444 | ADHD Tax Stories & Strategies with Rick Webster

444 | ADHD Tax Stories & Strategies with Rick Webster

In this episode, Rick Webster returns to the show! Rick has expertise in real-estate, entrepreneurship, and ADHD!  He has managed many domains in the financial and real-estate world, and in the last couple of years, he’s put his focus in helping people with ADHD make better peace and better “cents” of their finances. 

As CEO of Rena-Fi, Rick brings perspective, vision, and passion to an area of life he considers foundational: Personal Money Management.  His motto has always been, “It’s not just business; it’s personal.”

Eric and Rick share stories about paying the ADHD tax and its larger umbrella, the effects of chronic long-term stress, ways to change self-talk and self-identity to get things done, challenges we may encounter when developing financial habits, the shame we can feel when working on our finances, and forgiving ourselves.

Then, Eric and Rick talk about behavioral finance, why money management isn’t just about willpower, the impact of looking upstream, creating reminders and cues, and saying “no” to improve performance.

Finally, you’ll hear Eric and Rick talk about maintenance costs, other costs of homeownership, planning for upcoming maintenance, and the three primary reasons why the ADHD tax continues to happen.

Learn More about Rick Webster at

Other ADHD-tax stories shared on this episode:

  • “I have paid the ADHD tax so many times. I’d love some recommendations on extremely simple/easy budgeting tools.  A lot of budgeting books have too many steps.”
  • “I always do my taxes at the last possible minute and don’t know if I do them right, and I always owe a lot.”
  • “Didn’t pay a speeding ticket, license was suspended.  Pulled over again – arrested driving with a suspended license.  Then, I paid much more than the original speeding ticket for a lawyer, speeding tickets, and additional charges for reinstating my license.
  • “I pay the ADHD tax every day.  Paying late-fees, re-buying things I can’t find, spending impulsively, paying for things I’m not using because I didn’t cancel them or forgot to return them in time, expedited shipping because I didn’t order something on-time, ordering take-out because I wasn’t organized enough to have dinner ready, etc.  How can I be triggered to think things through at an early enough time that I can follow through in a way that lets me avoid the ADHD tax?”
  • “I’ve paid the ADHD tax on rush-orders. I’ve paid more on expensive repairs to my vehicles/yard equipment/house appliances, instead of the regular preventative maintenance that would’ve prevented the damage in the first place.  I have paid out-of-pocket costs for my meds because my insurance lapsed or I never sent in the reimbursement forms for what would be covered if I do the extra steps.  How do I know what the preventative maintenance tasks are on my big or expensive things (often appliances)? I feel like I “should” do many of them myself.  Would I be paying an ADHD tax by paying people to come do some of these easier tasks for my appliances because they at least know and will at least call me when they are due?”

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