The truth is that most small businesses never cross the seven-figure mark. As a business coach, I always say to own the business you want. Don’t get caught up in the revenue. You can own a profitable, beautiful six-figure company that supports your lifestyle and balance.

Have you ever noticed how often we equate success with more? Whether that’s more products, more profits, more activities or more accomplishments, we buy into the belief that we have to do more to have more to be more. And that will sum up to success. And then along comes The Great Resignation. Where employees are signaling that the “more” that’s being offered — even more pay, more perks, and more PTO — isn’t summing up to success for them. We visited with leaders who are redefining what success means now. Their answers might surprise you.

As a part of this series I had the distinct pleasure of interviewing Jennifer Dawn.

Jennifer Dawn is the founder of Jennifer Dawn Coaching and the creator of the Best Planner Ever. She began her entrepreneurial career selling apples off her grandfather’s tree because a lemonade stand was so “yesterday”. Jennifer is a serial entrepreneur who has grown two multi-million-dollar businesses and is a successful speaker and author.

She serves high-achieving entrepreneurs through private business coaching and hands-on workshops. Jennifer is a master at setting and achieving goals, problem-solving, profitability, and cash flow. She is also the host of the top-rated podcast, Happy Productive with Jennifer Dawn.

A mother of three children, Jennifer currently lives in Rhinebeck, New York with her family. She loves to spend time with her family, ride horses, travel, and coach/mentor others.

Thank you for making time to visit with us about the topic of our time. Our readers would like to get to know you a bit better. Can you please tell us about your professional background?

Thank you so much for this interview opportunity, Karen. I have a nontraditional career path.

While I attended Florida State University and worked full-time, I didn’t finish college and nor did I earn a degree.

When I was in my second year of college, my grandfather passed away. He was the father figure for all of us. We all loved and adored him, but when it came time for the funeral, my family said they would not pay to attend it in Arizona as we were in Florida. So, I decided to pay for the entire family to attend. I purchased plane tickets, made hotel arrangements, and rented cars — all at 19. But to do this I lost two weeks of work; I wiped out my savings; I maxed out every credit card — all of which got me into debt, so I had to withdraw from school and get a second job. I went back and took classes, but I never fully gained the momentum I once had.

At the age of 23, I started my first software company doing Point of Sale Ticketing Systems for waterparks and ski resorts. Although I didn’t know what I was doing, after years of trial and error, learning, and testing, I grew the company to seven figures and then sold it.

I then purchased a log home company in Montana. However, the real estate market bottomed out and I had to close my doors within a year. I went from being cash-rich to $178,000 in debt and was forced to take a job in corporate America. I took a position with a $54 million manufacturing firm, serving as the software division President.

At that time, I had just given birth to my third child. She was eight weeks old when I had to move across the country with three kids, three horses in the trailer, and nursing. I was there for about 2.5 years and grew revenues from $300K to $2.2 million in 18 months.

I discovered problems with the company’s software product. When I pointed the issues out to senior management, they ignored me and didn’t want to fix them. This was a very turbulent time, and I sought the help of a life coach who helped me navigate. I left the company and took a summer off to figure out my next move. It was during this time I met my now husband, moved to New York, and was asked to lead a national network of women entrepreneurs. While there, I tripled the organization’s revenue and developed a love of coaching and mentoring. That is how Jennifer Dawn Coaching began almost a decade ago.

We all have myths and misconceptions about what success means. What are some that you used to believe professionally?

This is a great question — I would have to say I used to believe I had to be perfect; I had to be able to do everything. I had to have all the answers from parenting to entrepreneurship to relationships — which, of course, is crap.

How has your definition of success changed?

I am an advocate for doing whatever makes you happy. I coach my clients to do the same and to avoid falling into stereotypical traps such as you must keep up with the Joneses. Define success on your terms. What works for me, may not work for everybody else.

The pandemic, in many ways, was a time of collective self-reflection. What changes do you believe we need to make as a society to access success post-pandemic?

Throughout the pandemic, I did not have much time for solitude and self-reflection. Working with business owners most of them lost revenues and had to make cuts. Business coaching is a luxury item, so guess what? I was one of the first expenses that had to go — which hurt my income too. I ended up telling each of my clients we are in this together, and I’m going to either stop or significantly reduce your coaching fees for the next three to four months during the pandemic. That is what we did, and luckily all the clients stayed in business and some of them ended up having record-breaking years, which was exciting.

But to answer your question about the changes we need to make to access success post-pandemic are treating our planet and each other better.

What do you see as the unexpected positives in the pandemic?

One unexpected positive was the end to people commuting, with the drastic reduction in pollution.

Another unexpected positive of the pandemic was it made all my clients look at their businesses differently, and the clients who succeeded had to pivot and create new products. They had to be nimble and agile. They essentially had to learn how to adapt to this ‘new normal.’

What are five ways that we can redefine success now?

Here are my top five:

1. Work-life balance, it’s so important. We all need it. The folks who say, “Oh, it’s not work-life balance; it’s a work-life transition,” and they try to change it, but it all means the same thing. Practice work-life balance in whatever way works for you. Just because some guru says, ‘this is how you must do it,’ doesn’t mean that’s how you must do it. For example, I work on vacations. I do an hour or two in the morning while everybody is asleep, and then I can be free for the rest of my day to do whatever I want.

2. The truth is that most small businesses never cross the seven-figure mark. As a business coach, I always say to own the business you want. Don’t get caught up in the revenue. You can own a profitable, beautiful six-figure company that supports your lifestyle and balance.

3. Instead of stressing out, create something in your heart. If you want a family and to run a successful business or have a successful career, it’s possible. There are always ways to make it happen. I always wanted both and learned how to merge the two successfully, and I’m so happy I did.

4. Make your health a priority. Don’t put off your health, no matter what. Even though growing a business is time-consuming and it’s easy to put your health off because you’re so busy, it’s a bad idea. When I prioritized my health, it increased my success in business, even though I was doing something for myself.

As part of number four, self-care is critical to redefining success. Take time for yourself by going on a retreat. Get a massage. Just do something you enjoy.

5. Don’t work with jerks or the wrong people. Life is too short. Be willing to fire a client, fire a vendor, or fire an employee. Surround yourself with those who are positive and encouraging. You will be much happier.

How would our lives improve if we changed our definition of success?

If we all changed our definition of success, there would be much more love in the world. We would love ourselves more. We would love each other more, and we would love our planet.

What do you think some of the biggest obstacles are that stand in the way of us actually being able to achieve that?

Well, number one is us. We tend to be our biggest obstacle. If we don’t get over ourselves first, if we don’t heal ourselves first, if we can’t love ourselves first, everything outside of us doesn’t have a chance of existing. But if we can redefine our success, set healthy boundaries, and take care of ourselves, it will be easier to care about other things. So, it starts with us. It begins with our actions and working on ourselves to show up better.

So, where do you look for inspiration when it comes to redefining success?

It will be spending time in nature, riding my horse, and being at the barn with my daughter. For me, that’s how I reconnect and find inspiration.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He, she, or they might just see this if we tag them.

Oh gosh, that is such a tricky question, but I would probably have to say Jennifer Aniston because she fascinates me. She’s one of my favorite actresses; she seems like a real person. It would be fun to hear her stories and see who she is as a real person, not what you see in the media.

How can our readers get in touch with you?

Readers can reach us at or via social media, and

Thank you for these fantastic insights. We greatly appreciate the time you spent on this. We wish you continued success and good health.