Introducing The Monthly Challenge App

Let’s do hard things together!

Dec 31, 2021
TLDR: We created The Monthly Challenge App. You can join for free and partake in doing hard things with friends. January is pushups everyday.
Over the last couple of years, I’ve embraced the monthly challenge. 
Dry December (crazy), No Spend November (super hard), No TV June (easy peasy), walk every day, do abs exercises every day… you get the idea.
I like challenges for their ability to bring focus, jumpstart a new habit, or just do something hard.
Sometimes a monthly challenge will change my daily habits beyond the month itself. Sometimes they are passing goals - won and done.
I have used the format for physical, personal, and professional goals. Everything from moving more, getting up earlier, taking care of house projects, eating better, using my time more efficiently, etc. 
Monthly challenges can also be used to achieve milestones along the way to much larger “resolutions” or major life improvements.
A year is a significant amount of time. But if we burst out of the gates in January with massive goals, and lose steam by February, a year can fly by with zero progress.  Take being fit. 
Fundamentally, this is a major lifestyle choice. It involves spending time working out and eating well most days. While cold turkey sometimes works, more often, I’ve needed a progressive plan to get me to my goals. 
The framework is simple: identify a small, attainable milestone and do it until it becomes easy. For example: 
  • Do 5 minutes of air squats every day. 
  • Add one serving of fruit or vegetables to each meal and eat it first
  • Write for 5 minutes a day.
As it starts to feel easier, and it will, add to it. 
Slow is fast.  
Doing things with friends is also helpful.
I tend to do things alone a lot. Maybe too much. I didn’t think I needed a community to push me, but over the last year, I’ve discovered how meaningful it is to have a team around you. 
Case in point: last summer my company held a “summer games” competition. Every minute of activity, even walking, earned you points. Because lifting is so intense and not something I can do for hours on end, I had to start walking to compete. 
The competition lasted for two months, but walking stuck for me. 
Let’s talk about consistency.
Consistency is very valuable. But let’s not see ‘consistency success’ as binary. 
If you set out on a monthly challenge, what happens if you miss a day or two? 
It’s easy to get caught up in worshipping consistency about all else. I know I have. Missing a day can easily feel like a failure. But it isn’t.
I’m the first one to tell someone else that perfection is the enemy of good enough. But I held unreasonable standards for myself. Last year, it finally struck me that partial achievement is worthy of celebration. 
New Year’s Resolution season is about to start.
Sometimes resolutions work. Often they don’t. 
Some of my best evolutions did not start in January, but I do enjoy slowing down this time of year, taking stock, and dreaming about what’s next.
2022 marks the first year my annual goal setting process is not filled with angst. It’s a really amazing feeling. 
I realized in November, when I usually start thinking deeply about the next year, that I’m not approaching 2022 with the deep-seated feeling that I am a failure and need to fix something fundamental about me.  Why’s that? 
Hot take: It’s not solely because I have found some inner peace and self-love. 
It’s because over the last couple of years I actually did hard work to become better. It wasn’t done in one fell swoop. It wasn’t linear. It wasn’t as fast as I wanted, but I did it and now I have momentum. 
So now I have confidence I can do hard things. 
I have goals, but they are about building and growing. 
To be clear, I don’t feel done. 
But I no longer feel like my goals come from fixing flaws. They come from doubling down on interests, gifts, passions, etc. 
Hold up, you said there was an app?
I love doing hard things and helping people do hard things. And Dane loves making everything a game. So we built The Monthly Challenge App over the holidays.
For January, we have one challenge - pushups every day!  The goal is to offer more than one challenge each month so do share your ideas! 
In the spirit of building in public, we’re releasing this before it’s in the various app stores. 
You can save a shortcut to it on your phone’s home screen. 
  • iPhone: Open Safari > go to challenges.thepleasantbox.com > click the share icon (box with arrow pointing up) > tap Add to Home Screen
  • Android: Open Chrome > go to challenges.thepleasantbox.com > tap the three dots at the top right > tap Add to Home screen  In the app, you can personalize your target. For example, my goal is to do 100 pushups a day for the month of January. Maybe your goal is to do 50 or 200. 
Note: You can signup for the app today, but the challenge won’t start until January 1, 2022.
Here is a short guide to proper pushup form and options for making pushups harder or easier. If you have never done a full pushup, I am very confident we can change that in January! 
At the end of the month, I’ll share stats from our collective effort. 
If you have ideas for future challenges, please comment or reply.
Welcome new readers! If you’re looking for inspiration for goal setting or doing hard things, I recommend these past articles: