Épisodes

  • 120. I Didn't Lose Myself in Motherhood. I Never Found Myself Before It with Libby Ward. April roundtable with Erin Holland.

    120. I Didn't Lose Myself in Motherhood. I Never Found Myself Before It with Libby Ward. April roundtable with Erin Holland.
    Apr 17 2026
    Libby Ward built one of the internet’s most recognizable platforms for honest motherhood, and she did it by saying the things most moms were too afraid to say out loud. Now she’s put it all in a book: Motherhood: On Losing My Mind and Finding Myself, published by Crown.In this co-hosted episode, Ashley and Erin sit down with Libby to trace the full arc, from the small town church community where motherhood was put on a pedestal, to the postpartum rage that finally broke her open, to the sociology class that reframed everything, to going viral on TikTok during a pandemic, to writing a book for Crown that she nearly wrote as someone else entirely.It’s a conversation about what happens when women stop doing everything for everyone else and start asking who they actually are, and why that question so often doesn’t get asked until something breaks.In This EpisodeWho Libby was before TikTok- a 26-year-old in a conservative church community trying to be every kind of mom at onceHow her second child’s higher needs broke the plate-spinning and sent her to therapy for the first timeWhy her postpartum depression showed up as rage, not sadness and why that made it harder to recognize and nameThe shame spiral of “what is wrong with me” and the therapy session that cracked it openThe sociology of sex and gender class that introduced her to the mental load, default parenting, and feminismFinding TikTok during the pandemic and posting as a form of dissociation, not really believing anyone would find herThe moment she stopped making humor content and decided she didn’t want to joke about things that were crushing her soulGoing no contact with her mom and how that coincided with the book deal coming throughThe writing process: imposter syndrome, a pivot away from research-heavy writing, and learning to trust her own storytellingWhy she didn’t lose herself in motherhood, she never found herself before itDoing it guilty: why waiting to feel ready or unashamed means never changing anythingWhat “honest motherhood” actually means and why it starts internally, not out loudQuotes From This Episode:“I didn’t lose myself in motherhood. I actually never found myself or knew myself when I was younger. Motherhood was the catalyst to help me find the self I never knew before motherhood even began.”— Libby Ward“It’s not that I’m exhausted because I’m not enough. It’s that the load is too much for any one person. That shift is so important.”— Libby Ward“How do you get rid of the guilt and shame? You just do it guilty. You do it feeling a little bit ashamed. And then you’re retraining your brain — actually, we survived. Actually, it’s okay.”— Libby Ward“I am so tired of women being the butt end of jokes. I no longer want to joke about the things that are crushing my soul.”— Libby Ward“You deserve to be well just for the mere fact that you’re a person who deserves to be well. Your kids just happen to benefit from that.”— Libby WardAbout the BookMotherhood: On Losing My Mind and Finding Myself by Libby Ward is available now wherever books are sold — Amazon, Indigo, and most major retailers.Find LibbyWebsite: libbyward.comInstagram: @libbywardTikTok: @libbywardofficialConnect with Ashley:Website: https://www.ashleyblackington.comPodcast website: https://www.andbothpodcast.com/Dovetail® App: https://apps.apple.com/us/app/dovetail-app/id6744341822Instagram: @mydovetail.appLinkedIn: https://www.linkedin.com/in/ashleyblackington/
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    1 h et 8 min
  • 119. The Mental Load Nobody Names: Reparenting Yourself While Raising Someone Else with Michelle Gibson

    119. The Mental Load Nobody Names: Reparenting Yourself While Raising Someone Else with Michelle Gibson
    Apr 3 2026

    What does it mean to break a cycle when you’re still inside it? Michelle Gibson is a psychotherapist, CEO of Gibson and Associates and the Nest Collective, and a mom of one, and she has spent her career helping people find language for experiences they were never taught to name.

    In this conversation, Michelle and Ashley cover a lot of ground: childhood trauma and the path into psychotherapy, the complicated terrain of parent estrangement, why adverse childhood experiences are disproportionately common in entrepreneurs, and what it looks like to lead a business and a family, from a place of genuine self-connection rather than survival mode.

