Face your scariest questions first—why loving hard news leads you faster to real success

Every creator or leader dreads the hard questions—the ones that, if answered wrong, could shatter your dreams. Would schools actually pay for my tool? Can I really get permission to use this data? Is this problem something people care enough about to spend money or time on? It’s tempting to avoid these topics, letting your hope guide the conversation and settling for signals that feel safe but change nothing.

But those who achieve progress, even if it means failing fast, learn to make their fear list explicit. They gather with their team and write down what would most likely destroy the project: 'Will teachers have money?', 'Are other teams competing in the same space?', 'Do users really find their current solution painful, or are they just being polite?' Once articulated, these questions become tools rather than ghosts. The habit becomes: in every conversation, check the list and ask at least one uncomfortable question, rather than hiding from potential disappointment.

It’s rarely easy, but this practice pays off. You walk away from scary talks with the kind of clarity that only honest confrontation brings. If there’s no money, no interest, or no path forward, better to know after two weeks than after two years spent building in the dark. Behavioral science and entrepreneurial research back up this approach, describing the 'premortem' (imagining failure in advance) and the value of active disconfirmation, where hard news leads to good pivots.

Grab a pen and jot down the riskiest reasons your project, event, or idea might fail. Turn each one into a critical question, even if it feels harsh or awkward to ask. In each meeting or chat, make a point to raise at least one of these tough questions, and don’t flinch from the answers—even if they sting. This habit is a game-changer: it replaces blind optimism with grounded strategy and lets you focus all your energy where it counts. Try it this week and see what happens.