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As we are witnessing nowadays with self-driving vehicles and robots performing collaborative tasks, and as it has been witnessed in the past, a disruptive technological innovation may cause a regulatory disruption. As a consequence, established regulatory frameworks need to evolve and, in this evolution process, regulatory excellence is paramount for guaranteeing appropriate risk taking, enabling innovators to innovate while efficiently complying to proportionate regulatory frameworks. In risk management theory, or better, in risk taking theory, Taleb has proposed the Barbell strategy, characterised by maximal certainty/low risk on one extreme of the barbell, and maximal uncertainty on the other extreme, as a means for developing anti-fragility, i.e., ability to gain from disorder. In this paper, we propose our vision consisting of a Barbell strategy-oriented regulatory framework and compliance management, where regulators and manufacturers/innovators, both, adopt a Barbell strategy for reaching an optimal solution in regulatory making, the former, and compliance management, the latter. Finally, conclusion and perspectives for future work are also drawn.