Planning a Monthly Calendar


Here’s a phrase that I’ve been working on as I’ve been getting better at planning my time in the past year. “If you can show me a person’s calendar, I can tell you their view of their future.”

It came from two older quotes that I hear quite a bit.

“Show me the stubs in a man’s checkbook and I will tell you what kind of man he is.” – G.K. Chesterton

Which I think it’s a play off of Miguel de Cervantes Saavedra’s quote,

“Tell me thy company, and I’ll tell thee what thou art.”

As I’ve come to realize over the years, both of these statements are true. Many times we see people who have to have the newest and the best things having the lowest self esteems. It makes sense, I used to be that way. I just wanted to fill a hole in my life. What I found out was that those who hold on to things and fix them when needed, tend to be happier. I can proudly say I’m part of the second group now.

The second quote, is another way of thinking about the saying “You are the average of the people you spend the most time with.” Again, very true. Whether or not you realize it, you’re being influenced by the attitudes and mindset of those that you’re around the most. This is why support groups and  masterminds are so important.

You are the Schedule that You Keep

It seems to me that those that plan the less, always let their circumstances plan out their day, their week, and maybe even their year. All they ever do is things for the now and the near future… not 5 or 10 years down the line. I think that comes from formal education failing them.

If there is something that formal education of the past is really good at is getting people to be followers. However, it doesn’t really help build leaders.

Even to this day I struggle with making a calendar. For me, every week is the relatively the same. I write my blog post, publish the podcast, do any marketing, and work on any upcoming products. When I’m not actively learning, I’m spending time with Maria. I think other people have similar structures of their week too. When they’re not at work or the gym, they’re hanging out with the family or getting things done around the house.

It really takes a miracle for something new to be added to our calendars.

However, by the end of this post today, I think you’ll have a little more guidance on how you can slowly change your life simply by planning it out month by month, week by week. It’s really helped me move forward in life, I expect it to do the same for you.

In fact, I don’t think I would have ever gotten to where I am today if I didn’t start making a calendar as I previously mentioned in my guide to planning a productive week.

Making a Monthly Calendar

Living a life to your full potential is all about intentionally deciding to live that way. We need to choose what you’re doing each moment. However, most of us are not used to living like that. One of the reason’s that jobs are so appealing, I think, is because we’re used to handing those choices over to someone else. Again, thank you formal education. (Side note: I think it’s important that we give kids options as they’re growing up. The more we do, the more they start thinking what consequences choosing one option over the other will have. Otherwise, they’re not going to know how to choose to do things when they’re older.)

So let’s make a monthly calendar to give ourselves a chance to better ourselves and our lives. How do we do that?

It’s actually fairly simple. You simply add themes, challenges, objectives, major events, and connect those all with the weekly plans that we’ve already talked about.

Let’s start with the important “large stones” first.

Major Events (Events Related to the Rest of the World)

You know what these are, and most people put these on their calendars if they keep them anyway. However, let’s look at what all we should include.

  • Birthdays (Yup. Of course.)
  • Anniversaries (Yes. This one is important.)
  • Weddings (Hey, you’ve probably known for awhile. Just write it down.)
  • Holidays (Any that you’re doing differently than what Google Calendar already does for you)
  • Vacations (You’ll want to do this just to make sure you’re seeing what you need to compress into the few weeks before hand.)
  • Extracurriculars (This might involve moving, adjusting to a new work schedule, having a kid, doc and medical visits, etc. You’ll have to adjust the actual dates based on when these happen.)

Whatever you can think up, you should mark it down. If you have a anniversary that’s going to include vacation time, mark it down. Specifically what it is and how long it’s lasting. Also, realize that if you’re having a kid, then there’s going to be time associated with adjusting with newborn. Likewise with vacation. More than likely you’re not going to do actual work on vacation. Figure out how much time both might take and communicate it with any people who need to know. You don’t need to cause yourself or them any confusion.

Themes, Challenges, and Objectives (Events Related to Your Life, Work, and Study)

Ok, now is the additional stuff that is going to really help you figure out how you’re shaping your own future. Each one of these will be broken down into further pieces, the weekly plans and then each day (again, what we’ve already covered).

  • Themes When you think of a theme, think of the highest level of things you’d like to change. Here at New Inceptions, we categorize themes as The 5 Pillars of Happyness. These Pillars are Relationships, Health, Purpose, Finance, and the Little Things. The first four are pretty easy to understand, the Little Things is anything that makes you happy (travel, shopping, gaming, etc.). So perhaps with relationships, you’d like to get married. Ok, well, we’re going to have to make time to find someone. Come up with strategies to do so, and then come up with times to date. Obviously that’ll come one step at a time, but you see where I’m going. These tend to relate to seasons and years.
  • Challenges and Objectives – These are essentially the same thing. Challenges are done for fun, while objectives are done for work purposes. Sometimes it’s hard to tell if it’s one or the other. (Dating would be a good example.) But, say, if you wanted to do a triathlon, that’d be a challenge. An objective would be losing so many pounds. Ideally these relate better with months, while their smaller counterparts, projects and tasks, relate to weeks and days, respectively.


Weekly Planning

This is what we’ve already we’ve already learned about (again, here’s the link).

It’s the glue of the month. However, they are simply a reflection of planning projects. Not actually planning meaningful action. Just because you have a theme, challenge, and/or objective identified, doesn’t mean you have the actual time allocated to get it done.


How’s your planning going? Have you been using the weekly planning guide? If so, how’s it working for you? I really hope this helps you add another level to your planning. What do you think about monthly or weekly planning? What have you seen as a result since you’ve started implementing it yourself? Would love to hear from you below, on Facebook, or Twitter!

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