    It’s an honest, warm, and unexpectedly funny conversation about doing the work while also just trying to get dinner on the table.


    In This Episode

    1. How Michelle’s childhood (alcoholism, trauma, adverse childhood experiences) led her to psychotherapy
    2. The magnetic effect of finding language for what you’ve been through
    3. Why social-emotional learning in schools is changing what middle school looks like for kids today
    4. Reparenting yourself while parenting someone else — and the double labor that involves
    5. The rise of estrangement from parents and what’s driving it
    6. Michelle shares her own experience estranging from her father — and why having a daughter changed the calculation
    7. Ashley shares her own experience with estrangement
    8. Why entrepreneurs so often come from hard childhoods — grit as a survival response
    9. The moment Michelle looked up from years of grind and realized she’d been in survival mode her whole life
    10. What it means to lead from a heart-led place versus a fear-led one
    11. The privilege of support — naming it honestly so other parents don’t compare their back end to someone else’s front end
    12. “Your parents’ ceiling is your floor” — and how Michelle thinks about expanding that for her daughter


    Resources & Links

    1. Gibson and Associates: gibsoncounselling.ca
    2. The Nest Collective: thenestcollective.ca
    3. Email: michelle@gibsoncounselling.ca or michelle@thenestcollective.ca
    4. Find Michelle on LinkedIn


    Connect with Ashley:

    Website: https://www.ashleyblackington.com

    Podcast website: https://www.andbothpodcast.com/

    Dovetail® App: https://apps.apple.com/us/app/dovetail-app/id6744341822

    Instagram: @mydovetail.app

    LinkedIn: https://www.linkedin.com/in/ashleyblackington/
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    1 h
  • 118. You Don’t Have to Be Strong: Rethinking Grief at Work & at Home with Sarah Kagan

    118. You Don’t Have to Be Strong: Rethinking Grief at Work & at Home with Sarah Kagan
    Mar 20 2026

    What happens when two of the biggest life transitions collide at exactly the same time? For grief coach Sarah Kagan, that meant losing her mother at six months pregnant and learning to live through loss while preparing to bring a new life into the world.

    Sarah is a mother to two young kids, a former corporate professional who walked away from her career to follow a calling, and someone who is building a platform to change the way we talk about grief, especially in the workplace.

    In this conversation, Ashley and Sarah dig into what it really means to grieve in real time, why the pressure to “be strong” is one of the most isolating things we do to each other, and what it looks like to hold loss and love at the same time, without having to choose between them.

    In This Episode

    1. What it means to be a “motherless mother” and why grief hits differently once you’re a parent
    2. The moment at her mother’s Shiva that taught Sarah everything about how we avoid grief
    3. Why “you’re so brave” and “at least she’s not suffering” do more harm than good
    4. The martyrdom trap — and how stepping out of it changed everything for Sarah
    5. The statistic that 51% of people leave their jobs within a year of a major loss
    6. How Sarah rebuilt her work life after leaving corporate — no 9-to-5, Wednesdays for arts and crafts, out by 4pm
    7. Why grief needs a better spokesperson (and what menopause got right)
    8. The problem with bereavement leave policies that tell you who you’re allowed to mourn
    9. Ashley opens up about losing her father to suicide and the shame layered on top of certain kinds of loss
    10. How to slow down after caregiving — and why your body will eventually make you
    11. Sarah’s grief workbook and creative morning kits: where does the love go when someone dies?

    Quotes From This Episode

    “There’s so much pressure to cover up or perform or just show up and be like, yeah, I’m fine. But it is a big deal and you need someone else to validate that experience for you.” — Sarah Kagan

    “Trying to put a period on something that’s an ellipsis.” — Sarah Kagan, on toxic positivity around grief

    “No one helps you speed up. They just throw it at you and you do it." — Ashley Blackington

    Connect with Sarah

    Find Sarah on LinkedIn: Sarah Kagan

    Website: keriahcoaching.com

    Instagram: @griefcoachsarah


    Connect with Ashley:

