Welcome to the Grief Series, a collection of conversations about the grief woven throughout our lives with some extraordinary women bringing their raw, vulnerable stories to the mic. I hope you see yourself somewhere in these stories.

…

This episode is for anyone who has ever had to keep showing up while watching someone they love disappear. My guest, Cait Howard, has experienced profound loss while building a business, raising three little girls, and navigating the many roles life has asked of her. Somehow, through all of it, she has kept moving forward. She brought so much honesty, wisdom, and heart to this conversation, and I think it’s one you’ll carry with you long after it ends.

TOPICS WE EXPLORE

• Losing two parents in a short period of time
• Being a new mom && a caregiver at the same time
• The guilt of being pulled in every direction at once
• How subconscious work changed the way she moved through her mom's illness
• Big G grief && little G grief
• How she protects herself through the grief
• Navigating a business partnership with your husband through loss
• What she wishes someone had told her

THE POINT

Grief doesn't have an endpoint. It has seasons && the only way through it is to let it be your own.

ABOUT CAIT

Cait Howard is the founder of Amplify Boutique, a podcast launch and management agency, and co-host of the Podcasting Moms Conference. She helps women get their voices && messages into the world through podcasting… she does it from just outside Nashville with her husband && their three little girls.

Find her on Instagram @heycaithoward and at amplifyboutique.com.

MENTIONED IN THIS EPISODE

• Amplify Boutique (Cait's podcast agency)
• Shamelessly Ambitious Soundcheck (free curated episode playlists)
• Work with Ash

Are you loving it? Send Ash a text!

MORE ABOUT ASH

I'm Ash McDonald — the Entrepreneur's Therapist. Trained therapist, seasoned entrepreneur, mom of 3, && the person you call when your business coach doesn't get your brain && your therapist doesn't get your business.

I built the thing I couldn't find anywhere else: whole-picture support that holds your strategy && your humanity in the same conversation at the same time.

LINKS:

• Work with me 1:1 → Deep Cuts
• Fast-track your results → The Green Room
• Solve one thing right now → Studio Sessions
• Burnout-proof your life && business → Mixtape
• Get your free podcast playlists → The Soundcheck
• Weekly emails that tell you what your business coach won't && your therapist can't → Subscribe to The Beat
• Website: ashmcdonaldmentoring.com

Welcome to the Grief Series, a collection of conversations about the grief woven throughout our lives with some extraordinary women && men bringing their raw, vulnerable stories to the mic. I hope you see yourself somewhere in these stories.

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This is episode 200 and I knew I had to make it count. I brought on my favorite person in the world, my husband Jake, for the most honest conversation we've ever had on record. We went into his grief around identity and purpose when I was the breadwinner, the resentment he carried for years, what it actually costs to be the supportive one, && what had to die in both of us for our marriage to become what it is today. This one is for every ambitious woman who has ever wondered what her partner is really carrying && every man who has never had the language to say it out loud.

TOPICS WE EXPLORE

• Jake's identity crisis when I became the primary breadwinner
• The grief of losing your sense of purpose and provider identity
• Resentment he buried for years and what it actually looked like
• How my ambition triggered his comparison and jealousy
• What I had to stop doing for him to step into who he wanted to be
• Why slowing down in my business saved our marriage
• The hyper-independence that was costing me the partnership I wanted
• What Jake sees when nobody's watching
• What ambitious women get wrong about their husbands

THE POINT

Sometimes the grief inside a marriage is a man who doesn't know how to say he feels purposeless. Sometimes it's a woman who's so busy holding everything that she never leaves room to be held. Both of those things can be true at the same time && both of them can change.

ABOUT JAKE

Jake is my husband, my best friend, my baby daddy, && the person who knows me better than anyone in the world. He showed up to this conversation with zero prep && more honesty than most people manage in a lifetime of therapy. We've been together 16 years, married for 12, raised three kids, traveled the world full time, filed for bankruptcy, rebuilt, && somehow ended up in the best season of our marriage yet.

MENTIONED IN THIS EPISODE

• Jake's week-long mental health onsite in Tennessee
• Work with Ash

Are you loving it? Send Ash a text!

MORE ABOUT ASH

I'm Ash McDonald — the Entrepreneur's Therapist. Trained therapist, seasoned entrepreneur, mom of 3, && the person you call when your business coach doesn't get your brain && your therapist doesn't get your business.

I built the thing I couldn't find anywhere else: whole-picture support that holds your strategy && your humanity in the same conversation at the same time.

