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Illustration by Jared Oriel

Quick — if I asked you to grade your money habits, what would you give yourself? An A+ or a B-, or maybe, if you're honest, an F? Would you even know the answer?

At the end of the year, most people can tell you how they rate in their careers thanks to annual assessments, but the same isn't always true of our personal money lives. I know that nothing says "dreadfully boring" like the phrase "performance review," but you have to admit that when you get feedback from one it often sticks.

Inspired by a number of high performers, I started giving myself a comprehensive personal annual review a few years ago. While I’ve abandoned some of the assessment categories, the financial review has stuck. Money allows so many other long-term goals to come to fruition — from travel and moving to changing jobs and buying property — that it’s worth its own review.

Let’s ease into this with questions you can consider right now.

1. Start your money review with a self-assessment

First, ask yourself: How do I feel about this year’s spending and saving?

Are you proud? Guilty? What feelings come up, and how do you wish you felt instead?

Listen to what your gut tells you when you think about your finances. If you feel like taking notes or journaling at this point, go ahead. After reflecting, move to step two.

2. Consider your money reality — the good, the bad, and everything in between

Here comes the fun part (kidding, this is the least pleasant step, but the most useful). It's time to audit yourself. This won't involve the IRS, but should be as detailed as if it did.

Survey your money tools

Which apps are you using? Which ones did you abandon after two weeks? Can you pinpoint a reason why? For instance, did you quit Mint because you never connected your bank accounts, or did you try YNAB and give up after a few days? Identify which ones you'd like to revisit.

Tally your account totals

See where you landed at the end of the year. Gather your checking and savings account totals, credit card and student loan debt, retirement accounts, and cash totals. Don't forget to check your Venmo and Paypal accounts to see if any money is lingering in there.

If you add these up, you can find your net worth.

Now, compare your totals to the previous year's: How much did you increase or decrease in each category? If you don’t know last year’s totals (and don’t want to dig to find them), use this year as your baseline going forward, but I do recommend going back at least one year. It’s crucial, in my opinion, to find out if you’re a chronic over- or under- estimator with your money.

3. Check in with your goals

After combing through your numbers, how reasonable were this year's goals? Maybe your 2019 wish was to save 25% of your income. But that didn’t happen because you bought a new phone with a payment plan, groceries were higher than estimated, and you had to replace the timing belt on your car. Or you wanted to save a few grand for a down payment fund, but midway through the year you ended up diverting that money to pay off a credit card bill. For each 2019 money hope, see how things actually turned out — good and bad — and then analyze why.

One year, I had told myself I wanted to spend no more than $250 a month on food (including groceries and meals out). But I was frequently exceeding this number because of dinners and drinks with friends, and a lapsed habit of bringing my lunch to work.

To see if I was meeting that goal, I had to go back and look through my credit card statements and total each month’s food spending, because I had lapsed on tracking my monthly category spending. It turns out I was going over by a lot — something I didn’t reckon with until I did the tallying work.

4. Set your money goals for 2020

Now that you have a clear idea of the money you have and what you've spent, it’s on to setting goals for next year. What seems feasible now that you know your finances down to the details? Maybe it’s throwing an extra $100 a month at Sallie Mae. Or, it’s maxing out your Roth IRA and setting up an account to save for that Caribbean cruise you’ve lusted over. Perhaps it’s $30 a week toward your car loan. Once you pick out your 2020 money targets, it’s on to the action step.

5. Finish your money review with a plan of action

Useful performance reviews leave you with a plan for how you’ll meet your next set of goals. You want to do the same for your money wants. Take, for instance, your budget. If you want to save 30% of your paycheck this year, calculate how much money you need to stash away each month, and each week.

Or perhaps you found that rather than a savings target, you’d be better off with a daily spending allowance. How much money are you planning on spending each day? What will your plans be if you go over this allowance?

6. Put your review and plan in writing

Fire up Google Sheets or grab a notebook and write down your plan. Moving your goals from your brain, where they can be mushy and nebulous, to a concrete list in black and white will allow you to start working toward them. It’s like going out for a run and setting up an actual finish line, rather than claiming you’ll stop when you get tired.

Once you’ve drafted your money goals and plans to reach them, keep it somewhere you’ll see it often, maybe tacked over your desk, or folded in your wallet. If you’re digital-only, add a calendar reminder that’ll ping you each month with a link to the document, so you see it regularly.

And to really commit to this concept, seal the review the way you would a corporate one — by signing and dating it, effectively making a contract with yourself for 2020.