the deep dig

the deep DIG with Catrina Mitchum

Ever wonder what happens when someone who’s spent decades perfecting the academic voice has to unlearn the whole thing? This week I’m digging in with Catrina Mitchum: learning experience designer, recovering academic, self-described new experience junkie, and (yes, really) winner of a fourth-grade readathon trophy for reading more books than anyone else in New Jersey.

We cover a lot of ground, from what learning experience design actually IS, to why AI can’t build your course for you, to Catrina’s LinkedIn strategy of seeking out people who swear in their headlines. (I love her.)

from the classroom to her own business

Catrina started teaching in person in 2008 and was fully online by 2010. Her community college had no instructional designers, so she became her own, diving deep into online course design, accessibility, and the Quality Matters rubric. Her dissertation looked at why online writing students leave.

Then COVID hit. She stepped into an interim director role when the people above her didn’t know what to do, burned out, and had an MS relapse she didn’t even recognize as one. The final straw? A new policy requiring her supervisor to write a yearly memo just to keep her on, despite multi-year contracts.

So she bought a course to pivot out of academia. It was garbage. And she thought, I can fix that. By October 2022, she had a website, a domain, and her first clients.

so what IS learning experience design?

It’s where instructional design meets user experience design, because traditional instructional design doesn’t always center the learner. Catrina builds the scaffolding so people from ALL kinds of backgrounds and learning histories can succeed, which, as she points out, overlaps a lot with good accessibility practice.

why AI can’t replace the humans (but can still be useful)

Catrina reviewed 15 course platforms on YouTube, and the ones with AI course generators? Her word: garbage. Surface-level, buzzword-mimicking, no real learning pathway. A great course starts with understanding what the learner actually wants and needs, and even subject matter experts often can’t articulate that. AI doesn’t ask the right questions to dig it out.

But she does use Claude, with strict rules: it can only use her own words, drawn from two years of transcripts, newsletters, and blog posts. Think less content generator, more souped-up search. Her parenting analogy is the best part: Claude is a two-year-old. Clear boundaries work. (Occasionally it acts like a three-year-old, and she reminds it of the rules.)

finding her voice again

Catrina was once accused of plagiarism in AP English for a speech that was just too good, and spent years believing she wasn’t a writer. Leaving academia meant unlearning the voice she’d spent decades honing. She found her way back to clear and direct through voice notes and a LinkedIn course from a friend who cusses like it’s her job. Her newsletter? Cut the Crap. Her offers, CourseMaker, Course Partner, and Course Designer, all came from her clients’ words, not Claude’s.

the book she refuses to call a memoir

She calls it an angry anthem. It’s about internalized ableism and what happens when you push through things you shouldn’t, including exercises that have now landed her at an orthopedic surgeon.

find Catrina

On LinkedIn, YouTube, and Threads, or just Google “Catrina Mitchum” (with a C) and you’ll get 13 pages of her and nothing else. Her kids confirmed it via the Google Nest.

https://www.cmlearningdesign.com

https://www.threads.com/@cmlearningdesign

https://www.linkedin.com/in/catrina-mitchum-learning-design

https://youtube.com/@coursecreatorplaybook

Bridget welcomes Kevin Chung, the person she credits with inspiring her to start the Deep Dig Podcast in the first place. Kevin helps creatives — currently focusing on authors — stand out by taking action on the projects they've been putting off, drawing on his background in marketing and his own long, winding creative journey.

The conversation covers:

Just start — Kevin's signature energy is one of calm, non-attachment to outcomes. He's helped Bridget (and many others) give themselves permission to begin before everything is perfect, to experiment freely, and to treat the creative process itself as the point — not just the result.

Working with authors — after years of trying to serve all creatives broadly, Kevin narrowed his focus to authors and the Substack ecosystem. The lesson: when you try to talk to everyone, you talk to no one. Niching down made it possible to actually speak the language of the people he wants to help.

Building community over broadcasting — Kevin makes the case that your superpower when you're small is the ability to connect one-on-one. Email lists are non-negotiable (he shares a vivid story of a Threads creator who was suddenly banned and could only reach his audience because he had email), and showing up in community — commenting, engaging, being present — is what actually builds an audience over time.

Asking for help — both Kevin and Bridget reflect on how hard it is to ask for support even when you know you need it. Kevin did a rejection challenge hosted by mutual friend Becky Mullenkamp, and found that when you ask people directly and authentically, the yeses far outnumber the nos.

