Meet a Mom: Leslie Randolph | Chicago North Shore Moms

Hello friendly faces! It’s that time of the week!  We’re back with a new CNSMoms’ Meet a Mom spotlight brought to you in part by Mary Gifford of Gifford Law.

This week we’re pleased to introduce Leslie Randolph, Highland Park Mom of two, life coach and founder of The Coach Chronicles.  Welcome Leslie!



Please introduce yourself. Where are you from originally? What city do you live in now? Please tell us one or two reasons why you love where you live. How many kiddos do you have and how old are they?

My name is Leslie Randolph, I am a Highland Park resident and a Highland Park native. I am actually a fourth generation Highland Parker, so the hometown pride runs deeps. I have two kids that are 6 and 8 years old who are both in the dual language program at Red Oak.


What is one thing people would be surprised to know about you…

My family and I lived in Johannesburg, South Africa for nearly five years. My son was 13 months old, and I was six months pregnant with my daughter when we moved for my husband’s job. We went knowing no one and nothing but we were committed to making the most of the experience. And we did. I have never been in a sorority, but I assume my day-to-day life looked a bit like rush– actively trying to meet new people and learn new things.

You might think this sounds super scary– and if you like to Google places before you go then you would definitely think it was terrifying – but I didn’t. I went into this experience with the mindset that it was going to be the best chapter of my life, and because of that perspective, it was.

I am not saying it wasn’t hard or that there weren’t challenges – there were loads. I dealt with a lot of anxiety about the unknown, of which EVERYTHING was. I struggled with panic attacks, spending hours in a hospital convinced that I was having a heart attack. I experienced homesickness, rejection, indescribable frustration and so much fear. There were many dark days. But when I reflect on my experience, I believe I always came back to the mindset that this chapter will be whatever I make of it. That thought was my anchor and with it I was able to get through each day, even the hard ones.


Please introduce your endeavor. When was it established? What brought you into that specialty? What is your professional background? We want to hear your story A-Z.

When I was living in South Africa, I experienced an identity crisis. I had worked my entire adult life, and for the first time, I was without a career to help define me. I felt lost. I love being a mom, but I also LOVE working. This is when I hired my first life coach.

I loved the unbiased perspective, accountability, and encouragement my coach provided as I navigated the next steps for my career and, unexpectedly just life in general. See, while I hired her to help me figure out my next job, the lessons I learned were applicable in every aspect of my life.

While working with her, I heard a voice in my head that said, “I would LOVE to do this for other women.” I’ve always been compelled to help others and to make the world a better place. This was exactly what my coach was doing. But that voice was quickly drowned out by a louder one that said, “Don’t be ridiculous! Life coaching isn’t a real profession” and “You can’t start a new career now!” I let the louder voice win the internal argument.  Shortly after working with my coach, our family moved home, and I made the choice to go back into public relations. I was working at my new firm for a month before Covid-19 was declared a pandemic.

Like so many others, I was navigating the new normal of being a mom, as well as a new employee who had really high expectations of herself. It was too much for me. I kept saying, “I feel like a waitress in roller-skates. I am going to drop something.” My anxiety and imposter syndrome were at an all-time high.

I once again hired a life coach. The story ends (or begins) with me finally listening to that voice which was showing me my calling. To do this work for others.

Last year I launched a life coaching practice which is dedicated to helping women and teenage girls get to know, love, and believe in themselves so they can live the life of their dreams.

I also started The Coach Chronicles as a platform to share my lessons learned as a coach and an eternal work in progress. I have been every woman I want to help so I welcome the opportunity to share my “AHA” moments.



What’s most rewarding about this endeavor?

There is no greater feeling in the world than supporting someone to make positive changes in their life, to achieve a goal, or to witness the subtle shifts that occur when someone starts to love and believe in themselves. Each client’s transformation is unique but greater self-confidence is a universal result of this coaching.


Who should hire a career (life) coach and why should people hire a career (life) coach?

Life Coaches can help individuals in every walk of life. I work specifically with teenage girls and women who want to feel empowered in their life, skin, career, and relationship. You might consider working with a life coach if you lack self-confidence, have lost your sense of purpose, struggle with imposter syndrome, feel out of touch with your dreams, are considering a massive life change, or are working towards a personal or professional goal


Who are your influencers and/or mentors that have helped you get to where you are today and/or continue to inspire you?

I come from a long line of hardworking women that showed me you can achieve anything if you believe in yourself. My grandmother was a wildly successful working woman before many women were even in the workforce. So too was my mother. They never apologized for their ambition or their accomplishments. I want to be that example for my kids and to also be there for the small moments that make up their amazing lives. By starting my own business, I am able to do both.


What advice can you give other mamas out there who are looking to start a new business in the current climate?

Anything is possible when you believe in yourself. It doesn’t matter what the current climate is or what skills you do or don’t have. If you believe in yourself then you will figure out the rest.


What are the 2 most common questions that people reach out to ask you?

People often ask, “How can I generate more self-confidence?”

Self-confidence is a muscle that needs to be stretched and strengthened every day. You can cultivate self-confidence by thinking highly of yourself and telling yourself every day that you are amazing. Chances are, you don’t do this (and you’re not alone). So many of us focus on what’s wrong with us, what’s lacking, and why things won’t work versus why we are perfect as we are, where we are excelling, and what’s possible. This is so subtle that you might not even realize you’re doing it or how long it has been a pattern. It has become your default setting. To generate more self-confidence, you need to disrupt the default thinking.

One easy way to make this a daily practice is to start intentional journaling. Take a few moments each day to write down something you are proud of achieving.

I also hear “How can I feel better?” often.

Your thoughts are going to determine how you feel, so if you’re focusing on the negative you are going to feel negatively and you are going to attract negative energy. If you want to feel better, then you must start thinking differently. Start paying attention to the soundtrack in your mind. What gets more airtime – your strengths or your weaknesses? What’s beautiful about your life or why others have it better? All the opportunities that lie ahead of you or the obstacles in your way?

This is not to say, “just think happy thoughts!” These past few years have been hard for so many of us. Loss, grief, sadness – these are real human emotions that need space and grace but if you are feeling stuck and WANT to make a change then you need to shift your thinking. And here’s the best news: every thought you think is a choice. If you don’t like how you’re feeling, then you can choose a different thought. When you do, you will feel differently.


What’s on the horizon for you personally AND your business?

Professionally, I am thankful to say that my practice for one-on-one coaching is thriving, and I plan to launch group coaching programs later this year.

Personally, I look forward to traveling again this year with my family. We all got bit by the travel bug when living overseas and have missed it so much. A few upcoming destinations include Austin, Scottsdale, and Panama!


How can we connect with you for more information?

Visit for more info or reach out at [email protected] and let me know how I can help you!

Connect with me on Instagram at @The_Coach_Chronicles, Facebook and on LinkedIn.

About Our Meet a Mom Sponsor

A very heartfelt thank you to CNSMoms’ Meet a Mom sponsor, Lake Forest mom of three and owner of Gifford Law, a solo Estate Planning Firm (wills and trusts). Mary, we appreciate your support of local moms in our North Shore communities! Learn more about Mary by visiting her Meet a Mom spotlight here!

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