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The Courage To Find Your Dream Job (Again) With Kerry Ann Rockquemore

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With the launch of Everyday Courage, Kerry Ann Rockquemore joins the show to share her journey. 

Kerry Ann’s Story

One thing that Kerry always knew about herself is that she wanted to be a teacher. In her family, many people were teachers and her father was a school principal. For her, success was growing up to be a kindergarten teacher.

Based on this constrained world view, she never planned on making a lot of money. Instead, she planned to go into the service of teaching with a safe and comfortable career. The epitome of success would be to become a kindergarten teacher and get married. Throughout her life, the root of this message was always centered around security.

The unspoken message is, pick something that is doable. Do that thing. Keep your head down. Stay quiet and good things will happen to you. 

However, the dream of becoming a kindergarten teacher changed as soon as she stepped into the classroom. She did not enjoy spending all day with 30 five-year-olds. In fact, one little girl told her that she was mean and didn’t even like kids. Spending some real-time in the classroom was a wake-up call for Kerry Ann.

Changing Paths

She realized that she didn’t want to be a teacher but she wasn’t sure where to go from there. Plus, this was the last year of her college degree.

At that point, she came into contact with a professor that changed her life. For Kerry Ann, this professor was not just a teacher but also an intellectual authority. It was an inspiring connection for Kerry Ann. In fact, it was the first time she had ever thought about being a professor. But the direct contact with this example of what was possible led Kerry Ann towards the career path of a professor.

There is so much power in proximity, and in community. I would say if I had a regret, or something I could do over in my 20s I would have spent more time, and more energy, and more money getting into proximity. Because it’s so hard to imagine things, to really rewrite your story and your identity outside of that proximity. 

Kerry Ann went down the path of becoming a professor by pursuing a Master’s and Ph.D. At some point, she decided to change trajectories again. She transitioned into entrepreneurship with the help of another female mentor. This entrepreneur laid out the process for Kerry Ann and believed in her ability to succeed. With encouragement from this entrepreneur, Kerry Ann found out that the path to entrepreneurship was not as long as she had once thought. Once she learned that, making the transition was more manageable.

A Path To Everything

If you want to achieve something, there is a well-worn path. However, you need someone to demystify it for you. Otherwise, you may believe that the path is 100 miles long when in fact it is just 5 miles down the road.

Once you see the path, then you just have to follow the steps. It might give you permission to start a journey that you thought was too overwhelming at first. This process starts with someone that believes in your dream. When someone sees something in you, it can encourage you to continue down the unfamiliar path.

We love seeing other people take action. The hope is infectious. Once people have walked the path they don’t think it’s that long of a path. Well that’s about a 100 mile jaunt there, like I don’t think I can even start. And people who’ve got are like ‘eh, it’s like five miles. It’s going to take some time, but this is not an ultra-marathon’.  

Find someone to talk to about your dreams that has already walked down the path. They may be willing to share their own experiences.


If you are struggling to find the right path, it can be frustrating. However, it doesn’t have to stay that way. Here is how Kerry Ann recommends moving forward.


Start with a piece of paper. First, draw a circle in the middle and fill it in with who you are. For example, Kerry Ann is a teacher. Next, draw lines around that circle with the possibilities for your future. Think of everything that you could do with your gifts and talents. Try to think of 10 to 12 possibilities.


Once you have some ideas, it is time to explore them. Simply start calling people that do the things you’ve thought of. Ask them what it is really like on a day to day basis. A conversation is the fastest way to move forward or cross it off the list.

Isolation is the dream killer.

If you are really trying to figure something out, you won’t be able to figure it out in your own head. A conversation with someone can really help. Your intuition will let you know if you are on the right path.


If you find something that you are excited about, then do a short-term experiment. Once you get yourself into something, you’ll know if it is a good fit. If something is working, you’ll feel energized instead of drained at the end of the day.

If we are really trying to figure things out, it’s not something we are going to figure out in our head. It’s something we are going to figure out by putting ourselves in positions that make us uncomfortable… that’s when our real self is going to show up. 

Think of this process as similar to trying on clothes. Not everything is going to fit just right, but that’s okay. You might find that you like certain parts of your experiment, but not everything.

Learn The Lessons

As an experiment of her own, Kerry Ann went to New Orleans for training to become a preacher. It did not go well. She figured out pretty quickly that being a preacher was not going to be a fit for her. But her teacher gave her some valuable feedback that changed her life.  He said

Baby girl, you gotta take up some space!… You are a very small person. You have to energetically take up space. You have to fill a room. You have to get all up in the bass of your voice and you have to learn how to project. You have to do more because you’re little… What is it that’s uncomfortable about being seen? Why are you hiding in your body?

It was a while before she understood what he was even talking about, but it sat with her. She went to therapy to figure out why she was hiding herself. And eventually, she figured out and today takes up all the space she wants!

So even though some might call the preacher training a “failure” since she decided not to become a preacher. But the lessons she learned have helped her life going forward, so it’s not a failure in any way.

Enjoy The Process

Kerry Ann enjoys the process of finding a path that will work for her and then making it happen. However, many people tend to love the outcomes but not the process.

Instead of focusing on the outcome, you should focus on the process. If you haven’t stuck your toe in the water, then you cannot fixate on the goal. After all, you might not enjoy any part of the process that would make that dream a reality. Many people want to have written a book but hate the process of actually writing it.

One amazing thing about financial freedom is that it gives you permission to lean into the question. You can experiment until you find what your unique gift is and offer it to the world. For Jillian, her unique gift is helping people laugh and cry and to hold conversations that facilitate that happening. Throughout this podcast, she hopes to allow people to laugh and cry on their journey.

In this episode, Jillian recommends Dropps. Dropps laundry detergent pods are both eco-responsible and economical. They contain no unnecessary fillers or dyes and they’re delivered in a 100% recyclable, compostable box. Use coupon COURAGE at checkout to get 15% off your order and free shipping.

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Choose FI has partnered with CardRatings for our coverage of credit card products. Choose FI and CardRatings may receive a commission from card issuers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities. Disclosures.
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