Moving to Costa Rica — after the 2024 election, Kevin and his wife decided to make a long-held dream real. They made the decision over a Valentine's Day dinner in February and moved on June 1st. The move involved going from self-described maximalists to letting go of almost everything — Goodwill runs, Facebook Marketplace, eBay, and simply handing things to whoever showed up to buy something else. A gallery-wall arch they'd found in a dumpster and accidentally turned into a watercolor painting ended up being one of the most meaningful things to part with.

Writing the memoir — Kevin is writing a memoir about the move and what it took to make it happen, originally as a Substack series that grew into something with a real through-line: anyone has the ability to transform their life, you just have to be willing to take the steps. He writes in 90-minute blocks twice a week, in a writing group, and lets himself follow the inspiration rather than forcing a rigid process.

Creative process — the conversation opens up into a wider discussion of how writers find their way in: fiction as a warm-up before harder writing, dancing before creating, dictating instead of typing, writing at 1AM because that's when you're awake. The throughline is the same one Kevin lives by — find what works for you, try it, adjust, keep going.

Find Kevin: standoutcreativebusiness.com | standoutcreativebusiness.substack.com

My guest for this episode of the dig deep PODCAST is Lauri Smith, a speaker, author, coach, and host of the Untamed Leader Podcast. She treats leadership as a sacred art that raises consciousness, guiding us home to our true selves. Lauri helps wild-hearted leaders and loving rebels transform the vibe in the room when they speak so they can ignite meaningful change.

Lauri helps coaches, healers, and entrepreneurs birth what they’re here to bring into the world through the spoken word — podcasts, red carpets, group programs, retreats. But before any of that, she was an executive assistant by day and an actor by night, wearing what she calls the “I’m Fine Face” through one world and channeling her whole self into the other. Until one acting teacher took off his glasses and told her to stop doing “whatever that is you’re doing in between scenes.”That moment cracked something open. And we spend this episode tracing where it led.

What we dig into

The box you can’t put back together. We talk about that Apple-unboxing feeling — once you’re out of the box, there’s no shoving yourself back in the same way. Lauri’s been out of hers since a college student told her, unprompted, that she coaches instead of professes. I’ve been out of mine since I found out, mid-audition, that a 5’4” dancer was never getting hired for a 5’10” soloist role no matter what I did.

Living your purpose vs. figuring it out.

Lauri’s line that stopped me: ”We are here to live out our purpose, not to figure it out.”* We talk about what happens when you wait for the fully-formed, logical explanation before you start — and who gives up entirely because they can’t articulate it perfectly first.

The Untamed Entrepreneur.

Lauri is wild on a stage, wild directing a play, wild in front of a room. Sit her down in front of a laptop to write website copy? Different story. We get into the gap between who she is everywhere else and who shows up when she’s building her business — and what it’s looked like to close it.

Sitting in the middle of the road.

One of my favorite images from this whole conversation: Lauri, picturing herself cross-legged in the street, old habits and hustle on one side, trust and intuition on the other, not fully able to get to the right side yet — and choosing to sit in the unresolved middle instead of scrambling back to what she knows doesn’t work.

Directing as coaching.

Lauri’s directing style — let people play, watch what happens, then shape it — is the same thing she does with clients. Holding the vision for who someone’s becoming until they can hold it themselves. This is also, not coincidentally, exactly what she did for me the first time I was on her podcast.**Who’s actually clapping.** We close on the standing-ovation problem — how easy it is to fixate on the one critic who didn’t get it, instead of following the people whose faces light up. Don’t pitch your new offer to your husband if he’s not your ideal client. Go toward the yeses.## A few lines worth sitting with- “We are both discovering and expressing our life purpose. All the time.”- “The world that’s looking for me can’t see me if I go back over there.”- “Sometimes we’re in the life-sized equivalent of that moment” — snotting all over yourself one minute, “it’s gonna be even better” the next.

What Lauri offers-

The Untamed Leader Collective— ongoing group coaching, ditching forced schedules for something that actually feels right-

Tune Your Talk — outside-director feedback on a talk you’re already giving (one client went from 4 sign-ups to 28 after this)-

Create Your Talk*— midwifing a brand-new talk into existence from scratch

Find Lauri

Sign up for her free offer:

Take the Speaker Alter Ego Quiz to reveal the mask that dims your one-in-eight-billion radiance — and step into speaking and leading from your untamed, soul-aligned voice.

sign up here

Website: voice-matters.com

Linkedin: linkedin.com/in/lauri-smith-voice-matters/

YouTube: youtube.com/channel/UCh91RFKkYB7WF83p4_DG9Ug

Instagram: instagram.com/voice_matters_llc/

ai disclosure: I used claude ai to summarize the show notes from the transcript. I used Canva to edit the podcast graphics.

