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Chelsea Leigh Trescott
Chelsea Leigh Trescott Breakup Coach and Podcast Host of Thank You Heartbreak
2y New York, NY, United States Story
Thank You, Heartbreak: Spotlighting Creatives #6

So much of our fear stems from or is perpetuated by the stories we hear and the stories we tell ourselves. Breakup stories are some of the worst and most damaging. Seldom do we hear of a breakup that makes us think, “Wow! If only heartbreak had motivated me in that direction, then, I would have let go sooner and feared less for myself.” The reality is, these stories are out there. You just have to ask for them. 

For this Q&A series, that is exactly what I did. Over the following weeks, various creatives will get honest with themselves and the Mogul community about how their breakups landed them on top. 

You’ll be hearing from women who attribute their professional success to heartbreak and credit their breakup for being the catalyst for personal transformation and professional reinvention. 

My hope is that these stories will encourage new thinking and even comfort you, that they will help you fear less and love greater. And perhaps most importantly, my hope is that they will help you breakupward and focus on all that is possible for yourself. 

A divorced mom, who transformed her family law practice in the DC Area after her own divorce in 2005, Regina DeMeo, 44, of N. Bethesda, MD has gone on to become a top matrimonial attorney in DC and MD, where she has been helping couples with custody and divorce issues for over 17 years. 

In 2010, the Washington Post wrote an article about her post-divorce transformation, paving the way for her to become a top legal commentator and media regular. Now focused on growing her family law practice while working on her column "Love & Money" for Wealth Strategies Journal, Regina opens up to us next about how she rose to new heights in the wake of her divorce. 

1. Do you think your success is a product of something you already had inside of yourself but relationship priorities either delayed or distracted you from going after or do you think solitude and loss themselves drove you to want more for yourself?

I definitely did not understand the emotional loss people suffered in a divorce until I went through it myself. As I came to understand the pain, the anger, and the uncertainty, I realized I needed to focus more on the emotional side of what my clients are experiencing, not just the legal side. My legal skills and writing abilities were always very strong, and I was able to use social media to disseminate my ideas. Certainly having more time on my hands helped.

2. How did you adjust your mindset after your breakup so, instead of focusing on what was lost, you focused on what you could gain?

You cannot go back and un-do the past. All you can do is learn from your mistakes and move forward. I had a business to run and a kid to raise, so I simply had to focus on planning for the future.

3. If every person that comes into our lives is truly an opportunity for us to learn and grow, what do you believe your ex was there to teach you?

I was with my ex-husband for over 10 years, and we had a lot of good times together. However, I was only 20 when I met him, and there were major core values that we did not share. Once my son was born, it was hard to ignore these major differences, and we drifted apart. But despite all our differences, we have worked together to put our child's needs first, and we both love him deeply. 

If it wasn't for my ex, I would not have my son, and perhaps I would not have started my own law practice (which he encouraged me to do). Also, the last 10 years on my own, I really have proven to myself (and others) exactly how strong and independent I am, and that has been a source of inspiration for others.

4. How did you grow up and grow into yourself because of the relationship?

When I met my ex-husband, I was only 20 and still in college. I had not gotten into law school yet, or experienced “real life” working a full time job, maintaining my own place, let alone dealing with work-life balance issues which began once I became a mother at age 31. My ex-husband was supportive of all my endeavors, in fact it was his idea that I should open my own law firm after our son was born so I could run my practice my way. He essentially saw me grow into who I am today. When he met me all I had was a vision of what I wanted to be, and what I love most is that he always believed in me.  

5. One of the most popular sayings is, time heals all wounds. What did you discover over time that helped you heal your wounds most?

After a breakup, you need time to analyze why things went so wrong, and what could have been handled differently. For me, having a life coach during this process was critical. At the same time, you need to remember who you are as an individual—what routines are important to you? What are your individual goals? You need time to reconnect with your family and friends, and let love back into your heart. 

For me, returning to my own rituals that make me happy, and hanging out with loved ones, always puts me back on course. I always try to plan a quick getaway and, while I am traveling and unplugged from everyone else, I map out my priorities and figure out my next steps to achieving the things that matter most to me. Also, daily exercise, meditation, journaling, eating healthy and getting plenty of sleep are all an essential part to my healing process. 

