[ad_1] Purchases like this really blow my budget. These days, I do a fair amount of informal financial coaching for both old friends and newer acquaintances. It’s a pretty amazing experience, almost as if I were a real doctor – people let down their guard and talk about the details of their financial lives, without the usual hangups and secrecy that tend to plague our society when it comes to the subject of money. Often, even taking this first step is a huge leap towards creating a more wealthy and prosperous life. Money conversations are not something we should reserve only for our paid professional advisers. We should speak about it openly with our friends and family, and support each other in a lifelong quest to make the most of our lives. Through these hundreds of little sessions, I have started seeing a pretty consistent pattern: People who struggle with money see the whole subject as a swirling, confusing mess. Income and spending, debt and retirement accounts are everywhere. They describe the situation in a long, meandering paragraph. People who are good with money have this stuff more mentally sorted. They can quickly list their income, their assets and debts, and most importantly they know how much money they spend each year. People who have been good with money for a long time have moved even further. They might not track it very closely, but they still maintain a growing surplus – because living well within their means is just a natural habit, which means there is no conceivable way they can run out of money in their lifetimes. People in this category sometimes need to be coached away from the habit of being too “cheap”, and towards making the most of the opportunity of a lifetime. As an MMM reader, you are headed straight for Option #3 above. But you may have to move through #1 and #2 to get there, which means sorting things out and tracking your spending. Tracking Your Spending is Fun, Useful, and Easy (Yes, really!) I can already hear your collective groan as I give you this prescription, but adding up your past year’s spending is one of the most useful things you can do with a Saturday morning, and here’s why: You can see where your money is going to waste and where you can make really easy improvements that completely change the course of your life You will get the courage to switch jobs, houses, cars, and other life decisions as your fuzzy swirling financial paralysis transforms to a crystal clear understanding of money – one of life’s most useful and fun tools. You can immediately see how much money you will need to retire. (just take your annual spending and multiply it by 25 as recommended by the 4% rule) I’ll show you my spending if you show me yours. Road Trippin’ in a Tesla. I keep this cost low by bartering carpentry or business help with Tesla-owning friends, or renting them on Turo. Now for the fun part. I like to think that I live in “Category 3” of that list above – most of my major life expenses (housing, cars, health, food, clothing) are lower than average, because I have simple tastes and I love optimizing things. Meanwhile, I have several sources of income which add up to many times more than my living expenses (stock index funds, real estate investments, this website, and side hustles like carpentry and operating the MMM HQ coworking space.) So I haven’t been tracking my spending for a while. But a couple of years ago I went through a major life change – the former Mrs. MM and I split up and moved to separate households in the same neighborhood. With the old routines shaken up, and new things like hosting more parties, outfitting a new home and increased friend/family/long-distance-relationship travel, how has my bachelor spending been transformed? It’s time to find out. How Do You Track Your Spending? My expenses are really easy to track: I funnel all my spending through a rewards credit card, which saves me about $2000 each year. (in 2019 I used the two highest-paying cards from Capital One which you can find here.) Meanwhile, I hook up a third party financial app to automatically monitor these transactions, alert me to any unusual activity, and – the best part – automatically categorize and add everything up for me. I’ve been using one called Truebill for a couple of years*, and it has the simplest interface of anything I’ve tried – you get results like this: Recent screenshots from my own Truebill account. (Sorry about all that cash sitting around earning nothing, I will put those little green employees to work ASAP!) Truebill is great for tracking and improving spending, and you can also track with Personal Capital, which I have used for the last five years or so mostly for keeping tabs on all my net worth (see my 2013 article on that). BUT you can also all this quite easily with no apps at all, just by downloading the full list of your 2019 transactions from your bank and opening it up as a spreadsheet. In Capital One (which I also use for my checking account), I just clicked on each account and there is a link for “Download Transactions” right at the top of my transactions list. For me, it was extra easy because I used the same bank for both checking and credit cards, so everything shows up on a single login screen like this – kudos for Capital One for doing this so well since most banks have pretty bad websites: Lots of useful stuff on my capital one home screen (don’t worry, balances and account numbers, etc. have been modified for public sharing) So whether you use an app or a conventional spreadsheet, tracking your spending is quite useful, to know where you are now. But the biggest message to take home from