    Website: https://www.ashleyblackington.com

    Podcast website: https://www.andbothpodcast.com/

    Dovetail® App: https://apps.apple.com/us/app/dovetail-app/id6744341822

    Instagram: @mydovetail.app

    LinkedIn: https://www.linkedin.com/in/ashleyblackington/
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    56 min
  • 117. When Life Hands You Everything at Once: Navigating Grief, Love, and New Beginnings with Caroline Benefield

    117. When Life Hands You Everything at Once: Navigating Grief, Love, and New Beginnings with Caroline Benefield
    Mar 6 2026

    In this episode, host Ashley Blackington sits down with Caroline Benefield—digital marketer, stepparent, and someone who found herself living a decade of life in 18 months. Caroline shares what it really means to become the third parent in a blended family, how she navigated losing both parents while building a new family dynamic, and what happens when your dream job turns out not to be your dream.

    Between January 2022 and June 2023, Caroline got engaged, bought a house, moved in with her fiancé and his two kids, lost both parents, managed two estates as an only child, canceled her wedding, got married on her back porch, left corporate life, wrote a romance series, and started a digital marketing business. Through it all, she's been learning how to show up as a secure, trusted adult in her stepkids' lives—with boundaries, intention, and a lot of therapy.

    In This Episode

    -What it means to be "the third parent" in a blended family—not the replacement, not the villain, but an additional secure adult

    -Why Caroline's approach is about enhancing existing support rather than reinventing the wheel

    -How she and her husband decided which parenting responsibilities she'd take on—and which ones stay with the biological parents

    -The importance of moving into a new house together rather than slotting into an existing family home

    -Navigating grief while building a new family—losing her father after a decade-long decline and her mother suddenly within 18 months

    -Estate planning lessons: why her mom's organized estate closed in 9 months while her dad's is still open after 4 years

    -What happens when your dream job (becoming a romance author) turns out not to be your dream

    -Why she started a digital marketing business specifically for moms and women—the people shortest on time with the most to give

    -The fiber arts connection: how teaching the kids to crochet and needlepoint became a way to share something her own mom taught her

    Key Quotes

    "My job as a stepparent is not to reinvent the wheel in their lives. My job is to come in and give them extra support and resources to navigate all of the complications and emotions that come with little bodies and little brains."

    — Caroline Benefield

    "If you are not married to your partner and you don't intend to be, please, please set them up for success. Please set everything up."

    — Caroline Benefield on estate planning

    Resources & Links

    Caroline's website: southerngritdigital.com

    Services: Digital marketing for creatives, entrepreneurs, moms, and women (email marketing, compliance audits, digital ads, full-service packages)

    Action Steps for Listeners

    1. If you're dating someone with kids: Ask yourself if you can be a safe and secure adult in their lives. That's the starting point.

    2. If you're in a blended family: Have clear conversations about boundaries and responsibilities before integration gets messy. Who handles discipline? What decisions require both biological parents?

    3. Estate planning reminder: Set up rights of survivorship, trusts, and clear documentation. Even if you have a will, it's not enough if things have to go through probate.

    4. If you're a long-term partner but not married: Make sure you're set up legally. Your partner's kids will be next of kin, not you, unless paperwork says otherwise.

    5. Therapy isn't optional: Caroline, her husband, and their relationship all have their own therapy. It's how they navigate the hard stuff.

    6. For moms and women entrepreneurs: If you're at the point where you know you need marketing help but don't know where to start, visit southerngritdigital.com.



    Connect with Ashley:

    Website: https://www.ashleyblackington.com

    Podcast website: https://www.andbothpodcast.com/

    Dovetail® App: https://apps.apple.com/us/app/dovetail-app/id6744341822

    Instagram: @mydovetail.app

    LinkedIn: https://www.linkedin.com/in/ashleyblackington/
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    1 h et 4 min
  • 116. Redefining Ambition, Identity, and Success in Life’s Transitions, a Roundtable with Dr. Anne Welsh and Ben Katt

    116. Redefining Ambition, Identity, and Success in Life’s Transitions, a Roundtable with Dr. Anne Welsh and Ben Katt
    Feb 27 2026

    This episode encourages embracing the messy middle, shedding old identities, taking small intentional steps, and cultivating a growth mindset as we navigate life's many transitions, personally and in parenting.

