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Tax Planning for Big Law Attorneys During Tax Season with Brian Leben

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Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money with Matt Smith, Episode 7

In this episode of the Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money, Matt Smith speaks with tax advisor Brian Leben, partner of Lulloff, Leben & Taylor, LLC, a tax advisory firm.

Tune in to the episode to hear about:

  • Tax planning considerations for big law attorneys during tax season

  • Avoiding steep underpayment penalties

  • Common gaps among high earners, including not maximizing pre-tax 401(k) and HSA contributions

  • Backdoor and “mega” backdoor Roth strategies, allowing after-tax contributions and in-service rollovers

  • A caution to popular social-media tax strategies (heavy vehicle deductions, conservation easements, intangible drilling costs, and the Augusta rule) are often inapplicable, complex, or not worth the hassle

  • Practical opportunities including properly applying composite/PTE state tax payments

Learn more about Brian Leben:

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About “Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money”:

You bill in 6-minute increments. Let’s get you some of that time back. “Sidebar with a CFP®” is your space for candid conversations about life inside BigLaw—the real stuff they don’t teach in law school or show in recruiter brochures.

Hosted by Matt Smith, CFP® and founder of Concert Financial Planning, this show pulls back the curtain on what it actually feels like to climb the ranks, navigate transitions, and make big decisions in a high-stakes career.

You’ll hear from Partners, Associates, and experts across law and finance—each sharing stories, surprises, and strategies for building a life (and career) that works for you.

This isn’t a money podcast. It’s a life-in-BigLaw podcast—with a CFP® in the host chair.

Watch or listen to more episodes of Sidebar with a CFP®: Pierce the Veil on BigLaw Life, Career, and Money:

Connect and learn more from your host, Matt Smith and Concert Financial Planning: