My Enrolled Agent Journey

Everything that mattered came from something unplanned

My father passed away last week after being quite ill over the last few months. Both writing a speech for his memorial service and being back in Philadelphia for an extended period made me reflect deeply on my past, present, and future. My career as an enrolled agent (EA) in the tax industry started in Philadelphia, and I first wrote about it in the EA Journal in 2020. Six years later, it is time for an update.

My journey as an EA started in 2008. I was 29 years old, living in Philadelphia, PA, near my hometown of Cherry Hill, NJ, working in student services at the University of Pennsylvania. I was a student leader in college, both during my undergraduate and graduate studies at the University of Delaware, so I went into higher education administration, which I had been doing for five years by then.

I always had a passion for numbers and personal finance, and I looked forward to doing my own taxes, which is not normal. I enrolled in the H&R Block course for non-practitioners to learn how to prepare taxes. It all clicked for me immediately, and by the end of the class, I was helping the other students — possibly an early indicator that I would become a tax educator. My instructor, Patricia Barrett, EA, encouraged me to become an EA after my first tax season.

Told I Would Fail

I worked for H&R Block for one season and decided to sit for the Special Enrollment Examination that summer. I told my district manager my goal at the end of the season, and he dismissed the idea, saying I would not pass because I did not have enough experience: “Don’t waste your time and our money,” I believe was the exact quote. Three months later, I passed all three parts; four months later, I became an EA; five months later, I joined the National Association of Enrolled Agents (NAEA).

Career Change

After my second tax season at H&R Block, I decided to transition to the tax field full-time. I moved to Baltimore, MD, and took a position at a new tax resolution firm, which was my first exposure to the representation side of being an EA. I also enrolled in the Master of Science in Taxation (MST) online program at Golden Gate University.

By mid-2011, I earned my MST and left that job because the business had slowed considerably. However, I leveraged my MST and tax resolution experience to secure a paralegal position at a small tax controversy law firm, where I performed much of the same tax work as the attorneys.

Life Shock

Working at a tax law firm was a tremendous learning experience, but also stressful, and it was where I began to hate the billable-hour model. In 2012, life veered in a different direction when I found out I had a very treatable form of leukemia. I still have it, and I will be treated for it for the rest of my life.

I chose to leave my full-time job and run my own business to gain the flexibility I needed to manage my health while staying in control of my destiny. I continued to work a part-time position at another tax controversy law firm for several years until my business and other ventures grew enough to support me fully.

Game Changer

I decided to take the U.S. Tax Court non-attorney admissions exam in 2014 and enrolled in the Tax Court preparation program taught by Sherrill Trovato, EA, USTCP. On the first day of class, I randomly picked a seat because I did not know anyone, and I happened to sit next to my future Tax Court exam study partner, colleague, and friend, Mary Beth Lougen, EA, USTCP.

I passed the 2014 Tax Court exam, and having the USTCP credential unlocked the next phase of my career. In 2016, I tiptoed into tax education, thanks to Kevin Huston, EA, USTCP, who invited me to teach some live classes with him. I spoke at two conferences, and I assisted with Sherrill Trovato’s Tax Court exam class.

Preparing for the Tax Court exam also allowed me to build relationships with Sherrill Trovato and Geri Bowman, CPA, EA, USTCP, and we launched Compass Tax Educators in 2017 with Kevin Huston to provide high-level webinar tax education.

Congress passed the Tax Cuts and Jobs Act at the end of 2017, and Compass then became known for providing accurate content on new tax laws. I won the 2019 NAEA Excellence in Education Award for my efforts to provide practitioner education on the new §199A deduction, which became a specialization of mine.

In 2018, I flirted with becoming a CPA. I took and passed Regulation, but as I began studying the rest of the material, I realized I would never use the content or the license. I was chasing letters I did not need, and I dropped the effort to focus on expanding my educational portfolio.

The Pandemic Pivot

Compass Tax Educators boomed during the pandemic because everyone had to move to online education, and the new tax laws gave us plenty of content to cover.

I started Tom Talks Taxes on a whim in December 2020, and I had no idea what it would become. It has now grown to almost 7,500 subscribers and is my flagship offering. When I semi-retire, I will continue to do Tom Talks Taxes.

