11. How to negotiate a raise and Chainsmokers show recap

Negotiation behind-the-scenes of a dream weekend: Alex recently performed an opening DJ set at The Chainsmokers show (nearly 10K attendees!) in San Francisco—LED screens, crowd-surfing friends, and even a robot DJ trying to steal the show. But getting there wasn’t straightforward: he was already offered to open for another major artist the same weekend, and chasing the Chainsmokers slot meant taking a risk. We break down how our “maximize, don’t satisfy” mantra guided the decision—and how the whole experience became a real-life negotiation, balancing opportunity with long-term relationships.

Promotions vs. raises vs. brand-new offers:

Why companies usually put a cap on your raise by leveraging status-quo bias.
The hidden leverage in new job offers—and how sharing salary history undermines it.
Long game vs. quick win: why asking for a raise is a months-long campaign, not a one-email sprint.
Tactful transparency: what to say (and not say) if you’re courting external roles while staying on good terms internally.

Action homework: Answer a recruiter DM this week—even if you love your job—to test your market value.