Do you ever feel like, despite your success, something is missing or you haven’t quite “arrived”? It’s not as uncommon among women entrepreneurs as you think.

Jennifer Holaday built a solid, profitable custom window treatment business with a great reputation. Yet, for a long time, she felt capped. Instead of being stuck because of failure, she was stuck because of her own success and the cautious mindset that came with it.

In this episode of She Thinks Big, Jennifer opens up about the pivotal moments that helped her break through her limitations, stop playing it safe, and take courageous leaps of faith so she could reach the next level. Through her experience, you’ll see how true growth happens when you invest in yourself and your vision with decisiveness, not after you feel "ready."

2:53 – Jennifer’s introduction and the moment she realized she was stuck

7:12 – How receiving coaching is like learning a new language and vocabulary

9:33 – Decisiveness and a willingness to pivot as vital to being a CEO

11:09 – How Jennifer’s dream of a showroom came together more quickly than she expected

17:15 – Attracting the ideal client by having the ideal business for that client

20:38 – Why confidence is a benefit that comes after taking a big leap

22:47 – The impact of surrounding yourself with other successful women

25:29 – Jennifer’s expertise and what she offers ideal interior design clients 

Connect with Jennifer Holaday

Jennifer Holaday is the founder and CEO of the Nashville-based Brave Maggie Designs, a window-treatment resource that serves as a tribute to her grandmother, Margaret White. With a dedication to sewing instilled in her by Margaret, she brings a rich history of craftsmanship and a keen eye for detail to every project.

Her journey in the realm of textiles stretches over 15 years of crafting custom curtains, drapery, and shades for homeowners and interior designers. It’s a path that led to proud moments in 2023 when her creations received two 1st place accolades in design and fabrication at the prestigious IWCE-VISION Design & Workroom Competition. Another 1st place award followed in 2024.

Jennifer brings more than just expertise; she promises a journey of transformation that turns spaces into statements and houses into homes.

Brave Maggie Designs | Instagram | Facebook | Pinterest 

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Mentioned In Decision Diaries: How Decisiveness Changed Jennifer Holaday’s Business

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Untangle your time, reset your role, and build systems that don't depend on your every move. No more white-knuckling your way through success because you're not just scaling your business, you're scaling yourself.

Get the clarity and capacity to lead differently and ascend to your next level. Learn how and join us at andrealiebross.com/ascension.

The big, glossy postcard invites in the mail…the life-changing workshop email invitation, the networking event of the year…

You’ve seen them all and probably often wondered, “Should I go?” While some might be more convenient to attend, others might be a cross-country plane ride away and require time, money, and other resources that make it harder to orchestrate. 

And in the end, is the payoff worth it? Instead of blindly making decisions on which opportunities to attend, a practical framework can help you move beyond “fear of missing out” and convenience and ensure that every event you attend is a strategic step toward your business goals.

In this episode of She Thinks Big, you’ll learn how to confidently choose which events, conferences, and webinars are worth the investment of your time, energy, and money. Using personal stories to illustrate my points, I’ll discuss the challenges you’ll face, things you need to consider, and the exact decision-making filters I use that can help you decide which opportunities are worth your while.

4:41 – Events I’ve decided to go to using my decision filter framework

10:58 – Three challenges you’ll often face when deciding on which events to attend

12:49 – Three filters to help you clarify opportunities worth your time

18:26 – What you should define before attending any event

20:23 – Four things you need to consider to make the most of any opportunity

26:13 – Why the event itself isn’t the investment and your next steps

Mentioned In How Successful Women Decide Which Events Are Worth It

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Untangle your time, reset your role, and build systems that don't depend on your every move. No more white-knuckling your way through success because you're not just scaling your business, you're scaling yourself.

Get the clarity and capacity to lead differently and ascend to your next level. Learn how and join us at andrealiebross.com/ascension.

The biggest leaps in life and business often come from a willingness to get uncomfortable. Investing in the person you need to become to achieve your dreams is a big part of the process.

Laura Khesin has known this firsthand for a while now. As the visionary behind her budding empire, Society Beauty Bar, her bold decisions and high tolerance for self-investment have stretched and challenged her, transforming big risks into even bigger returns.

