Is it ever ok to move a deadline?

Have you ever set an unrealistic timeline to hit a goal or complete a project?

Actually, let me rephrase that.

Have you ever started a project and set a deadline by which the project should be done
– and then at some point realized that deadline was going to be harder to hit than you thought?

I’ll be honest: this has happened to me.

Multiple times.

In fact, in 2020 our team was working tirelessly to prepare for a big promotion. We had set a deadline and, after a few weeks, I realized that it was going to be hard to meet it.

I was talking this through late one night with JD and he asked me, “Why can’t you move the deadline?”

His question (though annoying in the moment) was brilliant. It helped me realize that I had unknowingly applied a meaning to the deadline – if we hit it, it meant we were a capable team.

But that wasn’t at all true. It was just a story I was telling myself.

So I started asking myself a different question: could I have the courage to change the deadline without it meaning something about myself and/or my business?

If the answer was yes, I needed a framework to know if changing the deadline was in the best interest of our team and our customers. If you’re in need of this framework – I call it the “decision to delay” framework – then click >>PLAY<< now to learn:

  • [00:29] How the best business owners think about deadlines
  • [01:22] The decision I faced in 2020 on whether to push back a deadline
  • [03:04] What I learned about the meaning I was applying to deadlines I created
  • [06:10] The decision I faced in February 2023 on whether to push back a deadline
  • [09:19] The “decision to delay” framework that I used with the team in February
  • [12:09] What I was thinking and feeling as a CEO back in February
  • [15:56] What I learned from choosing to delay

Click >>PLAY<< to listen now!

listen to the episode:

browse more recent episodes