Why 2020 Will be the Year of 30-Day Challenges (And How I’m Organizing Mine)

Dudefluencer: 30-day challenge

I’m not one for stagnation.

When I was a teacher, I sought out new lesson plans and experimented with new pedagogies. As the creator of Dudefluencer, I’m continually reshaping the website or tweaking old articles to make them more appealing for my readers. 

I’m always trying new things, failing just a little bit, and improving on those failures to grow. 

In 2020, I’m taking that iterative approach to my business life and applying it to myself. I’ve decided to focus on a series of 30-day challenges to build new healthy habits. Specifically, Matt D’Avella’s Youtube channel inspired me to get off the couch and start trying some new health challenges for myself. This next year will be about improving my mental and physical health while pushing myself to break some of the bad habits I’ve accumulated over the years, one 30-day challenge at a time.

But can you really change your life in 30 days?

What are the rules for a 30-day challenge?

While every challenge will have its own internal set of requirements, there will be an overarching set of conditions for all of them. 

1. Every month of 2020 must have a unique challenge.

I can’t do two similar challenges in a row. For example, while mindfulness meditation is on my shortlist, I can’t also do transcendental meditation as a separate challenge for another month. 

2. Every challenge must last 30 days

That means that if a month runs 31 days, I get a day off if I so choose between goals. Otherwise, the challenge must run 30 consecutive days over the course of a month. Except for February. February’s goal will run 29 days this year. 

3. Every challenge needs intermittent documenting

While reflecting on each challenge at the end of the month might seem tempting, it’s easy to forget the days in the middle when habit formation is most difficult. I’ll take pictures and log how the challenge is going to be summarized in an article about the 30-day challenge.

4. Every challenge gets an independent accountability article. 

Come on, I’m a writer. Of course, I’m going to write about these challenges. On the last day of the month, I plan on publishing a 30-day challenge round-up where I take you through all of the steps of my journey: from conception to completion.

Along the way, I also plan on giving tips and suggestions from what I’ve learned over those 30 days. I want to help you out any way that I can, so I’m going to share any books I’ve read, videos I’ve watched, or podcasts I’ve listened to that I believe are going to help.

All of my resources will become your resources as we build a community of people practicing self-growth throughout 2020.

What are the overarching goals of these 30-day challenges?

One of the most daunting parts of this process is selecting which challenges I’m going to take on this year. A quick Google of “30-day challenges” brings me back all kinds of results, like:

And of course, there are many other challenges I didn’t include from the ones listed above. 

So how am I choosing which twelve I will pursue? 

The answer must be “yes” to all three of the following requirements:

Requirement 1: Am I learning by doing?

Life is about the expansion of knowledge. 

A 2012 study by Marjan Laal focused on the benefits of life-long learning. It concluded the three most significant gains were: adapting to change, a bigger paycheck, and enriching and fulfilling our lives. While I would never turn down a higher salary, these challenges will be focused on adapting to change and enriching my life.

After going through my wife’s Tony Robbins’ Unleash the Power Within exercises, I recognized that my need for certainty often keeps me stagnant. I’ve been afraid to take risks or try new challenges because I love the safety of knowing what comes next. Learning doesn’t just come from online articles; I need to experience new activities in order to know what effect they’ll have on me.

Every one of my challenges will hopefully push me to learn a new activity while also pushing my comfort zone.

Requirement 2: Am I pursuing something creative?

Part of the reason why I love running Dudefluencer is because I feel like I am pursuing something that engages my desire for creativity. 

When I think of creativity, I’m always reminded of a Ted Talk by Dave Morris, an improvisational comedian from Chicago. Morris describes “the way of improvisation” by breaking the artform down into seven steps: play, let yourself fail, listen, say yes, play the game, relax, and have fun. While the entire video is worth a watch, I’m always particularly drawn to his description of play. Morris defines play as “the idea of engaging with something just because you like it.”

Morris tells the audience: as children, everything in life happens right in front of you. His hands stretch forward as he continues, “but as we grow up, we slowly start to lose our sense of play.” Play turns into work, and no one likes work, which is why it is so important we keep playing.