In this episode of She Thinks Big, Laura discusses her journey of turning strategic risks into remarkable success, from her early days as a real estate investor to building her thriving salon business. You’ll learn how she courageously navigated major financial commitments to not only grow her business, but also to grow as a leader.

3:10 – How taking a big risk on herself led to Laura’s business and how it (and she) evolved afterward

9:18 – Why high risk tolerance proved key to Laura’s entrepreneurial growth

12:22 – The crucial difference between strategic investment and throwing money at problems

20:30 – Tangible and intangible outcomes for Laura since making big investments into her business

28:10 – What else defines higher-level leadership for Laura 

33:00 – Laura’s advice for anyone hesitant to make a big investment

Connect with Laura Khesin

Laura Khesin is the founder and chief stylist at Society Beauty Bar, a boutique salon with locations in the Boston area. After her sophomore year at Suffolk University, she decided to focus on becoming a stylist. She spent five years working for a salon before becoming an independent stylist. 

Then in 2017, Laura opened her first salon as a rental property in Arlington. Five years later, she pivoted to offering commission-based salons, which combined the best parts of being an independent stylist with the traditional commission salon model. Through Society, stylists enjoy the same benefits of independent contractors without the nuances of working for themselves and can grow their careers with freedom and a salon family that supports them in their aspirations.

Society Beauty Bar | Instagram | Facebook 

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Mentioned In Decision Diaries: How Laura Khesin Took $30K Leaps to Grow Her Business

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Untangle your time, reset your role, and build systems that don't depend on your every move. No more white-knuckling your way through success because you're not just scaling your business, you're scaling yourself.

Get the clarity and capacity to lead differently and ascend to your next level. Learn how and join us at andrealiebross.com/ascension.

There’s something not on your calendar that still takes up a lot of headspace. It’s something that no one really talks about. And it’s this:

You can be fully booked—calendar, clientele roster, and all—and still feel completely lonely in your business. Why? Because you have no one to bounce ideas off or to serve as a sounding board for tough decisions. It’s just you at the top.

In this episode of She Thinks Big, you’ll learn about the impact of entrepreneurial loneliness on you as a business owner. I’ll discuss the isolationism of being the one in charge, the stages of entrepreneurial loneliness, and what you can do to protect yourself against it (emphasizing the importance of having a real support system early on). 

2:46 – The invisible weight of decision fatigue

5:06 – How entrepreneurial loneliness evolves in three stages

8:14 – How an iceberg resembles your business and you as its CEO

9:21 – What real community looks like for women entrepreneurs

11:58 – Self check-in, your assignment, and an invitation

15:08 – How to build protection against loneliness before it takes its toll

Mentioned In Why So Many Women Entrepreneurs Feel Lonely (Even at the Top)

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Untangle your time, reset your role, and build systems that don't depend on your every move. No more white-knuckling your way through success because you're not just scaling your business, you're scaling yourself.

Get the clarity and capacity to lead differently and ascend to your next level. Learn how and join us at andrealiebross.com/ascension.

On the outside, everything looks golden. You’ve built your business. Maybe you’ve grown it to six or seven figures. You thought this kind of success would equal freedom, but it feels more like a straitjacket. All those bookings on your calendar have you busy and burnt out.

So what’s this all about, and how can you embrace a new way forward?

In this episode of She Thinks Big, you’ll discover the hidden time poverty that even the most successful women entrepreneurs experience. I’ll teach you the mindset behind your calendar, practical tools to shift it, and the mental space you must reclaim.

4:36 – The success time trap that most people don’t talk about

6:27 – Your calendar as a mirror and the calendar confidence gap you need to close

8:36 – The importance of giving yourself time to think and not think

11:18 – How a calendar detox helps you shift your mindset (with a practical exercise)

14:53 – Takeaways and your calendar autopsy assignment for the week

Mentioned In Why Six-Figure Women Still Feel Trapped By Their Calendar

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Untangle your time, reset your role, and build systems that don't depend on your every move. No more white-knuckling your way through success because you're not just scaling your business, you're scaling yourself.