    Big question - What happens when the identity that once kept you strong… starts to burn you out?

    Dr. Anne Welsh shares her work supporting ambitious, working moms, and emphasizes the complexity of personal change. Ben Katt discusses his experience with spirituality, community, and social healing, focusing on midlife transformation. We touch upon letting go and the importance of small changes, especially in parenting and the evolving relationship with children, as well as the importance of celebrating small victories amidst self care.

    Discover practical insights on how small shifts, self-reflection, and celebrating milestones can transform your experience of change and growth.

    Key Topics:

    • How to navigate the fear of letting go of old identities and armor
    • The concept of the "hero's journey" and the call to adventure in midlife
    • Small, intentional shifts versus major life upheavals for meaningful change
    • The importance of slowing down, reflection, and micro-moments of joy
    • Parenting milestones as rites of passage and opportunities for celebration
    • Addressing grief and loss in parenting and personal transitions
    • Embracing a growth mindset about aging and continuous learning
    • Practical tips for self-trust, desire-led choices, and pacing oneself during change

    Connect with Anne:

    https://www.linkedin.com/in/drannewelsh/

    www.instagram.com/drannewelsh/

    www.drannewelsh.com


    Connect with Ben:

    www.benkattofficial.com

    Modern Elder Academy

    Book: The Way Home

    Within Prison Meditation Project

    Substack

    Instagram


    Connect with Ashley:

    Website: https://www.ashleyblackington.com

    Podcast website: https://www.andbothpodcast.com/

    Dovetail® App: https://apps.apple.com/us/app/dovetail-app/id6744341822

    Instagram: @mydovetail.app

    LinkedIn: https://www.linkedin.com/in/ashleyblackington/
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    49 min
  • 115. Live Fully, Die Ready: Why End-of-Life Planning Is the Ultimate Act of Love with Niki Weiss

    115. Live Fully, Die Ready: Why End-of-Life Planning Is the Ultimate Act of Love with Niki Weiss
    Feb 20 2026
    In this episode, host Ashley sits down with Nikki Weiss- digital thanatologist, project manager, and founder of Endevo, for a candid, eye-opening conversation about the intersection of caregiving, death planning, and our increasingly digital lives. Nikki brings not just professional expertise, but hard-won personal experience: she lost her father at 11, became her mother's primary caregiver at 21, later cared for her grandmother through dementia, and is now supporting her daughter as she navigates a caregiving role for her fiancé, diagnosed with stage four brain cancer.Together, they tackle the questions most families avoid and make the case for why starting the conversation early isn't morbid; it's one of the most loving things you can do.In This EpisodeWhat thanatology is and why the "digital" specialization matters more than everNikki's personal caregiving journey: losing both parents young and what that shaped in herThe "panini generation" why today's sandwich generation feels more squeezed than everWhy most caregivers wait until crisis to plan and the real cost of that delayThe project management approach to end-of-life planning: de-emotionalizing the process so families can actually do itHow to build a caregiving community instead of letting one person absorb everythingThe "silver wave" of late-life divorce and what it means for adult childrenDigital legacy: what happens to your phone, social media, subscriptions, and photos after you're goneGrief bots, digital avatars, and QR codes on headstones the emerging world of digital memorializationWhy you need a Digital Legacy Advance Directive alongside your will and medical POAThe Final Playbook: Nikki's framework for building a comprehensive end-of-life planKey Quotes"Live fully, die ready. Carrying an end-of-life plan is like carrying an umbrella on a rainy day — if you carry it, you won't need it. If you need it, you know where it is."— Nikki Weiss"Death is indiscriminate. It doesn't care how old you are. We'll all die one of three ways: sudden and unexpected, a terminal diagnosis, or a long decline. You better have a plan for all three."— Nikki Weiss"The most humanistic experience we will all go through is death, dying, and incapacitation. What keeps me focused is this concept of human equity."— Niki WeissAction Steps for ListenersHave the conversation before a diagnosis forces it. Pick a low-stakes moment (Nikki suggests the day after Thanksgiving).Know the three core legal documents: will/estate plan, power of attorney, and medical advance directive.Add a Digital Legacy Advance Directive — designate someone to manage your digital accounts and assets.Take inventory of your digital life: phone passcodes, social media accounts, recurring subscriptions, online financial accounts, and stored photos.Build a caregiving team — no single person should carry the full load. Identify who handles what before it becomes urgent.Visit finalplaybook.com to start building your own end-of-life plan.Connect with Nikihttps://official.endevo.lifehttps://www.youtube.com/@DigitalLegacyPodcasthttps://www.endevo.life/https://final-playbook.passion.ioConnect with Ashley:Website: https://www.ashleyblackington.comPodcast website: https://www.andbothpodcast.com/Dovetail® App: https://apps.apple.com/us/app/dovetail-app/id6744341822Instagram: @mydovetail.appLinkedIn: https://www.linkedin.com/in/ashleyblackington/
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    53 min
  • 114. What Happens When You Stop Waiting for the “Right Time” with Danielle Alvarez

