Embracing Uncertainty Early Paves a Path for Tax Career Success

A career in tax can take you to unexpected places. I started at a four-person boutique in a small city, never considering going to Big Law. I had heard anecdotes from friends about 20-hour days, seven-day weeks, clients who were never satisfied, and partners who never smiled—likely because they never slept either. That life wasn’t for me.

I learned over the years that these horror tales of Big Law can exist regardless of firm size, and in a smaller environment, there’s less chance of avoiding the unpleasantness. So three years ago, I joined Akerman with the goal of expanding my practice geographically and found unparalleled knowledge and experience among the corporate and tax attorneys I encountered.

Over two decades of practice, many of those years spent as the resident tax nerd, I amassed a number of experiences and a little knowledge that I hope those 20 years my junior might consider:

What you don’t know is as important as what you know. Tax law is complex, esoteric even, and some parts are much more complex than others. I remember walking into my first partnership tax class, where my professor, who was incredibly kind, uttered his first words: “This is the hardest class you will ever take.” He was correct. He was right again the second time that I took it during my masters program.

In tax practice, never be afraid to ask yourself and your client “What else?” As one of my mentors used to say to me daily, the law is the easy part; the facts are the hard part. He once told me a tale of the client that “forgot” to mention the millions of dollars sitting offshore.

Confidence wins, but a little humility goes a long way. Nothing is more important than being prepared before meeting with a client, or a partner, or opposing counsel, or the IRS. Preparation begets confidence.

Hubris, meanwhile, leads to mistakes, or, failing that, entrenchment and less ideal outcomes. Having both confidence and humility produces more opportunities; a reputation for professionalism will follow an attorney longer than a victory.

Don’t let the tax tail wag the dog. Every non-tax lawyer refuses to admit it, but taxes are in everything—real estate, corporate transactions, litigation, intellectual property—you name it.

Although the tax team often is called to review narrow portions of matters and provide guidance on the tax implications of strategies, proposals, or even settlements, taxes aren’t often the primary consideration for the client. Sometimes, the job involves reviewing and advising without the result for which we advocate. Because many times, the tax risks are outweighed by the other goals of the client.

Diversify your portfolio. Several years ago, a recruiter asked about my willingness to give up certain clients and certain work. I frankly, but politely, declined. The firm proceeded to offer increased compensation for me to not do certain work. I thanked her and explained that tax practice is cyclical.

There is some work that is in greater demand during economic expansion, and there are other areas of practice that are in demand during contractions. A broad practice allows me to stay busy, something my partners appreciate, whether the market is up or down. Tax laws change. Don’t specialize yourself out of relevance.

Find the right team. Tax law is tough. It can be a tough practice to fit with other practices. Personalities don’t always fit, and even if they do, practice models don’t always fit with other business models. Even today, there are still firms that have toxic or stale cultures. The right fit will be obvious very early in the relationship. There is tremendous pressure in a tax practice to be precise and fast while also efficient.

A firm supportive of the commitment to excellence that a tax practice requires—and with grace for the other eccentricities of a tax nerd—is key to career satisfaction. I’m fortunate to have that, even if it’s not where I would have seen myself two decades ago.

This article does not necessarily reflect the opinion of Bloomberg Industry Group, Inc., the publisher of Bloomberg Law and Bloomberg Tax, or its owners.

Author Information

Robert Wall is a partner in Akerman’s tax practice and an adjunct professor at Wake Forest University School of Law.

We’d love to hear your smart, original take: Write for us.