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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The Ugly Middle

The Ugly Middle


There’s a point in every project where things go from exciting to completely mundane. We’re calling this portion "the ugly middle."

If you were to zoom the lens out on any creative endeavor it would typically have three big phases:

  1. Planning and kickoff (the fun times)
  2. The actual work (aka the ugly middle) 
  3. Some sort of launch or state of completion (the goal) 

The unfortunate thing about these three phases is that the time spent to accomplish each phase is not equal. It breaks down to something like this:

  • Phase 1: 30% of the project’s time
  • Phase 2: 60% of the project’s time (the ugly middle)
  • Phase 3: 10% of the project’s time


While the ugly middle takes up the majority of your time, it’s also the most important part

Anyone can start a project. Anyone can take the first step toward a big dream or goal. But not everyone can persevere when they encounter the ugly middle—when all the real to-dos and work start piling up and sucking all of the hours out of your days. 

The ugly middle is where you learn if you truly want to accomplish what you set out to create. 

Once the excitement of the beginning of a project wears off, you find yourself with a seemingly insurmountable amount of work in front of you. This work, by most accounts, is not sexy or fun (boooo!). That’s not to say that the work and time it takes to create what you’re trying to build won’t be interesting, it’s just that your interest level can dwindle when the hill you have to climb is steep and long. 

The ugly middle is the part of every project where the real magic actually happens. Sure, the beginning is great because you come up with the idea, but the ugly middle is where you bring that idea to life. Where you stop dreaming about it and when you start making it a reality. 


Without the ugly middle part of a project, there isn’t any substance. You don’t have an actual thing. You just have an idea and a goal, with no way to connect the two.

When you drudge through the drudgery (as our friend Josh says), you CAN achieve your goals. When you design the fifth revision of the 14th page on your website. Or when you write 10,000 words and have to scrap half of them. Or when you share your creation with your first customers knowing they’re going to have tough feedback that will require going back and redoing a bunch of work. If these types of things don’t scare you away, you’ll be doing what’s necessary to get to your goal. 

How we’re making it through the ugly middle and how you can too

For us, the ugly middle isn’t done yet. As of writing this post, I’d estimate that we’re about halfway through our ugly middle phase. We still have to:

  • Design 10ish website pages
  • Get all those designs implemented in WordPress
  • Migrate/update 400+ articles
  • Build our monthly launch strategy
  • Finish our combined newsletter strategy
  • Create an ongoing plan for social content
  • Create an ongoing plan for YouTube content

Crap. Maybe we aren’t halfway? Haha. 

Nonetheless, we aren’t afraid of all the work in front of us. Sure, there are some days we’d rather be spending time on other things (I’m looking at you article migration!), but we’re okay with doing the less-than-exciting work because we know it’s important and necessary. 


One of the mistakes any creator can make (and we’ve made it time and time again) is thinking you’ll craft a perfect plan and schedule in the beginning. It's tempting to naively believe that a linear path will take your project from kickoff, through the ugly middle, to arrive safely at the final goal. Unfortunately, projects almost never go to their initial plan. 

That’s why we have daily meetings to get on the same page with what we’re working on. We also have weekly longer meetings where we reprioritize the most important items and shift things around (feel free to watch one of these recent meetings). 

It’s easy to get discouraged when an initial plan doesn’t work out.  For us, we thought 6 weeks was enough time to build and launch Wandering Aimfully 😂. As of writing this, we’re at 10 weeks and have a lot left to do. But we’re not letting our missed deadline get us down. Sure, it sucks that we had to move things around, but what was the alternative? Give up? Not gonna happen. 


It sounds simple, but if you accept the fact that an ugly middle phase exists, it becomes easier to embrace it. We know there is a ton of unsexy work happening right now. And while it’s not entertaining work, it’s some of the most important work we’re doing for this project. 

There have been multiple times when we’ve felt the daunting pressure of the size and scope of building Wandering Aimfully. But, we want the goal more than we fear the work it takes to get to that goal. 

We wish we had more exciting things to write about and share, but alas, we’re in the ugly middle

Instead of trying to force some drama or excitement in our content, we’re sticking to our to-do list. We’re removing any unessential tasks that take up time/energy (hence why we went dark on Instagram for a bit), and we’re giving ourselves permission to take a little bit more time than we initially planned. 

Our goal with this entire public build of Wandering Aimfully is to show you what it actually takes. And right now, what it takes is doing the work. 

We hope you’ll stick with us (and stick with whatever you’re creating!) because we know the ugly middle doesn’t last forever.

The First 60 Days of Building Wandering Aimfully, By The Numbers

The First 60 Days of Building Wandering Aimfully, By The Numbers

Build Diary: Week Eight (Things Are Looking Up!)

Build Diary: Week Eight (Things Are Looking Up!)