    114. What Happens When You Stop Waiting for the “Right Time” with Danielle Alvarez
    Feb 6 2026

    What does it look like to make a huge life pivot in the middle of raising small kids—and during a global pandemic?

    In this episode, Ashley talks with Danielle Alvarez, a mom of three who walked away from the business she’d spent years building and went to law school with a six-, five-, and one-year-old at home. Now a corporate attorney with her own small business-focused firm, Danielle shares what it really looked like to start over, and how she made room for ambition without sacrificing everything else.

    This is a conversation about redefining success, letting go of timelines, and figuring out what actually feels right—instead of chasing what’s expected.

    Whether you’re in the middle of a pivot, thinking about one, or just trying to hold your own dreams alongside your real life, this one’s for you.

    We talk about:

    – Making a big life change when the timing isn’t ideal

    – Doing things differently than the “traditional” path

    – Ambition, burnout, and the pressure to do it all

    – Parenting while building something new

    – Starting a business that reflects your values

    – Letting go of old expectations (and other people’s opinions)

    Connect with DanielleLinks + Resources:

    Website: sblslaw.com

    LinkedIn: Danielle Alvarez, Esq., MBA

    Email: danielle@sblslaw.com


    Connect with Ashley:

    Website: https://www.ashleyblackington.com

    Podcast website: https://www.andbothpodcast.com/

    Dovetail® App: https://apps.apple.com/us/app/dovetail-app/id6744341822

    Instagram: @mydovetail.app

    LinkedIn: https://www.linkedin.com/in/ashleyblackington/
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    Indisponible
  • 113. You’re Allowed to Want More Than Survival, with Iconoclast founder, Sarah Smith

    113. You’re Allowed to Want More Than Survival, with Iconoclast founder, Sarah Smith
    Jan 30 2026

    Burnout doesn’t always show up as falling apart.

    Sometimes it looks like holding everything together for too long.

    In this episode of AND/BOTH, Ashley sits down with Sarah Smith — founder of Iconoclast Innovations, mom of two, and self-described iconoclast — for a deeply honest conversation about motherhood, mental health, and rebuilding yourself after burnout.


    Sarah shares her experience navigating postpartum anxiety and depression during the pandemic, being laid off multiple times, starting a business while pregnant, and learning how to advocate for herself in a system that often loses sight of mothers after birth.


    Together, Ashley and Sarah talk about identity shifts after becoming a parent, why burnout is information (not failure), how community and support can be lifesaving, and what it really means to choose yourself and your family — even when it’s messy.


    This episode is for anyone who has ever wondered: Why does this feel so hard — and am I the only one struggling?

    You’re not alone. And you’re not doing it wrong.


    Connect with Sarah:

    Website: https://iconoclastinnovationsllc.com/


    Connect with Ashley:

    Website: https://www.ashleyblackington.com

    Podcast website: https://www.andbothpodcast.com/

    Dovetail® App: https://apps.apple.com/us/app/dovetail-app/id6744341822

    Instagram: @mydovetail.app

    LinkedIn: https://www.linkedin.com/in/ashleyblackington/
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    55 min