Why I Signed Up For A Crazy 21-day Challenge

Aron Croft
5 min readJun 29, 2020

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Can I eliminate procrastination and increase my productivity 700%?

“$250 if I miss one day!?” I asked.

“No. You pay $250 if you miss one day AND $250 if I miss one day,” my friend replied.

“We need to be invested in each other’s success too,” he explained.

I could feel my heart thumping.

I could hear every rational bone in my body shouting “no!”

So I shocked myself when these words slipped out of my mouth…

“F- it. Let’s do it!”

Announcing my 21-day challenge

I’ll briefly explain the rules and then tell you the six reasons I signed up for this crazy idea.

Here are the rules:

  • I have to publish 21 articles in the next 21 days on Medium.com (one each day)
  • My friend has to do a Facebook live stream every day for the next 21 days
  • We have a celebration meal booked on Sunday, July 19th assuming we succeed
  • If either of us misses a single day, we BOTH have to forfeit $250.

This idea is crazy: In the first week, I’ll publish more blog articles than I’ve published IN MY WHOLE LIFE.

So, let me share the 6 top reasons I signed up for this thing:

  • Change the Game
  • Eliminate Perfectionism and Procrastination
  • Increase Productivity by 700%
  • Improve Skills
  • Strengthen a Relationship
  • Skyrocket Confidence

Change the Game

Publishing articles is scary. Take it from someone who has published only a handful to date!

But a 21-day challenge — that’s a different game. That is my friend and I competing and cooperating with each other.

Instead of focusing on my fear of publishing, I focus on ticking a box each day.

I get to look forward to the celebration meal we have scheduled.

And I am relieved to know that he’s just as scared as I am! There’s something freeing about knowing someone else is experiencing the same fears you are — and also taking action in spite of them.

By creating the challenge, my focus has shifted from my fear of publishing articles to my desire to tick the box each day with my friend.

Eliminate Perfectionism and Procrastination

I have a confession to make… I am a perfectionist.

Not the Type A, OCD type that can’t relax when things aren’t “just so.”

But the type of perfectionist who just really fears “looking bad.” The type who likes to maintain an image in his head of “all the great things I can do” and is terrified of shattering it by testing it against reality.

I’m like the merchant in The Alchemist whose life dream is to go to Mecca, but he never will because the reality of going to Mecca might not meet his imagined expectations.

The 21-day challenge eliminates that for me.

Look at everything I have on the line if I don’t follow through:

  • Lose $250 each day
  • Hurt my self-confidence in my ability
  • Cost my friend $250 each day
  • Look bad in front of my friend

While I am terrified to write and publish articles, I am more terrified of these other consequences.

So, I write…

Increase Productivity 700%

Productivity is so important. Yet millions of people struggle with it. They read countless “life hacks” and yet only increase their productivity by 1–2%.

I have been in that boat many times.

My goal prior to this challenge was to write 1 article per week. Given that I’d never published a single blog post prior to this month, that seemed like a suitably ambitious goal.

But it was also a very safe goal. It wouldn’t cause me to transform. I could still procrastinate and be perfectionistic with my writing.

Instead, this challenge will increase my productivity by 700% by getting me up to 7 articles per week. My output is going up by 700%.

Our actions and our output are all we can control.

Improve Skills

The other benefit of increasing my productivity and output by 700% is that I also increase my experience by 700%.

Experience is the best teacher there is.

You can learn more by publishing for 21 days straight than you can by studying publishing for 21 weeks straight.

I will get reader feedback on my articles, both direct via comments and indirect via reading statistics. I will get feedback from my friend. And I will give myself feedback on what I produce.

The only way to learn a skill is through doing the skill.

Strengthen a Relationship

I have another selfish reason for doing the challenge: I really like my challenge buddy.

I want to spend more time with him.

I know that what we achieve together will be a positive, shared experience — and will likely lead us to create new, bigger challenges together.

The best antidote to fear is community. Strength in numbers. Togetherness.

I can fall flat on my face with my writing and have everybody laugh at me or hate me, but my challenge buddy will still be on my team.

We’re in this together and will support and encourage each other, despite any negativity from the outside.

To do scary, big things, you need a support network of other people who are also facing their fears to achieve something bigger than themselves.

Skyrocket Confidence

Self-signaling is the term psychologists use to describe how we develop confidence.

You see, we create our self-image the same way we create our impression of other people: by observing behavior.

So, when I watch myself publish 21 articles in 21 days, I am going to update my self-image. Such an action is not consistent with my current self image — but it is consistent with my future self.

When my present self sees those actions happen, it will start to update how it sees me. My confidence will improve because I will see myself as someone new.

Someone that produces 700% more, improves his skills, and strengthens powerful relationships.

Someone who overcomes procrastination, eliminates perfectionism, and takes action in the face of fear.

Someone who I want to be.

Someone who I am becoming.

You can do this too. Start your own 21-day challenge and let me know how it goes!

Call To Action

If you want to 5X your learning skills and eliminate procrastination, I created a free guide on Ultralearning.

Click here to download the free guide.

P.S. You’ll also get daily updates on my 21-day challenge. :-)

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Aron Croft

Harvard Grad. Master’s in Psychology. Screwed up jobs & marriage in 20s with undiagnosed ADHD. Sharing how I rebuilt my life and career. On YT and HiddenADD.com