The Start of the Month

At the start of each month – typically on the evening of the last day of the previous month or in the morning of the first day of the new month – I spend a couple of hours doing a monthly review of my life and my financial situation. I look back at the month just past, tie off any loose ends, and look ahead at the coming month and consider what it will hold.

Doing this kind of review is a pretty routine thing for me. I set aside time each week (about an hour on Sunday mornings) to do a similar weekly review and figure out major tasks for the coming week, and once a quarter I do a quarterly review where I set bigger goals. A monthly review sits somewhere in the middle, but it’s useful in its own way, which you’ll see shortly.

Why do so many “reviews”? The simple reason is that I’ve found that time spent reviewing my recent activities and planning ahead for the coming month is incredibly valuable. Whether it’s done on a weekly scale or a monthly scale or a quarterly scale or a yearly scale, it’s incredibly useful.

Why so many different time scales? I’m usually addressing different things depending on the time scale I’m reviewing. In a brief nutshell:

Weekly reviews tend to be centered around very tangible actions. I’m usually thinking about concrete things I want to achieve in the coming week and reviewing the concrete things I tried to achieve in the previous week. These reviews are almost always centered around direct action – I identify about three key projects I want to complete outside of my normal weekly routine, come up with plans for them, and add them to my calendar and to-do list as needed. For example, this week’s major actions are centered around planning for my son’s upcoming birthday, winterizing our home and automobiles, and completing a milestone on a writing project.

Monthly reviews, which are the real focus of this article, are centered around two things. One, bills and statements come out in a monthly cycle, so this monthly review often centers around reviewing those things. Two, I often take on “thirty day challenges” starting each month, so I tend to look back at the two or three challenges I did during the last month and think about what kinds of challenges I want to take on in the coming month. We’ll dig into this in a minute.

Quarterly reviews are usually ones where I step back a little more and look at how I’m doing on major life goals. I’m not so much setting those goals, but instead I’m looking at how I’m doing in terms of proceeding toward them. How did I move forward on each major goal in the last three months? What do I really need to focus on in the next three months? This sets a framework for the next three months and thirteen weeks.

Annual reviews are the ones where I really question my big life goals. What do I want out of life? What do I want my life to look like in ten or twenty years? This is very big picture stuff. For the goals that remain more or less the same, I try to assess the previous year. What worked? What didn’t work? I usually try to set some general initiatives for the coming year – the two or three areas I really need to work on the most to hit my big life goals.

So, to summarize:
annual reviews center around setting big life goals and defining what I most need to work on
quarterly reviews center around connecting those big life goals and areas of focus with what I’m actually doing on the ground
monthly reviews are in line with the billing cycle and help me define very tangible personal initiatives meant to establish better habits
weekly reviews center around figuring out the big tangible tasks for the week in line with that higher level stuff

My “daily review” is usually just a look at my calendar and to-do list in the morning and evening. During the week, I’m mostly just adding tasks and events as they come up and trying to knock them off as time passes. My intent is that my other reviews help direct all of that toward something more effective – on a day-to-day basis, I’m focused as much as I can be on action rather than on considering what I should be doing.

The time I devote to these reviews is invaluable. This is pure “sharpening the saw” time.

If you’re unfamiliar with the idea of “sharpening the saw,” it comes from an apocryphal Abraham Lincoln quote: “Give me six hours to chop down a tree and I will spend the first four sharpening the saw.” It’s very likely that he didn’t actually say this, but it’s still a clear summation of the idea that time invested in preparation tends to make the tasks you’re working on much more efficient and much more directed toward your desired outcome.

Reviews are very, very good “junk” eliminators, in other words. They’re really good at helping me figure out which tasks aren’t really helping me achieve what I want to achieve in life and which ones are, so that I can discard many of the non-helpful ones and retain the helpful ones.

It is very easy to fall into a routine that’s loaded with those “junk” non-helpful things and then continue doing them as a matter of habit. This includes things like incessantly checking social media, watching television without any real intent, playing unfulfilling smartphone games, and many other things, even seemingly productive things like checking your email constantly in the background of your work. It also include “junk” expenditures of money like convenience items, unhealthy foods, and so on, some of which are okay in moderation, but they tend to be utilized more often than we think.

Reviews are the single most effective tool I have in my repertoire for eliminating that “junk” – junk time use, junk spending, junk energy use. That’s why I do them so frequently. I recoup the time investment often within hours, and the financial savings is pretty impressive, too.

Today, however, I want to focus on my monthly reviews. My monthly reviews usually consist of two distinct parts.

Review of Bills and Financial Statements

Throughout the month, I put any paper financial statements that we get in the mail in a basket in our home. During my monthly review, I grab all of those statements and download others from various financial institutions.

Then, I spend an hour or so going through them.

One big area that I look at carefully is our bank and credit card statements. These statements are a window into how we’re spending money. Sarah and I rarely withdraw cash via ATMs, so almost all of our spending is recorded on our bank and credit card statements.

I usually go through these item by item, looking for patterns or things that seem out of place.

