Road to Kickstarter #08: Taming Chaos

Road to Kickstarter #08: Taming Chaos

Road to Kickstarter #08: Taming Chaos

Greetings Heroes,

Welcome back to another installment of our Road to Kickstarter series! This week, Ryan talks about our newest “Wonderland” otherworld. Meanwhile, Nick spills some beans on a new planner layout we’re testing in The Hero’s Guild this week, including a revisited habit tracker design, cleaner note space, and a new gratitude section. Kyle dives into some of the philosophy behind organizing one’s life and how Gertrude can help keep track of responsibilities and thoughts. And last but not least, John talks about how balancing design intuition with community feedback can be a delicate but vastly rewarding process.

*Read to the bottom to claim your free version 2 weekly spread!*

Ryan, Art

The preview page you’re getting this week comes from Yew’s adventure in an optical illusion wonderland! Things are a little topsy-turvy and everyone’s a bit mad, but it’s all a matter of perspective, right? Yew and Shadow Buddy pursue a dapper little creature in a waistcoat that’s either a rabbit or a bird (depending on how you look at it) who seems to know the location of the hidden glyph, but good luck keeping up when the floor is suddenly the ceiling…

I’ve been obsessed with optical illusions since I was a kid, so mashing them up with an Alice in Wonderland inspired world seemed like a perfect match. It was a lot of fun to draw this one, I just hope the illustrations aren’t too confusing to color in!

Nick, Product 

Weekly Spread Layout 2.0

We have once again made some edits to the layout of the weekly spread. I’m going to do a quick walk through of the changes we made for the pages we are sending to The Hero’s Guild. With just a few months from launching this project we are closing in on what will be the final weekly page layout.

Habit Tracker Revision

This is the biggest change we made from the last version to the current. We went bold with the habit tracker design before, and while it was fun to look at, we ultimately felt like it visually overwhelmed the page a bit. Since the goal is to have the hero feel at ease when using the planner… This version wasn’t right. So, Ryan came up with what I think is a really original take on the classic habit tracker. At the top left of the weekly spread you list the habits/chores/activities you’d like to track aside universe branded icons. Each habit will have an assigned icon. As you progress through the week, you’ll color or circle the icons that represent the habit you wanted to execute. This allows us to get even deeper into the lore of each monthly universe, and give the heroes a cleaner and more functional tracking system. AND, it doesn’t have to just be traditional habits. I’m super curious to hear what you think about this new style of habit tracker. Please leave a comment below!

Cleaner Note Space

In the last iteration the notes section felt a little off. Part of the notes sat under the SideQuest list. We decided to separate the notes and keep the bullet journal style dots to be a true “space of infinite possibilities” for your brain dumps, grocery lists, workout plans, steps tracker, or doodle space. It’s also a nice visual break from the heavy use of horizontal lines across the other parts of the page. In the comments, we’d love to hear your thoughts on this.


This is a brand new feature we wanted to put on the page. It’s so cliche at this point, but it really does work. Writing down the things in your life that you are grateful for really help you live a better life. So, we are make a space for it on the weekly spread.

So, are you a fan of the new changes we have made?

Kyle, Operations

For this Road to Kickstarter, I get to be the one who gets to talk about some of the philosophy around the planner since Nick is talking about the page layout.

This week the team had a lengthy discussion about the deeper benefits that organizing your life can have on our overall well-being. The benefit that stuck with me, personally, was that when you are keeping track of all the different events in your life, you are in a way keeping inventory of how you are spending your days then in so doing keeping inventory of how you are spending your life.

So as we look at the page this week with all of the brilliant optical illusions and mind bending fun, it acts as an analogy for the way life can feel when we do not keep track of all of our responsibilities. These tasks can start to morph and we lose track of what they actually are because they are distorted by the general chaos of disorganization.

A planner is not just a safe place to write down important tasks on specific dates, it allows us to write down our thoughts and organize them in such a way that we can see them for what they truly are versus being distorted and confused for something that they are not.

John, Community

As the resident Guildmaster for The Hero’s Guild, I act as the front door for all hero feedback and suggestions that come in for Gertrude. Balancing the various elements and preferences our passionate Guildmates put forth can be challenging. It’s a delicate balancing act, a dance between design intuition and responsiveness to the needs of our community. Ultimately as we navigate the ever-changing landscape of hero needs and expectations, we have to remain true to our vision for Gertrude while also remaining humble and adaptable to the wisdom of the heroes who are helping us test Gertrude every day. By continuing to follow this path, I’m confident that we’ll create a planner that is not only practical but also transcendent, reflecting the beauty of both The Hero’s Journal design team and our beloved communities.

Have suggestions or feedback you’d like to share for Gertrude? Let us know in The Hero’s Guild!



  • Janna

    I adore Escher and Alice and this is now my new favorite spread. I’m dying for a weekly spread and I can’t wait to see the rest of the Wonderland chapter.

  • Beth

    It looks really good well thought out, I can’t wait to see the finished product.

  • Jocelyn

    I Love your work and even more so now can’t wait until I can get more Wonderland themed things!!

  • ilissa

    It looks good. Well thought out.

  • Jasper

    Really love this habit tracker design!

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