Finding the Right Career Path Can Be Taxing

By the time I finished law school in 2009, the uncertainty over my career path was nerve-wracking, to say the least. You see, I had decided I wanted to be an entertainment attorney. I haven’t reached that goal yet—but I’ve learned some important lessons along the way.

The economy was at an all time low right after I entered law school, and the job market wasn’t any better by the time I finished.  However, I did have a plan. First, I planned on networking and attending as many entertainment industry events as I could.  Second, I decided to apply for every and any legal job that I thought I could qualify for, and pray!

My experience in the legal profession—if you want to call it that—was a mash-up.  The summer between my first and second years of law school I worked a temporary job as an executive assistant in business and legal affairs for a cable network. During my last two years of law school, I worked as a law clerk with a mid-size civil litigation defense firm, and was an intern with the Immigrations and Customs Enforcement and the Public Defenders office. The legal profession was a second career for me after the military, and I didn’t quite fit the traditional mold of the young lawyer. Ergo, a traditional law firm career path just didn’t make sense to me. So I took another route.

After taking the New York and New Jersey bar exams, I  applied for many, many jobs at law firms and with the government. As fate would have it, my first job was with the Internal Revenue Service as an estate and gift tax attorney in the small business and self-employed division. I can remember when I got the call for the interview. I was in Orlando and the interview was an in-person interview in Philadelphia. I didn’t know anything about estate and gift taxes. To get a better understanding of what the practice of estate and gift tax involved, I turned to my wills and trusts professor. I used the information she gave me to prepare for the interview. The extent of my knowledge in taxes was in preparing my own income tax returns, which was basically a Form 1040 EZ, but most of the job requirements were related to accounting and business which I had completed during undergrad and graduate school.

As luck would have it, the IRS provided training—lots of training.  The initial training was for six weeks, with an additional four weeks a year later, including annual conferences. I worked as an estate and gift tax attorney for a little over four years, conducting investigations nationwide for compliance with tax laws. I was able to develop my substantive and procedural knowledge of federal and state laws in wills and trusts, contracts, real and personal property, and corporations.  The world of estate and gift tax involved a lot of small businesses, and highly complex and intricate valuation problems in extremely large holding companies and closely held corporations of exceptionally high value. With the assistance of expert engineers and economist appraisers, I analyzed the gifts being made and assets of estates, which often included small businesses and closely held corporations, to determine the correct tax liability.

Practicing in estate and gift tax helped me to develop my investigative and problem-solving skills; analyze and apply financial, business or accounting principles; communicate orally and in writing at various levels internally and externally; research and analyze the law to make technically accurate and logical arguments, and negotiate to achieve voluntary compliance with the tax laws. In my experience with estate and gift tax, I realized I was merely scratching the surface. Estate and gift tax was a niche, and I needed to expand my knowledge and practice into other areas of tax, both individual and business.

Recently, I transferred to the Office of Chief Counsel, Los Angeles Division within the IRS, where that expansion in tax law is continuing to take place. Still within the small business and self-employed division, I now provide litigation and advisory legal support to the agents of the IRS. My new role involves providing legal advice to the client—the IRS agents we serve—and preparing for trial on matters relating to and involving individuals and small businesses, collection issues, estate and gift tax, fiduciary, and excise tax. I draft answers to petitions, motions, and pre-trial memoranda and conduct discovery. Recently, I litigated my first case before the U.S. Tax Court, dealing with whether a witness qualified as an expert, the admission of evidence, and conducting a direct and cross-examination of witnesses. That experience in Tax Court was very rewarding and fulfilling.

What about the entertainment practice? Well, I haven’t given up on that either. Interestingly enough, before transitioning to my current position, I was able to represent performing artists and talent in a broad spectrum of matters in both film and music.

I would say that I am at the beginning of what looks to be a very promising and successful career path. My path isn’t etched in stone, and I want to see where it leads me.

About the Author

Casinova O. Henderson is an attorney with the Office of Chief Counsel in the Internal Revenue Service’s Los Angeles office.  He can be reached on Twitter at @casinova06.

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