How to Start Journaling: A Guide for Men

If you’re curious about journaling but aren’t sure where to start, this guide will help.

Most advice on how to start journaling has one big problem: It comes from writers — people who already like to write, and probably do it every day.

However, if it doesn’t always feel like writing comes naturally to you, a lot of that advice falls flat.

That’s why in this guide, I’d like to take a different direction. I want to help you understand why you should journal, based on your personal goals and aspirations.

To do that, we’ll have to dispel some common myths about journaling, as well as ask a few big questions to help you clarify your motivations. 

By the time you’re done reading, if I’ve done my job well, you’ll be inspired to pick up paper and pen (or open a Google doc) and start writing!

You Don’t Have to Be A “Good” Writer

The number one hang-up that I see beginning journalers get stuck on goes all the way back to grade school — the expectation of being “graded” on your writing.

This kind of negative conditioning can run deep, and constantly critiquing your writing (even before you write it!) is the quickest way to make sure that you hate keeping a journal.

So before you put pen to paper, I’d encourage you to remind yourself: “This writing does not have to be good.” Heck, if you’re really dealing with that sort of negative self-talk, you can start every journal entry with exactly that line — “This writing does not have to be good.”

This is the same sort of attitude that really helps when you’re starting to work out. You wouldn’t expect to hit the gym for the first time and immediately bench press 315 pounds, so why expect yourself to be on par with great novelists as soon as you start journaling? 

At the end of the day, as with every skilled activity, journaling is more about showing up consistently and putting in your best effort — not comparing yourself to others, or to some imagined standard of perfection. Whatever you write, as long as you write it, is good enough.

Finding Your Why

So you don’t have to be an accomplished writer to start journaling. But you do need to understand why you want to start writing in the first place if you want to make journaling a regular part of your life.

I’ll put this in context by sharing my own ‘why.’ My older brother wrote all the time — and would read books to me all day long when we were growing up (he taught me to read too).

Unfortunately, he passed away at a young age, and I didn’t have much support after his death. So, remembering the example he had set, I started writing. It’s a habit that I keep to this day, 19 years later.

My ‘why’ was obvious, but yours may not be so clear at first. And unfortunately, there’s no real silver bullet solution that will reveal your motivations to you. 

But I have good news too: There’s a tried and true method of discovering your motivations, your why, little bit by little bit.

Asking questions (and writing about them).

When You’re Stuck, Ask Questions

The beginning journaler, if they don’t find writing immediately satisfying, will get stuck. That’s to be expected, and it’s a natural part of the process of writing, even for seasoned writers.

When you get stuck — whether that’s on a blank page, or 100 pages in — start asking questions. This is also the best way to clarify your motivations, giving you the fuel to keep writing day after day.

What kind of questions? 

Well, what kind of questions show up for you, in your experience of everyday life? What do you think about most often? What are you curious about?

Your journal will never be identical to a friend’s or a stranger’s, and that’s a good thing. That’s because once you get into the habit of journaling, your writing will start to reflect your unique experience of life.

Writing will give you access to deeper insight into the questions and topics you find most interesting (or most troubling).

If you’re really stuck and can’t even think of a question to ask, feel free to use one of mine:

• If I had the power to change one thing in my life today, what would I change?
• What would I like my life to look like in a month? Six months? A year? More?
• What am I doing really well on right now? What do I have to be grateful for?

There’s An Easy Way to Make Journaling A Habit

I’ve kept a daily journaling habit up for nearly 20 years not through Herculean effort and force of will, but by one simple action: I always keep paper and pen with me, wherever I go.

The biggest obstacle I see that trips people up as they’re trying to start a journaling habit is, quite simply, not having a way to journal when they feel like they have the time to write.

Think about it: When you’re idly browsing through the apps on your smartphone, if you had a pen and paper you could journal even a tiny bit instead.

That’s why, contrary to popular advice of having one “special” journal that you write everything in, I encourage beginners to have journals in a few sizes.

Rite in the Rain’s pocket-sized, waterproof notebooks have worked wonders for me.

I can stuff one in the pocket of my jacket even when I’m not carrying a bag for the day. (Check out this article for more pocket notebook recommendations). 

I use a Voyager Refillable Notebook most often, though. They’re just compact enough to throw into a backpack or sling bag, but provide enough space to write comfortably when sat on a desk.

Plus, they have refillable inserts so you can keep a collection of your previous journals without having to buy a whole new cover.

A few friends of mine swear by their Extra Large Moleskin Journals though, so I have to mention them here as well. They are an excellent quality notebook for a fair price and are great if you’re looking to really get immersed into your journaling.

Editor’s Recommendations

Like Brian, I’ve been journaling for a long time (almost daily since around 2012 and sporadically since I was eight). 

I also carry a pocket notebook with me pretty much everywhere I go. While I don’t often use it for journaling, I’ll write down my thoughts (or my grocery list), and copy important parts into my main, daily journal as needed. 

For me, what initially helped me to want to write was a desire to improve my penmanship. Over the course of a couple of years, I used journaling partially as a way to gradually turn my chicken scratch into a script that I’m happy with. 

Another game-changer was getting a pen that I liked. For me, it was a family heirloom vintage fountain pen. However, for you, the perfect writing implement might be a mechanical pencil with a thinner lead than you’re used to, or maybe a Parker Jotter.

I’d suggest that you try out a bunch of different pens and pencils and use whatever makes you want to write more! If you want some suggestions on what pens to try, here’s our roundup of the best EDC pens.

If I don’t have some deep topic I want to write about, I just jot down a couple of sentences about what I did that day. In fact, that’s what most entries are — simply a record of my day.

I refer back to old journals frequently and they help me to see how my life, and how I think, has changed over time. 

Frequently Asked Questions About Journaling

Here are some of the questions from the web we’ve seen asked most often about journaling:

How Do Beginners Start Journaling?

Beginners should make sure they always have a pen and paper with them, so whenever an opportunity presents itself to write, they can take it.

What Should a Beginner Journaler Write?

Asking yourself questions and writing about them is a surefire technique for beginning journalers.

Is Journaling Healthy?

Healthline certainly thinks so, and they’re quite a reliable source.

What Is the Point of Journaling?

Journaling doesn’t have to have a point. If you enjoy it, feel better doing it, or just plain find it interesting, then it’s a good activity to pursue.

Conclusion: Encouragement for Writers of All Types

I don’t know where my life would be without journaling. It’s given me a way to express myself when I didn’t feel like I had anyone else to turn to; a way to explore and understand my feelings and the world around me more deeply; and a way to start telling different stories about my own life.

That’s why it’s my sincere wish that the tips and observations in this guide have given you even the tiniest spark of inspiration to take up journaling for yourself, as well.

It’s a solitary craft by nature, but one that has deep returns in our hearts and souls. My best wishes go out to you, and I hope we can share our writing with each other one day.

Questions? Comments? Leave them below!