19 Financial Questions to Ask Yourself

By Ashley Kilroy · November 17, 2022 · 12 minute read

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19 Financial Questions to Ask Yourself

You may have questions you’d like to ask a financial expert, but did you know there’s also value in asking yourself some questions about your money? These queries can help you organize your finances to spend efficiently, save more money, and achieve your goals, such as retiring comfortably.

While making money might be straightforward enough (you work and receive a paycheck), using your hard-earned dollars to improve your quality of life and achieve your goals can be less clear. Healthcare expenses, education, and keeping up with daily expenses (plus inflation) can be all-consuming.

Fortunately, good money management can help you think big-picture as well as identify small-scale ways to improve your finances. And checking in with yourself can be a vital step.

So here are 19 questions to ask yourself about money that can help you save, spend wisely, and retire well. They’re grouped into categories (baseline, weekly, monthly, and annually) to make them easy to navigate.

Benefits of Keeping Yourself in Check Financially

Taking stock of your financial circumstances is more than a box to check off or a simple chore. It has numerous benefits for your bank account and mental health, such as:

•   Reflecting on and changing your spending habits

•   Creating a plan for achieving financial goals and building wealth

•   Gaining control over your finances and reducing stress

•   Adopting an investment style that fits your needs and risk tolerance

•   Reviewing your tax burden to see if allocating pre-tax dollars can boost your financial potential

•   Understanding how you can increase your financial security through budgeting and saving

•   Fostering a sense of confidence and independence

Now it’s time to dive into the questions themselves, including ones you can ask as a baseline, weekly, monthly, and annually to help keep your finances on target.

Baseline Questions to Ask About Money

Now that you know the benefits of investigating your finances, start here. These questions to ask about money can help you lay the groundwork for where you want to go financially. It’s a good idea to refer back to them throughout the year to stay on track.

1. What Do I Want Retirement to Look Like?

A precursor to financially preparing for retirement is asking yourself what you want it to be like. For instance, you might imagine yourself vacationing in foreign countries throughout the year or taking it easy at home with an occasional visit to the golf course. You might also consider part-time retirement, where you work around 20 hours a week, whether to pursue a passion project or earn extra money.

In any case, your desired retirement will determine your financial needs once you leave the workforce. Developing as detailed a picture as possible will help you answer the next question.

2. How Am I Preparing for Retirement?

Planning for retirement is more than starting a retirement fund contributing to a 401(k) or IRA (although this helps!). Your retirement age determines your healthcare situation, Social Security income, and investment strategy.

For example, if you’re planning on retiring at an older age, you’ll receive higher Social Security distributions, and your investment accounts can stay aggressive, earning you more money.

As a result, a sophisticated approach to retirement is crucial. Planning early and in depth will help you build wealth and afford the lifestyle you want. Foundational elements of a healthy retirement approach include diversifying your investments, figuring out when you can retire, and identifying your target annual income.

3. How Much of My Budget Should Be In Investments?

There’s no one universal rule that dictates how much you should invest per paycheck, and everyone’s financial circumstances are different. However, the following four guidelines can help you see where your are and then ensure you’re investing a sensible amount:

1.    Investing a specific amount might substantially lower your taxes. For example, if you make $95,000 per year and put $20,000 pre-tax dollars into investments, you’ll drop your tax bracket and pay a lower percentage of your paycheck to the government.

2.    Taking advantage of any available employer match is critical. If your employer-sponsored 401(k) usually has matching funds up to a certain percentage, budget to snag it. For example, if your employer will match the first 5% of your paycheck contributions to your 401(k) plan, it’s wise to invest up to that amount to double your investment. It’s free money, and that’s hard to beat.

3.    Sticking to your retirement plan is key. A detailed retirement plan should define a target amount to invest every month. For example, your plan might require you to invest $150 a month in an IRA. If you’re not saving for retirement already, it’s not too late to start a retirement fund.

