Jen Guidry Fassler: Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life

An Interview With Jake Frankel

Authority Magazine Editorial Staff
Authority Magazine
11 min readFeb 11, 2024


Pray more. Praying always gives me peace. Pray about your decisions and your thoughts. You will know deep down in your soul if what you are feeling is true. You will feel it and it won’t go away. That is when it is time to take the plunge.

Many successful people reinvented themselves in a later period in their lives. Jeff Bezos worked on Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Kroc was a milkshake-device salesman before starting the McDonalds franchise in his 50s.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Jen Guidry Fassler.

Recently retiring from being one of the Top Mortgage Loan Originators in America, one of the Top 10 Most Empowering Mortgage Women in the World and from leading teams and branches for almost her entire career, Jen Guidry Fassler has transitioned into a transformational coach for women who want to make profound changes in their life. She owns Brilliantly Bold (, where she works with women to show them how they can have high success and life balance. She is also a two-time award-winning author and a powerful empowerment speaker.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I am originally from Buffalo, NY. While I am glad that I don’t live there anymore, I am grateful for growing up in there. It put “hair on my chest” (HA!) for lack of better words. It was definitely a harder life, for sure. My childhood was filled with a lot of trauma, as we endured abuse…but also had some great times as well. Although times were mostly tough, I would not change a thing because it made me who I am today.

From the time I was young, I just knew that I wanted to do really well in life. Like I was always meant for something more. I started working when I was 11 and quickly learned the importance of a great work ethic. If I wanted something, I earned it, as it was not given to me. Although I hated it back then, I appreciate those life lessons because they made me stronger.

When I was 19, I quit school, sold everything I owned and moved to Southern California. Through a series of serendipitous events, I got into the mortgage business.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“It is not where you started, it where you end up that counts.” I don’t even know who originally said that, but it has been my mantra since the first time I read it as a kid. It showed me that it didn’t matter where I came from or how I grew up. I could do something with my life. It was up to me.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

I believed I could. I remember back in the 4th grade, I got my very first “A.” Mrs. Brown was my teacher back then and she used to be so encouraging to me. I remember she told me that I was capable of so much more than I was giving myself credit for. From that moment on, I got all A’s. I even received an academic scholarship to college and was in the honors program. That ONE “A” changed my life. I believed I could do anything from that moment on. I always thought I was meant for something more, but I was really limited in my thinking. My good grades propelled me into a whole different mindset. What ELSE could I do? The possibilities were endless…but I was going to find out.

I worked hard. I talk about this a lot when I speak to my audience. Work ethic eliminates fear. When you work, give it your all and you will never be hungry. Success is not something that you just get. You have to work at it every day. Work hard. Get better every day. When you are at work, work.

Be Resilient. Recently, someone asked me what my best quality was, and without even thinking, I blurted out, “resilience.” To me, it is the art of dusting yourself off and getting back up when you get knocked down. In life, you WILL have pain…but you get to choose whether it is the pain of being a victim of your circumstances or the pain of growth. This girl has been knocked down so many times with major illnesses, betrayal and setbacks and each time, I just got better.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

I was the youngest everything in the first 10 years of my career. Youngest loan originator at my company, youngest branch manager at a national company ever, youngest regional manager and so on. I didn’t climb up the latter, I flew up…and quickly. Wherever I went, I was at or near the top in production. Before exiting the mortgage business just this past year, I was named one of the Top Most Empowering Mortgage in the World. I was one of the Top Women Loan Originators in the USA, and the Top Loan Officer in San Antonio for many years.

I made a very good living (sometimes in the millions) and I could have easily stayed on that track, but I kept on getting “tugged” in a different direction.

And how did you “reinvent yourself” in your Second Chapter?

Most everyone thinks I am crazy…giving it all up to start all over, but I am trusting my intuition. God has other plans for me. So, I gave up a career where I was and could have continued to be completely “set” in. I could have gone on for another 10 years easily on autopilot, continuing to make a beautiful living.

BUT, those “tugs” were relentless and finally, I had the courage to just do what I had been talking about for many years. So, I took the leap of faith.

I know that I am meant to coach and to speak to other people. I want to show others how to do what I did. I want to show them that it doesn’t matter where they came from or what happened to them in life, that they can be both successful AND balanced.

I completely started over. The “old Jen” that everyone knew as this mortgage powerhouse is now “Jen 2.0” and I have never felt happier.