Is there an expense – particularly a big one – that is related to something I can’t remember? I try to figure out what that expense is.

Am I seeing any patterns of expenses, particularly unnecessary ones? I try to make note of those patterns.

Am I spending too much on my own hobbies? I’ll tally up spending that seems to be related to my hobbies just to make sure that I’m not overrunning my hobby budget.

How are we doing on food spending? We “over budget” for food basically every single month so that we don’t have to feel worried about buying something like truffle oil once in a while. I usually check and make sure that our total spending at grocery stores and restaurants remains in a reasonable place. This is usually very steady and usually substantially below our monthly food budget, but food can be a widely varying cost month to month, so I like to keep an eye on it.

In a given month, I usually find two or three things that are out of place in our bank and credit card statements, usually related to our spending behavior. Usually, these are calls for me to correct something about my own spending habits or to talk to Sarah about our overall spending habits in a positive way, like a “Hey, we ate out a bunch last month compared to normal, so let’s try to eat at home a lot this month.”

I tend to examine other bills and statements mostly to make sure there aren’t any unexpected charges or other things going on. You’d be surprised how often cell phone providers and other businesses love to tack on a new fee or a new small charge whenever they can, and I like to be aware of those changes.

I usually don’t make a big deal out of a minor new charge or a small bump in cost, but what I often do is compare a regular bill to what I was paying a year or two ago, and if it’s significantly higher, I know it’s time to give that company a call.

So, let’s say I see a charge that I don’t quite understand on my cell phone bill. I’ll pull up that bill from a year or two back and see if the charge is there and see what charges I’m paying now versus what I was paying back then.

If it looks like there’s been a significant amount of things added in the last year, it’s time to give that business a call to renegotiate things, and if that doesn’t work, it’s time to shop around. I typically add such things as a task to my to-do list.

This takes probably half an hour to forty five minutes for all of my bills and statements. Most months, I wind up with one or two actions that I’m taking as a result of those bills – talking to Sarah about some spending issue, calling a business about escalating fees and charges, shopping around for a new service provider, or something like that. Each of those actions, when completed, usually results in some significant savings that month on spending or a notable decrease in a particular bill going forward. In short, this little thirty minute review of bills and statements ends up saving a lot of money over the long haul.

I usually review our investment accounts very quickly. I’m not really interested in changing our investments at all – I’m very much in the “buy and hold” mindset when it comes to investing – but I just want to make sure that things are moving along as expected. Were there regular deposits into the account? Did they go to where I wanted them to go? Everything’s good, then. This takes just a moment or two and virtually never results in any sort of action.

Review of “30 Day Challenges” and Setting of New Challenges

The other big part of my monthly review – and this is probably the most important part – is the review of my just-completed “thirty day challenges” and the setting of new challenges for the coming month.

So, a quick review: a “thirty day challenge” is simply an agreement with myself to adopt some new behavior for the next thirty days as a trial run. I’m trying to see how a particular behavioral change will affect my life. Sometimes, a “thirty day challenge” is a repeat from the previous month, which is a situation where I found the previous challenge to be a big success and I want to instill it as a permanent habit in my life (I’ll often do “thirty day challenges” for three or four months in a row until a new habit becomes completely normal if it’s a clear “home run.”)

Here are some examples of recent “thirty day challenges” in my life:
+ Do one plank to exhaustion and then four more planks of 60% of that time each day (in an effort to improve my core strength)
+ Trade, sell, or give away one board game each day (in an effort to trim my board game collection)
+ Do an hour of deep reading and note taking each day from a particularly challenging book
+ Average 15,000 walking steps each day
+ Spend no money on food outside of the produce aisle (in an effort to pare down the contents of a bulging pantry)
+ Be completely honest
+ Write a handwritten note of thanks to a mentor or influential friend each day
+ Buy no books
+ Spend thirty minutes deep cleaning and purging the trouble spots of our home each day
+ Don’t use Instagram for thirty days, either to post or to browse
+ Each day, drink some matcha green tea and follow it immediately by a twenty minute mindful meditation

Most of these “challenges” are attempts at behavior changes. Some of them are experiments to see how my body reacts to something new or my lifestyle reacts to something new. Sometimes, a “challenge” is breaking down something big and intimidating into smaller tasks.

Usually, the goal of all such challenges is to make my life better in some dimension. Like almost everyone, I tend to go through life following a path of least resistance – what’s the most direct path from here to getting the things done that I want to get done so that I can have some time to enjoy things I want to enjoy? Thirty day challenges are a simple way for me to force myself to try a new “direct path” and see if it’s better than the old one. If it is, I try to make it into a permanent change. If it isn’t, I mark it up as something learned.

Most things tend to work better if you repeat them over a long string of days. It’s hard to assess how good a change is after a day or two. I find that thirty days is a really good target number for figuring out if the change is a desirable one, but it usually takes longer than that to make a change permanent, which is why I often repeat thirty day challenges if they were really successful the month before.

