a podcast, blog and lifestyle brand by Maddie & Lauren Orlando

  • thesisterdiary

How I Journal & Plan My Life

Updated: Apr 27, 2020

By: Maddie

Hi, happy Monday!

I thought that this would be a fitting blog post to share not only on a Monday, but also during the month of January, when most people (including myself) are overly motivated and focused on goal setting, planning and making resolutions. I feel like I have been making to do lists and scheduling my life since I was a little kid. I am a very type-A, like-to-be-in-control person. I remember being so excited to go shopping for school supplies and to buy a new planner every summer before a new school year started, and I am abnormally obsessed with making lists and crossing off tasks as I accomplish them. In addition to this, I have recently started journalling. For me, journalling gives me a chance to actually look back and reflect on the goals and checkpoints I create for myself, which to me is an essential part of actually achieving success. Today, I wanted to get specific and break down what exactly I write in my calendar and journal every morning. I figured that this would be better to write about than speak about on the podcast, so you can actually see what I’m talking about. If you’re not a visual learner and want Lauren and I to discuss this as well, just let me know!

Digital vs. Physical Planners


I use both digital and physical methods of planning/journalling. I have a MacBook, so I just use the iCal calendar application that comes on the computer. I have a bunch of different calendars that are color coded for different purposes - work, personal, workouts, podcast (shared calendar between me and Lauren), Orlando family (shared between all my family members) and then JOHNNY ORLANDO (shared between the label and my fam lol). If you don’t have a MacBook, I suggest using Google Calendar. It does the exact same thing, is easy to use, and the calendars can be shared with other people as well.

The digital planning is pretty straightforward. I add appointments, calls, meetings and events to my calendar as they come up and color code them depending which category they fall under. For example, for my workouts, I like to plan out what I am going to do and what time I’m going to do it for a week in advance. If I plan it, I am way more likely to actually follow through and go. Once it’s in your calendar, it’s REAL, you know?

I also use the calendar to block off chunks of the day for doing work. Let’s say I have an event in the calendar that says WORK: YOUTUBE on Tuesday from 2pm-4pm. I know that during that time, all I’m going to be focused on is YouTube. In the “notes” section of the event, I can write specific reminders and to do’s that I want to accomplish during that two hour block.

The last digital planning element that I use is the “Reminders” app on my iPhone. I recently put this in the bottom task bar thing on my phone (not sure what that is called) so that I remember to actually use it. Basically, I write down anything that I remember that I have to do when I’m out and about or trying to fall asleep so that I don’t forget to do it. I review this list constantly and check off/delete things that I’ve done.


The only physical paper that I use right now is a lined, empty journal - no planner or agenda. Every morning, ideally before I do anything else or even look at my phone, I write out a bunch of different things in this journal to prepare me for the day, both mentally and logistically. It’s part of my morning routine now and I notice a huge difference when I do this vs. when I skip it.



I write out any appointments or plans that I’ve made for the day, with all the relevant details that pertain to them. For example, I’ll make a note of what time I’ll have to leave to be on time to make it there.


This part is super important, but we have to go back a little bit first so you understand the context of the “daily goal” section.

At the start of the year, I made a list of approximately 8 big goals in all different areas of my life that I am working toward this year. These are my BIG GOALS. I made a very specific plan of how I am going to get to these goals by breaking them down into sub-steps. It looks like this:

BIG GOAL: ___________

6 month goal: what do I need to have accomplished in 6 months, by the end of June, in order to be on track to achieving my goal by the end of the year?

Monthly goal: what do I need to have accomplished by the end of January in order to be on track to achieving my goal by the end of the year?

Weekly tasks: what do I need to accomplish this week in order to be on track to achieving my goal by the end of the year?

Daily tasks: what do I need to accomplish TODAY to be on track to achieving my goal by the end of the year?

At the start of every month, I create a new monthly goal. At the start of every week, on either Sunday night or Monday morning, I create a few new weekly tasks. At the start of every day, I create a list of daily tasks that I need to accomplish that week. Each little step moves me forward in the right direction so that I get closer and closer to being successful in reaching my goals.

These daily tasks are so essential. It is the small things that you do everyday, that seem unimportant, habitual, mindless and just “the way that things are” that either propel you forward or leave you stuck in the same patterns.


This is something that I was introduced fairly recently by my friend Mimi Bouchard, who is the queen of AM routines! I make two lists: one list of things that I am grateful for today, and one list of affirmations, or positive words about myself. To be honest, this seemed kind of stupid to me at first. I’m not exactly a reflective or spiritual person, and I am generally very hard on myself, so I kind of felt like “what’s the point”. However, practicing gratitude and positive affirmations are huge hacks for changing your mindset from negative-positive. Eliminating negative self-talk and practicing positivity was the key ingredient that I was missing from achieving my goals. You can goal set for years and write out as many lists as you want, but without belief in yourself that you can actually be successful, you simply will not be. Here is an example of the types of things I write down:


  • I am grateful for my family and the opportunities that I have because my parents support my dreams and visions

  • I am grateful to be in California right now, where the sun comes out in the winter (lol)

  • I am grateful for my health and that I am able to workout today


  • I am one step closer to achieving my goals every single day

  • I am incredibly successful at anything that I set my mind to

  • I am confident and sure in myself and my beliefs

Depending on the day, how much time I have and how I’m feeling, I write out a small or large list of gratitude and affirmations. Sometimes they are kind of trivial, like how I’m grateful for the weather, and other times they are more deep and complex. The important thing here is that you take a second to reflect and actually feel what you are writing down. You have to believe these things in order to change your mindset.

That’s pretty much it for my journal! Plan for the day, daily goals, gratitude and affirmations. This usually takes me 20 or so minutes which is the perfect amount of time for me to set aside before I start my day.

Lastly, at the end of the night, before I go to sleep, I start a new page called “PM Reflection”. On this page, I basically write out any thoughts that I have and reflect on my day. Did I have a good day? How did I feel, mentally? Did I do the tasks that I wanted to do? This helps me a lot because it keeps me accountable and on track. It also allows me to fall asleep more easily, because I play through and think about the day before I lay down and try to sleep.

I hope that this helps you in any way! You can take away what you wish, and remember that I have more time on my hands now to do this in-depth journaling because my schedule is flexible. Let me know if you are a planner/journal-er and what your method is :)

Maddie xx

516 views7 comments

Recent Posts

See All

2020 Holiday Gift Guide

If you're in search of a gift for someone special (including yourself!), you've come to the right place. Here are some of our all-time favorite items, and a few new ones that are on our list this year

23 Things I Learned at 23

In honor of my birthday this week, I thought I'd keep the tradition going and reflect on 23 things that I learned in my 23rd year of life. 1. The true meaning of presence. If this year has taught us a

Updated Skincare Routine

We hate to be stereotypical "influencers" that are like, "so many people have been asking us about our skincare routines" when no one actually cares... but it really is one of the most commonly asked