How to Overcome Deadline Sabotage?

We previously spent some time talking about why deadlines are useful. But you probably still don’t like them! Deadlines force you to contend with many core personal obstacles, including (but of course not limited to) your concern about commitments (do I really want to agree to this deadline?), perfectionism (how much work will it take to do this right?), procrastination (can I do this later?), and failure (can I pull this off?).

So what are the two most common obstacles that come up when dealing with deadlines?

Deadline Avoidance

The opportunity arises to take on a project or task, but you never commit to getting your work done by the deadline in the first place. You haven’t made it clear what specifically will get done or when it will get done by.


Deadline avoidance is one version of a fear of commitment (which ties in with a fear of failure). We don’t want to say we’ll get something done and then not produce the expected results. So instead, it’s easy to just avoid committing in the first place. The thinking here is that if we never commit, we’ll never fail.

Truth is, deadline avoidance won’t give us the success we want either (to say the least). In some sense, it’s like we’ve set ourselves up for failure before anything has begun. Life in the shadow of ignored commitments is draining — is that a big surprise?


The catch with a fear of commitment or failure is that it’s virtually always rooted in one or more negative past experiences. Overcoming a fear of commitment means getting 100% closure on those past experiences, where there is no more emotional charge about what happened.

Making peace with old unfulfilled commitments or perceived failures frees you up to make new commitments and take on new projects. And of course, with new commitments come new successes to enjoy and new failures to grow from.

Deadline Dismissal

You commit to a task, but then dismiss its importance. It’s like saying to yourself you’re going to read the TPS report by 5pm tomorrow, only to have that time come and go on your calendar. It’s not forgetfulness — it’s a very deliberate moment at 3pm when you remember this task still needs to get done, and then you tell yourself, “Eh, whatever. This doesn’t matter. I’ll do it later, when I feel like it.”


Dismissing deadlines is a way to mentally check out. You basically give yourself permission to ignore the deadline you committed to. It might not seem harmful, but distancing tends to quickly build into a habit.

If you keep letting yourself off the hook, many of your deadlines (and in fact, probably all of your self-enforced deadlines) will completely lose their effectiveness. Then your results will totally depend on your mood. Can you get how unproductive it can be to wait until you finally “feel like it” (or the pressure’s gotten high enough to complete the task anyway)?


Overcoming deadline dismissal is simple but not easy. It involves doing whatever you need to do to hold yourself accountable to what you say you will do. An accountability structure can take lots of different forms. The form itself doesn’t matter so much. What matters you drawing a line in the sand and placing value on your word. That includes the promises you make to yourself as well as the promises you make to others. Sound hard? Great! Welcome to humanity.

What deadline patterns do you find yourself trapped in that keep your effectiveness down?

This post is the second in a three-part series on deadlines. The other two articles are “Why Deadlines Are Useful” and “Deadline Damage Control (Or, Why Hope Had to Die)“.