In order to succeed, you've got to fail along the way.

As someone who has spent a lot of time tinkering with productivity – with both the various systems and tools that are available – I’ve come across a lot of successful ones. But I’ve come across a lot of things that just didn’t work, either. I found that these failures seemed to be more plentiful in my early days of studying the art of being productive, and as time progressed my chances of success did as well. It wasn’t often about the system or tool either.

It was all me.

When you’re trying to figure out what will work best in boosting your productivity, you rarely know what will work for you at first. You may be a paper person, but using it just isn’t practical to track all you’ve got going. Even a paper prophet like Patrick Rhone (of Minimal Mac fame) spends time in the digital world in order to keep on track. And while you may be excited about what your devices can do to make you a more productive person, there’s a chance that when it comes to actually being productive that a pen and paper are best suited for you. That’s why it’s so difficult to teach someone how to be more productive; there’s more to it than the old “Just Do It” assertion. A number of factors have to be weighed, making it a very subjective thing.

So if you’ve tried to become more productive through trial and error, you’re not alone. You’re more than not alone. Here are 3 of my own failed experiments with productivity. You may relate to some because you’ve given them a go or you may be inspired to try one of them because maybe your mind can wrap your head around it better than mine could. This isn’t an intervention or a warning; it’s an admission that even those who have lived in the world of productivity have fallen down. The trick is to keep looking for something until you’ve found something that allows you to get back up a whole lot faster and easier.

1. Two Systems: Personal and Professional

Since I didn’t want to bring my work home with me back when I had a 9 to 5 job, I kept a planner at work for work stuff and had a planner that went with me everywhere for personal stuff. Anything that was work-related never went in my personal planner and vice versa. Turns out there would be problems with this strategy.

By keeping two planners I was unable to be very nimble. I actually handcuffed my productivity rather than let it flourish. Instead of having one place to put stuff, I had two. And I had to decide on them with every action that came my way. I was working smarter…and harder.

In addition, I had essentially created a separation that really wasn’t there. There was no fluidity between work and personal stuff, and there needs to be. Work is part of life. So are personal matters that need attending. These feed off each other as well – maybe not in a technical sense, but certainly in an emotional one.

Time spent on this failed experiment: 4 months

2. Colour-Coded Paper Planner

This seemed like a good idea at the time. I used to use coloured pens and highlighters that were associated with a legend so I could tell what each task was associated with and how far along they were to completion. Different coloured pens were used for the “context” of the tasks (keeping in mind I had no knowledge of how contexts are defined in most productivity systems at the time) and the different coloured highlighters were used to signify the progress of the tasks.

One of the biggest problems with this experiment was that I was carrying around a pencil case for the first time since school. I also wound up using one of those multi-coloured pens that you had to flick to change colours. Not exactly the most pleasant writing tool.

Furthermore, I had to keep tabs on what each aspect of the colour-coding represented. I was either pulling out the legend regularly to make sure I knew what was going on with certain tasks or I inadvertantly would use a wrong colour and throw everything out of whack. Well, at least it felt like everything was out of whack. What it really was: not the best solution for my personal productivity.

Time spent on this failed experiment: 1 year (yes…1 whole year!)

3. Things

When I first dove into using apps for productivity purposes, Things won out over OmniFocus. The price was cheaper and it seemed to have everything I needed. The user interface was simple and elegant, the developers had built a complementary iPhone app and I was able to use it with relative ease and get a whole lot done.

Until I was away from my Mac for too long with my iPhone. Then “Things” wasnt working out so well. It had no over-the-air sync at the time. That was a problem for me. Others felt the same way.

So I ditched Things for OmniFocus. Moving stuff over took time, but not nearly as long as reconciling Things between two devices would’ve taken me over the long haul.

Time spent on this failed experiment: 6 months

Fail FTW

As I was writing this there were several other failed experiments with productivity that came to mind. I’ve made note of them (in the trusted system I use today, which is a combination of different tools I use) and may revisit them in the future so I can share them with you. There’s a lot of material to work with.

As for what I’m using now…well, that’s another post as well. But I can tell you that through these failed experiments I’ve been able to concoct my own winning productivity formula. It’s been the failures that have led me to my successes, which – when you put them into perspective – could indicate that perhaps they really weren’t failures after all.

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