I also launched the Inner Circle in 2021, a small-group program in which credentialed practitioners bring me their real client cases during recurring calls, and I challenge them to build successful businesses that prioritize work-life balance. It is the most direct teaching I do, and it keeps me close to the problems practitioners are actually hitting rather than the ones I think they are.

Collaborations and Mentorship

I have also developed partnerships with other EAs and organizations in the last few years:

• Providing tax planning education through the American Institute of Certified Tax Planners with Dominique Molina, CPA, CTS.

• Executing advanced in-person seminars with Brass Tax Presentations, owned by Ryan Reichert, EA, CFP, and Shannon Hall, EA.

• Providing in-person education for state and local professional associations.

• Building the InCite community focused on technical knowledge and business practices with Natalie Kolodij, EA, Brad Messner, EA, PhD, and Matt Metras, EA.

• Offering an innovative approach to the use of artificial intelligence in tax research by launching AskTomG.ai with Josh Youngblood, EA.

After a several-year pause from working with national organizations, I will be doing some exciting future collaborations with the National Association of Tax Professionals (NATP). I left NAEA, which is unfortunate, as I spent many years as a member, volunteer, and instructor. There need to be some cultural shifts for me to consider rejoining NAEA, such as respecting member feedback and disagreement.

I never had a traditional work-to-death tax practice. Today, I focus mostly on IRS and U.S. Tax Court representation, and I prepare some tax returns to stay current. My business is profitable but intentionally very small since I do a lot of other things.

Last year, I started a yearlong program for early-career EAs called EA Launchpad to equip them with the knowledge and skills to build a business and shape the industry. I am excited about how it turned out and have plans to offer another cohort next year, starting in July. The program is 100% free to give back to the EA community, and I plan to launch an ongoing initiative for EA Launchpad alums.

If I went back to 29-year-old Tom and told him where I would be today, simply from enrolling in the H&R Block tax course, he would not believe it. I cannot tell you where I will be professionally in five to ten years. I am going to keep going forward and let my instincts and the universe guide me in those choices. They have not led me astray yet.

Lessons Learned

Life and health always come before work. You never know when your last day could be. You will regret missing out on experiences with family and friends. You will not regret doing too few tax returns.

Take the road less traveled. For me, it did make all the difference. You need to take calculated risks for the best career rewards.

Invest in yourself by getting the best education available to you. If you settle for the cheapest, low-quality education to get it done, you are doing both you and your clients a huge disservice.

Pick your people and your organizations deliberately. I do not partner with people I do not know or trust, fake “influencers,” or self-appointed social media “thought leaders.” I do not partner with organizations if I cannot get behind their actions.

Relationships compound. Every meaningful step in my career came from a positive professional relationship: the instructor who pushed me toward becoming an EA, a classmate I sat next to at random, and colleagues who became business partners.

Teach what you know before you feel ready. I started teaching in 2016 with doubts about whether I could do this. Teaching is the fastest way to find the gaps in your own understanding, and there is a shortage of people who can do it well.

Own your platform. Newsletters, communities, and courses that you control are the difference between a career that depends on others and one that does not. Start smaller than you think is worthwhile and keep going longer than feels reasonable.

Experience is not a prerequisite for competence, and having experience does not automatically make someone competent (e.g., “I have been doing it this way for 40 years…” when it is completely wrong).

Professional jealousy is endemic. People attempt to take out others they perceive as successful. There is plenty of opportunity for everyone, and we should actively support the success of others who are competent and act in good faith.

What My Father Showed Me

My father was a cop to pay the bills, but his life was music. He performed and worked with musicians for 60 years, well past his retirement from the force. He stopped trying to make music a full-time job in his 20s, and police work is what made the next six decades of music possible.

I went the other way. I found what I loved at 29 and rebuilt my career around it. Even though I have a career I love, there are parts of it that I do not love. More and more, I want to stop doing those things and focus on the rest, regardless of the revenue I give up. That is my work for the next few years, as I approach 50 and my goal of early semi-retirement. And giving back to the EA community that got me here.

Join the Conversation

If you are a paid subscriber, you can talk about this topic or ask me questions in the comments section. Please keep the discussion related to this edition’s topic.