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How Personal Challenges Propelled Jennifer Dawn’s Coaching Success

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Carolyn Young is a business writer who focuses on entrepreneurial concepts and the business formation. She has over 25 years of experience in business roles, and has authored several entrepreneurship textbooks.

How Personal Challenges Propelled Jennifer Dawn’s Coaching Success

Jennifer Dawn, the visionary behind Jennifer Dawn Coaching, turned a period of personal adversity and injustice into an empowering business venture. After facing significant challenges due to a former partner, Jennifer emerged stronger, channeling her experiences into a successful coaching practice. In this interview, she shares her journey, insights on entrepreneurship, and practical advice for aspiring coaches and business owners.

Jennifer Dawn

From Adversity to Empowerment

SBS – How did you start your coaching business, and what was the main idea behind it?

Jennifer – I started my coaching business because I got screwed over by my partner. That’s what happened.

After I left corporate, I decided I needed to do something new, but I didn’t know what it would be, so I joined a networking group and ended up hitting it off with the owner. She gave me a position in this national network of women entrepreneurs. I was there for a year or two, and while I was there, I tripled their revenues and grew the organization. It was the first time that I had been coaching and mentoring, and I found a love for helping business owners with their businesses. However, my agreement with her had been equity in the company and a small salary. When it came time to honor the agreement, she chose not to do it, so I ended up having to resign. I was emotionally devastated by the whole thing.

Some of the women that I had been working with told me they still wanted to coach with me. That’s how my coaching practice was literally born overnight. I had clients right from the get-go, and I went on to grow this business. Now, we are a seven-figure coaching business.

That situation with my former partner was a great learning opportunity. You never know what can happen. Great things can be born from adversity. I always look back to that and remember that it’s okay if things aren’t going the way I want them to go right now. I should flow with it and see where it takes me.

As for that woman, people show you who they are. Evil would be a good word to describe her. I didn’t want to believe it. I didn’t want to see it. It was my husband who told me she was using me. I did not want to hear that but later realized it was the truth. She has since gone out of business, by the way.

Coaching Principles

SBS – Is it difficult to coach people in different niches, or are the principles the same?

Jennifer – We work with business owners across all industries. The principles are the same for me because when I coach a business owner, I always start from the inside out. I’m looking at their mindset, emotions, and belief systems because those are the things that are going to get in the way of the tactical actions that we take in the business. Everybody, of course, is unique and different, but the process I use is absolutely the same, and it applies to everybody. 

Common Challenges Entrepreneurs Face

SBS – Are there some common challenges that most entrepreneurs you work with face?

Jennifer – Yeah. Mindset. Mindset is the number one most common thing because as we think, we create stories that guide us regarding our successes or failures. This is not a bad thing, but the stories and thinking that we bring to this are everything. It really and truly starts with the mindset. That’s why I start with that in coaching.

We are all the same because we’re all human beings. Even though my belief system might be different than yours, and I might have to coach you differently than I would coach somebody else, in the end, we are the same.

Goal Setting

SBS – How do you approach goal setting with clients?

Jennifer – First, we get clear on their long-term vision — where they want to be in 3–5 years. Then, we do goal setting. After we look at their plans, we reverse-engineer them. For example, we take what needs to happen in 12 months and then break that down into 90-day objectives. What do you need to do in these 90 days to reach the twelve-month goal? The twelve-month goal drives to the three-year or the five-year goals. That’s the tactical, the action part of it.

We also get clear on the outcome of who you want to be as a person by the time you reach your goal. It’s not just about the money. The money is a benchmark or lets us know we’re on the right track. But at the end of the day, we’re all looking to achieve goals because we think it will make us feel a certain way — satisfied, happy, free, at peace. Yes, we want to work on the tactical actions, but we also want to work on the outcome of who you become as you achieve that goal. We tie the two together.

Essentials for Creating a Successful Business Strategy

SBS – What do you believe is essential for creating a successful business strategy today?

Jennifer – We’ve already touched on the mindset side of it, but today, to be successful in business, you also have to have determination and resilience. Business is tough, and you are, too, but you have to have that resilience and focus only on where you want to go and what you want to achieve. Pay less attention to what everybody else is saying and doing and other things that can distract you from your goal. 

Enhancing Marketing and Sales through Coaching

SBS – Can you help businesses improve their marketing and sales? 

