It’s Both — Living in the Messy Middle

Waiting for permission to start over is its own kind of messy middle. Jess Lattif spent ten years building a career in tech, at Meta and beyond, and joins me to talk about the identity shift that happened long before she ever left, and the transition anxiety of sitting in the unknown after she did.

In this episode — the line in the sand that finally made her stop ignoring the truth she already knew — the offsite trip and the performance conversation that became her breaking point — the difference between the discomfort of growth and the dread that means "hell no" — how "Not Working in Tech" was actually born out of being on leave, not out of quitting — and why she believes burnout isn't a personal failure, it's a systemic one.

Jess Lattif is the founder of Not Working in Tech, a platform and consulting practice built around the belief that your job should never cost your health. Find her at notworkingintech.com.

If this resonates, the Messy Middle Workbook was made for exactly this space — five sections, real prompts, and a companion meditation for each one. Link in the show notes.

Get Connected & Support the Show:

- If you're in the messy middle right now, the workbook was made for this. Or you can grab your free resource.

- Follow Jess on Instagram or visit her website 

- Listen to the companion podcast: It's Both- Guided Meditations for Anxiety, Emotional Regulation, & Real Life Transitions

- Subscribe, rate, & review It's Both on Apple Podcasts

This is starting over with no guarantee it gets easier. Amber Lewis Stewart joins me to talk about the identity shift that started long before she and her wife ever left Tennessee, and the night they finally decided to leave the country for good.

In this episode — the lines in the sand they drew years before they crossed them — what it felt like when a friend group they trusted turned distant over the decision to leave — the same night they got the news their last fertility treatment failed and chose to go anyway — what it means to feel certain about a decision without ever feeling at peace with it — and how gardening and uprooting became the actual metaphor for starting over.

Amber Lewis Stewart is the founder and editor of Unbordered Magazine and author of In the Garden: An Almanac for Uprooting, out now. 

If this resonates, the Messy Middle Workbook was made for exactly this space — five sections, real prompts, and a companion meditation for each one. 

Get Connected & Support the Show:

- If you're in the messy middle right now, the workbook was made for this. Or you can grab your free resource.

- Follow Amber on Instagram or visit her website 

- Get her book In The Garden

- Listen to the companion podcast: It's Both- Guided Meditations for Anxiety, Emotional Regulation, & Real Life Transitions

- Subscribe, rate, & review It's Both on Apple Podcasts

This is transition anxiety, recorded live instead of explained after the fact. In this solo episode, Nikki checks in from a friend's basement mid cross-country move, mid job loss, and mid everything else, letting you into the version of starting over that usually only gets told once it's resolved.

In this episode — the real timeline of moving from Nashville to Denver with three kids in tow — the liminal space of no lease, no house, and no plan yet — what it actually feels like to start over with nothing certain — and how she's holding gratitude for the choice and grief over how hard it is, at the same time, without picking one.

Get Connected & Support the Show:

- If you're in the messy middle right now, the workbook was made for this. Or you can grab your free resource.

- Listen to the companion podcast: It's Both- Guided Meditations for Anxiety, Emotional Regulation, & Real Life Transitions

- Subscribe, rate, & review It's Both on Apple Podcasts

In the messy middle of chronic illness, self-worth, and giving up good for great, Amy Lenius joins me to talk about the three core wounds that quietly run our lives — unlovable, unwanted, and defective — and how healing starts long before we feel ready.

In this episode, Amy shares her decade-long fight for an endometriosis diagnosis, the moment she chose to trust her own body over a system that kept dismissing her — the one question she now asks before every hard choice to protect her self-respect — why giving up something good for something great always feels like chaos in the middle, not clarity — and how something as small as painting her nails a new color became actual identity work.

Amy Lenius is the director of group coaching at Next Level University and a holistic self-improvement coach specializing in the three core wounds framework. 

If this episode resonates, grab the Messy Middle Workbook — five sections of prompts and meditations to help you actually sit with your own messy middle instead of rushing past it. Link in the show notes.

