A Man's Life, Personal Development

Jumpstart Your Journaling: A 31-Day Challenge

H.G Ponting. Captain Scott+s Antarctic Expedition 1910 - 1912. 7th October, 1911. Profile view of Captain Scott sitting at his desk as he writes his journals in the Winterquarters hut.

There’s been plenty of talk on AoM recently about journaling with our articles on The Diary Habit as well as 9 habits young men should adopt. Seeing a few of the comments confirmed a notion I already had about the practice of journaling: many men would like to, but few men do to the extent that they would like. And the main reason why? A simple lack of direction. When presented with a totally blank slate — that open journal, with pen in hand, and nothing but white pages — we freeze up. It’s been said that constraint actually gives way to greater creativity. When we have clear boundaries, or direction, we no longer have to think about the act itself. We don’t have to think about what to journal, we simply have to journal based on a prompt.

With that in mind, I’d like to present a 31-day roadmap and challenge for your journaling. Doing something for around 30 days is a great way to not only build a habit, but to also explore if it’s right for you. Maybe journaling isn’t for you, and you just have never taken the time to really prove that to yourself. Or maybe you love the practice, and simply haven’t gotten into the habit yet. Either way, I hope this calendar presents you with ample opportunity to take the journaling bull by the horns and experience all its benefits.

All of these can be accomplished in just 20-30 minutes per day, and often less. If you can’t make time for that, perhaps journaling isn’t as important to you as you really thought, and you’ve discovered right there that it’s not for you.

In this roadmap are many questions. In your journal — whether digital or by hand — you can simply write out the question at the top of the page, and answer as if having a conversation. Don’t worry about formality, how it may sound out loud, grammar, etc. Just write your thoughts. It may seem mundane, but there is a magical quality in writing something down that cannot be fully explained. You just have to trust me and try it out.

Note: I am of the opinion that this exercise should be 31 continuous days. However, you can also decide to do it over the course of a couple months, or just on weekdays; remember, this is for you, so if don’t enjoy what you’re doing and are just stressed out by the thought of it, it won’t work.

Day 1: Start with answering the question of why you want to journal, and beyond that, why you decided to embark on this 31-day experience. Write out what you’d like to get from journaling.

Day 2: Continuing to work within that idea of constraints, try to write a 6-word memoir of your life so far. This idea is rumored to have originated from Papa Hemingway. The benefit is that with only six words, you really have to filter your life to what you deem most important. It may take you many iterations, but you’ll end up with something that speaks largely to who you are, if not in toto, then at least in this moment in time.

Day 3: Decide on one positive habit you’d like to implement in your life. Whether seemingly mundane (like flossing) or perhaps life-altering (exercising every day), think of something you’d like to add to your life that will be beneficial. Then, think about the steps you’ll take to get there, and how you’ll keep yourself accountable.

Day 4: Via negativia; today, pick a habit that you’d like to eliminate from your life. Bad habits are like armpits, we all have ‘em and they all stink. Whether cutting soda out of your life, or putting a stop to your porn addiction; either way, as with yesterday, think about the steps you’ll take in order to put the kibosh on that negative habit. And again, also think about how you’ll keep yourself accountable to that goal.

Day 5: Write a letter to a loved one. Chances are high that there is someone in your life that you’d like to say something important to. Maybe it’s a wife, a parent, a grandparent you never really got to say goodbye to…take the time today to write that out. It can be positive, negative, or anywhere in between. The beauty of this letter is that you aren’t sending it in the mail, you’re simply “voicing” something that needs to be said. Should you choose to share it later, that’s okay, but you don’t have to. Doing this can be a great way to heal anger that’s been pent up inside, or to release a pressure valve of sadness we may have been harboring over something lost.

Day 6: Pick a quote from our 80-ish quotes on manhood and reflect on why it stands out to you. Does it reflect a man that you aren’t yet, but hope to be? Does one of them remind you of a great man in your life who you’ve tried to model? If you can’t seem to reflect on a single quote, just take the time to write out a few of them that you like. Doing so will keep them top-of-mind and perhaps lead to some thoughts later down the road.

Day 7: You’ve made it one week! Reflect on what this newfound practice has been like. Getting through the first seven consecutive days is truly the hardest part. Have you enjoyed it? Has it been difficult? Has it been what you expected?

Day 8: Take some time today to reflect on your career. Jot down a timeline of it, including all the ups and downs. What was your best experience? And the worst? What would you like your future to look like, in terms of your career? If you’re a young man and haven’t started in yet, focus on that future part. What do you want your work to look like?