Get the clarity and capacity to lead differently and ascend to your next level. Learn how and join us at andrealiebross.com/ascension.

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.

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

Liddane Tutoring | Facebook | Instagram | LinkedIn | TikTok

Mentioned In Why Successful Business Owners Still Struggle with Decisions After Years of Experience

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Untangle your time, reset your role, and build systems that don't depend on your every move. No more white-knuckling your way through success because you're not just scaling your business, you're scaling yourself.

Get the clarity and capacity to lead differently and ascend to your next level. Learn how and join us at andrealiebross.com/ascension.

Do you lie awake at night, feeling that nagging urge to throw in the towel even though your business is thriving? 

Many women entrepreneurs hit their revenue goals, have adoring clients, or finally upgraded their systems. Yet, they still fantasize about walking away for something simpler, like becoming an employee again or living in the Swiss Alps as a dog walker. However, what looks like craziness or ungratefulness on the surface is just a sign of a much-needed internal shift. 

In this episode of She Thinks Big, you’ll learn why you feel like shutting your business down even when everything looks perfect on the surface. I’ll teach you why burnout isn’t from your efforts, why success can feel like a trap, and the crucial role of your mindset, self-talk, and support system in sustaining your entrepreneurial journey with renewed energy, power, and purpose.

1:20 - Why you’re not crazy or ungrateful if you want to quit or burn it down

4:24 - Why it’s about your brain, not your business being broken

6:52 - Why mindset is a daily recalibration, not a bubble bath

10:18 - Why you need new self-talk, not a new strategy (with a personal example)

16:24 - Why who you surround yourself with matters more than you think

20:35 - Take five minutes to answer these four questions 

Mentioned In I Built the Business I Wanted, So Why Do I Feel Like Quitting?

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Untangle your time, reset your role, and build systems that don't depend on your every move. No more white-knuckling your way through success because you're not just scaling your business, you're scaling yourself.

Get the clarity and capacity to lead differently and ascend to your next level. Learn how and join us at andrealiebross.com/ascension.

Like so many women, resiliency and recovery coach Lina Midla initially saw fitness through the lens of fat loss and weight management. But she discovered that what you could gain was actually more powerful. Through movement, breath, and cold exposure, she helps women build real resiliency, joy, curiosity, and compassion.

In this episode of She Thinks Big, Lina provides three takeaways that will transform the way you look at fitness and movement. She unveils how movement is an underrated superpower, why regulating your nervous system isn’t optional, and the power of tapping into your body’s feminine energy and wisdom.

Discover why getting in shape isn’t just about chiseling the outside. Using her array of tools, Lina’s powerhouse insights will help you connect with your inner self and find joy in the process.

1:24 – Introduction to Lina and how she transitioned from focusing on weight management to resiliency coaching for women

7:13 – How movement acts as a supercharger for your confidence, connection, and energy

10:30 – How functional strength training differs from traditional fitness approaches for women

14:12 – Recovery and nervous system regulation as foundational and how breathwork and cold exposure impact the nervous system

21:37 – The power of approaching a problem, goal, or situation from your whole being and not just logical thinking

24:50 – The importance of honoring your feminine energy and the gift of a quiet pause

30:56 – Recap of Lina’s three key takeaways and how you can start implementing them today

33:12 – Lina’s vision for the third space she wants to create for women and her final thoughts

Mentioned In Why Nervous System Regulation Isn't Optional for Entrepreneurs with Lina Midla

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Untangle your time, reset your role, and build systems that don't depend on your every move. No more white-knuckling your way through success because you're not just scaling your business, you're scaling yourself.

Get the clarity and capacity to lead differently and ascend to your next level. Learn how and join us at andrealiebross.com/ascension.

Jamie Lee is an executive coach, certified hypnotist, and true big thinker. Connecting years ago in a mastermind, I’ve been a devoted follower of her work ever since. She’s dedicated to empowering women and people of color to reclaim their power, advocate for themselves, and build unshakable confidence to achieve bigger and better things in their careers. 

