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/