Earning a high income and building genuine long-term wealth are two very different things, a reality that catches even the most successful attorneys off guard.
Niraj Chhabra, managing director of SideBar Advisors, has spent nearly two decades advising lawyers on their personal finances and has developed a clear view of where high earners quietly lose ground.
Chhabra joined Steve Fretzin on the podcast “Be That Lawyer” to discuss the specific financial pitfalls that tend to follow attorneys throughout their careers, regardless of how much they earn.
According to Chhabra, one financial mistake stands out above all others and remains consistent across every stage of a lawyer’s professional life.
The conversation also challenged one of the most widely held assumptions about retirement planning, specifically the belief that deferring taxes always delivers a financial advantage in later years.
The common logic runs that income drops sharply after retiring, bringing tax brackets down with it, but Chhabra explained why that reasoning often breaks down for lawyers specifically.
“In other occupations, it’s an on-off switch. One day you’re in the office, one day you’re not,” Chhabra said. “Attorneys nowadays, it’s more like a dimmer.”
That dimmer effect means many lawyers continue generating income well into what would traditionally be considered retirement years, undermining the tax-deferral strategy many rely on without question.
Fretzin raised a pattern he has observed repeatedly through years of coaching attorneys, noting that lawyers earning $300,000, $400,000, or $500,000 or more annually are not automatically saving or investing that income wisely.
A strong income, as both Fretzin and Chhabra made clear throughout the discussion, provides opportunity but not a guarantee of financial security or a well-structured retirement.
The conversation highlighted that a lawyer’s financial plan cannot simply be written once and left to run without adjustment as circumstances inevitably change over time.
Income levels rise, tax brackets shift, family situations evolve, and retirement for most lawyers bears little resemblance to the clean, abrupt exit that traditional financial planning tends to assume.
The central message across the discussion was direct: lawyers at every career stage benefit from treating financial planning as an active and ongoing discipline rather than a single decision made and forgotten.