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Have you ever had a server at a restaurant tell you to say, “When,” when he or she has put the right amount of ground pepper on your food? That’s usually a fairly simple ask, since it’s rather easy to know when the amount will be the right amount. It’s something you’ve likely done for yourself enough times to know when to say, “When.”

Have you ever asked yourself when you’ll know when to stop trying to accomplish a goal or when you’ve reached it? Do you know how long you have to keep trying your best to satisfy your boss or how long you have to keep asking someone to do something before it becomes automatic for them or for you to no longer feel like a nag? There is a simple answer to the questions, but only you will know when you’ve reached that, “When.”

Whether it is a business, professional issue or a personal, relationship issue, you must clearly define what success or the goal is. What does it look like and feel like? How will you know when you’ve reached it? If success is getting a direct report to be self-directed, assuming that they have the wherewithal to do so, you will know it when they accomplish what you want them to accomplish without your having to constantly remind them. If it is getting a student to turn in assignments on time and properly without your having to constantly remind them or their parents, you’ll know when that goal is accomplished. The main point is, you have to clearly define the goal and what success looks like. As with getting your child to keep their room clean and the bed made, you must clearly define to your child what “clean” and a “made bed” look like, especially with teenagers since your definitions will likely be different. Unless you clearly define the goal, neither of you will know when it has been reached.

So, “When is When, When?” How long do you keep asking, reminding, following up, micro-managing, working your tail off, nagging your child, and so on? The simple answer is, “Until.” You keep going, until. You keep working at it, moving closer and closer every day, until you’ve accomplished your goal or until you decide it is no longer worth pursuing. The answer is still, “Until.” You go until you know it’s time to stop. Regardless of what you decide, you will know when, when is when because you will have reached your “until.” Reaching “until” is always a great feeling, one of accomplishment and also of relief. How cool is that?


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