4.    Your debt burden might be more pressing than depositing money in a retirement account. For example, let’s say your investment portfolio has an estimated return of 6%. However, you also have credit card debt with an APR of 25% and an auto loan with a 7% interest rate. These debts are accruing faster than your investments. Therefore, it’s a good idea to pay them off ASAP so you can invest efficiently.

4. Do I Need to Have a Financial Advisor?

If you feel in over your head when asking yourself financial questions, a financial advisor can help. Financial advisors create customized financial plans and investment strategies. While they usually are competent across most financial subjects, you can also get specialized financial advice.

Remember, financial advisors charge you for their services. Usually, you’ll pay a percentage of the assets managed (around 1% for a human advisor, while robo-advisors can be as cheap as 0.25%) or a flat fee. However, if you’re feeling lost trying to organize your finances, the price can be well worth it.

5. How Can I Improve My Financial Literacy?

From student loans to home ownership, the financial world has many complex aspects. If you are feeling as if you could use more insight in one or more areas, educate yourself. There are plenty of books, podcasts, and websites that share knowledge on a multitude of financial topics. It’s also likely that your financial institution has content on money topics.

6. What Are My Financial Values?

Asking yourself this question can help shed light on your money mindset. Your financial values drive your decisions, whether you’re aware of them or not. For example, you might scrimp and save every penny but not pay any attention to investment opportunities. This value of preserving rather than growing your cash could be detrimental to your long-term financial health.

Or, you might buy luxury items as status symbols but be unable to afford a much-needed vacation. Writing down your financial values and asking yourself if you need to change any of them can help you evaluate your beliefs and direct your money to what matters most.

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7. Am I Happy With My Job?

This question could help you understand your financial and/or emotional health. For example, your job might be financially stable but unfulfilling. In that case, you might need to weigh if it’s worth continuing in a job you don’t enjoy.

On the other hand, your job might not provide the income you need to reach your financial goals and retire comfortably. In this situation, you might consider whether you should ask for a raise or look for a better-paying job. Boosting your income might require going to school part-time to get a degree or evaluating the pros and cons of a part-time job.

Recommended: 23 Ways to Make Extra Income from Home

Questions to Ask About Money Weekly

You will likely benefit from the previous questions on big-picture topics. However, the following are applicable in a weekly personal check-in. These financial questions to ask yourself don’t take long to answer and can help you readjust your spending.

8. Is My Budget Proper and Up to Date?

Budgeting is the structure that makes your financial plan realistic. As a result, updating it regularly to reflect your monthly expenses can help you focus your progress. For example, suppose you signed up for a new streaming service or changed internet providers to save money. You can revise your budget accordingly (reallocating any surplus money to investments can be a good way to get ahead). Or you might also realize that you need to cut back on spending and decide to, say, minimize dining out for the next couple of weeks.

9. Am I Staying Consistent in Saving Money?

Eyeballing your total income versus expenditures over the last few weeks can help you answer this question. If you’ve been able to set aside your target amount of money every paycheck, then you’re on track.

Quick Money Tip:Typically, checking accounts don’t earn interest. However, some accounts will pay you a bit and help your money grow. An online bank account is more likely than brick-and-mortar to offer you the best rates.

10. Do I Have Enough Money for a Financial Emergency?

A crisis, such as job loss or needing a new furnace, can throw your finances into a tailspin. Gradually building up an emergency fund of three months’ of expenses can help you handle whatever comes your way. Earmarking even a few dollars per week can help you get there.

Recommended: What Is Considered a Financial Emergency?

11. Is There a Way to Increase My Income?

When you ask yourself this financial question, you might decide to work weekends or ask your employer for a raise. Remember, your income isn’t set in stone, and increasing it is a matter of considering your options and taking action.

Questions to Ask About Money Monthly

Every month or so, you might want to check in with how your spending habits are evolving and whether you’re on the path toward achieving financial security.

