237: Why Successful Business Owners Still Struggle with Decisions After Years of Experience
You survived the start-up phase, made money, and built a team. Now, several years later, you think you should have the ins and outs of running a business all figured out by now. Yet, even though everything looks great on the surface, it can feel exhausting, chaotic, even uninspiring on the inside…especially when you’re still wearing all the hats.
That’s where Andrea Liddane found herself with her 20+ year tutoring business. As the founder and CEO of Liddane Tutoring and Learning Services, she’s served hundreds of students and hired over 30 tutors. But after all this time, she realized she was emotionally and physically tired and felt uninspired by her passion. So she took a bold step and sought a guide who wouldn’t just hand her a map but take the journey with her.
In this episode of She Thinks Big, Andrea shares what it really looks like to be an experienced business owner who still needs support and why seeking coaching later in the game can sometimes be the most strategic move of all. As she and I have fun with revealing her story through forest analogies, you’ll see why knowing what you’re doing as an entrepreneur doesn’t mean you should have to do it alone.
What’s Covered in This Episode on Why Successful Business Owners Struggle with Decisions
4:36 – Introduction to Andrea Liddane, her business, and why she took the leap to hire a coach
9:02 – Why Andrea felt her business was stuck despite its success
12:00 – The need for an outside voice to get on the path to making the best business decisions
17:02 – Examples of distractions (or “squirrels”) that kept threatening to push Andrea off track
21:07 – The turning point when Andrea “jumped across the stream” and made a big decision in her business
25:11 – How Andrea makes business decisions differently now and what keeps people stuck in indecision
28:47 – The power of having a sounding board to help you make quicker decisions and free up real estate in your brain
33:28 – Andrea’s advice if you think you should have it all figured out by now as an established entrepreneur
36:46 – How having a coach has helped Andrea reclaim inspiration for her work
38:07 – The return for Andrea on her investment in business coaching
41:14 – How Andrea feels about the future of her tutoring business
Connect with Andrea Liddane
Andrea Liddane is the founder and CEO of Liddane Tutoring & Learning Services, a trusted educational support organization she launched in 2001. What began as her personal mission to combine meaningful relationships with creative, student-centered learning has grown into a team of experienced, empathetic tutors serving students from preschool through college—both in person and online.
With a background as a public school teacher and private tutor, Andrea brings deep experience to her leadership. She’s known for prioritizing personalized instruction, professional development, and collaborative problem-solving—ensuring that each student gets the thoughtful support they need to thrive.
Under Andrea’s direction, LTLS offers academic tutoring across all subjects, executive function coaching, study skills development, standardized test prep, and college application support. Her team also specializes in working with students with learning differences such as ADHD, autism, dyslexia, and more.
Behind the scenes, Andrea continues to consult with families, schools, and professionals—always centering trust, understanding, and holistic support. And in keeping with her lifelong commitment to educational equity, LTLS quietly offers support to a small number of students with financial need—reflecting her belief in access, dignity, and community care.
Liddane Tutoring | Facebook | Instagram | LinkedIn | TikTok
Mentioned In Why Successful Business Owners Still Struggle with Decisions After Years of Experience
She Thinks Big by Andrea Liebross
Quotes from the Episode
“We're standing in front of this forest of life. There are so many different paths. As women, we have this notion that we can do everything and figure out the best path forward if we just look or try harder.” - Andrea Liddane
“As business owners, we can watch a million videos and listen to YouTube, podcasts, books, everything. But it's not the same to almost have someone in your court.” - Andrea Liebross
“It wasn't that long ago that I was taking client notes by hand, like on a napkin in the back of my minivan. I mean, that's really how I started. And there's certain parts of the business that aren't that far from that.” - Andrea Liddane
"Now that we're here on the other side, I feel like I have somebody who's learning about my business, who's understanding some of the sticking points, but also can make those decisions in the best interest of me as a human." - Andrea Liddane
"I don’t want to spend the next 20 years trying to figure out what the next step should be and making all the mistakes. It’s really inefficient to do it without a coach sometimes." - Andrea Liddane
Links to other episodes
152: How to Combat Decision Fatigue in Everyday Life
135: Where Do You Need More Freedom in Your Life or Business?
62: How to Make Decisions From a Place of Abundance Instead of Scarcity
60: How to Be Confident in Your Decisions
[fusebox_transcript]
Take The Quiz
Are you overwhelmed with business and life and think there is never enough time in the day? Are you tired of being reactive vs proactive in your business?
Learn how to show up as your best self in business.