Start a 5 year journal

A practical guide to developing follow through & long-term thinking

Photo by Jan Kahánek on Unsplash

Over the years, I’ve tried many different kinds of journaling and ways of documenting my life. Everything from daily habit tracking in Notion to Obsidian's daily pages. Bullet journal planning, morning pages, daily logging -- oh my, indeed. But without fail, they always ended up abandoned within a month or two (on a good run).

I would find a trove of people on YouTube who had made a hobby, sometimes a career, out of showcasing their long term commitments to documenting their life, be it through daily vlogging or bullet journaling. Their portfolios were impressive, inspiring, and would lead me to pick up their medium of choice. Though time after time, I would abandon it shortly after.

This lack of follow through has made itself known in plenty of areas of my life: abandoned business plans, untouched domains renewing year after year, a dozen different productivity tools left half setup, and an electric guitar slowly detuning in the spare bedroom. (Just to name a few.)

When I turned 25 this year, I was ready to change that.

Looking at the graveyard of journals and apps, seeing this quarter-life number, I was inspired to start looking over the long-term. It probably doesn't help that I was reading Cal Newport's Slow Productivity at the time, a book that focuses on doing meaningful things over a longer time horizon.

So I wanted to see if I could commit to a daily practice for 5 years. A 5 year daily journal.

I decided to go analog, since I wanted this to be something I could physically hold, flip through, and look at on the shelf as a time capsule of years 25 through 30. I wanted to create a present for myself on my 30th birthday.

How to do it

There are plenty of options you can choose for the pre-made route, including Leuchtturm's Some Lines A Day, Midori 5 Year Diary, and the Hobonichi 5-Year Techo. But personally, I wanted more control over the layout, so I opted for a dot grid 400 page Moleskine - the Classic Notebook Expanded (Hardcover).

It's readily available, pretty cheap ($20 on Amazon at time of writing), a good balance between paper thickness and journal bulkiness, and you get to choose how to lay it out. 

What’s this layout, you ask?

I split it into two sections: 35 pages at the front, and 365 pages at the back.

5 Year Planning & Review

For the 35 page section in the front, that gives me 7 pages per year for planning, reviewing, setting goals, or having some traditional bullet journal collections. For me, I opted to use these in the following way:

1. 5 year plan

   1. I have one of these each year, since I'm pretty sure that this is going to change from year to year

2. Yearly Plan

3. Yearly review

4. (through 7) 1 page per quarter

   1. Option 1: Split the top half and bottom half for planning and review

   2. Option 2: Split into 3 sections to have one for each month (could also split each these in half [grid of 6] for planning and review)

Daily Pages

For the 365 page section, you get one page for each day of the year. The Moleskine expanded has 40 vertical spaces, so divided by 5, you get 8 lines per day, per year. (It’s almost like it was made for this.)

This makes it a pretty small daily commitment, taking just a few minutes most days.

I most often do my daily entry the next morning, while I’m sipping on my morning coffee, but it can also be a great end of day shut down ritual. Sometimes I’ll go a weekend without doing the pages, and backfill them on Monday. 

What to write about

Planning

So far, I'm almost 3 months in, and I've been scared to fill out the planning section. For the 5 year plan, I do have a draft ready, I just need to put the pen to paper. Here are a couple of frameworks I've been thinking around:

From Cal Newport: 

• Craft & Career (Lifestyle Centric Career Planning)

• Community (Relationships)

• Contemplation (Spirituality, Religion, Philosophy, Mental Space)

• Constitution (Health)

Wheel of Life: (h/t Ali Abdaal) 

• Health: Body, Mind, Soul (spirituality/life purpose)

• Relationships: Romance, Family, Friends

• Work: Mission(Fulfillment/Purpose), Money, Growth

Other Considerations:

• Travel plan & goals

• Life Upgrades (Where you live, What you own, etc.)

• Identity (The kind of person you want to be)

Daily entries

Here’s how I set up each daily page:

Next year, I’ll append “ - Thu - “ to “2025“ and just rely on the date at the top. (And probably underline 2025 too.)

Within the 7.5 lines remaining, I’ll usually journal about some combination of:

• What did you do today?

  • Content you’ve consumed (books, media, games, etc.), places you've went, projects you’re working on, meetings you’ve had, etc

• How are you feeling? 

  • Generally? About work? About life direction?

• What's been on your mind?

How it's been

I haven't done too much reflection on my entries yet, but seeing the bookmark progress downwards through the journal is a stark reminder that time is going to continue on moving, regardless of what I do on a daily basis, and has helped push me towards trying to make the most of the little time we have. Not to mention, it's provided a steady, daily check in to see how I'm feeling, and reflection on what actions are contributing to that.

Your turn

If you're reading this shortly after this has been published, July 1st is a wonderful day to start. If not, the monday after you read this is great too. The start date doesn't matter, what matters is the practice. If you're truly concerned about the aesthetics (I get it, I had to wait a bit too) then January 1st, 2025 is 6 months away, and is a wonderful time to start a 5 year journal. If you do wait for that, then in the meantime, pick up a cheap notebook to start today and practice over the next 6 months.

It doesn’t matter when you start it, just that you start it. The purpose here isn’t aesthetic, it’s to start considering the long term, the bigger picture, and to start building the habit of follow-through.