Jennifer Dawn

Find and use tools that work for you. Don’t leave your goals to chance, find tools you can use every day no matter what’s going on to keep you focused, productive, and on track.


Jennifer Dawn is the owner of Jennifer Dawn Coaching and founder of Best Planner Ever. She’s a serial entrepreneur who has grown two multi-million dollar businesses, loves working on her third now, is a successful speaker, and author. She serves high-achieving entrepreneurs through private coaching by helping clarify their business vision, refining their goals, and executing a strategy to achieve them.

Where did the idea for Jennifer Dawn Coaching come from?

I was asked to lead a national network of women entrepreneurs accountability and masterminding circles. I loved the work and from that found a love of coaching and eventually went out on my own.

What does your typical day look like and how do you make it productive?

Each day varies but it usually consists of client work and then working on my businesses. I have two companies – Jennifer Dawn Coaching and Best Planner Ever. To make each day as productive as it can be I use the daily planner (I created) and apply the principles to my own day. I start each day by getting clear on my A tasks (the 1-3 actions each day that will really move the needle on my goals) and then the rest of the day can be things like client calls, vendor meetings, interviews, staff meetings, etc… This way I’m certain to make sure no matter how busy the day gets, I’ve always done something to move forward.

How do you bring ideas to life?

I start with adding them to my Vision. Once there, I spend time thinking and planning about how I want to bring the idea to life. I used to just have an idea and then launch into the action steps to get it done. But I found that I made more mistakes, would have to re-do work, or the work ended up being wasted because a better idea came along. Now I spend a lot more time thinking and planning BEFORE I get busy. I’m finding I’m able to launch new products faster and easier than ever before.

What’s one trend that excites you?

The transition to PAPER planners. It’s one that I never left, but I’m seeing so many more people trending back to traditional paper and I love it.

What is one habit of yours that makes you more productive as an entrepreneur?

Every single day I get clear on my A tasks for the day. To be clear an A task isn’t just important, it’s something that pushes me outside my comfort zone. It’s something I might otherwise procrastinate or chicken out of. By doing 1-3 of these each day I’m constantly opening up new opportunities.

What advice would you give your younger self?

Slow down. Get help. Breathe.

Tell us something that’s true that almost nobody agrees with you on.

Happiness is a choice. Too many people think being happy is something that just happens automatically. I disagree. Being happy is without question a choice we make.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Find and use tools that work for you. Don’t leave your goals to chance, find tools you can use every day no matter what’s going on to keep you focused, productive, and on track.

What is one strategy that has helped you grow your business?

Be honorable and trustworthy in all that I do. Word gets around. People talk. Always, always do right by everyone.

What is one failure you had as an entrepreneur, and how did you overcome it?

I bought a log home company the same year as the real estate market collapsed. I ended up closing my doors within a year. It really sucked but I fought my way back. I took a job in corporate, paid back all the debt, and then eventually went back out on my own. It was a hard experience but now as a business coach I’m so grateful to have gone through it because I’m better equipped to coach my clients.

What is one business idea that you’re willing to give away to our readers?

Figure out more creative ways of reducing waste on our planet!

What is the best $100 you recently spent? What and why?

I purchased a new pair of muck boots. Very exciting I know. But in all the rain we’ve been having in upstate New York they are invaluable when I’m out at the barn. Having the right gear in bad weather makes all the difference!

What is one piece of software or a web service that helps you be productive?

My coaching software, Coach Accountable. I could not live without it and it’s made my coaching practice so much easier.

What is the one book that you recommend our community should read and why?

Essentialism by Greg McKown. We should all be saying a lot more NO’s and focusing on the one big thing we are really good at. A must read.

What is your favorite quote?

You’ll never do a whole lot unless you’re brave enough to try – Dolly Parton

Key Learnings:

  • Invest in a good daily planning tool that really works for you and will help you be more productive (not just getting more stuff done).
  • Get help in your business. It’s worth the investment in yourself and will shorten your curve.
  • Failure isn’t the end. It’s really an opportunity for growth. Yes, it may suck while you are going through it but you will come out stronger and better.


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