12. Did I Pay Myself First This Month?

The purpose of paying yourself first is to allocate money towards your goals — usually retirement, savings, or an investment account — before all other expenses. While this strategy might make money tight the rest of the month, it can help you stay disciplined directing money toward what matters most.

13. Am I on Pace to Reach My Goals?

Asking yourself this financial question regularly can spare you from getting to December first and realizing, oops, you forgot to reach a goal. By checking in monthly, you can reset your budget or, if necessary, lower your goal accordingly. Your budget should reflect your financial capabilities, not set discouraging standards.

14. Do I Need to Make Any Financial Adjustments?

Making adjustments is a topic to tackle head-on and often; tweaks are what making a budget is all about. That’s what helps it provide the right guidance and guardrails. You may find that your budget is working perfectly or that there’s a bit of extra money you could be saving or an unnecessary expense to eliminate from your budget.

15. Have I Regretted a Recent Purchase?

You’re not asking this question to rub salt in the wound. It’s possible that you made an expensive purchase outside your budget and your conscience is catching up. When this happens, it can be wise to forgive yourself. Your budget is a guide, and next month is your opportunity to follow it and stay disciplined.

Questions to Ask About Money Annually

The following questions have a broad scope and can help you analyze your overall financial health. As a result, revisiting them annually or semi-annually can provide helpful reminders for creating financial stability.

16. Am I Getting Closer to Financial Freedom?

Financial freedom may look like being able to retire without working. Or, you might define it as living without debt. In any case, finding ways to financial freedom likely entails accumulating savings, contributing to an investment account, and repaying debt. Asking this money question annually can help you prioritize these habits and progress toward financial freedom.

17. How Is My Credit and Could It Be Improved?

When was the last time you checked your credit score? Generally, lenders consider credit scores of 670 or higher as “good,” with better scores garnering consumers lower interest rates and favorable loan terms. Therefore, solid credit can help you get a less expensive mortgage or credit card. If you review your credit reports, you can pay down high-interest debt and report any mistakes you found as first steps towards improving your score.

18. How Am I Preparing for Retirement?

Having a dollar goal to save for your later years is crucial, but so is preparing a retirement plan to get you there. Checking in on your retirement assets can be a very wise move.

If you have an employer-sponsored 401(k), you can see whether there’s a way to increase your contribution in pre-tax dollars from your paycheck. This may be a highly accessible asset for retirement (not to mention your employer might match your contributions, doubling your investments). Otherwise, a traditional or Roth IRA can be your primary investment account for retirement.

19. What Are Your Personal Priorities for the Coming Year?

Life moves quickly, and your financial priorities can, too. When asking this question, you can zero in on key goals, such as paying for sleepaway camp for your child or reaching a specific dollar amount in your emergency fund. Setting your budget while also factoring in your personal goals can help you put money aside throughout the year.

The Takeaway

Managing your money well is an important responsibility, and it’s one that requires frequent check-ins to ensure you’re accounting for life’s twists and turns. The path to building wealth can involve asking yourself questions annually, monthly, and weekly to assess how you’re doing. You can then make necessary adjustments — from tweaking your budget to opening a retirement account — that keep you oriented toward your goal.

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How can I change my financial goals?

You can change your financial goals by asking yourself what you’d like to achieve and then saving money for a new purpose. For example, if you add a child to your family, you might want to start a 529 plan to pay for their future education and make monthly contributions.

How do I financially plan?

You can financially plan by making a budget outlining your monthly income and expenses. Besides life’s essentials, such as food and housing, your expenses can also contain allocations for your goals, such as contributions to your retirement account or deposits into a savings account. A budget allows you to direct your income toward various priorities and re-assess as needed.

How often should I ask myself financial questions?

It’s a good idea to ask yourself financial questions regularly to keep tabs on your financial health. Some questions you can ask annually (such as those about retirement), but others are best asked and answered weekly and monthly. This allows you to course-correct in real time if you hit any issues with spending and saving.

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