Last episode I got raw about uncertainty && not having it figured out. This one is the follow-up… because once you admit you've been standing still, the next question is: what does moving actually require? && the honest answer is sometimes it requires doing the shit you don't want to do, whether it feels aligned or not.

TOPICS WE EXPLORE

• Why "does this feel aligned?" can become a very sophisticated excuse
• The difference between discomfort as a message && discomfort as an invitation
• Why discomfort isn't the same as wrong
• Does your behavior match what you say you want?
• The hard && fast rule that keeps our family sane
• Feeling fully alive requires willingly experiencing shit that doesn't feel good
• Love && grief. Ambition && disappointment. Business && selling. You don't get one without the other.
• What I think this next season is actually going to require of me

THE POINT

Somewhere along the way we started treating discomfort as evidence that something is wrong… it isn't. The version of you that goes all in is still in there, and now it's time to resurrect her.

MENTIONED IN THIS EPISODE

• Episode 206: Shamelessly Not Having It Figured Out
• MIXTAPE waitlist (opens September 21st)
• 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

I didn't know what I was gonna say when I hit record, truthfully… I'm in a funky season. I'm newly 39, && I'm noticing something I didn't expect: the more I know, the less certain I become. This episode is me processing that out loud.

We're talking about the certainty epidemic, why we buy it, what it's costing us, && what I actually think it means to be a 39-year-old woman who is ambitious as hell && has absolutely no idea what comes next. This one is unpolished, unscripted && exactly what it needs to be.

TOPICS WE EXPLORE

• What the data actually says about stress at 39 && why it felt like a permission slip
• The hidden load epidemic && why millennial women are the most burned out demographic
• Admitting out loud that I sometimes want a life where I don't have to work
• Why certainty is profitable && what that means for who you're buying from
• Homeschooling, travel, business models && the things I've changed my mind on
• All in or all out: my unpopular belief about half-measures in business
• What I actually want back: unbearable belief that success is inevitable

THE POINT

Maybe the wisdom isn't in finally having all the answers. Maybe it's becoming a hell of a lot less threatened by the fact that you don't. && maybe the unbearable belief that success is inevitable is the only thing that ever actually mattered.

MENTIONED IN THIS EPISODE

• Wealth Walks (WLTH Walks, Denver)
• MIXTAPE waitlist
• 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

It's my birthday week, I'm turning 39, && I'm coming in with a raw one. This is a full behind-the-scenes Ash Unplugged episode, which means personal updates, business updates, && the thing I've been sitting with lately that I had to say out loud: it's kind of chic to know where you suck.

We're talking about the gaps that actually cost us, why self-awareness is the highest-leverage business skill most people aren't using, && a list of things I genuinely believe are underrated right now. Plus: what's been hard this summer, what's coming with MIXTAPE, && why I'm coming back to social media for a few weeks.

TOPICS WE EXPLORE

• Turning 39 && what this season of life actually feels like
• What's been hard this summer
• MIXTAPE opens September 21st && what's inside it
• Coming back to social media for the first time since April
• Why "fake it till you make it" isn't the whole story
• Self-witnessing over perfectionism && what that looks like with a client
• Self-awareness as the highest-leverage business skill you're not talking about

THE POINT

People don't plateau because of their weaknesses, they plateau because they pretend not to have any. Knowing where you suck is not a liability… It's the most honest && efficient thing you can do for your business && your life.

MENTIONED IN THIS EPISODE

• MIXTAPE waitlist (opens September 21st)
• ashmcdonaldmentoring.com (new website && rebrand)
• 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

I've talked a lot about burnout, but so has everyone else in this space. I'm starting to think we've been diagnosing the wrong thing, because the women I work with aren't always JUST exhausted. They have capacity, however they seem to be lacking the desire they once had. They're functioning, often even performing well, but they feel flat… uninspired && disconnected from the drive that used to make them insatiable.

That's not simply burnout, that's disconnection. In this episode I'm breaking down the difference, why it matters, && what I've been doing to actually reclaim the aliveness I thought I'd lost.

