Meet Jessica Medina

We caught up with the brilliant and insightful Jessica Medina a few weeks ago and have shared our conversation below.

Jessica, thank you so much for making time for us today. We can’t wait to dive into your story and the lessons you’ve learned along the way, but maybe we can start with something foundational to your success. How have you gone about developing your ability to communicate effectively?

I didn’t always want to be a lawyer. In fact, I dreamed of a career in musical theater when I started high school. I loved drama class, being in the school plays, chorus, and all the Broadway hits of the time. But I was also very good at academics and thought I might pursue something on the intellectual side…enter law! It seemed like the perfect mix of performance and intellectual rigor.

Uh, not really.

But I carried my performance skills with me to law school, winning Best Oral Argument during our mock trial competition.

I also honed my communication skills working as a retail clerk at the (then) popular clothing store, Express. I was in charge of the “wrap desk” which meant I dealt with customer returns, opening credit cards, and checking out customers. There were lots of personal interactions throughout the day and I learned to listen with empathy, to ask clarifying questions, and to provide clear explanations for our policies and procedures.

This all served me well once I started counseling clients as a lawyer.

And it continues to serve me well as an Accredited Financial Counselor helping lawyers figure out the money.

I am adept at asking good questions, listening for details, and empathizing with my clients’ struggles and worries. I’m also very good at explaining complicated financial concepts in a way that makes sense.

And with my performance background, I make it fun!

Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?

First came law, then came passion. I practiced law in the DC metro area for nearly 14 years before deciding to pursue my true calling: financial coaching.

I was a single mom of twins, had graduated from Columbia Law School with hundreds of thousands of dollars of student loan debt, and was just trying to keep my little family afloat while I juggled a new life as a law firm associate.

To say those times were stressful would be quite the understatement!

I spent eight successful years at a large DC law firm(several more than originally anticipated), but always saw myself as a public servant.

I left Biglaw for the United States Securities and Exchange Commission (SEC), taking a hefty salary cut but loving the idea of working for the people.

The Division of Enforcement at the SEC works tirelessly for those who have been defrauded by the financial industry, and my work there opened my eyes to how shady characters in this area can be and how regular folks are in need of personal financial guidance to avoid becoming vulnerable to such schemes.

My five years at the SEC were also a turning point in my personal financial journey.

I realized I was not passionate about the practice of law, just the part that involved helping people, and I needed to get my financial house in order so I could retire from my legal career and still support my family.

I achieved that goal in 2018 and left the SEC to pursue my certification as an Accredited Financial Counselor® (AFC®.)

The AFC® training and examination broadened my knowledge and experience both in the space of personal finance education and counseling. I have been working with clients on their personal financial journeys since I left the SEC and look forward to continuing to pursue the highest standards of excellence in educating and tailoring my guidance to each client’s unique situation.

I’ve now helped hundreds of attorneys reframe the way they think about their finances and how they affect their career and life choices. I’ve also assisted many of them with creating a path to student loan repayment (often times including forgiveness!) And it’s always a win when I get an update from a client that they’ve taken that new job, payed off their debt, moved into their dream house, or hit their savings milestone and they’re feeling so confident about all the money stuff.

My career has taken many turns, but I now see how each phase fit perfectly into the grand scheme of becoming a financial coach and serving those attorneys who are ready to pursue their true passions, no matter the salary.

My many years as a lawyer honed my counseling and listening skills so I can be a better ear and accountability partner for my clients.

My stint at the SEC heightened my sensitivity to the shady underbelly of the financial industry and the great need for objective, unbiased guidance.

My AFC® training refined my personal finance knowledge and deepened my counseling acumen.

And, my own journey taught me how changing habits and planning can open up new possibilities.

I believe lawyers are some of the smartest, most effective people in the world (self-serving, but true!). And every attorney deserves to use their law degree however they choose to put more good out into the world.

I may not practice law anymore, but I still think like a lawyer. So my clients never get a rigid set of rules, but rather the best solutions for their specific facts and circumstances. It’s the best way to create a life you absolutely love.

Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?

I believe making money more approachable and fun is a big part of my success. And some of the most important skills I developed over my career include my command of personal finance topics important to lawyers, my listening skills, and my sense of humor.

One of the things that helped me build up all three of those skills was free speaking engagements.

I did free webinars, workshops, and presentations for Bar Associations, law school alumni groups, lawyer coaching groups, for local libraries, and on my own for three years before someone offered to pay me.

And those years of speaking cemented my reputation for expertise and approachability when it comes to lawyers and money.

I also met a ton of people this way who then were able to speak about my work and stay connected to me either on social media or my email list.

I’m now a paid speaker and continue to share my expertise in this format in order to increase my overall impact and make sure potential new clients can get a taste of how I work and my philosophies when it comes to money.

I also put on a pretty good show!

Alright so to wrap up, who deserves credit for helping you overcome challenges or build some of the essential skills you’ve needed?

One of the things they don’t teach you in law school is marketing. And selling your services as an attorney in a Biglaw firm is practically frowned upon, though that may be changing. But it was definitely shunned when I was practicing so I never really understood sales other than my days at Express.

So I was a total newbie to social media when I started my business.

I made the mistake of thinking I needed to completely redefine myself and who I was in order to show up in a space I had not traditionally participated in.

As a lawyer, I spent my days reading other people’s emails and social media posts as part of litigation…so I was pretty hesitant to use the platforms myself!

And when I started, instead of going where I might feel the most comfortable, I thought I HAD TO BE on Instagram.

I knew nothing about Instagram.

I did not like hanging out on Instagram.

And I was trying to give financial tips on a platform that really prefers photos to financial strategies.

So I dreaded it.

And I wasn’t very good at it.

But when I allowed the “old” parts of me to be incorporated into my business — the lawyer part of me to be exact — and I switched my focus to LinkedIn my social media experience completely changed.

I was now speaking more directly to lawyers and their money issues.

I was on a platform that rewarded long-form written content.

And I was talking about something I understood quite well, the life of a lawyer and what it felt like to struggle with money.

This struck a chord with my target audience and folks started reaching out.

I’ve booked many consults from a single LinkedIn post because I know how to reach my people and they like my message.

So my advice to those looking to market themselves on social media is show up where (1) your people already are; (2) you’ll be most comfortable; and (3) you can be yourself.

And then be yourself!

The magic will happen on its own from there.

Contact Info:

Image Credits

Alicia Loos
Theo Widharto

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