Play, to me, is no different than creativity: an opportunity to create and express ourselves through various art forms. I’ve always loved video editing and podcasting, and I don’t think I’ve ever spent enough time “playing” around with them. That’s why creativity will be an integral part of my 30-day challenges, even if it’s just at the end-of-challenge round-up article.

Am I prioritizing my health?

My first year in Virginia, my pepperoni pizza and fried chicken-focused palette became even more limited after having to go grocery shopping for myself for the first time. That meant lots of pizza, hamburgers, and bacon. Lots and lots of bacon.

Too much bacon.

The first time I cooked a package of bacon, I ended up grilling the whole pound and mixing it between homemade turkey club sandwiches and bacon Buffalo chicken wraps. I ate half on Sunday and packed two turkey club sandwiches for work the next day.

I should note that at that point, I had recently volunteered to help out with the drama club at the high school I was working with—the final rehearsal was that Monday. After devouring a pound of bacon over 24 hours, I found myself crashing by 1 P.M. and asleep by the end of the school day bell.

Next thing I remember, it was 6 o’clock, and the janitor woke me up by slamming his broom into my desk. I missed the rehearsal.

The moral of this story: I don’t know how to take care of myself.

That’s why, for a majority of these goals, I need to be able to clarify how this habit will help me prioritize either my physical or mental health. Whether it is modifying my diet by including more vegetables or meditating, the end result of the habit has to be a net positive.

Okay, well, what challenges are you going to attempt?

Hard ones.

Alright, that’s a shitty answer. 

The truth is that with these 30-day challenges, I plan on starting small and building around where I want to grow the most first. I’m not going to try and change my entire physical appearance in 30 days, nor am I planning anything that might be harmful to my body. Instead, I’m focusing on self-care routines that have helped me before in the past alongside some new challenges that will push me outside of my comfort zone for the sake of new-found healthiness.

That’s where we will begin for January 1: practicing mindfulness. Over the next 30 days, I plan on meditating for at least 15 minutes daily. 

Dudefluencer: Meditation

Meditation as a habit has always been something that fascinated me and seeing a bevy of resources tout meditation’s positive health effects, I didn’t want to pass up this opportunity.

Other planned tasks include getting at least 11,000 steps a day, turning off electronics after 7 P.M. and no complaining for an entire month. Yet the one that will be hardest (and scariest) for me looms in the summer: Going vegetarian. When I told Rachel about that one, she raised her eyebrows, glanced at our Instacart history, and said, “Are you sure?” 

I’m not. But that’s part of the point. 

One thing I should note is that I also will be reading one self-help or business book a month for the next 12 months as well. The goal is to find new ways to improve Dudefluencer and myself so that I will be in peak performance shape by the end of the year.

Are you going to stop these challenges after 30 days?


I’m not really sure. I’m hoping that a lot of these habits provide enough benefit that they are worth keeping for longer than a month, but I honestly won’t know until the 30 days are over. At the very least, I want to establish a collection of healthy routines that will build upon each other so that by the time December 31, 2020 rolls around, I will have a toolbox of healthier habits.

The point of a 30-day challenge isn’t to necessarily change every aspect of my life, but instead, slowly introduce better habits replacing bad ones (like eating as much pizza as I do). Research conducted by Phillippa Lally found that it takes 18 to 254 days to make a habit. And unless the habit proves to be beneficial in the short and long run, I doubt I’ll be building towards 254 days.

But my mind is going to be open, and the truth is, I hope some of these habits stick. I want to live a long time for my wife, my family, my future children, and myself.

Time to get started!

I might have mindfulness meditation planned out for January, but I am looking for ideas for the following 11 months. Let me know what you think I should try in the comments, and I’ll keep you updated as I progress forward. 

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2 Responses

  1. I love the way you have set your goals out. I love seeing how other people reflect and set themselves challenges. I also love that one of your challenges is meditation, oh my goodness the difference that this simple practice makes to my life is beyond words amazing! All the best of luck with it!

    1. Thank you so much. I’ve started small with my meditation work but I can already feel a difference.