Freedom Through Bookkeeping: Tools, Tips, and Community Support for Your Career Change

The Stay-At-Home Bookkeeper Academy Podcast

The Stay-At-Home Bookkeeper Academy Podcast
Freedom Through Bookkeeping: Tools, Tips, and Community Support for Your Career Change
Jan 26, 2026
Tiffani Higgins

Are you ready to ditch the overwhelm and build a bookkeeping business that actually fits your life? In today’s episode of the Stay-at-Home Bookkeeper Academy podcast, host Deanna Rogers and mentor Bill Rogers sit down with Rob Hamilton, Head of Go-To-Market at Digits, for a conversation packed with practical insight, real talk about technology, and empowering advice for bookkeepers at every stage.

If you’ve ever wondered how AI is changing bookkeeping—or worried if it’s going to take your job—this episode will put your mind at ease. Rob Hamilton breaks down what “agentic general ledger” actually means, why relationship-building is still your superpower, and how automation can make your work faster (and maybe even a little more fun).

We cover:

Why you don’t need a fancy degree or tech background to succeed as a bookkeeper

Actionable tips to define your services and pick tools without getting stuck in overwhelm

How Digits is making cleanup work way less intimidating (spoiler: more time for what matters!)

What advisory services mean for your future—and how you can start offering more value, even as a newbie

Stories from the trenches, including remote team hacks and real-life business leaps

So if you’re someone craving freedom and flexibility, or just want bookkeeping to feel simple, welcoming, and doable—hit play. You’ll leave with more clarity, confidence, and maybe a new favorite tool for your business journey.

Ready to take the next step? Book a free clarity call and learn how the Stay-at-Home Bookkeeper Academy can support you—no permission slip required.

If you're interested in the Academy, fill out this form we'll give you some details asap!!
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Episode Artwork Freedom Through Bookkeeping: Tools, Tips, and Community Support for Your Career Change 42:23 Episode Artwork From Introvert to Influencer: Casey Eberhart’s Real-Life Networking Strategies 43:06 Episode Artwork From MLM Fails to Bookkeeper Wins: Alicia Porter’s Guide to Starting Messy and Staying Authentic 46:09 Episode Artwork Accidental Bookkeeper: Robbin McManne’s Journey From Corporate Burnout to Family Freedom 45:23 Episode Artwork Leaving the 9–5 for Good: Bookkeeping, Family, and Redefining Success with Bill Rogers 43:06 Episode Artwork Real Talk: Juggling Multi-Million Dollar Business and Family with Sarah Jenkins 35:54 Episode Artwork From Homeschool Mom to Multiple Businesses: Kirstin Reeder’s Bookkeeping Journey 45:05 Episode Artwork Making Double: How Ben Stein Built Tools to Help Bookkeepers Earn More with AI 26:19 Episode Artwork Mastering Time, Income and Independence. Kelly's Journey to Entrepreneurial Freedom. 52:02 Episode Artwork Learn ALL About How TO Grow A Profitable, Sustainable Bookkeeping Business 2:11:08 Episode Artwork A Powerful Couple's Successful Bookkeeping Journey with Academy Student Robbin McManne 43:38 Episode Artwork Quitting the Conventional Corporate World - with Gabby Ianniello 32:28 Episode Artwork Breaking Cycles, Building Dreams - with Kim Guillory - The Integrative Life Coach 28:09 Episode Artwork A Journey on the Entrepreneur Roller Coaster - Jennifer Lukas Bourgeois 24:26 Episode Artwork From Mom To Entrepreneur with Carey Bentley, The LifeHackMethod 22:09 Episode Artwork Investing in the Bookkeeper Academy...Completely Changed Her Life 29:55 Episode Artwork How Kristen's Academy Journey Transformed Her Life 37:45 Episode Artwork Kelsey's Bookkeeping Journey to Financial Freedom 27:57 Episode Artwork Christina's Transition from 9-5 to Thriving: An At-Home Business Success 38:50 Episode Artwork McKenzie's Journey from Side-Hustle to Full-Fledge Business 48:54 Episode Artwork Kaylie's Journey from Pharmacy Tech to Business Success 33:20 Episode Artwork From Chalk to Charts: How Kate Traded Teaching for a Thriving Bookkeeping Business 49:42 Episode Artwork How Joining the Bookkeeper Academy Doubled Jen's Income in 1 Year 55:07 Episode Artwork How Diving into the Bookkeeper Academy Led To Massive Success 52:55