Hi! We're Jason and Caroline, a husband and wife creative team taking you behind-the-scenes of building our new business from scratch. Poke around and watch us figure it out as we go!

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Why Deadlines Are Equal Parts Beautiful and Completely Arbitrary

Why Deadlines Are Equal Parts Beautiful and Completely Arbitrary

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Setting a deadline is absolutely instrumental in making any idea a reality.

Have you ever wanted to launch a project of your own, only to get stuck staring at a blank screen or page with overwhelming feelings of being paralyzed? Where do you start? How will you make time for everything? Does anyone actually care if you make this thing??

We’ve learned, from years of painstaking, paralyzing experience, that setting an initial deadline for a project is one of the most powerful motivators. 

Why deadlines are crucial to getting things done

When you work for yourself, you’re fighting a constant battle between the things you know you should do and all the things your easily-excitable monkey brain wants to do (new notification! new tweets to read! new emails to check!).

Setting a deadline helps give your monkey brain some focus. You’re essentially saying: "Hey furry mammal in my mind, pay attention to this date in the future! We won’t be able to eat bananas unless we meet our goal by that date!"

A deadline creates focus. And focus is incredibly helpful when you’re trying to take an idea in your head and make it into some sort of tangible thing. 

For us, and for Wandering Aimfully, we set an initial launch date of May 1. This date was picked completely out of thin air earlier this year. May 1 was months away when we started our initial planning. As it got closer and we actually got started, we had 5 weeks to build ALL THE THINGS.

We knew this initial timeline was aggressive, but we also knew from previous experience that if you set a longer amount of time to create something, guess what happens? You somehow end up taking that amount of time! 

Funny enough, this idea is not new, and it was made popular in 1955 when Cyril Northcote Parkinson wrote part of it in an essay published in The Economist. Parkinson's law (as it became known) states: "work expands so as to fill the time available for its completion." Ohhh look at that fun fact. You feel smarter, don't you?

This is why we believe whole-heartedly in the power of constraints. By limiting the timeline to a very finite number of weeks, this actually allows us to use time more efficiently. This is why we didn’t give ourselves more time, despite the aggressive deadline. 

But, as our Google Calendars crept closer and closer to May 1, I bet you can guess what happened? That little monkey in our brains started to get nervous. He knew if we weren’t done by May 1, he wouldn’t get any delicious satiating bananas.

We've learned (painfully) in the past that when this happens—when you realize you're closing in on your deadline and there's still much to be done—you can do two things: (a) freak out, drop everything and pull all nighters to get as much of it done as possible, probably cutting corners in the process, OR (b) move your deadline back so you can still enjoy the process and build your business to the vision you initially had. 

Remember that your own deadlines are also completely arbitrary

This brings us a very important lesson: It’s important to remember…

The deadlines we set for ourselves are completely made up.

When you set a deadline, circle a date on your calendar, and train your monkey brain to pay attention to that looming day, you can inadvertently create for yourself a very slippery slope. That date can become so defined in your brain that you forget one important detail: you made it up.

If you work for yourself, YOU are the only one dictating the consequences of not meeting that deadline. 

You might laugh, but this has legitimately been something we've had to remind ourselves of in the past. 

So, taking our own advice, to calm the nerves of those trained monkeys in our heads, we extended our launch deadline by a few weeks to May 21. 

Sure, we really wanted to hit our initial deadline, but our sanity—and the sanity of the folks working with us to build Wandering Aimfully—were more important than some date we randomly plucked from the calendar. 

Deadlines, especially the arbitrary ones we make up, do not deserve our stress.

Had we stuck with our aggressive 5-week timeline and launch date of May 1, we would have driven ourselves insane. Building Wandering Aimfully would have gone from a fun project we were building together, to a potential disaster on multiple levels (biz + relationship). 


Now, that being said, there's a caveat to pushing back your launch date. Of course you still want to keep your audience engaged, and you don't want to use it as an out to  procrastinate. In our case, to stay somewhat tied to that original deadline, we decided to follow through with our pre-order and open the doors to actual paying customers.

When someone has given you money for something, it’s as though you’ve signed a secret agreement to not let them down. 

Our pre-order buyers helped do one very important thing: Test that assumption our monkey brains had that no one would purchase our Wandering Aimfully membership. It may sound silly, because this is simply an evolution of a product that has already sold well, but we are changing things up, and change brings about a lot of unknowns. 

We don’t want to let our existing customers down, but now we REALLY don’t want to let our new pre-order customers down. They’ve bought in on just the idea, with nothing (yet) to show for it. That’s a huge motivator for us to get this sucker out the door. 


One thing worth mentioning that we highly recommend is making your deadlines public. It doesn't have to be emailed to all your subscribers or plastered on the homepage of your site. (However, those could be even more motivating.) Just sharing your deadlines on social media or a mention here or there via email could help you stick to it, if you're one of those people in the first category that has a hard time adding constraints to your projects. 

We're also doing some additional public accountability with a live sneak peek/Q&A call this week. For us, showing people (live) what we've been working on is an extra incentive to push through the tough moments and long hours and deliver an amazing product.

Want to join us and catch a sneak peek of the WAIM dashboard/website?

Click here to register for our live sneak peek call on May 9 at 2pm PST! 

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