Get Connected & Support the Show:

- If you're in the messy middle right now, the workbook was made for this. Or you can grab your free resource.

- Follow Amy on Instagram or visit her website 

- Listen to the companion podcast: It's Both- Guided Meditations for Anxiety, Emotional Regulation, & Real Life Transitions

- Subscribe, rate, & review It's Both on Apple Podcasts

The messy middle of betrayal isn't just heartbreak. It sits in your body. It changes how you trust yourself. And it hits differently than any other kind of pain — and Dr. Debi Silber has the research to prove it. She went back to school at 50, in the middle of her own betrayal, to figure out why. What she found became groundbreaking research and a whole movement. In this conversation we talk about what post-betrayal syndrome actually looks like in your everyday life, why most people get stuck and never fully heal, and the five stages of betrayal recovery that change everything. There's also something she said that I haven't been able to stop thinking about — the people who heal the fastest aren't the ones who hurt the least. They're the ones who were the most willing.

In this episode:

If you've ever been betrayed by someone you loved and trusted — a partner, a parent, anyone — this one was made for you.

Get Connected & Support the Show:

- If you're in the messy middle right now, the workbook was made for this. Or you can grab your free resource.

- Take the Post Betrayal Syndrome Quiz

- Follow Dr. Debi Silber on Instagram or visit her website 

- Listen to the companion podcast: It's Both- Guided Meditations for Anxiety, Emotional Regulation, & Real Life Transitions

- Subscribe, rate, & review It's Both on Apple Podcasts

The messy middle of becoming a mother doesn't end when you leave the hospital. It lives in the identity shift, the mom rage you don't talk about, the grief for who you were before, and the joy that exists right alongside all of it. Dr. Nicole Pensak is a licensed clinical psychologist who specializes in perinatal mental health — and she went through severe postpartum OCD herself, right in the middle of COVID, while her husband worked on the front lines. In this conversation, we talk about what actually happens to your brain when you become a mother, why postpartum is a developmental stage nobody told you about, and what it means to hold the grief and the love at the same time.

In this episode:

For anyone who has ever loved their child fiercely and also felt completely lost inside that love — this one is for you.

Get Connected & Support the Show:

- If you're in the messy middle right now, the workbook was made for this. Or you can grab your free resource.

- Buy her book Rattled

- Follow Dr. Nicole Pensak on Instagram or visit her website 

- Listen to the companion podcast: It's Both- Guided Meditations for Anxiety, Emotional Regulation, & Real Life Transitions

- Subscribe, rate, & review It's Both on Apple Podcasts

The messy middle isn't always something you can think your way through. Sometimes it lives in your body — in the shallow breath, the held-back cry, the emotions you've been managing instead of feeling. Jon Paul Crimi is a breathwork teacher who has spent 15 years helping people release what their minds can't process alone. He found this work through his dear friend Matthew Perry — and the grief of losing him is woven into every class he teaches.

In this conversation, we talk about what circular breathwork actually is and why it works, what it means to let go of the life you planned to step into the one you're actually meant for, and why you can't shut yourself off from the hard emotions without also losing access to the joy.

In this episode:

For anyone who lives in their head, knows exactly what they're feeling, and still can't seem to feel it — this one is for you.

Get Connected & Support the Show:

- If you're in the messy middle right now, the workbook was made for this. Or you can grab your free resource.

- Follow Jon Paul Crimi on Instagram or visit his website 

- Listen to the companion podcast: It's Both- Guided Meditations for Anxiety, Emotional Regulation, & Real Life Transitions

- Subscribe, rate, & review It's Both on Apple Podcasts

The messy middle of relationships isn't always dramatic. Sometimes it's the slow, quiet erosion of yourself — giving and giving and giving until you don't know where you end and everyone else begins. And not having a name for it until someone finally says it out loud.

Vanessa Bennett is a licensed depth psychotherapist and author of The Motherhood Myth. She spent over a decade in corporate New York feeling disconnected underneath a life that looked felt great on the outside. She left, rebuilt, moved to LA, spent years creating exactly the community she wanted — and then lost her home in the LA fires in January 2025. Now she and her family are in Costa Rica, still following the breadcrumbs.

