want you to understand that I am very good at things LOL.

Here’s what nobody tells you about being the capable one in a relationship like this: I got things, and I want to be honest about that, since it’s the part that gets cut from this genre. I got the things I wanted and he went along with it, and I’m endlessly grateful to him for that part.

I have the dream house and the land and the ridiculous number of chickens. I have my two little boys. I have work I love, a name that opens doors, fifteen years of building things that help people. I’ve been the primary earner for all of it, which I know is a sentence a lot of women say through a clenched jaw, but most days I like it about myself enormously. I can buy what I want. I can support my aging parents. I can move through the world mostly unencumbered by scarcity (which is big for me given my childhood). My competence is the best thing about me. I have talked women through the worst weeks of their lives with it. I have carried whole companies on it. When my partner collapsed in a hotel gym several states away, it is the reason our lives (and businesses) stayed intact.

And it is also the reason I have almost never had to find out whether I really wanted any of it.

That’s the thing I’ve been circling since this spring. If you can make anything work, you never have to ask whether it’s the right thing. Choosing means picking one thing and letting the rest go, and we weren’t built for that. The infamous 90’s parenting told us we could be anything, which our little overachiever brains translated into we’d better be everything. So we don’t choose. We add it to the pile, competently, and we get told how strong we are, and then we drift a little further from the answer every year. We were raised to strive and achieve and take care and check the box, and not one person ever taught us how to want anything. And I don’t mean wanting a bigger house or a better title or more money. We’re all exceptional at that. I mean discernment. The kind of wanting you’d have to trust yourself to know.

So we built enormous lives out of things we did for every reason except true desire. Because it was available. Because it was impressive. Because it was the next logical step. Because someone else did. Because someone needed us. Because we should. Because we could.

And then those lives no longer fit the way we thought they would. And we have to change.

So here I am at almost 44, with the house and the boys and the work and the reputation, asking a question I hear from women constantly now and never used to hear at all: I thought I wanted all of this. I figured out how to get it. I got it. And then it didn’t feel the way I assumed it would, and I’m not sure anymore that it’s what I actually want…but how do I know what I actually want?

That’s what this publication is for.

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I’m not going to tell you how to choose the right things. I think we all have to figure that out for ourselves. What I can do though is go back through my life experiences and look at what I “figured out” without asking myself what was true. I suspect I’ll have a long list to examine. I suspect you will too.

I’m going to write about all of it here. The mental load. Raising boys. Millennial identity. Cultural conditioning. Fifteen years of building businesses, including the parts nobody mentions outside the mastermind rooms. What I learned in my parents’ house about money and men that nobody ever said a word about. What happens to a marriage when one person’s competence becomes the other person’s ceiling. Whether the fairy tale of a steady, competent, boringly dependable partner to match my elder millennial oldest daughter energy is a fantasy I should put down or a standard I should hold (nod to Emily Henry for giving me (false?) hope). I honestly don’t know the answer to that last one, which is sooo confronting.

As for me and RT. We’re taking it slowly and we’re doing it as transparently as possible. He is deep in the work now and is finding his way to the answers he seeks about himself and the world. I’m proud of him for that. He’s a good dad, the boys love him, and he’ll be just down the street. So far the hardest part of splitting up hasn’t been any of the things I braced for, thank God. It’s been the ordinary logistics of dismantling a life you built together, especially with kids involved, and how kind and peaceful it all feels…which sometimes makes me second-guess my decision. After everything, we do still love each other. We were together for ten years, we made two little amazing humans, and we got each other through the worst year either of us could have imagined. I feel deep reverence and appreciation for him, even amongst the wounds that live here too.

It’s been a wild journey, and as cliche as it sounds, I’m happy it happened the way it did. It’s my life’s dharma. Fodder for my work. Lessons for this lifetime of my soul.

For now, it’s late here. The boys are asleep. The house is quiet in the new way it’s going to be quiet from here on out, and I notice I’m not dreading it. Deep breath. I have a lot of exciting things and big plans (obviously)...and a lot of open loops and uncertainty (of course).

But I’ll figure it out. I always do. And for the first time it doesn’t feel like the loneliest thing about me.