Chris Hannah
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Playing Around With Experimentation and Challenges

Setting yourself goals can be an excellent way to push yourself towards a target and keep yourself heading in the right direction. But something I've discovered recently is that breaking a goal down into actions and turning them into challenges can be very beneficial.

The first question that comes to your mind is probably, what's the difference between a goal and a challenge?

My answer to that would be that your perspective changes when you have a challenge rather than just a goal. Because goals usually don't come with any information on reaching them. They're only a target that you would like to achieve, and the journey is yours to figure out.

Something I've discovered relatively recently is the benefits of setting yourself challenges and using experimentation to improve skills, make informed decisions, and ensure that you stay on track.

What Makes a Good Experiment?

In my opinion, a good experiment has a clear goal in mind and a way that you can track progress. I also think it helps if there is a planning stage before a challenge is set or before any experimentation is started.

From a goal, you should be able to extract actionable tasks to help achieve that end goal.

For example, I had the goal a while ago to sort my email out and build a system that worked for me. As a goal, I would probably write it as "I want to have a better email system". But instead, I broke it down and examined what exactly it was that I was looking for.

Turns out, I didn't want a whole new email system. I just wanted to deal with the one address/account instead of the three I had previously. And to have an automated mechanism that filtered junk, sorted some valuable but not urgent emails, and kept my inbox for anything that I either had to deal with relatively soon or manually organise.

Once I did that, I set myself a fixed duration of 1 week and got on with my experiments. I also found that keeping a log of my decisions and opinions helped keep me on track too.

So What Are the Benefits?

I'm sure there are countless benefits to setting yourself challenges, and experimenting, rather than just introducing a goal. But at least from my perspective, here's what I've found:

It's easy to track progress. Especially when you keep records throughout the process as you make decisions.

It keeps yourself honest throughout the experimentation as you have a clear goal in mind and actions that should get you there.

Making informed decisions become more straightforward. If you perform an early analysis and identify your requirements early on, the decisions you make during and at the end of the process are more informed and more likely to be based on logic than your current thoughts or emotions in a particular moment.

Challenges I Have Set for Myself

Since really thinking about this idea of using challenges, I've set myself two of them. First, to find an email system that suited me, and more recently, to explore the market of writing apps to see if they fit my needs.

The email challenge was rather strict. I had a clear goal of fixing my email system and requirements that I wanted to meet at the end. And I also set myself a week to complete the challenge. I think I benefitted thoroughly from developing the initial requirements, as I found myself veering off the path a few times, but I was pulled back after re-reading my original plan.

I think that keeping a log of my decisions throughout the week also helped. Because although there were benefits of being honest to myself, I was left with a record of my thoughts and decisions at the end of the week as I tried new things. Which meant I could do better analysis at the end and make a better final decision.

The challenge to find a new writing app has been a more flexible one. Mainly since it was more exploratory, I wasn't aware of each app's intricacies, or in fact, what apps were available. So I went in with an open mind and precise requirements (which were refined over time) and decided to test a few apps until I thought there wasn't any more left to try out.

In retrospect, I think I would have benefitted from some more limitations. For example, coming up with an early list of apps and doing a basic research level. Because that would have filtered a few choices out early on.

This kind of reflection is another aspect of experimentation that is also important since it can only improve future challenges' efficiency and success rate.

Final Thoughts

By breaking down goals into steps and setting yourself challenges, I think you're more likely to take action and actually achieve them. And by doing controlled experiments with fixed criteria, you're more likely to finish with usable information that can help you make more informed decisions.

I want to explore challenges more, and I think I'll be doing some more myself. Maybe less around technology choices and more to do with life in general.

I'm interested to see if anyone else has used challenges and how useful they've been. So if you have any past experience, I'd love to hear it.