I’ve spent several years observing, studying and writing about tax noncompliance among small business owners. The pattern I keep finding has little to do with willingness to pay and a lot to do with the design of the tax compliance system itself.
The same traits that drive entrepreneurial performance – tolerance for ambiguity, fast pivots, sustained focus on the thing in front of you – leave predictable gaps under any regime built on deadlines, record-keeping and self-initiated filings. A W-2 employee with those traits is still tax compliant, because payroll withholding does the work. Move the same person to self-employment and compliance becomes a quarterly task with no prompt, no deduction at source, and penalties that compound in silence.
Outside of the tax world, I often notice business and personal behaviors in owners that look like the traits associated with ADHD. I am not diagnosing anyone. Most chronic non-filers have no clinical diagnosis and never will, and I have no standing to offer one. The useful framing isn’t “my clients have ADHD.” It’s that the tax system levies a hidden tax on executive function, and payroll departments have been quietly paying it on behalf of employees for generations. Independent operators pay it themselves.
That reframe changes what I can do about it. An automatic transfer to a separate tax reserve account on the day money lands beats any reminder to save for taxes. A standing quarterly appointment already on the calendar beats a filing deadline the client has to remember. Neither asks the client to become someone they aren’t. Building the automatic structure a payroll department provides is a service design option in the tax profession, and it belongs on the coaching side of my practice rather than the clinical diagnostic side, where I don’t belong at all.
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