For The Best Results — Start Messy

The first version of your business, product, or service is always going to suck.

At this point in my entrepreneurial career, I have about 30 projects under my belt. Some of have been very successful. Some have done just okay. Some have been complete flops. But they all have one thing in common: they started ugly.

You might think that project 29 or 30 started out perfectly, right? With 20+ previous experiences, I had to have figured out how to avoid all the mishaps, errors, and ugliness that go along with a new project.

Here’s a secret: every time I start a new project, even I think it’s going to be different this time. But alas, it’s not. Every project starts out with a hideous mess of disjointed ideas, thoughts, sketches, and assumptions.

Now, ugly means different things to different people. For the sake of this argument, I’m defining ugly as a version I’d be embarrassed to show a potential customer.

Most recently, the idea of starting ugly happened with my ofCourseBooks project with my friend Paul Jarvis, and our new friend Zack Gilbert. The three of us came together with the idea to create elegant embeddable workbooks.

But guess what? Things didn’t start out elegant at all.

The start of any project requires an ugly duckling phase

Sketches on paper. Really quickly thrown together designs. A bunch of bad ideas tossed in a Trello board. All of these things are necessary when starting a project.

It is 100% impossible to get a project from initial idea to beautiful and ready for the world in a straight, linear fashion. Instead, it looks more like this:

Yeah, it looks like a mess, and yeah, it often feels like things might crash and burn at any moment. But here’s the hidden beauty in the ugly duckling phase: if you accept that this phase of a project is necessary (or even mandatory), you can look at it from a completely different angle. You can embrace the ugly phase, and you can use it to your advantage to create without criticism or judgment.

With ofCourseBooks, we didn’t worry about everything being perfect from the beginning. We just allowed ourselves to create the first version of a logo. The first version of a branding guide. Definitely the first versions of the website framework and design.

And how many iterations did each of those “first versions” end up having?

• About 15 different logos
• 4 different branding guides
• 3 different website framework sketches
• 2 full website designs

Paul, Zack, and I all have experience working on previous projects, which helped us understand that things wouldn’t be perfect on the first go-round. We came together as a team and had conversations about letting go of perfectionism, and about our willingness to create new versions of things — without complaining about the extra work.

The ugly duckling phase doesn’t have to last long

This is where the word “iteration” actually means something. It’s not just a buzzword, people. It means making changes quickly and without hesitation. It means throwing away hours of work that no longer serve the greater good of a project. It means swallowing your entrepreneurial pride and realizing that no one ever makes anything perfect on the first, second, or even third try. Shifting your thinking in this way can help you reach the next milestone or level of success faster than you’d imagine.

I remember what it was like pining over designs for various projects, or even over words for various articles. It was tedious, nitpicky work. And it wasn’t until I made the big shift in how I defined the success of my art that I began to understand and embrace that my ugly ducklings could quickly become majestic and powerful mallards!

Nowadays, especially with writing, I just sit down and know that the first version doesn’t have to be perfect. There is no perfect, and an ugly duckling is okay. This single thought has completely removed writer’s block from my vocabulary and life.

Sharing the ugly can create interest

I learned in 2015 that people don’t need the perfect picture to be interested in buying something.

In 2015, I wrote a daily journal for 60 days on Medium. In that journal, I shared my heart, soul, and ugly thoughts about what it took to create my next big project (BuyMyFuture). I was scared to publish many of the daily entries I wrote because they were ugly and vulnerable. One in particular was titled, “Does anyone even care?” Here’s an excerpt:

Every single day I think to myself: “Does anyone actually care about this journal or my new project?”

That’s simply the honest truth. I believe a lot of people who are creators (or business owners) can relate to that feeling. When you’re working on something, even if you have validation of the work you’re doing, it can feel like there is a lack of public interest because the amount of interest could never possibly match your effort. I’ve poured well over 200 hours into Project Galaxy [BuyMyFuture] already. Not to mention the hours that other people have poured into this project. The small moments of public validation are fantastic, but it would take an insurmountable amount of them to match up to the hours that have been invested.

A funny thing happened when I shared these relatable thoughts. People became even more interested in the project. How interested? Over half of the 165 buyers of BuyMyFuture said they read the Medium journal and that it influenced their buying decision!

Being relatable and willing to share my ugly helped generate over $80,000.

(The first year of BuyMyFuture was sold at $1,000 per spot.)

Going back to ofCourseBooks, we shared a public Google Doc with our podcast listeners and email subscribers. In that doc (as you can see), we shared all our ugly versions and a bunch of our thoughts along the way. Remember, our definition of ugly may vary to your definition of ugly.

And surprise, surprise: many of our founding members say they purchased when they did because we shared the behind the scenes (read: ugly versions). They saw the progress and knew we’d continue to improve our next versions of the product.

Make starting ugly a mantra, and embrace its usefulness

Say this out loud: “I know this is the ugly phase. I’m 100% okay with making mistakes and having to redo work.” The more you say it, the better the outcome of whatever you’re working on will be.

Whether it’s writing an article, building a piece of software, designing a new logo, or all the other millions of ways you can create things nowadays, be okay with having an ugly duckling phase. Understand how beneficial it is, and shift your mindset from worrying about it to leveraging it in the creation of something even better.

Be okay with starting ugly. It doesn’t last forever, but it’s completely necessary.