^^^ Sometimes that's what it takes.
My fiance is new to cycling, and started riding because I offered her a Schwinn 10-speed that I'd tuned up. Eventually, she asked me to "take off all those heavy gears," because she never shifted anyway, so I SS'ed it (with a flip-clop hub and a lighter wheelset).
Eventually, she decided she wanted to try fixed, so I flipped the rear wheel and she rode fixed with 2 brakes and platforms for a while.
A month or so later, she asked me to put on some toeclips, so she could control her speed better using her legs. I don't expect her to go brakeless any time soon (nor would I recommend it for her), but she's made a natural progression as she became more comfortable with her bike, and with riding in general.
Initially, when I would suggest changes or offer advice, she'd get flustered and upset; turns out, she just needed to evolve at her own pace.
I suggest a similar approach in your case. It's all about the "comfort zone" and pushing the boundaries gently.