Jennifer – I can. I created a tool called Inside-out Results Roadmap. We analyze a business from top to bottom to identify strengths, weaknesses, and gaps. We’re then able to create a strategic plan to address those gaps. Two of the things on our roadmap are the sales and marketing processes.

We took marketing a step further because we created an in-house digital marketing agency for our clients a few years ago. I was struggling with my marketing, and I saw my clients struggling with theirs. There are many agencies that charge a lot of money and don’t deliver, and there are many freelancers who claim to have skill sets that they don’t have. I got tired of all that, so I started my own agency and vetted all our contractors, so we know we work with people who know what they’re doing. In the process, I learned a lot more about marketing, too. You can coach on marketing and tell people what to do, but when you have an agency, it’s on you to demonstrate results because now the burden of responsibility shifts to you.

We also do a lot for sales, but very authentic sales that feel good to do. That’s what we teach and use in my business.

The Profit First Method

SBS – How can the Profit First method enhance business finances?

Jennifer – Profit First is a truly amazing tool. It’s one of the few things in business that, if you stick to it, absolutely works. I love it. I discovered it when I was leading that networking group of entrepreneurs. I brought Mike Michalowicz, the founder of Profit First, in as a speaker, and I remember sitting in the audience and listening to him speak. I realized I would have spent millions of dollars better if I had had this tool years ago.

When I left the networking group and started my own practice, Mike found out, and he invited me to lead his mastery group. For a couple of years, I led his mastery group, helping all of his coaches, bookkeepers, and accountants get on the Profit First system. Then, my business started taking off, and I had to step away, but I still use this system in my own business and with all my clients. I think it’s such a simple way of managing the cash in your business, making financial decisions better, and really understanding the finances behind a company. You don’t have to be a CPA and understand financial statements. Anybody can know how the cash flows through their business using a tool like Profit First.

Measuring Success in Coaching

SBS – How do you measure the success of your coaching? 

Jennifer – Nothing makes me happier than seeing a client get results. The result is that they hit their revenue goal, increased their close rate, improved marketing, or their business became everything they ever wanted it to be. A real result for me is seeing a belief system shift when I can change somebody at a core level of their being, helping them destroy an old belief system that wasn’t serving them and create a new one, fuel it, and then start to live in it every day. That’s the work that I love doing the most. Yes, I love the agency and doing email strategies. But when I can change somebody at the core and help them step into who they’re meant to be and start living in that potential, that, for me, is ultimate. That’s when I know my coaching is working.

Transformative Success Story

SBS – Can you give us an example of a client that achieved a major change in their lives with the help of your coaching? 

Jennifer – I have an amazing client whom I’ve been working with for six years. When she first came to me, her business revenues were on the decline, and she absolutely hated her business. She was super frustrated and wanted to get rid of it. When we started working together, we made some changes in the business that helped her start loving it again. 

She had never hit a million in revenue, though she had gotten close (when she came to me, the revenues were around half a million). In our first year of working together, we got revenues back in the right direction. In the second and third years, we were on track to reach that million. Then COVID hit. Her clients are schools, and those shut down, so she was so afraid that she would lose her business. However, she didn’t.

We pivoted and created a digital product. That first year of COVID, she hit her goal of seven figures and ended up having her highest revenue year. Now, we’ve quadrupled her revenues, and she loves her business more than anything.

She wrote the forward in my new book, Apple Stand because she was proof of how this really and truly works. If she had gotten rid of her business back then, it wouldn’t have been worth much. Now she’s going strong, has a beautiful business, has grown the team, and has quadrupled revenues.

Advice for New and Aspiring Coaches

SBS – What advice would you give someone who just started their coaching business or is planning to? 
Jennifer – If you’re going to start a coaching business, my advice is to get a coach. How will you sell coaching if you’ve never invested in it and don’t understand what that process is or what it feels like to invest in yourself or put a big chunk of money down and take that risk? I can speak from experience. I’ve helped so many coaches shorten the curve on getting their business off the ground because if you get a certification and they teach you how to be a great coach, they don’t teach you anything about running a business and getting a new business off the ground. You may think you’ll have all these clients. Will you, though? It will be pretty tough if you don’t have a business and a marketing strategy and know how to close on a discovery call. Coaching for yourself will be the best investment you can make and will help you launch a successful coaching practice.


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How Personal Challenges Propelled Jennifer Dawn’s Coaching Success