Decades ago in law school, my tax professors said you just couldn’t sell tax planning to middle‑market clients. In my experience, that’s mostly true. The focus of my professional study and expertise was compensation and benefits planning. As a non-attorney, I felt forced to find a different way to bring these services to the market through an online platform; but that’s a different story outside of this post.

Lately I see tax industry influencers promoting the sale of tax planning to tax professionals nervous about the impact of AI on their tax preparation business. It would be disingenuous to not recognize that I have an inherent conflict of interest in discussing this topic.

My bias is that long‑term satisfaction with tax planning sold as a stand‑alone product is lower than our industry likes to admit. A meaningful portion, maybe 20%, of my current work comes from unwinding failed tax plans or supporting litigation that seeks recourse for prior “tax planning” that was sold to the client and did not age well. In three cases over the past year the errors and omission carriers seemed poised to cover my fee for unwinding a tax plan gone bad, although I am not directly involved in the legal settlements. It seems that once I developed a reputation as a “fixer” of failed tax planning, frustrated clients and their attorneys brought more of these failed tax planning cases than I knew existed.

These days, I find the best long‑term, high‑value tax savings happen when tax planning is woven into broader strategic planning and supported by executive coaching agreements that keep everyone accountable over the multi‑year time frame that it takes for good tax planning to stand up. Tax planning blends in seamlessly with other life and business planning, and naturally evolves over time as circumstances change. I see little value in separating and selling tax planning services, per se, to middle market clients.