Hear me out.

You need one of these.

It’s a base to check in with every so often. How often? Meh, it’s up to you. I check in with mine once a month. I have reminders set up to review it. Ask myself how I’m doing with it and any changes that need to be made. I log these reviews so I can look back on my progress and weak areas.

I make changes often and add to the Wisdom section when I come across something I like. Some are my own thoughts, others are “borrowed” from books and blog posts that I’ve come across.

It doesn’t have to be fancy, complex, or well-written. Keep it simple.

Write it out in your favorite notes app and set a reminder or calendar event to review it every month or so.

Using mine monthly has improved my life in so many ways.

I’m going to share parts of mine with you so you can see what I mean. It will show you my structure. Change yours to whatever makes sense for your life.

Here are portions of mine: (edited to remove really personal stuff)

This is a living, breathing document just like life. Things can and will change. Be Honest with yourself and how you are doing with your goals.

Once a month, check in on how you are doing and what needs to change. Where have you drifted? What was your most delightful moment last month? What was your best use of time? What was your worst? What went wrong, and what lessons did you learn? What are you looking forward to and why?

Big Picture

  • Happiness
  • Love
  • Friends
  • Simplicity: less stuff, spend less. Less really is more.
  • Work less, play more, take more pictures.
  • Outside: wilderness, camping, exploring, hiking, road trips, photography of all kinds, getting up early with a cup of coffee and smell the air, listen to the birds, listen to nature, listen to Mother Earth, she is trying to teach you.
  • Meditate every day.
  • Take pictures every single day. Print your pictures, hang them in your office, give them away, post them online.
  • Write every day, somewhere, anywhere, journaling, blog posts, Obsidian, Notes, send letters/cards to friends and family.
  • Help people, inspire people, encourage people, be a good human. Smile more.

Questions

  • Does this “thing, object, want, desire” fit into the big picture above? 
  • Will this purchase fit into long-term plans and needs? Will it still be useful or used in 3 months?
  • Can you live without this thing? Is it something that truly will enhance your day-to-day?
  • Is this thing worth going to work extra days…? 

You

  • What kind of person do you want to be?
  • What kind of husband, friend, son, do you want to be?
  • Check your drift; have you drifted from your values? From who you want to be?
  • What situations or triggers make you become someone you don’t want to be?

Housing

  • Think, don’t rush. What do you want in a house/apartment/condo?
  • Property, room for a shop, garden, trailers, room for the dogs to run around. Or small and super simple. Being able to lock the door and leave for a month without worry? What is important to you in this current stage of life?

Work

  • It’s complex… But it doesn’t have to be.
  • Keep it simple.
  • Attitude: be happy. Don’t be a dick. You don’t know how somebody’s day has been. Nobody likes working with a grumpy SOB.
  • Exude positivity.

Vehicles

  • Two total.
  • One small, efficient commuter.
  • Goal: One truck with a camper or a van for extended road trips.
  • No loans, use savings. If you don’t have the cash, you can’t buy it.

Money Saving

  • As much as possible! 
  • Goal: Be debt-free and borrow from yourself.
  • No more loans ever. (except home loans)
  • No more credit card debt. Period. 

Technology

  • (Big Area) Danger! Danger! 
  • Does it bring you happiness? 
  • Keeps you going back to work, you lose days off.
  • Usually fails down the road, causing even more stress.
  • Do you really need this? Or do you want it?
  • Put it in your cart, and wait two weeks. Still want it?
  • The upgrade isn’t worth it.
  • Keep it simple.

Wisdom

  • Only boring people get bored.
  • I’m fanatical about new projects; slow down, spend less.
  • Less IS more.
  • Spending money is giving away freedom. Money is freedom. Are you willing to give up $1,000 in freedom for that new iPad? With money, you have the freedom to do what you want, to take more days off. No money means going back to work, your freedom taken away. 
  • Truth: You can skip the pursuit of happiness altogether and just be happy.
  • Environment matters a lot; move to where you can flourish most. Put yourself in environments where you have to perform to your utmost; if you can get by being average, you probably will.
  • Later, you’ll be nostalgic for right now.
  • Figure out what your primary focus is and make progress on that every day, first thing in the morning, no exceptions.
  • Pay attention to your production-consumption balance. If you’re only consuming and not producing, change that.
  • Lean into the good kind of fear.
  • No matter how bad things seem, everything passes. Everything.
  • Do a review of your year every year: write it out in Obsidian, figure out what was good and what was bad, and use this to set your goals for the next year.
  • Doing things is energizing; wasting time is depressing. You don’t need that much rest.
  • Form opinions on things and then find the strongest critique of those opinions. Repeat. Strong opinions loosely held. Be open to changing your mind.
  • Know your ‘triggers’ / what makes you the worst version of yourself.
  • There is some wisdom in “fake it till you make it”.
  • Don’t “slow down” as you get older; speed up. Lean into changes; be curious about new things.
  • Be honest about whether something is learning or entertainment. Real learning is hard and effortful.
  • Think in writing. Write in Obsidian, scrawl in notebooks. This extends working memory arbitrarily and allows your thoughts to compound on each other.
  • Luck isn’t a constant; it increases with surface area: be in the right places, have lots of conversations, put yourself out there, ask for what you want, and be optimistic and positive.
  • The most valuable feedback usually hurts a lot.
  • If you want to think originally and differently, seek uncorrelated inputs. Read minor works, older things, obscure journals.
  • Read as much as possible and remember what Doris Lessing said: ”There is only one way to read, which is to browse in libraries and bookshops, picking up books that attract you, reading only those, dropping them when they bore you, skipping the parts that drag – and never, never reading anything because you feel you ought, or because it is part of a trend or a movement. Remember that the book which bores you when you are twenty or thirty will open doors for you when you are forty or fifty, and vice versa. Don’t read a book out of its right time for you."

Beyond this, “Cliff538 Life Manifesto”, I usually write out my monthly reviews so I can see trends and have something to look back on. Write out three or four questions you want to ask yourself every month for your check-in. Writing this out gives you time to reflect on what truly needs to change and why. And most importantly, how.

I also do a “Cliff538 State of the State” where I write out what my usual day consists of, what is working, and what is not. I list options and what changes I’m going to make.

Another suggestion is to write out in detail about who you want to be to your spouse, friends, family, etc.

All of this is mostly because I honestly forget a lot of this and just need a monthly reminder to stay on track. It can seem cumbersome at first, but after a few months of check-ins, you’ll start to see improvements in your life. I truly believe you will.

Note: If you want a really deep dive into this stuff and see a whole role system, I highly recommend MacSparky’s Productivity Field Guide.