A Quiet Afternoon With a Stack of Cards Picture a slow Sunday afternoon. There's a cup of coffee on the table, a short stack of index cards, a handful of envelopes, and a pen that writes smoothly. You're working through a short list of sweepstakes, carefully printing...

Becoming a sweepstakes regular can sound like a big commitment, the kind of thing reserved for people with endless free time and elaborate spreadsheets. In reality, it's much simpler. Regulars are just people who have built a handful of habits that make entering...

Every sweepstakes has a life cycle. It launches, runs for a stretch of days or weeks, winds down to a deadline, and then moves into a quieter period while winners are drawn and notified. Each phase of that cycle offers different opportunities and different risks, and...