Jessica Medina is a financial coach who helps attorneys create financial freedom. As a former big law attorney herself, she brings unique insight into the challenges and pressures her clients face. In this interview, Jessica discusses how she’s designed her business to accommodate her lifestyle while serving her clients effectively, including her unique approach to seasonal client acquisition and her journey from law practice to financial coaching.

Jessica Medina: My business has morphed over the years, with much of the design responding to my personal life and needs for personal time. In 2022, my husband’s 50th birthday present was to follow the Atlanta Falcons around in our RV—a season-long endeavor requiring extensive travel and potential non-internet spaces. I crafted my business that year to allow me to take that quarter off from selling. Client fulfillment is easier than selling, which requires significant creative and engaged energy. I knew I wouldn’t be available to the market as usual, so I filled my client roster in the first six months. It worked well, so I’ve continued this cadence in my sales activity. I always do the Client Creator Challenge at the beginning of the year, and summer tends to be a good time for people to sign up since they’re gearing up for fall. Those are my two big selling seasons. I use the other seasons to ensure my clients are moving through the programs well and preparing for the following year.

Jessica Medina: I practiced law in the DC metro area for nearly 15 years. Across those years, I worked for a large law firm, which is where most students of top law schools end up. I was somewhat unique because I graduated from law school as a single mom of twins. I needed that big law money to manage my family and my $200,000 of student loan debt from law school. I always wanted to be an attorney and thought I would be one for the rest of my life. I fell out of love with the practice around the four to seven year mark. When I was looking around during my existential crisis, I wasn’t sure what I wanted to do next, and I found financial coaching. I’m an accredited financial counselor, and I’ve been working with clients since 2018 when I first took the AFC exam. I’ve been operating as a profitable business since 2020.

Jessica Medina: My core offer is a six-month coaching program, and I work with my clients for at least six months. I give them a year to complete the entire program because my clients are attorneys who sometimes get pulled into trials or deals. In that six months, we work through three major frameworks. First, we create a vision for their money and do long-term financial planning. Most of my clients want to make a transition, often taking a pay cut, and I help them map out how they could do that. We examine both the short-term ramifications of lifestyle changes and the longer-term implications for reaching their goals.

After establishing high-level strategies, we move into cash management, which is my favorite part. I build them a personalized cash management system based on principles from various experts and my own experience. I teach them the system I built for myself, and we run it for the rest of our time together, ensuring everything works smoothly. Because many clients experience major life changes while we’re working together—a new job, a move, a baby—we revisit their long-term strategies and high-level goals to ensure everything still fits.

Jessica Medina: I wanted something more accessible in terms of price point and client commitment than my six-month program, which is designed for attorneys going through or planning a transition. I have a particular passion for helping people struggling with student loan debt because there aren’t many great resources available. While free resources exist, they’re often confusing, and it’s difficult to get personalized guidance from someone knowledgeable. Many of my clients already have financial advisors who don’t understand how to handle their student loans—the advice is always to pay them off as quickly as possible, which isn’t the best approach for everyone, especially those planning to take a pay cut.

I created a specialized, streamlined student loan offer based on my free student loan resources, but including one-on-one time with me. That’s a core part of my company—I believe financial coaching must involve some one-on-one element because it’s so personalized. I don’t see myself creating a course or DIY product. I don’t prefer them for my clients, and I don’t want to execute them.

Jessica Medina: I am now a well-paid speaker on the financial wellness circuit for law firms and bar associations. I give workshops for summer associates, new associates, and all attorneys at firms. When I took action on speaking, everything happened fairly quickly because I had established myself in the market as someone knowledgeable. I had done considerable free speaking and built connections in the financial wellness world for attorneys.

Speaking has become a major revenue source in my business and allows me to impact many more attorneys than I could with one-on-one practice. I’m developing a curriculum focused more on teaching while maintaining my individual client work. I’ve already gained individual clients from speaking engagements, so it serves as a marketing funnel while satisfying my love for travel. It was an overnight success after two years of work.

Jessica Medina: When I focused on lawyers in particular in 2020, my business took off. They appreciated that I had practiced before. It opened up a way to market that felt authentic—instead of just talking about money and personal finance, I could speak directly to the lawyer experience and the emotions wrapped up in big law practice, particularly how that stress manifests in their finances. People were relieved to find someone who understood both the money part and their day-to-day life. When I started marketing specifically to lawyers, my revenue increased tenfold from 2020 to 2021.

Jessica Medina: Many of my clients have mortgage-sized student loan debt, just as I did. I consider it one of my superpowers as a financial coach that I intimately understand what it feels like to enter a profession that’s supposed to take care of that debt, only to find that isn’t the reality. For years, I didn’t have a plan—it was just something I thought I would take to my grave because I’m old enough that the forgiveness programs weren’t in effect when I graduated.

When I started coaching clients, I still carried student loan debt, but I had a clear payoff date and had been intentional about which debts to prioritize. I could articulate my strategy confidently and help others create paths that made sense for their finances. I’d attacked my loans in different ways throughout the payoff journey, so I understand that sometimes you can’t go full force—sometimes you need to adjust for other financial priorities or take advantage of relief programs that appear unexpectedly.

Jessica Medina: Things take time, even for the most successful coaches. Early success doesn’t guarantee immediate repeatability forever. Give yourself time to really try new approaches. If you’re new to social media, don’t abandon it after two to three weeks—it takes about six months for something to start working. With new offers, you might have amazing success with your first run, then your second run flops. That has happened to me, and it was disconcerting.

The key is to ask yourself: Do I love this offer? Do I want to figure out how to sell it because I know my people need it? When I’ve answered yes to these questions, the offer has become successful—it just didn’t happen as quickly as anticipated. It’s a combination of understanding the practical realities of building a business, breaking into a new market, redefining yourself, and accepting that sometimes you need to try harder. If you believe in what you’re doing, you will figure out a way to make it work.

About Jessica Medina

Jessica Medina is a lawyer turned Accredited Financial Counselor on a mission to help attorneys create the financial freedom they need to do big things. She graduated from Columbia Law School in 2004 as a single mom of twins with over $200,000 in student loans and went straight to work at a Biglaw firm. After eight years she switched roles and became Senior Counsel at the Division of Enforcement at the United States Securities and Exchange Commission. She left the government to work in an area of the financial industry outside of the securities world and now teaches other lawyers how to use their money to finance their dream lives. She is a graduate of the Financial Coach Academy®.