Retention offers are designed to make leaving feel costly and staying feel cheap — but 'cheap now' can simply be 'expensive later.' The practical, least-regret response is to accept a short-term retention discount only as a trial and to set a reassessment reminder. That means: if the vendor offers 50% off for six months or three months free to stay, use that period deliberately as an experiment. Track your actual usage and perceived value during the discount window. If the service genuinely meets your needs more often than not, it may be worth continuing — but you should make that decision with current data, not with the inertia that retention offers try to exploit. Setting an explicit follow-up reminder (calendar entry, phone alert) is crucial because the discount can end silently and the vendor may quietly resume full price.

Practical template for handling retention offers: (1) Accept only if you explicitly schedule a reassessment date in your calendar that's a few days before the discounted period ends. (2) Add a one-line objective to the calendar event: 'Have I used X at least N times this month?' or 'Did X deliver Y value?' (3) If the answer is no, cancel before renewal; if yes, consider whether long-term value justifies the full price. Also log the actual renewal price so you don't assume the discounted rate continues. Treat the retention window like a scientific test, not a hostage negotiation — short-term discounts can be useful but they should never substitute for intentional long-term decisions. Lastly, beware of 'we'll keep you on the lower price if you accept now' scripts; always verify with a written confirmation and set your calendar reminder before saying yes.