Sunday Special: Systems and Planning

Fail to plan, plan to fail.

I know I’m not the only one out there who feels like the world runs on hyper speed nowadays. Everything comes at you fast and everything seems like it’s the most important thing. This seems to be true for all facets of life. From parenting to work to just sitting scrolling on social media. Every where you look, it seems someone is selling something to help hack your time or coach you in some way.

Recently, I have tried to take a step back and look at these things with a different view. Every time I see a post or article like these, I look deeper and realize it’s literally just someone or some company trying to sell you on why you should spend your time and money on their product. And most of the time, their product is worthless or just a way to do things that probably aren’t much different than what you are doing now. Then you read the comments and half the people out there are either agreeing or arguing that their way is better. A lot of times, this shit is completely useless and after spending five minutes thinking about it, you realize it too.

I get that sometimes there may be some glimmer or morsel of information you can pick up from them, but mostly it’s the same regurgitated bullshit that people have been selling for as long as there have been self improvement advice and information out there. You know, the self help, self improvement gurus out there that if you look even 3 inches below the surface, you can see right through their bullshit and see that they are just trying to make money.

You don’t need their system to help you get things done, you need one that works for you in the stage of life that you are in. These things are in fact simple concepts, they’re just not easy to put into place and keep up with.

I’m not here to sell you on anything and don’t claim to be a productivity expert with a course. Frankly, I don’t care if you tell me what I am about to write is a complete waste of your time. That’s great. But here’s the thing, it works for me. And that is all that matters. I’m going to give an overview of my system that works for me, mostly because I have been thinking a lot about it recently. I usually do when the new year starts or when I have a lot of stuff to do. And both of those are true right now.

Planning is key.

The first thing I usually do when I have a lot bumping around in my head, is do a brain dump. This is where I empty my brain of all the things that I can think of. I take about 30 minutes and dump out all my thoughts onto a piece of paper in a physical notebook or into a page in Notion or OneNote. From there I categorize all of the items and break them into sections and topics.

The next step is to then assign priority and see when they need to be completed. I then add them into my task manager - Todoist for personal items and Planner or ToDo for work. (On a separate note, I like to keep work and personal separate because I work for a company in an industry that is highly regulated with security for data. If I worked for myself or a company less regulated, I would combine them into one.) Once the items are in the task managers, I assign due dates to them. This step is important because it shows me what needs to be done in the near term and what things can be pushed off for a little. The key for the items that can wait is that they are on my to do list with a date in the future. It allows me to not keep them rattling around in my dome and allows me to know that I have accounted for them and will get to them when I need to.

Once the items are scheduled, now comes the hard part. Actually doing them. Planning is great, but if you don’t execute the tasks and complete them, you’re going to end up in the same place as when you started. A bunch of tasks and things that you have to do and no time to finish them all.

Once I have the tasks with due dates, I add them to my calendar in time blocks. There are many studies out there that show time blocking, when done correctly, helps you get things done. I don’t add specific tasks to my calendar, but instead batch the tasks together into one block so my brain can focus on that particular subject without having to switch between things and lose focus. That part is key. Plus, it’s taken me awhile to realize this, but everything always takes longer than you expect it to. That’s why figuring out which tasks can give you the most bang for you buck, and completing them first. It helps you build momentum and actually lets you feel like you accomplished things.

One more note about tasks, when you write them, they should be broken down into actionable steps. I find when I make things too vague or large — plan vacation— I usually don’t do too well with them. Break it down into smaller pieces. For example, decide where to go on vacation. Then book hotel, flight, etc. That way when you look at the tasks you don’t have to think more about it.

I do a couple of different planning sessions. I conduct a monthly planning session at the beginning of the month to see the big things coming down the road. I also conduct weekly planning sessions — Friday afternoon for the week ahead at work, and Sunday morning for my personal time. I know that these are locked in and that’s where I plan my week ahead from the big items in the monthly session. I also look and adjust the plans on a daily basis because things don’t always go as planned. As Mike Tyson said, “Everyone has a plan until they get punched in the face.” (Not sure if it was exactly that, but you get the point.)

As a Dad, husband and director of technology, I know there’s a lot to do and things always pop up that are unexpected. I feel if you do not have a plan and fly by the seat of your pants, you get caught off guard and always work to put out fires and not move things down the field. I have resolved myself to always move the ball down field. Even if that is one yard at a time. Sometimes you get a big chunk play, other times you take a loss. The key is to keep moving forward and moving down field. Whether that means, rearranging and rescheduling things because a kid got sick, or there was an outage. If you don’t have a plan of what you want to do, you can’t adjust because everything becomes important. Fail to plan, plan to fail.

This is the system that works for me. As I said up top, I’m not here to sell you anything. This was more for me to reconfirm what my system is and how it works for me. Planning is key. And so is being flexible and not rigid. Life doesn’t care what your plan is, and will always throw curve balls. The idea is to have an idea of what needs to get done and when the curve balls are thrown, you can adjust.

I’m planning to go a little deeper into each of the software I use in my system in future posts. For now, this is what works.

Enjoy the football today and tomorrow because we are down to only six meaningful football games (college and NFL) left this season until September.

Until next time.