So, the first thing I do is review the challenges of the previous month. I usually keep track of my thirty day challenges in an app called Way of Life, where I detail each challenge and mark it off as I complete it. Lately, I’ve also been “scoring” my effort toward each challenge each day, as I discussed when talking about the book Triggers by Marshall Goldsmith.

So, I’ll pull up all of that data and sometimes also look at my journal entries and reflect a bit on each challenge. Did it go well? Did I get results like I was hoping for? Did I stick with it?

For most challenges, I usually find that I stuck with it and that it had a bit of a positive return, but the time investment or other commitment needed to permanently alter my routines wasn’t worth the benefit I got from it. Some of those challenges are hard, and unless I’m starting to see some really good results or at least have a sense that good results are coming, I’m probably not going to try to permanently adopt that challenge.

There are a few challenges, though, where the benefits are screamingly obvious to me. Over the last few years, here are some of the challenges I’ve done that have just been downright home runs for me:
+ Buying no new games and paring down my board game collection by one game a day
+ Giving up smartphone games entirely
+ Mindfulness meditation for fifteen minutes in the morning
+ Writing “Three Morning Pages” in my journal
+ Drinking both coffee and green tea as I write in the morning
+ Turning off my cell phone from 5 AM to 7 AM and then again from 8 AM to noon, every single day.
+ Doing a few exercises to exhaustion once a day, then doing a few sets later in the day to about 60% of exhaustion
+ Doing a meal prep every Sunday, then using one of those meals every Monday, Wednesday, and Friday (did this during a busy month and it was revelatory in terms of evening time efficiency and saving money)
+ Eating vegan until 6 PM every weekday

Those things have become permanent parts of my life, either in that exact form or in a similar form. They were all borne from thirty day challenges.

So, what I’ll do is I’ll just go through my challenges for the past month and just see what I learned from each of them. If a challenge is an absolute home run, I’ll repeat it again for the next month unless I feel like it is a permanent part of my life now, at which point I’ll drop it as a “challenge” and just continue doing it. Otherwise, I’ll think about what I learned from it a bit – this usually becomes journaling fodder and sometimes transmogrifies over the next month into a new thirty day challenge for a subsequent month.

Then, I define three non-overlapping “thirty day challenges” for the following month. Sometimes, one or even two of those is a repeat from the previous month.

Usually, I have a large number of challenge ideas that I want to work on. What I try to do is focus those challenges on areas of my life that I feel are out of alignment and underappreciated.

For example, if I feel like I’m letting some long term relationships slip, I might have a challenge related to shoring them up. If I’m feeling out of shape or ready for some other approach to fitness, I might try a fitness related challenge. If I’ve noticed an ongoing financial concern, one challenge might be related to spending.

I’m also often influenced by compelling ideas I read about or hear about. If I hear about a particular productivity tweak, I’ll often use that as a thirty day challenge in an effort to make my days a little more efficient. If I learn about a particular mindfulness practice or something like that, particularly one that seems like I could reasonably incorporate it into my day, I’ll make that into a challenge.

I’ll usually just brainstorm a list of challenges based on what’s on my mind in terms of underappreciated areas of my life and ideas I’ve picked up on recently. I’ll choose one, two, or three of them to complement the ones I may be repeating from the previous month to ideally choose three challenges for the coming month.

This month, these are my three challenges:

Each day, sell, give away, or throw away five items from my office drawers or closet. Late this month, I’m moving my home office to another room in the house, and I’ve realized that I’ve accumulated a bunch of random things in the drawers and the closet in my office. Most of it is things I’ll likely never use, but someone else might find a use for (or else it’s just complete junk). So, each day I’m going to find ten items to either trash or give away or, in a few cases, sell off. I want to see how this makes me feel about the tools I keep around for work and for some aspects of my personal life.

Each day, work while standing for at least one minute longer than the previous day. One thing I have for my new office arrangement is a standing desk, which I’m switching to for health reasons. However, I know that an abrupt shift from a sitting desk to a standing desk is going to be rough, so I’m challenging myself to gradually switch using a “makeshift” setup that I devised for the next few weeks. On the first of the month, I’m going to work while standing while it’s comfortable – as soon as it stops being comfortable, I’ll stop. Each day, I try to beat my standing time from the previous day. This is really preparation for a permanent lifestyle change, as I plan to work at a standing desk going forward (it may even eventually become a treadmill desk that moves at about one mile per hour).

Buy no new books or board games. None. I’m spending nothing on my hobbies this month. I went over my hobby budget in both September and October and the truth is that I have a lot of things left untouched in both collections, so this is a month to focus on what I already have and appreciate those things.

I load these challenges up into Way of Life, as noted above, and add them to my listing of triggers to review, also noted above, and some elements find their way into my to-do list app (OmniFocus).

That’s it. I feel ready to tackle the next month. I’ve tightened up my finances and established some ongoing steps toward improving myself for the next thirty days.

I highly recommend this kind of monthly review, particularly if it’s a part of ongoing reviews in your life at other time scales. It’s incredibly effective at helping you figure out good and bad patterns in your life and setting you up to maximize the positive and minimize the negative.

Good luck!