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/

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 Episode

1. What thanatology is and why the "digital" specialization matters more than ever
2. Nikki's personal caregiving journey: losing both parents young and what that shaped in her
3. The "panini generation" why today's sandwich generation feels more squeezed than ever
4. Why most caregivers wait until crisis to plan and the real cost of that delay
5. The project management approach to end-of-life planning: de-emotionalizing the process so families can actually do it
6. How to build a caregiving community instead of letting one person absorb everything
7. The "silver wave" of late-life divorce and what it means for adult children
8. Digital legacy: what happens to your phone, social media, subscriptions, and photos after you're gone
9. Grief bots, digital avatars, and QR codes on headstones the emerging world of digital memorialization
10. Why you need a Digital Legacy Advance Directive alongside your will and medical POA
11. The Final Playbook: Nikki's framework for building a comprehensive end-of-life plan

Key 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 Weiss

Action Steps for Listeners

1. Have the conversation before a diagnosis forces it. Pick a low-stakes moment (Nikki suggests the day after Thanksgiving).
2. Know the three core legal documents: will/estate plan, power of attorney, and medical advance directive.
3. Add a Digital Legacy Advance Directive — designate someone to manage your digital accounts and assets.
4. Take inventory of your digital life: phone passcodes, social media accounts, recurring subscriptions, online financial accounts, and stored photos.
5. Build a caregiving team — no single person should carry the full load. Identify who handles what before it becomes urgent.
6. Visit finalplaybook.com to start building your own end-of-life plan.

Connect with Niki

https://official.endevo.life

https://www.youtube.com/@DigitalLegacyPodcast

https://www.endevo.life/

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/

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/

What do you get when you mix startup experience, mother-of-a-newborn energy, and a deeply broken system for working parents?

You get Recess.

Amy Kiska is the co-founder and CEO of Recess, a platform parents are calling “the Booking.com of kids’ activities.” In this episode, she joins Ashley to talk about building a tech company while parenting a newborn, the invisible mental load of managing care coverage, and the bold decision to solve a problem most people don't recognize until they’re drowning in it.

Amy shares what it took to launch Recess, including fundraising 10 days postpartum, and how she’s designing a business that helps families and providers thrive.

This conversation covers:

• The truth about camp registration (and why it feels like the Hunger Games)
• How Recess supports both parents and activity providers
• The underestimated power of mom-founders
• Building a company without pretending you’re doing it alone
• And why some of the best ideas are born in the bath 🛁

Connect with Amy:

Website: hello-recess.com

Social media @hellorecess on Instagram and TikTok

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/

What if fertility and reproductive health were treated like skincare or mental health, something we talked about before it became a crisis?

In this episode of AND/BOTH, Ashley sits down with Sam Diamond, co‑founder of Bird & Be, to talk about building a clinically‑backed fertility company in the middle of a global pandemic, and why proactive, inclusive fertility care matters more than ever.

Sam shares the deeply personal experiences that shaped Bird & Be’s mission, including miscarriage, fertility treatment, and the gaps she saw in education, access, and support for both women and men. Together, Ashley and Sam explore why fertility conversations are still too reactive, how male fertility remains stigmatized, and what it looks like to build a company rooted in science, ethics, and care.

They also talk about:

• Launching a startup during COVID — and why at‑home testing was harder than expected
• Why male fertility must be part of every fertility conversation
• The shift from “cute” branding to clarity as Bird & Be entered retail
• What it took to land Bird & Be in Ulta — and why placement mattered
• How early education and testing can shorten or even prevent long fertility journeys
• Why women are not “small men” — and how research still fails women’s bodies
• Blending motherhood and entrepreneurship without pretending it’s balanced

This is a conversation about health, agency, science, and building systems that actually support people, not just sell to them.

Connect with Sam:

Bird&Be site: https://birdandbe.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/

This week on AND/BOTH, I’m joined by Nomiki Petrolla, founder of Theanna and a mother of four who is reshaping what early-stage entrepreneurship can look like for women in tech.

Nomiki has spent 15 years in the tech world, sitting beside founders, engineers, and venture-backed teams, often as the only woman in the room. That experience eventually led her to build Theanna: a platform designed to support women tech founders from idea to launch.

In this episode, we talk about:

• Why women are turning to entrepreneurship not out of ambition alone, but out of a desire for agency
• The realities of building a startup with four young kids
• How AI is completely changing what’s possible for early-stage founders
• Why venture capital isn’t the only — or even the most aligned — path for most entrepreneurs
• The difference between building your first business for money and your later ones for meaning
• How motherhood sharpens clarity, decision-making, and boundaries
• What Nomiki is noticing about the next wave of women building tech
• Sustainable entrepreneurship vs. the unicorn mythology we’ve all absorbed

It’s a conversation about choosing your own path, understanding your season, and building something that fits your actual life, not a version of life you’re supposed to pretend you have.

Connect with Nomiki:

Instagram, TikTok, LinkedIn: @nomikipetrolla

Theanna: @theannaio

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/

In this solo episode, I’m taking a moment to pause, look back on Season 9, and share what’s coming as we head into a new year and our tenth season of the AND/BOTH podcast.

This season brought so many meaningful conversations on the mental load, the realities of modern motherhood, how we build community, what comfort and safety look like in hard seasons, and the ways we try (and often fail) to carry less than we’re used to. We also continued our roundtable series, with thoughtful, deeply resonant conversations about grief and holiday burnout that so many of you reached out about.

I talk through:

• The themes that kept surfacing across episodes
• What these conversations revealed about burnout, expectations, and the pace we’re all trying to keep
• The “colander list” moment with my friend Meg and why it hit me squarely in the chest
• What it’s been like to grow a tech company, run a podcast, and raise four kids during a very full season
• Why we’re taking a short break before Season 10
• What you can expect when we return in the new year

And I share an invitation: if you’ve listened to the show and haven’t yet heard your version of motherhood reflected, I would love to bring more voices and stories into the mix. You can submit a guest interest form at andbothpodcast.com.

We’ll be back in January with Season 10—rested, reset, and ready for the next chapter.

Wishing you a holiday season with at least one hot coffee, a moment of actual rest, and something small that fills your cup.

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/