My guest today is Jacki Hayes (she/her) is a systems strategist and project manager for website designers in the messy middle - overwhelmed by running the business and less time for focused creative work. She was also the host of the podcast Here’s What I Learned, which ran from March 2021 until April 2026.

This wide-ranging conversation about running a sustainable, spacious business — one that actually feels good to show up for, and using your strengths — and getting your systems set up so you can do your creative work.

Jackie shares how she helps clients move from frantic, reactive days to ones with real breathing room. A key insight: she asks clients about their favorite day rather than their ideal day — because “ideal” invites judgment and “shoulds,” while “favorite” grounds you in something real and achievable.

The conversation covers:

SOPs (Standard Operating Procedures) — what they are, why every business owner needs them even if you’re solo, and how the humble peanut butter sandwich is the perfect metaphor for why unclear instructions fail.

Time tracking — why brain-dumping everything you do for two weeks every quarter is one of the most eye-opening exercises you can do, and how it reveals where you’re spending energy that isn’t moving the needle.

Hiring smart — why a VA isn’t always the right first hire for service providers, and how bringing on an assistant in your actual craft (design, social media, etc.) can free up far more of your time.

Tools & systems — Jackie’s “tool agnostic” philosophy, why you should always try a tool for 90 days before buying the annual plan, and the hidden cost of switching tools.

Emergency SOPs — what happens to your business if you’re suddenly out for a week, a month, or permanently, and how to create a simple contingency document before you need one.

AI in your workflow — how Jackie uses Claude to turn Loom walkthroughs into drafted SOPs, and why using AI as an editor rather than a writer is often a far better use of your time.

Find Jackie:

WEBSITE: jackihayes.co

THREADS: @jackihayes_obm

EMAILS: jackihayes.co/subscribe

Listen to Bridget’s episodes on Jackie’s podcast, Here’s What I Learned (100+ episodes in the archive).

The Deep Dig Podcast

Episode: This one's got owning a knitting magazine, decorating cakes, and therapy in book form with my guest: Kate Gilbert

Kate Gilbert is a business coach, certified GHL expert, and the author of Social Media Group Therapy, a book for small business owners who know they need to post but just don't want to. She's been called a "hand-holder/butt-kicker" by her clients, which is honestly a pretty accurate description of her supportive but no BS style.

Kate’s road to coaching started back in 2008, when she founded and ran her own online knitting magazine for a decade — work that ended up changing how the whole industry paid designers. A decade later, after burnout, single motherhood, and a cancer diagnosis, she stepped away, took a university job, and then the pandemic happened. Suddenly everyone she knew needed help figuring out how to run a business online. She started taking calls. It became the best part of her week. Someone finally asked why she wasn’t charging for it, and — boom. Business.

We also get into:

being the person you needed — Kate coaches the way she wishes someone had coached her, back when she was running the magazine solo.

you can’t read the label from inside the jar — why even the people who give the best advice still need someone else in their corner.

dressing for yourself, not for a gaze — a black jumpsuit, a redrafted pattern, and a mini meditation on what your closet says about who you’ve been and who you’re becoming.

her book, Social Media Group Therapy — out now on Amazon, and it’s not another content calendar. It’s the anxiety, the comparison spiral, the avoidance — the actual emotional mess underneath “just show up online.” Includes her manifesto process, which she uses with every coaching client to find their real brand voice.

Kate’s reframe, and honestly the whole point of this episode: if you’re not showing up, you’re not protecting anyone. You’re just keeping the people who need you from knowing you exist.

find kate:

kategilbert.com

IG @kategil

Book: Social Media Group Therapy: From Anxiety to Action: a no-BS social media reset for real results on socials

pisode Summary

Bridget welcomes Brian Perry — authentic communication coach, singer-songwriter, and one of her favorite newsletter writers anywhere — for a conversation that goes deep fast and stays there. Brian describes himself as being in a reinvent stage, though he’s quick to note that reinvention has basically been his whole career.

The people Brian works with are grown-ups who’ve gotten very good at adulting — checking all the responsibility boxes, being a different person in every room they walk into — and who arrive at a point where they urgently need to finally write the book, give the talk, open the business, or have the big conversation. What they discover is that somewhere along the way, sounding like themselves has become the scariest thing they could do. Brian’s job is to help them find their way back.

