Automate Winning and Choosing to Fail

Strategies, tactics, and systems can set you up to win without having to make a decision.

There is no secret to winning. If you choose a direction and put in the work, you will see success. It doesn’t matter what that thing is; these statements are a universal truth. Success takes work – you have to put in the hours, build the systems; you’ve heard this all before. Instead of talking about the ways that systems will benefit you, let’s talk about how to automate your success using systems. 

Tools and systems will allow you to set up automated winning. This flips a lot of ideas on their head. What I’m saying is that there is a way to automate winning in such a way that you will need to choose to lose, rather than choose to win.

Making better choices is not bad advice, but what if we instead set ourselves up so that all we have to do is show up to win without having to make decisions. We can raise our baseline to the level that we want to operate at rather than having to decide to climb the hill to success. 

Think about the power in that idea. You don’t need to decide to work out, work on that side project, eat right – all of those things that you are trying to do to level up. You can get yourself to a place where all of that is a given and you have to choose to do those things that are hurting you. It is a powerful shift in perspective. Automating winning makes the choices you face far easier. Deciding not to do harmful things is easier than having to choose to do beneficial things.

Each decision point you leave yourself is an opportunity for failure – it is a weak point. Every decision is prone to influences like stress level, energy levels, surroundings, and any number of other factors. The idea here is to remove as many of those decisions as you can and leave the decisions that you do have to make as easy and obvious as possible. 

Humans are pulled to the path of least resistance; it’s attractive and comfortable. We have to choose to do hard things. So, make winning the path of least resistance and make losing difficult. Let “do hard things” be about pushing yourself out of your comfort zone in training or new experiences rather than trying to stay on track with your goals. 

Alright, that’s likely enough build-up. Let’s get into the meat of this article – the strategies and tactics.


The first stop is creating routines for ourselves. Most common among routines are morning and nighttime routines, sure, but you can make anything repetitive a routine. Think about a lunchtime routine, for instance, or a “start of workday” routine. 

A routine is anything that has a set timeframe and a set of tasks. The advantages of having routines is that it removes decisions. 

Think about it – if you’re morning routine takes an hour and includes:

  • Wake up
  • Shower
  • Get dressed
  • Breakfast
  • Journal

…those are the things you do for the first hour of the day. There is no thinking involved – as long as you shuffle your feet from the bedroom to the bathroom to the kitchen, you’re starting your day off on a good foot and setting yourself up for success. 

Then, maybe you have an hour-long nighttime routine and a one-hour lunchtime routine. 

With only those three routines, you have automated three hours of your day. Assuming you include important and productive activities within your routine, that’s three hours of automatic wins. This is basic, but explains the concept.

You can create more routines for whatever you do daily – how and when you check your email and social media alerts, how you do work activities, how you work out, the possibilities are endless and each routine has the same effect of automating a chunk of your day with wins.

Project this out to starting that new side hustle or business, getting that promotion…

Calendar / Schedule

Using a calendar or a planner is a powerful tool to organize your routines. If you look at routines at the micro scale,, your calendar will organize your routines into sequences that make sense and move you through your day on a more macro scale. I am not breaking new  ground here, just setting it up.

I like using Google Calendars, but any electronic calendar works because they all generally allow you to do a few things:

  • Color code activities
  • Maintain different calendars
  • Schedule recurring activities

I am not going to belabor calendars, but instead give you some ideas to begin to look at macro scale systems.


It is difficult to audit from memory. Auditing your calendar will quickly show you where you have inefficiencies, where you are over or under-estimating the time it takes to do different things, and it keeps you honest – you can’t argue with what is written down.

Build a Day With Intention

When you lay a day out ahead of time, you can build it in a meaningful way. I use this idea for content creation for this blog, the Initiated Lifestyle Podcast, and social media content. An example I use for content creation stacks out similar to this. 

  1. Outline and idea for content
  2. Write blog post (further think through and organize my thoughts)
  3. Outline then record the corresponding podcast episode
  4. Write corresponding newsletter
  5. Write social media content around the same idea.

You can see how I build a day from a rough content idea, into a blog post to do most of the heavy lifting in organizing and fleshing out how I present concepts, into a podcast, and then moving down into shorter-form but more specific content to highlight some of the finer points of the content. I am using the tasks that came earlier in the day to expedite the activities I am performing later in the day. This gives me a week of content across 4-5 platforms in a day, which is pretty good.