LINKS:

• Work with me 1:1 → Deep Cuts
• Fast-track your results → The Green Room
• Solve one thing right now → Studio Sessions
• Burnout-proof your life && business → Mixtape
• Get your free podcast playlists → The Soundcheck
• Weekly emails that tell you what your business coach won't && your therapist can't → Subscribe to The Beat
• Website: ashmcdonaldmentoring.com

If you've been white-knuckling your way through a season and calling it productivity, this one is going to hit. Sometimes grief isn't about loss… sometimes it's about the story you've been telling yourself so many times it started to feel like fact.

A few weeks into summer, I caught my own brain running a narrative I didn't even realize had taken over. I was ending every day feeling like everything was too much and the issue wasn’t my schedule but instead the stories I was telling myself. In this episode I'm sharing exactly what I shifted and how to do it yourself.

TOPICS WE EXPLORE

• The mental load that doesn't show up on a calendar
• How I caught myself in a spiral I didn't even know I was in
• What my inner voice has been dictating in my life
• Why your structures and systems can be working and you can still feel like you're drowning
• The story your brain tells before you even open your eyes
• How to get back in the driver's seat when your mindset has taken over
• Why this is a practice && not a one-time fix

THE POINT

You have the life you're willing to put up with. The circumstances don't have to change, but the story does.

MENTIONED IN THIS EPISODE

• Ash's new website and brand relaunch
• Work with Ash (Studio Session, Deep Cuts, The Green Room, MIXTAPE waitlist)

Are you loving it? Send Ash a text!

MORE ABOUT ASH

I'm Ash McDonald — the Entrepreneur's Therapist. Trained therapist, seasoned entrepreneur, mom of 3, && the person you call when your business coach doesn't get your brain && your therapist doesn't get your business.

I built the thing I couldn't find anywhere else: whole-picture support that holds your strategy && your humanity in the same conversation at the same time.

LINKS:

• Work with me 1:1 → Deep Cuts
• Fast-track your results → The Green Room
• Solve one thing right now → Studio Sessions
• Burnout-proof your life && business → Mixtape
• Get your free podcast playlists → The Soundcheck
• Weekly emails that tell you what your business coach won't && your therapist can't → Subscribe to The Beat
• Website: ashmcdonaldmentoring.com

Welcome to the Grief Series, a collection of conversations about the grief woven throughout our lives with some extraordinary women bringing their raw, vulnerable stories to the mic. I hope you see yourself somewhere in these stories.

…

This episode is for anyone who has ever looked around and realized the people who were supposed to show up simply haven't. My guest, Emily Merrell, is a connector by nature, the founder of Second Degree Society, a business coach, and a two-time boy mom based in Denver, Colorado. She brought her whole, unfiltered heart to this conversation, and we both cried. We go deep into the grief of friendships that fall apart without explanation, the grandparent village that never materialized, and what it actually costs to need your mom and find that who she is now can't meet you there.

TOPICS WE EXPLORE

• When your friends don't show up for your business
• The slow fade of a deep friendship and the loop that never closes
• Being ghosted by people who you thought were your friends
• How ambition triggers the people closest to you
• The grandparent grief nobody talks about
• Asking for help once and being let down
• Grieving your mom while she's still alive
• Building a village when the one you expected never arrived

THE POINT

Sometimes the hardest grief isn't the loss of someone. It's the slow realization that the village you were counting on was never coming, and you have to build it yourself.

ABOUT EMILY

Emily Merrell is the founder of Second Degree Society, a networking community that takes the awkward out of connection by handpicking who you meet. She's also a business coach passionate about helping people grow, scale, and open the right doors. She's based in Denver, Colorado, and is a two-time boy mom who turns human connection into both a superpower and a business.

Find her on Instagram @emilyamerrell and at seconddegreesociety.com.

MENTIONED IN THIS EPISODE

• Second Degree Society
• Let Them by Mel Robbins
• Work with Ash

Are you loving it? Send Ash a text!

MORE ABOUT ASH

I'm Ash McDonald — the Entrepreneur's Therapist. Trained therapist, seasoned entrepreneur, mom of 3, && the person you call when your business coach doesn't get your brain && your therapist doesn't get your business.

I built the thing I couldn't find anywhere else: whole-picture support that holds your strategy && your humanity in the same conversation at the same time.

LINKS:

• Work with me 1:1 → Deep Cuts
• Fast-track your results → The Green Room
• Solve one thing right now → Studio Sessions
• Burnout-proof your life && business → Mixtape
• Get your free podcast playlists → The Soundcheck
• Weekly emails that tell you what your business coach won't && your therapist can't → Subscribe to The Beat
• Website: ashmcdonaldmentoring.com

Welcome to the Grief Series, a collection of conversations about the grief woven throughout our lives with some extraordinary women bringing their raw, vulnerable stories to the mic. I hope you see yourself somewhere in these stories.