In this episode of She Thinks Big, Jamie unpacks three transformative takeaways that will revolutionize how you approach your career and life. She challenges the notion that speaking up is selfish, reveals why uncomfortable conversations are essential for growth, and shares how harnessing your mental state can lead to unprecedented success.

So get ready to examine your perceptions of self-advocacy, embrace uncomfortable conversations, and discover powerful tools (including hypnosis) to cultivate unwavering self-confidence and achieve your biggest goals!

3:17 – Jamie’s background and her work as an executive coach to women and people of color

5:05 – Why self-advocacy is an act of service that also benefits others

9:40 – Why everything worthwhile is on the other side of a “risky” conversation

16:32 – Two ways to make work/business conversations feel less risky for you

19:46 – A sign that it’s time to leave your position

21:50 – Why you’re doing it right if it feels awkward to advocate for yourself

23:16 – How hypnosis/visualization serve as powerful confidence-building tools

29:05 – A two-minute method to use ahead of a high-stakes or risky conversation

Connect with Jamie Lee

Jamie Lee is a coach and hypnotist who helps women, BIPOC, neuro-divergent, and the marginalized reclaim their power and achieve mastery through practical neuroscience and coaching. She’s delivered many talks about self-advocacy in the workplace, but her true passion is digging into the inner workings of the human mind. Following her fascination, she obtained certifications in life coaching, feminist coaching, and integrative hypnosis.

Jamie’s work is rooted in the conviction that true personal power lies not in chasing after other’s approval but in tapping into the potential of the brain’s vast neuronal connections. She works individually with those who don’t fit the traditional mold of leadership, find conventional wisdom too stifling, and want to forge new paths in their careers and lives.

Jamie Lee Coach | LinkedIn | Instagram | YouTube | Substack

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Untangle your time, reset your role, and build systems that don't depend on your every move. No more white-knuckling your way through success because you're not just scaling your business, you're scaling yourself.

Get the clarity and capacity to lead differently and ascend to your next level. Learn how and join us at andrealiebross.com/ascension.

You’ve got the big thinking ideas, but are you still thinking small when it comes to protecting them?

When I re-branded to She Thinks Big, it wasn’t just about titling my book or renaming this podcast. It encompasses my entire brand and business. I had to trademark it to ensure nobody else could claim it, and Cheri Andrews was the attorney who helped me do it.  

In this episode of She Thinks Big, Cheri reveals everything you need to know about trademarks. Whether you’re just starting your business or have been at it for a while, she’ll clear up the confusion about when, why, and how to trademark your intellectual property. 

3:18 – What intellectual property (IP) is, the different types, and its purpose

7:58 – The best time to start thinking about trademarking 

10:08 – What to consider when choosing a name to trademark and the cost of having an un-trademarkable one

13:34 – What you can expect during the trademarking process and how long it takes

21:28 – The surprising truth about the trademark and registered symbols and when you can use them

23:00 – Why you can lose the rights to your trademark even after it’s registered

25:54 – The impact of a trademark on the value of your business

27:30 – Misconceptions about LLC business names and trademarks being reserved for big business

30:08 –  Your next best steps if you’re thinking about trademarking an IP

Connect with Cheri Andrews

Cheri Andrews is a speaker, author, small business attorney, and expert in intellectual property. After an award-winning career with over 30 years of legal expertise, she left law firms and corporate settings to start a company where she could practice law her way and donate a percentage of revenue to charity. She works primarily with heart-centered, service-oriented, women entrepreneurs to help protect their business, move forward with confidence, and sleep better at night. With a holistic approach, she addresses concerns you may not even know you have and proactively resolves them so that they don’t turn into legal problems.

Cheri D. Andrews, Esq. | Facebook | LinkedIn | Instagram | YouTube

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Mentioned In She Thinks Big, So She Trademarked It with Small Business Attorney Cheri Andrews

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Untangle your time, reset your role, and build systems that don't depend on your every move. No more white-knuckling your way through success because you're not just scaling your business, you're scaling yourself.

Get the clarity and capacity to lead differently and ascend to your next level. Learn how and join us at andrealiebross.com/ascension.