Timing and Flow

Laying out a day will bound the time frames in which you work on different tasks and shows you how you’re going to flow from one activity to the next. You will take the guesswork out of “what am I supposed to work on next” and “how long is this going to take”.

You answer both of those questions when you plan out your day. You will increase focus and decrease distractions when you give yourself a limit on how long something is going to take. This also requires you to put some thought into how you are going to organize your day and also forces you to think about how you are stacking your activities in a meaningful way.

I also suggest keeping the same recurring activities at the same times of day if possible. If you go to the gym at the same times on the same days, that helps you in a lot of ways. For example, you can eat at the right times to support the workout and you are taking more decisions away from yourself.

Combine this with auditing your schedule to find out how long activities actually take you to do so you are not short-changing yourself or giving yourself too much wiggle room to get distracted. This optimization takes a few iterations to get right, so go in with the mindset that this will be a work in progress and let it get better over the course of a few weeks.

Note Taking and Journaling

The biggest productivity killers are those little fires that pop up and distract you. These are the insignificant tasks that are quick to address, so you decide to address them to get them off your mind. The problem is that these tasks break focus on what you’re currently doing and you then need to get back into the frame of thought to continue working. As a one off, it may not be a huge deal, but stack a small handful of these throughout a day and the inefficiencies add up. 

Get a system together where you can write down these things as they come up, jot down a few notes to remind yourself, and then keep focus on the work item you are currently on. 

I like to use Evernote for its scratch pad feature, note tags, notebooks, and use across multiple devices. Keeping my notes somewhat organized on the go kept them at hand and easy to find once I developed my system. 

The most important thing to mention here is to plan time into your day to review the notes you took. The notes are great, but if you aren’t reviewing them regularly to remind yourself of the thoughts you wrote down, you may as well have not written them down at all. If you have too many scribbled notes to yourself, they quickly become disorganized and the thoughts are lost, anyway. 

Meal Prep

Meals are another potential time killer and decision point that can be optimized. You can either prepare a bunch of meals at once so all you have to do is heat them up and eat when it’s time, or, if you prefer and have the ability to make fresh food, have one or two staple meals that you can make quickly and that have easy ingredients. The idea here is that when it’s lunchtime, you go and eat lunch. You are not spending time deciding on what you want, where you’re going, do you even have those ingredients – none of that. When it’s lunch time you eat lunch.


Setting time to plan all of this out is the mission-critical step. Talking about using a calendar to plan out work is great just like having all of those one-off thoughts written down is going to help you remember them. Attempting to do any of this without leaving yourself the time to create your plans and review your notes is fruitless. 

You need to set aside time daily, weekly, monthly, and yearly to look at the different levels of your systems and your larger plans for where you want to go. 

The common trap is that people don’t see this as a productive use of time and forgo it in favor of physical work. What people fail to realize is that the efficiencies gained by setting aside this planning time gives them returns exceeding the time they spent putting the plan together. 

Wrap Up

If I haven’t made it clear how powerful automation is – it’s really powerful. By enacting the ideas presented here, you are removing the potential to make unproductive decisions and you are setting yourself up for the best chance at consistent successes. All you have to do is show up to each of your “appointments” that you create for yourself, and you win. To decide to deviate from your plan is deciding to fail. 

If you start to think about things from this perspective, winning is easy. When winning is the expectation, it is difficult to lose. 

Nothing above happens overnight – it is important to understand that it will be frustrating at the beginning. Going from an unstructured day to having something with this level of structure is not going to be smooth until you learn how long to assign different things and which order you work in best. This is fine. Just like I mentioned in the planning section that the time spent creating the plan returns larger dividends, the same goes for these systems we are discussing here. 

If you stick with it and strengthen your systems, you will automate success. The more time you automate, the less time you have to make unproductive decisions.

If this all sounds mechanical or robotic, well, it is. There is a reason factories moved to robots rather than having people work the machines. Robots are efficient at doing the same things repeatedly. They do it with high precision and consistent results. Why not use those same principles when we talk about our successes? Build mechanical and robotic systems for doing those things that need to be done repeatedly to get us to our goals. 

Save the spontaneity for your fun times. When it’s time to work, get to work.

Yours in strength,


There is a lot going on at thebeardreport. these days.

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