…

This episode is for anyone who has ever walked away from something they built, a career, a marriage, an identity, and wondered what the hell comes next. My guest, Delia Monk, has done it more than once. She came to this conversation with the full story: leaving journalism, building a six-figure copywriting business she eventually had to grieve, navigating divorce as a single mom, and making one of the scariest leaps of her professional life.

TOPICS WE EXPLORE

• Leaving the career you built your identity around
• When AI devalues your trade overnight
• The $12,000 rebrand that didn't save it
• Fear laced with excitement vs. fear laced with scarcity
• Cutting the rope and going all in
• Grieving the life you thought you'd have after divorce
• Giving up half your child's childhood
• The scrappy list: 100 ways to make money
• What opens up when you finally let go

THE POINT

Grief is the price of going all in. You can't grieve what you didn't love, and you can't become who you're meant to be without leaving someone behind.

ABOUT DELIA

Delia Monk helps people who are ready for their next chapter figure out what that actually looks like and how to talk about it. After years working in messaging and copywriting, she pivoted into transition and pivot coaching, helping women who feel unfulfilled or called toward something new discover what comes next and position it with clarity. She's British, based in Barcelona, and entirely worth finding.

Find her on Instagram @delia.monk and at deliamonk.com.

MENTIONED IN THIS EPISODE

• deliamonk.com
• The Mixermind (networking community mentioned by Ash)
• Work with Ash

Are you loving it? Send Ash a text!

MORE ABOUT ASH

I'm Ash McDonald — the Entrepreneur's Therapist. Trained therapist, seasoned entrepreneur, mom of 3, && the person you call when your business coach doesn't get your brain && your therapist doesn't get your business.

I built the thing I couldn't find anywhere else: whole-picture support that holds your strategy && your humanity in the same conversation at the same time.

LINKS:

• Work with me 1:1 → Deep Cuts
• Fast-track your results → The Green Room
• Solve one thing right now → Studio Sessions
• Burnout-proof your life && business → Mixtape
• Get your free podcast playlists → The Soundcheck
• Weekly emails that tell you what your business coach won't && your therapist can't → Subscribe to The Beat
• Website: ashmcdonaldmentoring.com

Welcome to the Grief Series, a collection of conversations about the grief woven throughout our lives with some extraordinary women bringing their raw, vulnerable stories to the mic. I hope you see yourself somewhere in these stories.

…

This episode is for anyone carrying grief that doesn't have an obvious name. My guest, Chrissy Powers, is a therapist, ketamine-assisted psychotherapy practitioner, and someone who has personally held space for me in some of my own deepest healing work. We talk about the grief that lives inside a marriage you're still in, the mourning of watching your children grow up, the loss that comes with deconstructing your religious upbringing, and what it actually takes to feel your way through grief instead of solving your way around it.

TOPICS WE EXPLORE

• Complicated grief vs. the grief we're taught is acceptable
• Grieving inside a marriage you haven't left
• Watching a partner struggle and the ultimatum that protects your family
• The invisible loss of your children growing up
• Outgrowing a partner who isn't on the same healing path
• Raising emotionally literate sons in a culture that discourages it
• Deconstructing religious upbringing and what it costs
• Finding a guide, trusting your body, and reclaiming intuition

THE POINT

Grief isn't reserved for death. It lives inside the marriages we stay in, the children we watch grow, and the beliefs we outgrow, and the only way through any of it is to feel it instead of fix it.

ABOUT CHRISSY

Chrissy Powers is a licensed therapist and the founder of Paradigm Wellness Collective, a group practice in Southern California. She's trained in psychedelic somatic therapy and ketamine-assisted psychotherapy, and has spent over 16 years in practice helping people heal through embodiment, vulnerability, and deep inner work. Her book, Woman Embodied: The Practice of Coming Home to Yourself, releases October 27th.

Find her on Instagram @chrissyjpowers and at chrissypowers.com or email her @ chrissypowersmft@gmail.com.

MENTIONED IN THIS EPISODE

• Paradigm Wellness Collective
• paradigmwellnesscollective.com (find a practitioner)
• Woman Embodied: The Practice of Coming Home to Yourself (Chrissy's book, out October 27th)
• Work with Ash

Are you loving it? Send Ash a text!

