9. Make more bold moves.

“I’m living like there’s no tomorrow, because there isn’t one." Don admits this unhindered approach to Rachel Menkin in season one. Several episodes earlier he'd stormed out on a meeting because she was too demanding, and mere episodes later she's seen throwing her morals (and panties) to the wayside for the married ad man.

Don applies a no-rules attitude towards life, and it's this mentality that makes him the master of the unexpected bold move. He unleashes them with such regularity that we almost expect him to do the unexpected. Force fingering Bobbi Barrett to get her to appease a client? A shocking (possibly deal-breaker) moment for any other man, but for Don, the sexual power-play only serves to solidify Bobbi's desire (and convinces her to coax Jimmy into apologizing to Don's client). 

While we don't suggest engaging in similar semi-violent behavior, there is something to be said for the way Don levies left-field moves. He doesn't think twice before showing up at school teacher Suzanne's door. He fires clients on a whim ("too traditional" seems to be his favorite reason). He has no qualms about manipulating others to get what he wants, whether it be with coworkers (remember when poor Roger vomited at the feet of clients after Don's elaborate "broken elevator" scheme?), his employers (that whole "fire us so we can start a new agency" strategy), or the general public (penning that ingenious letter to the New York Times about quitting smoking after being dumped by a tobacco client).

Don's message here? I'm a man who knows what he wants and stops at nothing to get it.