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We’re squarely in the midst of tax preparation season which means we are forcibly engaging in looking back at last year to answer questions like: How much were my medical expenses?   How much did I give to charity?  Do Girl Scout cookies count as a charitable deduction? (Sadly, they don’t.)  Pulling all this information together can be a drag, but I must say I appreciate a bit of mandatory reflection.  In fact, it was pulling my tax information together one year that started what has become a bit of a ritual for me.

While tracking down my deductions a couple years ago, I logged in to my American Express account since I run almost all my expenses through it.  Sitting there waiting was a year-end summary of everything I’d spent on my credit card the prior year.  I’m sure you’ve seen these year-end summaries before.  There is nothing particularly magical about them; they simply organize your transactions and show you things like where you spent the most money and which types of expenses you favored over others.  It can be a pretty helpful document for tax preparation, but I have started using it as something more.

I see my annual summary as a representation of my year.  It’s almost a type of journal that I make a point to review.  With each entry, I am reminded of somewhere I went or something I did.  When I view it at the micro level, I am reminded of the day I went tandem bike riding with my husband, the day I took my parents to the carousel at Smale Park or the amazing meal I had on my birthday.  It’s astonishing how many of these things have already faded to the back of my mind, having happened less than a year ago.  This little ritual of looking back over the year brings me so much enjoyment that I need no other reason to do it.

When I view my spending at the macro level, I have a different goal.  It still has to do with reflection, but in the sense that I am evaluating whether my spending is an accurate reflection of who I am.  I look at the top places that I spent money through the year and I try to imagine what a stranger would think about me if they had nothing else to judge me on but this.  Would they be able to tell what is important to me, or what I like to do?  Would the things that make me happy be evident or would my spending be misleading?  I can say I love to travel, but does my spending demonstrate it?  I can say I want to focus on having experiences, but when it actually comes time to part with my cash do I buy activities, or do I buy more stuff?

This part of my ritual is about accountability to myself.  It’s examining my reflection through the prism of my spending, so I can explore whether I am spending in a way that aligns with what’s important to me.  It’s a litmus test to see if my intentions match my actions and if they don’t, it’s an opportunity to consider different choices.

The first year that I did this, I was struck by the level of my charitable giving.  Volunteering and giving have been important to me since I was Key Club president in high school, yet as I looked at my year the importance of that value was reflected nowhere in my spending.  When I compared how much I’d given that year with how much I’d spent on meaningless purchases, it was obvious that this wasn’t about having the means to give.

Reviewing my spending in this way enabled me to recognize an issue I probably wouldn’t have noticed otherwise.  Stepping back and taking a 10,000-foot view was different.  I wasn’t balancing my checkbook.  I wasn’t trying to stay within my budget.  I wasn’t evaluating if I could afford something.  I wasn’t trying to eek out a little more for savings.  This was not about the minutiae of day-to-day spending.  It was about looking at how my spending behavior was shaping my life and whether I was fulfilled by that.  The way a CFO directs a company with his or her decisions, we can govern the direction of our life by making more intentional choices with our spending.  We can choose to funnel more money into the things that give us a higher degree of fulfillment.  It’s a different way to think about the return on your money.

As I contemplated the discrepancy between my charitable values and my actions, I realized I hadn’t made a conscious decision not to give.  In fact, I found myself diverting from my values because I hadn’t given it much thought at all.  And so, I decided I would give myself time to think about these things every so often and looking at my annual spending summary seemed like a logical time to do that.

We can eternally debate the degree to which money can bring us happiness.  What I believe is that reflecting on what we do with money can absolutely make us happier.  Reflection can mean finding joy and gratitude by looking back at how many great meals you had, how many new places you saw, or how much care you provided to your family.  Reflection can also mean looking inward and deciding how you can architect a life you love through your spending decisions.  In both cases, a small investment of time and attention can result in pretty meaningful returns.