The one where self-imposed deadlines are generally flexible

This was written on Saturday instead of Friday.

Hi friend,

This is showing up in your inbox on a Saturday because, well, I was so wrapped up in the Govalo pre-launch that I forgot to write an email.

I’m a creature of habit. I close my rings on my Apple Watch almost every day, have a ~64-day Peloton activity streak, maintain inbox zero, and tend to send out an email every single Friday. When I fall off my habits, I really fall off and it’s hard for me to get back into it.

Knowing this about myself, I’m very careful about setting self-imposed deadlines. I used to get really down on myself whenever I’d miss one. It turned into a pattern of negative self-thinking, so I’ve since changed my mind on how to handle deadlines. As entrepreneurs, we live lives that are constantly in flux with every day being different. I genuinely believe we need to handle deadlines a little differently because of this.

There are two kinds of deadlines: hard and soft. Hard deadlines are the ones that absolutely cannot be moved. You need to launch a project before a client begins a sale. You’re attending an event on a specific day. Someone else gave you the deadline.

Soft deadlines are much more flexible. Most self-imposed deadlines technically fall under the soft deadlines category. This newsletter is about soft deadlines.

I’ll be the first to admit that not everyone will agree with me on this topic. There are plenty of people who need to be told their self-imposed deadlines are not flexible in order to hit them. My take is that there are plenty of other actions you can take to keep on top of your deadlines and hit them while still providing yourself the grace to move the deadline if needed.

I usually ask myself:

Is this a truly important deadline? I used to go out of my way to keep a streak going for the sake of keeping it going. Like, do a 5-minute meditation on the Peloton app just so I keep my daily streak going. Keeping that self-imposed 11:59 PM deadline every single day is probably the least important thing to keep on my mind. Are streaks fun? Absolutely. But if something is not worth the stress, don’t stick with it.

Why did I set this deadline? Why am I keeping this deadline? This newsletter is a good example of this one. I set a deadline of Friday morning for this newsletter when I first started sending out emails a few months ago. I know newsletters are meant to be consistent for increased readability. But stressing over keeping my Friday morning send time is not going to make or break my readership a huge amount. Some may not see the email with it coming in on a Saturday, and that’s fine. It’ll be in their inbox on Monday. (A future hello to you Monday readers!)

Is shifting my deadline negatively impacting anyone else? If someone is depending on you, shifting a self-imposed deadline could have a negative impact on someone else. If you absolutely cannot hit the deadline, speak with those impacted and give them a heads up before you miss the deadline. Don’t wait until after you miss it. Transparency and communication are key to any successful relationship, whether in work or in your personal life.


If you’re going to set self-imposed deadlines, just make sure you’re doing it for the right reasons and that you can allow yourself the grace and forgiveness to shift the deadline if it’s not going to work out for a given reason. We all lead busy lives, and our days as entrepreneurs tend to change all the time.

Until next week,

Kelly