Ep 28: Money Shame, Avoidance, and How It Sabotages Your Business Growth with Morgaine Trine
“Avoidance of the bookkeeping is like the single most common behavior I see around bookkeeping.”
Morgaine Trine
Today’s conversation with my friend Morgaine went places. We started with queso and girl lunch energy and somehow ended up unraveling the emotional, psychological and operational roots of bookkeeping, money shame, childhood conditioning, nervous system patterns, the accounting industry collapse, digital nomadism and why most business owners are absolutely avoiding the one thing they say they want: clarity.
If you’ve ever felt like bookkeeping is confusing, overwhelming or “I’ll figure it out later” energy, this episode is going to hit. And if you’ve been telling yourself your messy books are a personal failure, I need you to hear this clearly: nope. There’s a whole ecosystem of systemic, emotional and operational things that collide inside your profit and loss statement.
Morgaine is one of the few bookkeepers I’ve met who gets the financial side and the psychological side. Today we unpack both.
What You’ll Hear in This Episode
How VIP Day–style bookkeeping cleanups can change your entire onboarding experience
Why asynchronous cleanups were breaking Morgaine’s process
How the accounting industry is aging out, shrinking and shifting
What bookkeeping actually is (hint: not data entry)
The two levels of bookkeeping: compliance vs management
Why business owners avoid their finances and how shame shows up
How our childhood money experiences shape our adult patterns
Why “treat yourself” culture is deeply tied to nervous system regulation
Why some businesses are thriving and most are struggling right now
How to talk about money with kids without recreating your own wounds
What it means to build self-trust through money decisions
A VIP Day That Changed Everything
Morgaine has been a bookkeeper for eight years, and like most service providers, she kept running into the same issue: cleanup projects were dragging on forever. Clients wanted books fixed yesterday, but then disappeared for months. She could never get the information she needed on time, and the back-and-forth was draining her team.
Then someone in her network mentioned doing cleanup as a VIP day.
And baby, it worked.
Her first one? Nine months of cleanup done in a seven-hour day. Three team members, tight structure, kickoff call, closing call, and the rest of the day inside a client portal with rapid responses.
It wasn’t about speed for the sake of speed. It was about clarity, focus and eliminating decision fatigue. And honestly, it highlighted how much bookkeeping relies on context, interpretation and partnership. There’s so much nuance in categorizing expenses, understanding multi-business transfers, interpreting weird account names and digging into one-off charges.
This is the part business owners never see. You think your bookkeeper is sitting there tapping numbers into QuickBooks. No. They’re basically financial anthropologists.
Why Business Owners Avoid Bookkeeping (Spoiler: Shame)
When I confessed to Morgaine that I avoid reconciling my expenses when I’m feeling emotionally crunchy, she didn’t blink. Avoidance is the most common bookkeeping behavior she sees.
Money activates shame more than almost anything else.
You’re shamed for having too little, too much, wanting more, spending “wrong,” saving “wrong,” charging “wrong,” pricing “wrong”… it’s endless.
And when shame shows up, we hide.
We make ourselves small.
We delay the very tasks that would give us relief.
This is why so many people have resistance around hiring a bookkeeper. It’s not the money. It’s the exposure. It’s the fear that someone will look at your numbers and think you’re stupid or irresponsible or doing business wrong. (Spoiler: they won’t.)
The bookkeeping conversation isn’t just spreadsheets. It’s nervous system regulation, self-trust and emotional literacy.
Compliance vs Management: The Real Reason Bookkeeping Matters
One of the biggest mic-drop moments in this episode was when Morgaine explained the two types of bookkeeping:
1. Compliance-Level Bookkeeping
This is the bare minimum.
Get the IRS the information they require, in the format they require.
This is where the “data entry” misconception comes from.
2. Management-Level Bookkeeping
This is the strategic stuff.
The stuff that lets you make decisions.
The stuff that helps you understand patterns, opportunities, margins, investments and how your business actually works.
You cannot make strategic financial decisions without clean historical data. You also can’t jump to strategic analysis without getting your emotional relationship with money regulated enough to look at the numbers.
This is why bookkeeping is not admin work.
It is leadership work.
Why the Accounting Industry Is… Kind of in Crisis
This blew my mind:
Before the pandemic, the average age of an accounting professional was 67. Not only did the pandemic cause mass burnout in the industry, but many retired or passed away. On top of that, new grads with accounting degrees are fleeing the industry for better-paying finance jobs.
So we’re left with:
Fewer bookkeepers
Fewer CPAs
Higher demand
More complexity
More legislation
More tech confusion
And because bookkeeping requires interpretation, precedent understanding and tax awareness, AI isn’t about to magically fix it.
No wonder business owners feel lost.
Money Patterns Start Young
We got into upbringing, class backgrounds, and how wildly different our childhood experiences were. Yet both of us still ended up with emotional money patterns that needed untangling.
Morgaine made a powerful point: kids don’t need the granular details of your finances. What they need is nervous system modeling. They need to learn that money can feel safe, flexible and manageable. They need age-appropriate transparency about priorities, values and choices, not stress dumps.
Money conversations are less about dollars and more about regulation, self-trust and emotional context.
Why Most Businesses Are Slow Right Now (According to the Data)
Because Morgaine sees the real numbers behind dozens of businesses, she has a bird’s-eye view that most people don’t.
Her take:
About 10% of businesses are crushing it.
90% are slow right now.
But here’s the twist — even with lower revenue, many of those same business owners feel more grounded, centered and emotionally well than ever. People are investing in therapy, coaching, nervous system work and personal development.
It’s like the economy is having a reckoning and a reset at the same time.
And honestly? I’m seeing the same thing.
Chapters
00:01 Girl lunch, queso energy
03:40 Parenting, height genes and Ugg boot scams
04:20 Morgaine’s new VIP day cleanup model
06:30 Why async bookkeeping cleanups weren’t working
09:00 How she structures VIP days
10:50 The expectations clients need to show up for
12:40 Onboarding, cleanup and setup fees
13:50 Why late bookkeeping exponentially increases effort
15:10 My own avoidance patterns
18:10 Money shame and why we hide
20:40 Pricing, moralism and nervous system alignment
22:10 Morgaine’s money upbringing
24:40 Talking to kids about money without scaring them
29:30 Helping kids build self-trust around spending
32:30 Dopamine, spending patterns and instant gratification
36:10 My relationship with coffee, wine and treat culture
38:50 Emotional buying vs aligned buying
40:00 Bookkeeping and operations are inseparable
43:00 The recession vibes and why 90% of businesses feel slow
46:00 The accounting industry collapse
50:00 Why so many bookkeepers go MIA
55:00 How Morgaine became a bookkeeper
01:03:00 Why bookkeeping is NOT data entry
01:08:00 Compliance vs management bookkeeping
01:11:50 Why niching by psychographics matters
01:14:00 The microcosm of the US economy inside client books
01:16:00 Where to find Morgaine
Resources & Mentions
About the Guest
Morgaine Trine is the founder of Honestly Bookkeeping, a firm that helps visionary founders who’ve moved beyond the hustle and are now building something that can help them stabilize, strengthen, and sustain their financial infrastructure in a way that supports actual decision-making and long-term leadership. Her ecosystemic approach to bookkeeping reduces reactivity, supports calm, and creates systems that scale with you.
Connect with Morgaine
Interested in Being on the Show or Working with Emylee?
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