The conversation covers:

Tuning the radio — Brian describes his coaching like dialing an old analog radio. You’re listening through the static, past all the stations that are clearly wrong, for the signal that’s unmistakably yours. The work happens in the space between the I don’t knows and the I absolutely knows.

The once-in-a-lifetime story — Brian’s central belief is that every person has a story only they can tell, and when they live it out loud, they lift everyone around them. He acknowledges this doesn’t land with everyone he says it to — partly because people genuinely believe they’re boring, and partly because uniqueness has been said so many times it’s lost its charge. But the reason it’s true hasn’t changed.

Pain as knowledge — Brian weaves together Epictetus (we’re not disturbed by things, but by the view we take of them) and a Jerry Seinfeld conversation with Trevor Noah about pain being knowledge rushing in to fill a gap. The stub-your-toe example: now you know there’s a table there. For Brian, this reframe changed everything — not just intellectually, but as a way of actually moving through uncertainty as a creative entrepreneur who has never once had a 9-to-5.

Bell’s Palsy and the return — Brian shares publicly for one of the first times that he had Bell’s Palsy — a virus that attacks the facial nerve and creates temporary paralysis on one side of the face — not once, but three times, switching sides. At a moment when he had just decided to get back up, start speaking again, start making music again, his voice changed in ways he couldn’t reverse. He pulled back. He got quiet. And then, during the pandemic, he found a songwriting community called Thinking Outside the Blocks (Allie Moss and Bess Rogers), which helped him fall in love with the music he could make now, and slowly, trust his voice again.

The Indigo Girls and not being done — watching Emily Salyers of the Indigo Girls announce that the voice she was known for was gone — and that they were going to find a way to keep going anyway — was the moment Brian looked at his guitar and decided he was done playing dead.

The Martian — the conversation lands on the scene where Matt Damon, stranded on Mars and out of options, wraps himself in a blanket and says: I’m not dying here. And then the montage begins. Brian’s point: in movies the hard part takes two and a half minutes. In life it takes two and a half years. But the moment of deciding you’re not done — that something else gets to show itself in the dark — that’s the pivot.

AI as a quickie — Brian offers what might be the most memorable AI analogy on this podcast so far. He’s a fan of sex. He’s not a fan of only quickies. AI is the quickie: useful, even great in the right context, but not a substitute for the messy, slow, vulnerable, collaborative, human process of actually figuring out what you have to say. When you let AI write for you, people aren’t responding to you — they’re responding to something that doesn’t know the text.

What Brian is building — YouTube and Substack, developed more intentionally going forward, focused on authentic voice, navigating uncertainty, and permission to just be making it up as you go.

Find Brian: yesbrianperry.com | on Instagram, on Substack, and on YouTube

References

The Indigo Girls

Stoicism

Epictetus

The Martian

The Deep Dig Podcast

Episode: The One Where Tracy Stanger Talks Doing Business Your Way

Guest: Tracy Stanger (she/her) Host: Bridget Baker (@bridgetbakerbranding) Find Tracy: Instagram @tracy.stanger | tracystanger.com

Episode Overview

Tracy Stanger — business coach, questioner, and future author — joins Bridget for a wide-ranging conversation about rejecting the "right way" to run a business, building your offers and marketing around your actual personality, and why the most radical business move might be simply doing things your way.

What We Cover

The Current Mood Tracy opens by admitting she's pissed off — and that anger is fuel. She's been deep-diving into off-grid living (voltage, amperage, food storage), questioning every system in business, religion, and government, and channeling all of it into her upcoming book, The Most You Business Book.

The Business Guru Cycle The conversation digs into a frustrating pattern: big-name coaches selling you "the secret to business" — then years later telling you everything they taught you is now dead, and selling you the new secret. Sound familiar? Bridget and Tracy compare it to fashion trends: everything cycles. Knowing that frees you from chasing it.

Personality Typologies as a Tool (Not a Box) Tracy uses frameworks like Gretchen Rubin's Four Tendencies, DISC, Clifton Strengths, and the Enneagram in her work — but not as rigid labels. She's a Questioner (Four Tendencies) and an Enneagram 1, and she's clear that these tools shift over time based on stress, life circumstances, and growth. The point is to use them to find your way, not to lock yourself in.

