Sherlocking My Systems

How to step back to go forward

Illustration by Maria Hagsten Michelsen.

As a freelancer, I have to motivate myself. To do this I have a lot of systems in which I set goals and plan ahead. In other words, I structure my life like a madwoman. There is a ton of advice out there about how to be structured and hundreds of productivity apps for building systems. This article will not be about all that. Rather, it’s about my favorite part of having systems: that their data can save me from going off track by revealing the patterns of my life.

When I Planned Myself Off The Track

But there is a danger to such systems. They might work so well at keeping me on the track that I don’t notice it’s the wrong track. In the daily hustle and bustle of following my plans, I risk forgetting my desires and my dreams.

To combat this I have a planned date with myself and my systems once a month where I reevaluate and adjust. However, one day I realized that when I planned this way it still kept going wrong … and I wondered why.

In time, I came to understand that the issue was my mindset. When I planned to plan, it became another task in the system. I would take my planning post-it note and say to myself “it’s time to plan.” Based on last month’s goals, I would make a new set of rational SMART goals and consider the planning-task as completed. However, in this process, I was handling the task as a “worker,” whose main focus was to complete the task.

But planning your life should be more than a continuous chain of SMART goals. You are after all planning for your future happiness. The mindset needed for such a task should be broader than just “the worker.” It should also include the mindsets of other parts of one’s human character like the “philosopher,” the “innovator,” the “critic,” and the “optimist.”

My planning routine prevented me from utilizing such a broad mindset. It’s like in a company, where you notice things that need improving or adjusting. You inform your boss, who says it’s something that should be addressed at the yearly planning meeting. At the planning meeting, you get a list of last year’s goals and are asked to create new ones. In such a setting you forget the things you wanted to change and instead focus solely on the goal-setting.

Being a freelancer, I have the freedom to run my business the way I want to. So, when I realized that the monthly planning didn’t work as I had hoped, I experimented with finding a new solution. The solution I came up with was far more organic than structured. Far more human than planned.

Break Out the Sherlock Emergency Kit

The Sherlock Emergency Kit. Illustration by Maria Hagsten Michelsen.

What was the solution? Well, I still keep up my planning date every month, but I now also stay open to the organic point of planning. It’s the point when the subtle whispers of my mind and body inform me that something is off. These whispers are puzzling questions or vague feelings that persist over a period of time. They are never concrete, which might be why I used to ignore them. But I don’t ignore them anymore because they are an emergency alarm that inform me that replanning is needed.

So, now when I feel that I’ve reached an organic point of planning, I follow my new emergency routine and break out my four-step process.

Sherlocking My Systems — The Process

Step 1: Take time. Step 2: Sherlock your systems. Illustrations by Maria Hagsten Michelsen.

Step 1: Take Time

Step 2: Sherlock Your Systems

Step 3: Relax your mind. Step 2: Solve the puzzle and replan. Illustrations by Maria Hagsten Michelsen.

Step 3: Relax Your Mind

Step 4: Solve the Puzzle & Replan

The Organic Replanning in Action

With that knowledge in mind, I modified my systems so they had better time-tracking features and were optimized to show when I started to fall behind on a task. For the next couple of weeks, I tracked my time vigorously to better understand my time-use. I realized that I grossly overestimated what was possible to cram into a week.

I needed to make my plans more realistic, so I started to replan. I felt awful while doing it. Taking down goals, which I had expected to be able to reach, made me feel depressed and claustrophobic. It was the anti-feeling to the success color-change of my conditionally formatted spreadsheets. But it had to be done, otherwise, I would have collapsed completely under the weight of my own expectations. As an added bonus it also made me realize which of all my goals really meant something to me.


This process helps me adjust when I do something too much or too little. It helps me find the balance between the things in my life I need to do, want to do and dream of doing.

And by the way, I don’t smoke a pipe and I don’t own a deerstalker hat. So in real life, it looks more like this (it’s a Scandinavian licorice pipe):

Maria Hagsten Michelsen

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Graphic Designer / Illustrator / Regex Crossword Writer / Productivity Nerd /