MORE ABOUT ASH

I'm Ash McDonald — the Entrepreneur's Therapist. Trained therapist, seasoned entrepreneur, mom of 3, && the person you call when your business coach doesn't get your brain && your therapist doesn't get your business.

I built the thing I couldn't find anywhere else: whole-picture support that holds your strategy && your humanity in the same conversation at the same time.

LINKS:

• Work with me 1:1 → Deep Cuts
• Fast-track your results → The Green Room
• Solve one thing right now → Studio Sessions
• Burnout-proof your life && business → Mixtape
• Get your free podcast playlists → The Soundcheck
• Weekly emails that tell you what your business coach won't && your therapist can't → Subscribe to The Beat
• Website: ashmcdonaldmentoring.com

Welcome to the Grief series - a collection of conversations about the grief woven throughout our lives with some extraordinary women bringing their raw, vulnerable stories to the mic. I hope you see yourself somewhere in these stories.

…

This specific episode is for the women in their 30s, 40s, 50s, and beyond who are entering a new season, physically, emotionally, and mentally. My guest, Bryn Daylor, brought her whole heart to this conversation and bared it all from her grief around physical changes, ambition shifts, and comparison as we age.

TOPICS WE EXPLORE:

• The identity shift underneath every physical change
• Grieving the attention you used to get
• Aesthetic procedures, the pressure, the fear, and the nuance
• Losing reckless abandon
• Building ambition from belief instead of survival
• Starting a family later and doing the math on time
• How comparison kills your output
• What shamelessly ambitious looks like when you stop performing

THE POINT:

Aging is the grief that lives in the gap between who you were and who you're becoming, and the only way through it is to name it.

ABOUT BRYN:

Bryn Daylor helps women unmask themselves through creative expression so they can have the life and love they really want. She works with women to strip back layers of conditioning so that when they go to share themselves, whether through storytelling, writing a book, or putting a creative project into the world, they are doing it from the core of who they actually are. Find her on Instagram @bryndaylor and on her podcast, Seen.

MENTIONED IN THIS EPISODE:

• Bryn's podcast: Seen
• Vanquish Vitiligo (product for vitiligo coverage)
• Work with Ash

Are you loving it? Send Ash a text!

MORE ABOUT ASH

I'm Ash McDonald — the Entrepreneur's Therapist. Trained therapist, seasoned entrepreneur, mom of 3, && the person you call when your business coach doesn't get your brain && your therapist doesn't get your business.

I built the thing I couldn't find anywhere else: whole-picture support that holds your strategy && your humanity in the same conversation at the same time.

LINKS:

• Work with me 1:1 → Deep Cuts
• Fast-track your results → The Green Room
• Solve one thing right now → Studio Sessions
• Burnout-proof your life && business → Mixtape
• Get your free podcast playlists → The Soundcheck
• Weekly emails that tell you what your business coach won't && your therapist can't → Subscribe to The Beat
• Website: ashmcdonaldmentoring.com

Welcome to Ash Unplugged, the behind-the-scenes monthly episode where nothing is off the table and the real shit gets said.

In this episode we’ll explore the full rebrand reveal, the complete list of things I hate right now, the red flags me and my husband built together, and how I’m actually running our summer successfully.

TOPICS WE EXPLORE:

• The rebrand
• Everything I hate right now
• My red flags and what l’m doing about them
• How I’m structuring my summer to be present, but still successful in my business
• The guest series coming up.

THE POINT:

The things that make me successful are not just the pretty ones… it’s the walks at 6:30am, the plan that never waits until morning, the self-coaching loop I often use on myself, and the willingness to say exactly what I think, including the things I hate.

MENTIONED:

• Rebrand team: Catie Cupples (copywriter), Christina at Gem Creative (designer), Katie at 26 & Then Some (naming strategist), Dallas (VIP strategy session)
• Work with me

Are you loving it? Send Ash a text!

MORE ABOUT ASH

I'm Ash McDonald — the Entrepreneur's Therapist. Trained therapist, seasoned entrepreneur, mom of 3, && the person you call when your business coach doesn't get your brain && your therapist doesn't get your business.

I built the thing I couldn't find anywhere else: whole-picture support that holds your strategy && your humanity in the same conversation at the same time.

LINKS:

• Work with me 1:1 → Deep Cuts
• Fast-track your results → The Green Room
• Solve one thing right now → Studio Sessions
• Burnout-proof your life && business → Mixtape
• Get your free podcast playlists → The Soundcheck
• Weekly emails that tell you what your business coach won't && your therapist can't → Subscribe to The Beat
• Website: ashmcdonaldmentoring.com