The Work Tracy Does Her offer, The Space You Want, includes:

Most You Biz Space — her entry-level community, built around the Sort, Purge, and Organize course

The Junk Drawer — a small cohort format for working through it together

1:1 Coaching via Voxer — async, on your schedule, because she's never wanted to do 10 Zoom calls a day (or any, really)

The Voxer model wasn't just a workaround — it was a deliberate choice made when she had a one-year-old and couldn't reliably be anywhere at a specific time. And it turns out her clients love it for the same reason: when you're in the middle of a crisis, you don't want to wait until Thursday's call.

Why "Sort, Purge, and Organize"? Think of it like a home organizer coming to your kitchen. You pull everything out, look at what's actually in there, and figure out what you've been hiding in the garage that you wish you had space for. In business terms: what are you actually doing, what do you actually want, and what revenue do you actually need to support the life you want — not the life a coach told you to want.

The 10K/Month Trap Both Bridget and Tracy push back on the default metric of "make 10K a month" (or 7 figures, or now apparently 8 figures). Tracy's work helps people figure out their number — which might be $3K, might be $15K — and then reverse-engineer an offer and a marketing approach that actually fits. One client realized she only needs to sell 7 of her premium offers per year. That's her scaling strategy, and it energizes her.

What AI Can't Do Tracy is openly not into AI. The conversation gets into why: AI can handle the checklist-style coaching that's already too formulaic to be valuable. What it can't do is hear the change in a client's voice when they're in their luteal phase, or notice that the panic spiral at 11pm is cyclical, not a sign to burn the business down.

On Writing the Book Tracy has always known she'd write a book. The motivation: she got pissed off that the business book she needed didn't exist. The Most You Business Book is meant to be the antidote to generic business advice — a guide to building offers, marketing, and daily work around who you actually are, not who the gurus say you should be.

Living Like You're Already Retired Tracy's been saying since college that she wants to live like she's retired — not waiting until 65 to enjoy her days. The conversation unpacks what that actually means: not quitting work, but building work that fits your life, not the other way around.

Quotes to Remember

"Fuck you to the way business is done — building your offers, your marketing and sales, and literally what you do each day, around you." — Tracy

"Or just don't do that shit to begin with. We don't have to pay someone else to do it if it's a thing that doesn't need doing." — Tracy, on the VA-and-AI trend

"When you do the thing that is you, it calls in the right people." — Tracy

"Life is too short." — Tracy's friend, at 29

Resources & References Mentioned

Gretchen Rubin's Four Tendencies framework (Upholder, Questioner, Obliger, Rebel)

DISC personality profiles

Clifton Strengths (StrengthsFinder)

Enneagram

The 4-Hour Work Week by Tim Ferriss (and why Tracy has feelings about it)

The Devil Wears Prada (the cerulean sweater scene, specifically)

Tracy's Sort, Purge, and Organize course inside of the Space You Want

Tracy's upcoming Dream Days exercise

Episode 1: The Business That Found Katy Miller

Welcome to the very first episode of The Deep Dig! And what a full-circle way to kick things off — my guest Katy Miller of The Miller Social is the person who had me on her podcast years ago, so it only felt right to return the favor.

Katy Miller is a learning experience designer who helps entrepreneurs turn their expertise into digital offers like courses, trainings, or product suites. She's the founder of The Miller Social and host of Katy Calls BS podcast. Katy is known for combining strategy, structure and her no BS approach. She's a single mom to two boys, can't start the day without coffee, and loves Taylor Swift.

Her top values are: Empowerment, Honesty, Innovation, Practicality, Motherhood or Parenthood, Respect, Education

In this conversation we get into all of it: burnout, boundaries, the winding road that led Katy from "I'm going to be a classroom teacher" to "wait, I forgot I have a master's degree," and why building a digital product might be the best business preparedness move you're not making.

What we dig into:

How Katy went from social media manager → strategy → course designer (and how burning out became the turning point)

Why she almost forgot she had a master's in instructional design — and what finally made her lean all the way in

The biggest misconception about courses: you can't just build it and wait for money to appear

Why the content isn't the problem — it's how your audience needs to receive it

The course platform conversation: you don't actually need one (yes, really), and if you do invest, what to look for

Why Katy considers digital products a "safety net" — and why you should build yours before you need it

Her personal anti-burnout stack: mental health runs, house projects as digital detox, and firm boundaries around access and weekends

Connect with Katy:

Website: themillersocial.com

Instagram: @themillersocial

Podcast: @katiecallsbs

My episode on Katy Miller's podcast aired January 22, 2024 on the Real Background of Branding.