Philip Wolf received his JD in 2019 from the University of California, Hastings College of the Law, with a formal concentration in taxation. He is a member of the California State Bar and the U.S. Tax Court bar.
In this article, the author describes embarking on a tax career and how he continues to build his professional skillset after being laid off from his job as an entry-level tax lawyer because of the coronavirus pandemic.
On my first day as a tax associate I was excited about putting into practice skills that I had learned in law school. I was surprised when my boss told me, “Philip, when I was in your shoes starting at my own first job, I also thought I was very well equipped. I quickly discovered that tax has a steep learning curve. You will have to climb that curve as well.”
My boss explained that a good tax lawyer needs to write persuasively, interact professionally with different taxing authorities, communicate honestly with clients, and be familiar with fundamental accounting principles. I watched carefully how my boss demonstrated each of these skills, and I tried to emulate him. I came to admire him highly.
It quickly became apparent that the writing I had been trained to do in law school was not the same as the writing I would be doing on a day-to-day basis in a professional tax practice. One of my professors told me that my writing would always need to answer a basic question: “So what?” I observed how, in practice, my boss also wrote each paragraph — even each sentence — with advocacy in mind. He worked and reworked his documents until he was satisfied with their quality. I asked him what standard I should strive for, and his reply was quite simple: “Only the best is good enough.”
My boss explained to me that “the way to become a good writer is to write, write, write.” He told me that when he worked for the IRS, despite having a newly minted law degree, he bought a legal writing book. Every morning at 7, he would head to his favorite coffee shop and write until it was time to go to the office. He did every exercise in the book — and then he bought another.
I also watched my boss carefully, sitting with him in his office while he spoke with government tax agents. I noticed how he maintained his calm, no matter how unfairly or unreasonably an agent might behave, and even in the rare instances when an agent tried to provoke him. At the end of one of the calls, he turned to me and said, “Philip, it’s important to develop a reputation as a straight shooter. By doing so, you can gain the trust of the government bureaucrat and turn them into an ally.”
In the same vein, my boss taught me how to communicate with clients honestly and dispassionately. He had me write memos that broke down complicated tax issues like partnership tax into clear and understandable language so that the client could appreciate our advice and the reasons behind it. He emphasized the importance of not overpromising a result or overselling a case.
Finally, although I had chosen a tax controversies practice in part because I didn’t see myself as a numbers guy, my boss disabused me of the notion that I could dismiss accounting altogether. He had me organize clients’ financial data into spreadsheets that he could use for his discussions with the IRS. I learned the importance of synthesizing data as well as ideas.
Unfortunately, five months after I started as a tax associate, my position fell victim to the COVID-19 economy. After being laid off so soon after embarking on a career that I had spent years training for, I went through a period of intense self-reflection. My first impulse was to wonder if I’d come up short: Did my performance fail to meet expectations? My mind kept revisiting and tallying every mistake I’d made, and I wondered how many I may have missed. I agonized that I hadn’t improved quickly enough, failed to adequately understand tax fundamentals, or, worst of all, was simply incompetent.
But then I remembered that my former boss had repeatedly said he was pleased with my work product. I realized that he wouldn’t have kept me for several months, and wouldn’t have promoted me from a law clerk to his associate, if he didn’t like my work. I was performing well — or at least as well as an entry-level associate could be expected to perform.
I reached out to another mentor of mine for insight. Robin led the FBI’s Behavioral Analysis Unit before leaving to write about psychology and trust. During law school, I read one of his books to learn more about communication in the professional workplace. After finishing the book, I reached out to Robin. He became a trusted adviser who provided useful guidance at critical points as I prepared for and began my legal career.
I told Robin that I’d lost my dream job and was doubting my ability to succeed as a tax attorney. He responded that the key to success, both professional and personal, is self-awareness. Self-aware individuals analyze their flaws realistically. Instead of getting hijacked by their emotions, they come up with plans to turn their weaknesses into strengths. Robin made me realize that I needed to stop worrying about my flaws; I needed to use this time wisely and work to improve my skills. I had to be proactive instead of reactive.
I thought about the skills that made my former boss an effective tax lawyer. I bought the books he’d used to teach himself writing. I study from them every day. I even force myself to get up at 7 a.m., although coffee shops are out of the question these days! I am actively seeking out opportunities to practice writing, including regularly submitting my work to Tax Notes. I am improving my ability to organize my thoughts into coherent articles. I always return to my professor’s advice making sure that I answer the question: “So what?”
Most taxing authorities in this country have curtailed their operations, but I am still learning how to interact with government officials through my volunteer efforts. On one project, I am in communication with a county supervisor. I am making an effort to speak calmly and clearly to convey my client’s needs and advocate on its behalf. I am sending regular progress memos to the nonprofits I’m advising, making sure that I communicate honestly, explain concepts appropriately, and refrain from overpromising results.
One of the things my work as an associate taught me is that I need a firmer grasp of accounting and technical concepts. I have enrolled in a community college class to learn financial accounting, and I am taking courses online to improve my Excel skills.
In all these ways, I am still trying to emulate my former boss and to learn the entry-level skills that will make me a better tax lawyer, even if I’m learning them in unexpected ways. As a child, I was a huge Star Wars nerd. (OK, I still am.) So, at this particular moment in my career, I find myself turning to yet another mentor. In the wise words of Master Yoda, “Named must be your fear before banish it you can.”
I still have a lot to learn, but by being persistent and thinking outside the box, I am confident that when the job market finally returns to normal I’ll be ready for the next opportunity to serve the public and the tax community.