Jennifer Dawn | The Real 50 over 50

About me

Jennifer Dawn coaches business owners to seven figures and beyond without sacrificing their personal life. She’s the creator of Best Planner Ever, author of The Joy Guide: Finding Your Joy In A World of Crap, and founder of Jennifer Dawn Coaching & Consulting. Jennifer 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”.

What do you do and why do you do it?

I am a business coach helping entrepreneurs to cross the 5% barrier. Less than 5% of business owners ever get to seven figures and only 2% of those are women. I think this is crap. I’ve done it multiple times and now I want to help others do the same.

We offer coaching not just for the business, but also for health and life. We don’t believe in only focusing on revenues, we coach the entire person.

I believe when I help a small business owner be more successful, they go out and make the world a better place. That’s how I change the world – by helping them.

What changed for you after age 50?

It became very real I would not live forever. No other birthday affected me like this. I now recognize my time here won’t last forever so I want to make the most of it even more than ever.

What would you tell the 20 or 30-year-old YOU?

Get more coaching help – don’t try to go it alone.
Heal the pain from your childhood now – it did affect you – so heal it sooner.
Be more present and enjoy the moment.

What do you think you’ll tell yourself in retrospect at the end of your life?

You did a good job. Well done.

What impact do you think increased visibility can have on your business?

We will be able to serve more business owners who are hurting or struggling.

Who or what inspires you and why?

The Susan Boyle audition video inspires me. Whenever I’m feeling hard on myself I watch it. If she could get out there on a stage in front of thousands of people shaming her and then bring down the room – I can too.

Something else I’d like to share

Our Unbreakable Retreats came from my personal experience. I set out to do three Spartan Races and ended up doing 12 in one year. That same year my business revenues TRIPLED. The correlation between a physical challenge and your business are absolutely connected. I love helping others make this often overlooked connection in our business retreats.

“Turning 50 felt like a huge accomplishment AND an ‘I’m not going to live forever’ wake-up call.”

Jennifer Dawn

The Brief

In summary, Jennifer Dawn shares how she started her entrepreneurial journey at the age of eight with an apple stand, because a lemonade stand was so yesterday. She continued through various career and business pivots until she launched Jennifer Dawn Coaching. Throughout her journey, Jennifer took what she learned and implemented in her own life and business. She was overwhelmed so she created the Best Planner Ever. She wrote The Joy Book: Finding Your Joy in a World of Crap to help entrepreneurs prioritize what really matters. And in her coaching and retreats she mentors entrepreneurs to grow exceptional businesses without giving up their lives. 

Jennifer emphasizes the importance of prioritizing wellness and self-care, especially after recently turning 50. She shared what she is learning from her experiences with health issues and menopause; and advises others to slow down and focus on the present, allowing time to expand and enabling a more grounded and peaceful state of mind.

Watch the entire video and be sure to connect with Jennifer. 

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Wisdom Panel: Grief + Gratitude

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