Are Challenges a Trap?

I love a challenge. I always have.

“The instructions say it takes two adults two hours to build this Barbie camper van? Challenge accepted.” Okay, so maybe I didn’t say “challenge accepted” as a 7-year old child, but I did build that van by myself in 90 minutes on Christmas morning. I felt like Rockstar Barbie.

Yet, while I’ve always known challenges bring out my tenacious side, a few years ago, I tried to distance myself from a certain type of challenge. I began judging my affinity towards time-bound endeavours, like 30 days of X, or 100 days of Y. My inner monologue started sounding the alarm, questioning the credibility and effectiveness of these challenges. If they are so great, why do you keep ‘needing’ them? Just do the thing you want to do—you don’t need it to be a ‘thing’.

Simply put, I convinced myself challenges were for weak people who can’t simply show up and take action. But over the past year, my opinion has shifted and evolved thanks to two realizations.

New perspectives

First, I gained more insight about how my brain works. After an ADHD diagnosis in 2024, I learned about the disconnect between knowledge and execution. How even when a task is important, its importance is not enough motivation to initiate action. It helped me understand all those years of watching with admiration and envy as others around me simply ‘did the thing’ because it was important. Instead, I would think about the important thing I should be doing until it became urgent.

But what about all the important things that never become urgent? Those actions I want to take that never have a deadline? No one else is waiting for those things from me.

So when I read Extra Focus: The Quick Start Guide to Adult ADHD by Jesse J. Anderson where he described how people with ADHD primarily find motivation through interest, novelty, challenge, and urgency, I felt seen. If a task is important but not interesting, novel, challenging, or urgent, well, odds are good I’ll spend my time doing almost anything else.

Side note: if you’re wondering why people recently diagnosed with ADHD can’t seem to stop talking about ADHD, consider the fact their world is finally starting to make sense after years of wondering why they can’t ‘just do’ what others can.

Second, after developing the Momentum Formula framework, which emphasizes the importance of taking action as a way to discover the ideal Method, Mode, and Mindset for lasting change, I read the book Tiny Experiments by Anne-Laure Le Cunff. In the book, she describes the value of creating a pact as a form of personal experimentation. It’s about committing to taking an action for a set duration.

Sounds a lot like a challenge, right? In many ways a pact is a personal challenge, but an important distinction of the pact is the experimentation element. It’s about about paying attention to what happens when you take action. In other words, it combines action with learning.

Getting into action

Momentum starts with the first step. Once you are in motion, it takes less energy to take the next step. And while you often know the first step you should take and how important it is, it can still feel daunting if you don’t have any sense of what comes after. Your brain might think, “So, wait. I take the first step… and then… I just keep going forever?!?”

In other words, without structure, clarity, and boundaries, it can feel overwhelming to imagine what comes after that first step. Faced with this uncertainty, it can feel safer to stay put.

Challenges are appealing to many because they provide a clear path with a set date. It removes confusion and focuses on specific action over a set time period. Getting started is easier because you know not only the first step, but the second, the third, etc.

But, not all challenges include personal experimentation and reflection.

An experimental mindset involves taking on the role of observer. It’s about being curious to see what happens when you [insert action here] for [insert time frame here]. Your job is to review the experiment like a researcher who is gathering evidence about whether this approach was effective for you or not.

The wrong lesson

Remember all that self-doubt I was having about challenges? It wasn’t just about wishing I could ‘do the thing’ like others did. It was also questioning whether I was becoming reliant on a challenge as the only way to change my behaviour.

Whether you realize it or not, you are always learning from your experiences even if you’re not conscious of the lessons. Without taking the time to pause and reflect, your brain can take a shortcut and draw an unhelpful conclusion.

In my case, I subconsciously ‘learned’ challenges were the only way I could stay ‘on track’ and as soon as I wasn’t part of a challenge, I was ‘off the rails’. I had drawn a false equation:

Challenge = Success

While technically, I was taking desired action during a challenge (my desired outcome), I was attributing the success to the challenge itself (a false attribution).

Unfortunately, humans are masters of drawing unconscious conclusions, aka. assumptions, regardless of their validity. You are collecting unquestioned assumptions all the time, often without any awareness.

Be a curious researcher

If you are someone who is drawn to challenges and falling into a pattern of ‘on or off’, it’s a sign to add in some personal reflection. True experiments provide data and results, so start thinking like a curious researcher:

• What are you learning from your experience?
• What aspects of the challenge worked for you and what didn’t?
• How can you integrate what worked into the future regardless of a challenge?
• How can you let go of what didn’t work?
• What variables can you adjust for a new experiment?

By taking the time to treat any challenge like an experiment that includes intentional reflection, you can incorporate what’s working into a longer term system that supports taking consistent forward action in the absence of a challenge.

For example:

• External accountability. Many people who like challenges are the type who respond well to some form of external accountability. You can incorporate external accountability into your life on a regular basis without requiring a time-bound challenge.
• Following a clear plan. Challenges typically come with a pre-determined plan or enough structure so it’s clear what you are expected to do each day. No guessing or daily decisions. If you feel lost outside of a challenge, focus your attention of crafting a clear plan (which may also be helped with external accountability).
• Preparation. Often a challenge will have you do some preparation leading up to the start date or even as one of the first actions to take. This sets you up for success by removing friction and making it easier to take action when it’s time. You can use this knowledge to set-up your own form of preparation based on what worked well for you. Again, this may be helped with external accountability (yes, it’s a theme).

In other words, if you feel like you are flying blind without the structure and guidance of a challenge, this is valuable insight about how you are wired and what will work longer term. Because even if your brain loves a challenge, the nature of a challenge is temporary. If you tried to keep a challenge going indefinitely, your brain would stop seeing it as a challenge and the impact would fade.

Side Note: It’s common for some individuals who join a challenge to learn and/or kickstart a new skillset and then never look back. It’s simply a springboard that gets them into action. But, perhaps it’s obvious by now, this post is not for that individual.

Finding middle ground

As a person who swung from one extreme of challenges all the time to the other extreme of swearing off challenges altogether, I’ve managed to find a healthy middle ground that works well for me.

What has helped most is recognizing where challenges fit into my personal experimentation. The more I use the Momentum Formula in my own life to establish lasting habits, the more intentional I can be about the type of experiment I run. Sometimes these are challenges, like the Momentum90 writing experiment, where I really am pushing myself to do something outside my usual comfort zone. I also embrace traditional external challenges run by outside groups when the goal is aligned with my own, like a 30-day piano lesson challenge, a 100-day Peloton streak, or a work-focused challenge hosted within a professional community.

But, not all experiments are challenges. Sometimes the experiment is making a small adjustment to my Method, Mode, or Mindset, like changing up a morning routine for a few weeks to observe what happens.

It all comes down to discernment. Intentionally pausing to think about the change you want to make, what you want to learn about yourself in the process, and what’s the best path for you right now. A challenge may be an ideal option for you to get into action—just make sure you don’t skip over the part where you learn what really works for you.

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