AND/BOTH Podcast - Real Conversations, Shared Experiences, and the Community You've Been Missing

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

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/

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
What thanatology is and why the "digital" specialization matters more than ever
Nikki's personal caregiving journey: losing both parents young and what that shaped in her
The "panini generation" why today's sandwich generation feels more squeezed than ever
Why most caregivers wait until crisis to plan and the real cost of that delay
The project management approach to end-of-life planning: de-emotionalizing the process so families can actually do it
How to build a caregiving community instead of letting one person absorb everything
The "silver wave" of late-life divorce and what it means for adult children
Digital legacy: what happens to your phone, social media, subscriptions, and photos after you're gone
Grief bots, digital avatars, and QR codes on headstones the emerging world of digital memorialization
Why you need a Digital Legacy Advance Directive alongside your will and medical POA
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
Have 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 Niki
https://official.endevo.life
https://www.youtube.com/@DigitalLegacyPodcast
https://www.endevo.life/
https://final-playbook.passion.io

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 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: [email protected]

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/