After 36 years in the tax profession, enrolled agent Alan Pinck makes a surprising admission when he speaks at conferences: “I’ve been doing this for over 30 years, and I’ll be the first to admit I know nothing about taxes.”
This isn’t false modesty from the successful Northern California practitioner and Tax Talk Today moderator. Instead, it reflects the realities of running a tax practice—the rules change so fast that what you knew yesterday might not apply today. As Alan told Federal Tax Updates hosts Roger Harris, EA, and Annie Schwab, CPA, “If I figured it out, I’ll quit. Once I stop learning, I don’t want to learn anymore.”
From Hospitality to Tax Practice: An Unexpected Journey
Like many tax professionals, Alan never planned to enter this field. After years in the hospitality industry, he reached a breaking point. “I got to the point where I didn’t like people anymore,” he admits with a laugh. “So I knew it was time to get out.”
His father, a retired enrolled agent who had recently bought a practice, offered Alan and his siblings the chance to join him. The practice turned out to be more than his father could handle alone. Alan, who was living on the East Coast at the time, decided to give it a shot. “I wanted to get into a regular life. That’s what I thought at the time,” he recalls.
He started with a year at one of the big box tax preparation stores, doing returns with pencil and paper—no software in those days. “Back then, they used to have the numbers at the top of the form so you know how to write the numbers where they wanted them,” Alan remembers. “You couldn’t put a loop in your zeros or put a dash in your sevens.”
After that foundational year, he moved to California, became an enrolled agent in 1993, and, as he puts it, “couldn’t stop myself.”
The Case That Changed Everything
For years, Alan followed the typical tax practitioner’s path: intense work during tax season, then scrambling for income the rest of the year. Many practitioners try bookkeeping to fill the gap, but Alan found the repetition wasn’t for him. “I’m all about numbers. Numbers don’t lie,” he says. “But the repetition was no fun.”
The turning point came through a friend whose wife ran a home daycare. Instead of using the standard hours-based calculation for the home office deduction, Alan took a different approach. The client had converted their garage into a dedicated daycare facility with its own entrance and bathroom. This justified using a percentage-based deduction for the entire space.
“I knew when we filed the return it would be audited,” Alan recalls. In fact, of the nine audits of his own work that he’s represented, he knew eight would be audited when he prepared them.
When the audit notice arrived, Alan walked into the IRS office without really knowing what he was doing. But he knew his client and understood the position he’d taken on the return. Most importantly, he approached the auditor with respect and professionalism.
“The main thing was I was nice to the auditor, and the auditor was nice to me,” he explains. In the cubicle next to them, he could hear another representative arguing with an auditor. The contrast was stark, and so were the results.
Choosing Your Lane: Examination vs. Collections
That first successful audit representation opened Alan’s eyes to a different business model. Unlike tax preparation, which is seasonal, representation work is year-round. But he quickly learned that not all representation work is the same.
“I’m a big one in believing in staying in your lane,” Alan emphasizes. “You really have two types of representation. You have examination and collections.”
Examination:
Defending positions taken on tax returns to prove that deductions were valid, income was reported correctly, and tax law was properly applied. This builds naturally on tax preparation knowledge. “You’re dealing with a tax return that you may have prepared or somebody else prepared, but tax law is tax law,” Alan explains.
Collections:
Negotiating payment arrangements for people who owe taxes but can’t pay in full. This includes offers in compromise, installment agreements, and currently not collectible status.
Annie has an idea why many practitioners struggle with collections. “It’s too emotional. I feel like I’m going through a bad divorce or something when I’m trying to negotiate what they can pay, what they can afford, and what the IRS will accept.”
Alan chose examination work as his specialty, only handling collection cases when clients don’t actually owe the assessed amounts.
Building Relationships, Not Battles
One of the biggest surprises for practitioners entering representation work is how collaborative it can be. Forget the TV drama image of lawyers battling IRS agents. Successful representation is about problem-solving together.
“I’m on a first-name basis with a lot of auditors,” Alan reveals. These relationships run so deep that when the IRS offered the Departure Readiness Program, auditors personally called him to say goodbye.
This relationship-building starts with mutual respect. Alan makes auditors comfortable when they visit his office, offering them conference space and even spare monitors. But he also sets boundaries. “I don’t care what time you want to start, but at noon I break for lunch and I close the office,” he says firmly.
As Roger notes, “You’re going to get a lot more agreements if you get along with someone than if you’re adversarial with them.”
The Learning Never Stops
Perhaps the most striking aspect of Alan’s approach is his commitment to continuous learning. Beyond handling cases, he teaches at IRS forums, moderates Tax Talk Today, and speaks at conferences nationwide.
“If you want to learn something, you have to teach,” Alan explains. “It takes me a good eight to ten hours of writing and research to put one hour of education together.”
For practitioners looking to enter representation work, Alan recommends the National Association of Enrolled Agents’ National Tax Practice Institute (NTPI).
“This is not taught out of a book. This is the real world,” Alan emphasizes.
Taking the First Step
For practitioners tired of the feast-or-famine cycle, representation work offers a path to year-round income.
“Take one case at a time. Don’t worry about a mistake the first time because you get a chance to learn,” Alan advises.
As the conversation wrapped up, Alan offered one final piece of wisdom: “Plan what you’re going to be doing on April 16th and make sure all your plans are in place.”
Listen to the complete conversation with Alan Pinck on the Federal Tax Updates podcast to hear more about his journey and practical advice for building a sustainable, year-round practice.
And for help navigating representation work, practice management, tax support, marketing, and technology, learn more about having your firm join the Padgett network.