TOPICS WE EXPLORE

• Why burnout && disconnection are not the same thing
• The difference between anxious-overwhelm && depressive-flat
• Why resting your way through disconnection makes it worse
• Curiosity as a North Star instead of certainty
• How to find aliveness in micro moments
• The body-brain connection && why transition routines aren't optional
• Why I stopped trying to minimize my ambition && what changed
• Language as identity: "I'm overwhelmed" vs "I'm feeling overwhelmed"
• What reconnection actually looks like in practice

THE POINT

You can recover from burnout && still feel completely, utterly disconnected from your life. If resting isn't working, maybe what you need is to reconnect.

MENTIONED IN THIS EPISODE

• MIXTAPE waitlist (opens September 21st)
• 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 watched a business they built go from printing money to something they barely recognize, and had to figure out who they are on the other side of that. My guest, Megan Yelaney, built her coaching business to insane heights during the golden era of 2018 to 2022, five-x-ed her income, lost her father-in-law && then her dad within fifteen months of each other, had a miscarriage, got pregnant, had twin boys, && came back to a business that just wasn't working anymore. She's one of the most honest people I've had in my corner, and she brought every bit of that honesty here.

TOPICS WE EXPLORE

• The golden era of online coaching && what happened when it ended
• Watching your income decline && pretending everything is fine
• The imposter spiral when your numbers don't match your reputation
• Coming back postpartum to a business that tanked
• What she had to let die to rebuild with integrity
• Comparison, viral moments, && the benchmarks that rob you of joy
• Why unsexily consistent is the only thing that actually works
• Building back to 100K months in under 30 hours a week

THE POINT

The grief of a declining business isn't just about money, it's about watching an identity you built your whole entrepreneurial-life around stop fitting. The only way out is to stop comparing yourself to a version of you that was built on circumstances you can't recreate, && start building something that actually belongs to you now.

ABOUT MEGAN

Megan Yelaney is a business coach && strategist who helps online coaches && service providers find and message their distinctive edge, the specific combination of story, process, && approach that makes them unmistakably them. She's based in Babylon, New York, is a theater girly, && is mom to two-and-a-half-year-old twin boys. After a complete rebuild in 2024, she had an almost $200K cash quarter && she is just getting started.

Find her on Instagram @meganyelaney && on her podcast Business Not as Usual.

MENTIONED IN THIS EPISODE

• Business Not as Usual (Megan’s podcast)
• Ash on Business Not as UsualWith Megan
• 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 bringing their raw, vulnerable stories to the mic. I hope you see yourself somewhere in these stories.

…

This episode is for the woman who fought hard to build something she loved, then had a baby && came back to her desk crying because she hated all of it. My guest, Sophia Rose, is a marketing coach, strategist, and IVF mom based in London. She had a business she was deeply proud of, a husband who showed up, and a clear picture of the kind of mom she wanted to be. None of that prepared her for sitting at her to-do list a few months postpartum && feeling like she was wearing someone else's shirt. She brought all of that here, one year out, still in it, && more honest than most people ever let themselves be.

TOPICS WE EXPLORE

• The identity crisis nobody warned her about (even though her friend tried)
• Coming back to a business she'd built from the ground up && feeling nothing
• The fog of postpartum grief
• Saying goodbye to breastfeeding without knowing it was the last time
• The duality of motherhood: joy && grief in the same breath
• How navigating loss reshapes your tolerance for things that don't matter
• The superpowers that come on the other side of falling apart
• What she wants women to know before they have their first baby

THE POINT

You don't graduate from the grief of motherhood. You just get better at walking through the doors it keeps opening. && if you can stop fighting it, it will change you in the best possible way.

ABOUT SOPHIA

Sophia Rose is a marketing coach, strategist, host of Marketing Unfiltered, and co-host of Relatable with the Roses alongside her husband Bradley, a Peloton cycling instructor. She helps business owners cut through the noise and market in a way that actually works, and she does it from London with her IVF son Grayson.

Find her podcast Marketing Unfiltered && Relatable with the Roses.

MENTIONED IN THIS EPISODE

• Marketing Unfiltered (Sophia's marketing podcast)
• Relatable with the Roses (Sophia's podcast with husband Bradley Rose)
• Ash on Marketing Unfiltered - Breaking the Cycle of High-Functioning Burnout
• 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 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.

---

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