6. Ingrid Bergman famously said, “Success is getting what you want; happiness is wanting what you get.” What do you have today that you wouldn't have imagined could make you so happy?

I agree that success is how you define it for yourself, but equally important is the ability to be at peace and just enjoy what you have versus constantly wanting more. So for example, I am enjoying being on my own, spending time with family and friends versus lamenting the lack of a suitable male companion. 

Also, since my divorce, I have not been able to purchase a big house, but I've come to appreciate that owning a 2 bedroom condo is really all I need, and I don't actually miss having to pay someone to clean the house or mow the lawn. I also no longer drive a Mercedes that costs $800/month, but my 5 year old Mini Cooper that's all paid off runs just fine and is super easy to park. I may not have a yard where I can grill, but I actually enjoy interacting more with my neighbors who I see every day as we get the mail, or share the elevator ride, or when we BBQ by the pool during the summer.  

I didn't plan on being a single mom but it turns out as a result I've developed a far better appreciation for what my clients and my own mother went through. Also, I've learned to enjoy being with my son when he's with me, and finding time to pursue my own activities like yoga or running when he's with his dad. 

Ultimately, I love the insight I have been given into the importance of financial literacy and the complexity of relationships, and the real reason I have that depth of knowledge on these topics is because of my own divorce—getting through it and moving on.

My biggest take away is this: The humility you gain from suffering a major setback actually can be turned into one of your greatest assets. Overcoming painful losses, and moving forward, is the best way for you to recognize your own strength. And if you can forgive yourself for the mistakes you make along the way, let go of the anger and disappointment, and instead reframe things by appreciating what you have accomplished and obtained to date, that is really the only way you can sustain any long-term sense of happiness.   

7. What would you tell someone who was in need of finding the silver lining in their breakup?

You may not see the reason why things had to happen the way they did for years, so don’t focus too much on the why and torture yourself thinking about what was once there or what could have been. The point is to focus on what you want to do moving forward. The goal should be to take this opportunity to figure out what you want to do for yourself.

When you are on your own, you can really think about what you want to put on your agenda without having to compromise or sacrifice for others. What’s on your bucket list? What is your mission in life? What is your vision for the future? How will you define success for yourself?  Answer the key questions, make an action plan, and then go do it with no apologies. 

As you work through all of this, you’ll start to see the silver lining and, in fact, you may just find that your success blasts away any and all doubts that the breakup was unfortunately a necessary step to self-actualization.

8. If you could say or ask one last thing to your ex, what would you rather do? And what would the statement or question be?

Well, when you have kids, you have to stay in touch with your ex. I guess if there ever came a point where I knew I’d only be able to say “one last thing” to him, I would definitely say “thank you—not just for my son, but for believing in me and sharing some great years together.”

9. In your opinion, what does it mean to breakupward? What would that look like to you?

I take that to mean that you break up and move not just forward but up, onto bigger and better things. To me, that means that each one of us would take the set back as a learning opportunity and we’d all grow from that experience (something Brené Brown advocates for in her book “Rising Strong.”) 

Ideally, we should all be able to appreciate both the good and the bad things from each relationship and, as we move on, we step forward with greater insight, more mindful of our needs and wants, as well as those around us, and as we trek ahead we learn to maintain appropriate boundaries, live with greater honesty and integrity, and above all show mercy and grace towards those that cross our path in the future.

Connect with Regina yourself on LinkedIn, Twitter, her YouTube channel GenXSmartie, and find out how you can work with her next on her website


An Advice Columnist and Breakup Coach trained and certified in Solution-Focused Life Coaching, Chelsea Leigh Trescott helps her clients turn their sob stories into silver lining breakups. For a chance to be featured in her HuffPo advice column or Mogul Q&A series write [email protected]

Visit for coaching services. 

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Chelsea Leigh Trescott
Breakup Coach and Podcast Host of Thank You Heartbreak

A Breakup Coach trained and certified in Solution-Focused Life Coaching, Chelsea Leigh Trescott is the host of the podcast Thank You Heartbreak and the founder of Breakupward—a movement encouraging men and women to use heartbreak and setbacks as an opportunity to launch themselves to a greater [...]

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