After years of living paycheck to paycheck, I learned to ask myself 4 money questions every week, month, and year

• After living paycheck to paycheck in my early 20s, I decided I needed to come up with a different approach to my money dates during different times of my spending cycles, each with its own set of priorities.
• Now, I check in with my money every week, month, and year, and ask myself four questions each time.
• They include "What are my biggest goals and, subsequently, my biggest expenses?" (yearly), "Is this system working for me?" (monthly), and "How much did I spend this week?" (weekly).
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After college, my finances were an enigma to me. I had spent four years as an undergrad working low-paying jobs and living paycheck-to-paycheck. I did what I needed to scrape by, and I managed to follow some basic rules to make sure my credit remained in good shape.

But soon, I learned about the concept of a "money date." The idea was simple: A money date is a regular financial check-up. 

A money date can either be with yourself, alone, or between you and the people you share your finances with.

I decided to try having self money dates once a week, initially just to track my spending. But I soon realized there are many layers to strategizing around money. What if I needed to make a major purchase? What if I wanted to switch to a zero-sum budget?

I decided I needed to come up with a different approach to my money dates during different times of my spending cycles, each with its own set of priorities. Now, I check in with my money every week, month, and year.

To figure out exactly what I should be asking in each of these check-ins, I spoke to Maggie Germano, Certified Financial Education Instructor and financial coach for women, who agrees with me that some money dates are for looking at spending, while others are for asking bigger questions.

Here are the questions I ask myself to help focus and guide my strategy, with some feedback and suggestions from Germano.

Yearly money questions

Let's start with yearly money dates, because they often set the priorities for your monthly and weekly budgets. I like to do yearly monthly dates at a ceremonial moment that makes sense for me. It can be at a birthday, but January is great because it's a fresh start (and a fresh calendar).

Yearly money dates are for asking big questions, such as:

1. What are my biggest goals and, subsequently, my biggest expenses? Plan it down to the biggest quarterly expenses and make sure each is on your radar.
2. What's the best way to save $__ by this time next year? Opportunities to save include utilizing monthly automated savings, tax returns, or savings from a side hustle.
3. What kind of budget will work best for me this year? Decide how to budget like a boss.
4. What is standing in my way, and what can I do better? Identifying your resistance is key. "It's important to forgive yourself for your past money mistakes," says Germano. "Use your past mistakes to inspire new habits and more positive ways forward."

Monthly money questions

Monthly money dates are about refinement. In the beginning of the month, I like to perform a mini-review of the previous month before looking forward to the month ahead. I scan my spreadsheet to see if and where I overspent, underspent, and if I have any rollover savings after paying myself first at the beginning of the month.

Monthly money dates are a great time to ask:

1. Did I pay myself first this month? It's not a self money date without putting some upfront money into savings.
2. Am I being honest? I've learned the ways I hide my spending habits from myself. Learn how to look at your numbers (and your habits) squarely in the face.
3. Is this system working for me? Turn off autopilot and ask yourself if your tracking system is making your life easier or more stressful.
4. Am I still on track for my goals, and how do I feel about it? Sometimes, a plan that seems great on January 1 is not as important because other life events come up. It's okay to recognize when plans change. 

Weekly money questions

Germano says a weekly money date is the only way to make sure that your daily spending is aligning with your budget as a whole. But they can be short and sweet!

Here's what I ask:

1. Did I account for all of my purchases this week? This includes "invisible" purchases like automated withdrawals or subscriptions that happened without swiping your card.
2. How much did I spend this week?
3. How much is left for the rest of the month? If you have some wiggle room, consider putting extra cash into savings or give yourself permission to enjoy a small splurge.
4. Do I have the basics covered for the foreseeable future? Car fueled up? Fridge stocked? Check.

Money is meant to make us happy. Regular money dates are meant to remind you of this! 

If you feel resistance at first, keep your goals top of mind, says Germano. She recommends creating reminders for yourself as to why you're doing what you're doing with your money. This can be a picture of that dream house or a visual representation of the debt you're paying off.

Just make sure it's inspiring! 

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