I do still help Kristin, who took over my book of business on the mortgage side, but I no longer originate any loans.

The joy that comes from speaking success and hope into someone else’s life has been incredibly fulfilling to me…and now I am wondering, “What took me so long?”

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

It has been on my mind for a few years, but I was just too “comfortable” with my situation to take the plunge. But the feeling to make the change never went away. It is hard to describe…like I was constantly being pulled in a different direction that was scary as heck to me, but at my core, I also knew that this is what I was meant to do in this part of my life. Time to take the plunge and give back.

I also had to put my ego in check, which some people will understand. I was used to being known as the #1, now I am not. I had to be okay with that.

I have faith that my bold move will pay off, because I can feel it in every part of me. I have peace.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

I discovered that I had a powerful intuition about people and what they need. This is a skill that I knew I had, but really never maximized. Coaching my clients has been extremely rewarding in ways that I had never felt before. I get to see profound changes in them and it is amazing.

However, my skill set that I have really been using more is motivational and inspirational speaking in the corporate setting. I have realized that my story is powerful. The things I had to overcome provide moving lessons for others.

I have joined a speaking academy to really develop more of my speaking skills. It is a LOT of work, but I know that it will be worth it.

How are things going with this new initiative? We would love to hear some specific examples or stories.

I have had the privilege to work with a lot of women in coaching, really without having to do marketing (yet). It is like God is bringing them to me and when I am done with a session, He is like, “See? I told you THIS is what you were meant to do.” I just had to trust.

Also, I have had the chance to speak at a number of events. To look out in the crowd and see smiles or tears coming from someone’s face that my words touched…words cannot even describe how that feels. It just reinforces that I made the right decision.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My wonderful husband, Michael. He really has been so supportive of me. When everyone thought I was crazy for giving up my old career that had been so good to me, he said, “Jen, I support you 100%.”

He has been there next to me the entire way and I am so grateful to have such a great husband as him.

Can you share the most interesting story that happened to you since you started in this new direction?

I know you are probably expecting some great story about something that happened, but my answer is this: I came home to myself.

And it is about time.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

Sure, I did. Classic Imposter Syndrome thoughts.

I had thoughts like, Who would want you to coach them? Or, why would anyone want to hear your story? What if you fail and can’t make money?

So, I told those thoughts that they are not facts. Feelings are not facts. I WOULD want me as a coach. My story is powerful. I know that deep down, I am now doing what I am meant to do at this part of my life and there are a lot of people that can learn from me.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

Besides my amazing husband, I have some incredible friends. Everyone is excited and happy for me.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

I have a shirt that says, “Comfortably UNComfortable.” Getting uncomfortable is the only way to grow. To me, really it is about having faith.

Sure, I could have remaining in my old career path and have retired completely in just a few years, but I would have been full of regrets.

When I see my future, I see me on big stages. I see me helping millions with my books and my words. All of that meant me jumping off the ledge and knowing that the net would appear. It was scary. It has been very uncomfortable, this starting again stuff. However, I know that with every inch of my soul that I am stepping into something better than I can ever imagine.

What are your “5 things I wish someone told me before I started” and why?

  1. Listen to that voice inside of you. It is there for a reason. If you have thoughts that keep telling you that you should change your path in life, those “thoughts” are probably right.
  2. Don’t be afraid to be uncomfortable. The pain of growth is invaluable.
  3. Don’t give a crap what anyone else says. Yes, when you make a change that makes no sense to other people, they will think you are crazy or try to encourage you to NOT do it. Don’t listen. Trust your intuition.
  4. Pay attention to serendipity. Things start coming together and people will enter your life for a reason when it is time to make a change. Pay attention and you will be astounded at what or whom magically appears into your life.
  5. Pray more. Praying always gives me peace. Pray about your decisions and your thoughts. You will know deep down in your soul if what you are feeling is true. You will feel it and it won’t go away. That is when it is time to take the plunge.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I am a big “random acts of kindness” girl. It is one of my favorite things. Imagine a world where everyone just did random acts of kindness every day!!

We are very blessed that some very prominent 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 with, and why? He or she might just see this if we tag them. :-)

Brene Brown for sure. She was part of my inspiration because she was in her 40’s when she did her Ted Talk that changed the trajectory of her life. I was like, if she can do it, so can I.

How can our readers further follow your work online?

@thejenguidry — Instagram or my work website is

Thank you so much for sharing these important insights. We wish you continued success and good health!