As part of the Morning Lazziness series about empowering women who encourage and do incredible things with their ideas in society, I had the pleasure of interviewing Jennifer Dawn.
Jennifer Dawn helps business owners escape the hamster wheel of constant “doing”, unpredictable cash flow, and misaligned teams, empowering them to create a thriving company culture that is profitable, sustainable, and fulfilling.
She’s the creator of a signature two-step coaching method designed to get maximum results in minimum time by working from the inside out and has helped over 50,000 business owners.
Jennifer is the founder of Jennifer Dawn Coaching, creator of Best Planner Ever, and author of two books, The Joy Guide: Finding Your Joy In A World of Crap, and The Apple Stand: How To Rekindle The Love for Your Business.
She is a Profit First certified coach and host of the Happy Productive podcast. She began her entrepreneurial career at age 8 selling apples off her grandfather’s tree because a lemonade stand was so “yesterday”.
Here’s what we found out about Jennifer’s daily routine, followed by an exclusive Q+A.
What inspired you to become an entrepreneur, and what sparked the idea for your business?
My entrepreneurial journey began at age 8 when I decided to sell apples from my grandfather’s tree, choosing that over a ‘yesterday’ lemonade stand – and I’ve been innovating ever since! After building several successful businesses, I noticed many business owners stuck on the hamster wheel of constant ‘doing,’ which inspired me to create a coaching method that transforms chaos into clarity. My passion lies in helping others find both profit and joy in their businesses, just as I’ve found in mine.
As a woman navigating the business world, what challenges have you faced, and how did you overcome them?
Being part of the top 2% of women business owners who’ve broken seven figures has taught me that success isn’t about gender – it’s about mindset, strategy, and execution. Rather than focusing on challenges, I’ve concentrated on building multiple successful businesses by staying results-driven while leading with heart. This approach has not only helped me succeed but has become the foundation for how I help other business owners transform their companies.
How do you balance the demands of running a business with maintaining a healthy personal life?
I practice what I preach about escaping the hamster wheel of constant ‘doing’ by creating systems and developing strong teams that allow my businesses to thrive without my constant involvement. The key is to build your business around your life, not your life around your business – it’s why I help my clients transform chaos into order and reclaim their time. When you have the right systems and people in place, balance isn’t just possible – it becomes natural.
Which networking strategies have most effectively built meaningful connections within your industry?
I’ve found that genuine relationships trump traditional networking every time. Instead of collecting business cards, I focus on creating real value and fostering authentic connections through my podcast, speaking engagements, and coaching programs. The most meaningful partnerships emerge when you consistently show up as your authentic self and genuinely care about others’ success.
How do you approach mentorship, and how has it shaped your entrepreneurial path?
Having built three seven-figure businesses, I believe in the power of both receiving and giving mentorship. My coaching method was born from combining proven business strategies with genuine care for others’ success. The most rewarding part of my journey has been watching business owners transform their companies using the same principles that helped me succeed.
What strategies have worked best for selling your products and reaching your ideal customers?
The most effective strategy has been focusing on delivering genuine results – our clients’ successes become our best marketing tool. By maintaining a ‘results-first’ approach and truly caring about client outcomes, we’ve built a reputation that attracts business owners who are ready to transform their companies from chaotic to thriving.
Which marketing techniques have been most successful for your business, and how do you track their performance?
Our most powerful marketing comes from the real transformations our clients experience – from increased profits to reclaimed time and renewed joy in their businesses. We track not just traditional metrics but also the lasting impact of our work: client satisfaction, revenue growth, and quality of life improvements. This holistic approach to measuring success sets us apart.
Can you share a significant setback in your business journey and the steps you took to overcome it?
One of my businesses failed during the economic crash, taking me from cash-rich to $178K in debt – a devastating experience that forced me to take a corporate job to survive. But this setback became my greatest teacher. The lessons learned from failing, rebuilding, and climbing out of debt now form the foundation of how I help business owners avoid similar pitfalls or navigate through their own challenging seasons. It’s not just theory for me – I’ve lived both the breakdown and the breakthrough.
What’s the most important advice you’d give to women just starting their entrepreneurial journey?
Focus on building systems that serve both your business and your life – success shouldn’t require sacrificing one for the other. Remember that profitability and joy aren’t mutually exclusive; with the right strategies and support, you can create a business that delivers both. Your business should work for you, not the other way around.
Is there a mantra or quote that guides your actions and decision-making as an entrepreneur?
Dolly Parton said it best: ‘You’ll never do a whole lot unless you’re brave enough to try.’ This quote resonates deeply with my journey from selling apples at age 8 to building multiple seven-figure businesses, and even through my setbacks and comebacks. It reminds me that success requires courage, and I’ve seen this truth play out countless times with my clients who take brave steps to transform their businesses.