Day 9: On this day, simply write about your day. This may seem especially boring, but write out the events of your day. What time you woke up, what you had for breakfast, what your commute was like, what you did during at work, how you spent your evening. If you’re journaling in the mornings, write about the previous day. The beauty of this exercise is that you may discover something that you hadn’t realized. Maybe you weren’t very productive at work, and reflecting on it can allow you to analyze why. Perhaps you finished a big project on the house when you got home; you can think about what motivated you, how it made you feel to finish something big, etc. Don’t discount the seemingly simple task of writing about your day.

Day 10: Take a look at the hero’s journey, and identify where you are in that journey. Doing so can help you better understand where you are in life, and help you figure out where to go next. You can take it in the context of your entire life, or you can take it in the context of a certain phase of your life. Either way, you can be sure that you’re part of a greater journey, and knowing what comes next can help guide you along.

Day 11: Memento mori. “Remember that you will die.” Admittedly, this isn’t the most pleasant topic. There is, however, great benefit in meditating on the reality that at some point, you will in fact die. It motivates you to live the life right now that you want to be living. Meditate on this, and write out your thoughts. Does death scare you? Does it motivate you? It’s okay to be honest.

Day 12: Give stream-of-consciousness writing a try. This is where you basically just write out whatever comes into your head at the moment it comes into your head. It can feel bizarre, and it’s certainly not structured, but it can lead to some valuable insights into what’s going on in your mind. I’ll give you a 10-second example from right now, while looking out my window: “Boy, I have a nice-looking grill outside and the weather is beautiful…just what we need after all this cold and snow. That cloud looks like a ship from Star Wars… it makes me want to be outside.. maybe I need to spend more time outside and appreciate the fresh air. Perhaps I’ll open a window!” Random? Absolutely. Offering some helpful insight about my desire/need for fresh air? Affirmative. Try this out for 10-15 minutes. You may uncover something — no matter how small — you hadn’t previously realized.

Day 13: Perform a mind dump of everything you’re worried about. From the leaky dishwasher to your family member’s poor health — get it all out. Dwight D. Eisenhower did it, and it significantly helped him manage his stress. Just as your body needs to…cleanse itself of waste, so does your mind every once in a while. Getting all your stressors on paper may alleviate some of that pressure. Use David Allen’s GTD trigger list to help you out.

Day 14: Write a review of some form of entertainment you recently took in. Whether book or movie or TV show or Broadway play, write out what you liked and didn’t like about it. Was the acting/writing good? Could you follow the story? Is there anything you can take from it about life, or was it purely entertainment? This is often one of the most enjoyable entries to write, as it’s especially fun (and quite nostalgic) to go back and read these in the future. I can imagine that 10 years from now I will thoroughly appreciate my thoughts from this week on Roy Baumeister’s Is There Anything Good About Men?.

Day 15: Come up with your own Cabinet of Invisible Counselors. There are innumerable great men from history who we can learn from today. When thinking about your life or pondering some question or problem, yes, go to actual mentors and friends, but also take in the advice of men of yore. Write out who you would have on your list and what you admire about them. Having trouble coming up with a list? The comments in the post should offer plenty of ideas.

Day 16: Imagine that someone has decided to write a book about your life, just up to this point. What would the cover blurb say? Be honest here. Is it kind of boring? Are you happy with it? Now imagine what you’d like that blurb to say at the end of your life. What changes need to made for that to happen?

Day 17: Hop on the internet and search for the biggest news stories in the year you were born. Infoplease is a great resource for this. Think about how these news stories, or even statistics, may have shaped your childhood or who you are today. For example, the year I was born, it was discovered that 98% of American households had at least one television set. I could write about how television influenced my generation, and continues to do so today, either positively or negatively.

Day 18: Identify one project you’d like to complete with your hands. There’s something special about a man doing work with his bare hands, and most men today have lost that. Maybe you want to start a garden, or build a workbench in your garage. Maybe you’ve been meaning to upgrade your bathroom on your own volition. Once you identify that one project, write about what you have to do in order to complete it. Detail the steps, the resources, the help you’ll need, etc. Then, set about doing it. Come back to this entry as motivation when you see yourself wavering.

Day 19: Reflect on your romantic relationship(s), and identify one area in which you’d like to improve. Be it your wife, fiance, or new girlfriend, there’s sure to be something you can do to make the relationship even better. If you don’t have a romantic partner in your life, perhaps you can identify past failures that you’d like to improve in your future relationships. You can choose to talk about this with your partner, or not. Either way, you’ve now put your relationship top-of-mind and will be more attuned to being intentional about keeping it healthy.

