Are you a deadline dodger? Design deadlines that do you right

If you’re a creative type (or curious, or a questioner), you probably dislike being boxed in by “rules.” Including rules about when stuff gets done. After all, can’t you trust the process and your instincts to get where you want?

There is infinite creative possibility in allowing time and space to make things up as you go. And if you don’t have external structures like deadlines to shape your efforts and outputs, you’re making the process much harder or longer than it needs to be, in my humble opinion.

Before giving tips on designing deadlines I want to make a case for using them at all.

If you’re a deadline dreader/dodger, know that there’s plenty of evidence that deadlines can be (pleasantly) motivating. It’s how we relate to them and/or their source and implications that gets us all wound up.

Also consider that even for the most fluid and flexible among us, there is always some kind of logic and rhythm to how you order and prioritize both material things (such as your kitchen or household) and activities (such as social engagements and work flows). This can be because of the way you do things as well as external incentives/consequences. Typically it’s a combination.

For this reason, unless you’re in a period of profound personal development or wild experimentation, most people do things the way you’re expected to or the way they have in the past.

Self-designed deadlines break these patterns, giving you motivational juice and momentum. A friendly kick in the tush or a firm helping hand.

A few approaches to deadlines that support versus stifle you include:

  1. Declare a date that would make you feel great. Is there a timeframe that feels too good to be true? I often prefer this approach and it can be intimidating because there is (or seems to be) a high risk of failure. Sure, you could fail or feel stressed by the possibility, and a healthy challenge is naturally motivating. The point is not to doom yourself to failure or create negative pressure — it’s to not sell yourself short.
  2. Run the numbers. If you have “market data” or historical data to create a reasonable hypothesis about how long something will take, great. This is a very practical approach. Just keep in mind that work expands to fill the time allotted and that you may need to get creative if unknown variables throw a wrench into plans.
  3. Consult someone who is good at what you want to do, better yet several. This will give you a confidence interval, more social support and a more grounded sense of what to consider.
  4. Consider the long term or bigger picture goal and desired timeline, and set deadlines for short(er) term goals on a relative basis. This is particularly helpful if you’re naturally strategic and/or can already see the big picture.
  5. A combination of 2+ of the above. You can mix and match these approaches as best suits your preferences and position.

Deadlines empower performance and motivation because they give you something to rise toward and kick against in some cases. A deadline is inescapably real. If we’re too theoretical/open/formless about what we’re up to it can feel like we’re swimming in an ocean of possibility without going anywhere or changing direction haphazardly.

When can (performance) deadlines hurt more than help? When you’re truly just exploring something, or you’re burned out.

In this case creating learning, experiential and wellness goals (and yes, deadlines) can be more timely and fruitful.

Also if you’re perfectly content to make progress at the pace you’re making it and aren’t energized, inspired or excited by the possibility of creating your desired future faster, nor do you want to feel more excited, a deadline doesn’t really make sense. You may benefit from more play time, more partner time, or more peace out time instead.

Deadlines “work” when you take advantage of their ability to help you prioritize your efforts and activity: First thing’s first.

Want more work tips and inspiration? Subscribe to my weekly newsletter at caseyonder.com.

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