In this episode, Vanessa and I talk about the identity shift of recognizing your own codependency — and why almost all of us are codependent whether we want to admit it or not. We talk about the difference between caregiving and caretaking, why resentment is actually one of the most useful tools you have, and what depth psychology actually means in practice for someone who lives entirely in their head. We also talk about grief, starting over, and the transition anxiety that comes with following breadcrumbs through the messy middle of a life that keeps changing before you're ready.

This is also a really honest conversation about The Motherhood Myth — the lie we've all been fed that partnership and parenthood should feel natural and easy, and what it actually costs us when we believe it.

For anyone who gives more than they take, for anyone who calls themselves a recovering codependent, and for anyone who says they're definitely not codependent — this one is for you.

Get Connected & Support the Show:

- Grab your free resource and be the first to know when the workbook is live.

- Order Vanessa Bennett's book HERE

- Follow Vanessa Bennett on Instagram or visit her website 

- Listen to the companion podcast: It's Both- Guided Meditations for Anxiety, Emotional Regulation, & Real Life Transitions

- Subscribe, rate, & review It's Both on Apple Podcasts

The messy middle isn't always about a crisis you can name. Sometimes it's quietly losing your sense of self inside a relationship that looks fine from the outside — and not having language for what's actually happening until years later.

Dr. Jordin Wiggins is a naturopathic doctor, pleasure and intimacy coach, and founder of the Pleasure Collective. She built a thriving health clinic, checked every box success was supposed to look like, and was still disconnected, exhausted, and quietly unraveling underneath it — both in her business and in a relationship she didn't yet have language to call abusive.

In this episode, Jordin and I talk about starting over with your own desire after burnout, after betrayal blindness, and after losing your sense of agency inside your own home. We talk about why sexual dysfunction often isn't a personal failing at all — it's a power imbalance, an invisible labor problem, or a nervous system too dysregulated to access pleasure. We talk about responsive versus spontaneous desire, the orgasm gap, and why women's pleasure centers shut down in survival mode. And we get into what it actually felt like for her — a successful clinic owner who solved other people's problems all day — to rebuild her own identity, and her own desire, from nothing.

This is also deeply personal for me. We talk about my own relationship in my teens and twenties, and the both/and of loving someone while slowly disappearing inside that love.

This is a conversation about grief, identity shift, transition anxiety, and the messy middle of rebuilding your relationship to your own body, your own pleasure, and your own worth after everything falls apart. For anyone who has ever felt successful on paper and empty underneath — this one is for you.

Get Connected & Support the Show:

- Grab your free resource and be the first to know when the workbook is live.

- Order Dr. Jordin Wiggins book HERE

- Follow Dr. Jordin Wiggins on Instagram or visit her website 

- Listen to the companion podcast: It's Both- Guided Meditations for Anxiety, Emotional Regulation, & Real Life Transitions

- Subscribe, rate, & review It's Both on Apple Podcasts

The messy middle isn't always something you can talk your way through. Sometimes you just need a place to breathe.

This is a meditation for the waiting. For the unknown. For the transition anxiety that sits in your body when you've made a decision but can't get to the other side of it yet — the knot in your stomach, the tightness in your chest that won't turn off no matter how many times you check your phone.

We're not fixing anything here. We're not trying to be positive or push through. We're just finding a little awareness, a little steadiness, and a little permission to be exactly where you are.

Both things can be true — you can be scared and still be okay. You can have no control over the outcome and still have control over how you take care of yourself while you wait.

This meditation comes from the companion podcast It's Both Guided Meditations — available free wherever you listen.

Get Connected & Support the Show:

- Grab your free resource,What If You're Not Doing Anything Wrong — It's Just Hard Right Now, and give yourself permission to just be where you are.

- Listen to the companion podcast: It's Both- Guided Meditations for Anxiety, Emotional Regulation, & Real Life Transitions

- Subscribe, rate, & review It's Both on Apple Podcasts