Day 20: Think about the period of your life in which you have the greatest nostalgia for. For me, it’s definitely college. Staying up late with friends, being forced to be creative with date ideas because I didn’t have any money, doing nothing but learning all day long…it was fantastic. Once you identify that time period, think of why you’re so nostalgic about it. There’s a good chance that there’s something from that time that you’d like to regain or recapture. Maybe you realize the importance of having close friends, or perhaps you’ll come to understand your desire to be a lifelong learner. Nostalgia can be healthy if reflected on and not obsessed over. You may not be able to recapture the past exactly (see Jay Gatsby), but there are elements of it that may make you a happier fellow.

Day 21: Take a look at our excellent series on the four archetypes of the mature masculine. Read the descriptions, and think about which archetype you most strongly resemble, and that which seems to be your greatest weakness. Write about how you can achieve better balance between all four archetypes and identify the specific ways in which you can strengthen your weaknesses and harness your perhaps overpowering strengths.

Day 22: Imagine you’ve been provided with a livable income for the rest of your life. You have no need to work, but aren’t rolling in money either. How would you spend your time? Your answer will say a lot about you and what your passion may be. Perhaps this discovery confirms your career choice, or maybe it makes you realize you’re not actually where you want to be in life. If it’s the latter, think about how you could make money with that passion, and even draw up a game plan for getting to that point. As much of our lives are spent at work, to dislike what you’re doing will not only drain you of energy and willpower, but also leave you looking back and wondering why you didn’t do anything to change it.

Day 23: Make a list of things that distract you. Every man deals with distractions, whether at work or at home. It could be the internet in general, it could be a specific website, it could even be something that’s actually beneficial, and yet distracts to some degree from something that’s important to you. Making a list creates awareness, and you can better slay those distraction dragons.

Day 24: In modern times, men have become more spectators than doers; more consumers than creators. Yet one of the marks of a mature man is being someone who doesn’t just consume the culture around him, but actually helps create it. Think about all the ways you consume the world around you, and the time you spend doing it. Next, think about the ways you can reverse that, and start to actually be a creator. That’s an intimidating word to some, so come up with ways that you can get off the couch and do something productive instead of just mindlessly intaking.

Day 25: There comes a time in every man’s life where he just feels…meh. He’s not happy about things, but he’s not depressed either. In fact, it’s probably a place where many men spend most of their lives. Take a look at the 5 switches of manliness — the things that ignite passion within us to live fully. Which of these is missing from your life? It’s not likely that all five are fully present, so take some time to jot down ideas on how you can better integrate these switches into your life so that you can have the motivation to seize each day as it comes.

Day 26: For three days, we’ll work from AoM’s “Craft the Life You Want” series. While many things in life are out of our control, there are more things than we often realize that are in our control. Most often, we simply don’t realize that we have the power to change things in our life when we aren’t happy. Today, work on crafting a life plan. It can be a long process, so if you’re short on time, start by defining your various roles as a man, and your ultimate purpose and goals within those roles, including specific action steps.

Day 27: The importance of where you live: our home and environment have a tremendous impact on our lives. Take a look at the eight factors that should be considered when choosing where to live. Maybe you’ve never actually chosen, and you’ve just ended up where you are by default. Take the time today to think about the idea and importance of place. You may determine that where you are is perfect, or you may realize that you belong somewhere else.

Day 28: Finally in this three-day journey, you need to gather the tools necessary to make your life a masterpiece. Take a look at the article, and define the various tools that you will need and use to work towards those purposes and goals you laid out a couple days ago.

Day 29: Try writing out your own personal manifesto. I’d describe the benefits and the how-to, but this short post does it much better than I could.

Day 30: Jot down a list of all the things you’re grateful for. It could be as simple as “Family, Job, Home…” or as detailed as “The bacon I had for breakfast, the weather being warm today, the chance to sleep in this weekend…” When we aren’t feeling chipper, thinking about what we’re thankful for can help get us in the right mindset. No matter how down and out you may be, there is always something to be thankful for.

Day 31: Reflect on the last 30 days of journaling. Did you enjoy the experience? What did you learn about yourself? What was most difficult? Will you continue the practice? If so, take some time to map out how you’d like your journaling habit to continue. It can be entirely up to you; don’t worry about following a set of rules. Maybe you want to write every day, maybe you’re okay with a slightly longer session every month or so. Just make sure it’s something that you want to do.


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