Go on a date with… your money??

Written by Briana Cavanaugh

October 11, 2021

Yes, I’m telling you that managing your money can be fun!

If “fun” sounds too hard, then start by making your money routine less agonizing. Either way, you need a routine. Why not make it as pleasant a routine as you can?

Think of money as a romantic partner. Maybe you’ve been on the rocks for a long time. Your money hasn’t taken you on any magical vacations in years, it’s neglected your needs, even deserted you. And maybe you’ve been treating your money like you’re mad at it, too — neglecting it, telling yourself you’re better off with as little as possible, and on and on.

The reality is (unlike a relationship with a real person) you can’t live without money. And no amount of yelling at money or holding grudges at money is going to fix things. What do you and your money need to make beautiful music together?

Write out a plan to renew your relationship with money and get your business into a better financial position.

Weekly, biweekly, or monthly dates

Going on a date means setting aside a special time. It means you plan an experience that will feel good. It means you focus on feeling good in your body, feeling good with your partner (money), and focusing on having special time with your partner (money). Making good memories on a regular basis helps build resilience into a relationship so that you’ll keep trying when difficult circumstances crop up to make things harder.

Wouldn’t it be great if your difficult money times were less stressful? Imagine what it would feel like to look at a month of unexpected expenses or low revenues and say to yourself, “I got this!”

Some couples have date nights once a week. On the other hand, if there’s not a lot going on with your money or if you have an assistant who helps with your money stuff, maybe you don’t need to have dates with your money more than once or twice a month.

Write down: How often will my money dates be? How much time will each date take? (Remember, your plan doesn’t have to be perfect! Give it a try, and you can change it later if you need to.)

Set the mood for your money date

Unlike a date with a monogamous partner, on a money date you have the option to bring someone.

Do you have a sweetheart who’ll rub your back, or a friend who needs to work on their money stuff too? Do you have a virtual assistant who pays your bills and saves your receipts? Do you have a bookkeeper who categorizes most of your transactions and pulls financial reports for you? Maybe this person should be there for the beginning, middle, and/or end of your date with money.

What else can you bring to your money dates that will help you look forward to getting started? Chocolate, tea, incense, music, candles, a beautiful workspace?

(If you’re meeting in person with your sweetie / friend / assistant, be mindful that you’re co-creating a space for both of you. What agreements will create a container where you both find delight and safety?)

It’s also important to start your money date in a space of tender self-love. No amount of yelling at yourself will make your relationship with money improve. If you feel bad about the money mistakes of the past, maybe you need to do some releasing work in order to forgive yourself. Some people meditate before their money date, say affirmations, or ask a friend for emotional support.

Write down: Where will my money dates occur? Who will be there? What will I do to set the mood?

What needs to get done on these dates

Make an agenda of what you need to look at on each money date.

  • Pay your bills, payroll, and debts
  • Deposit checks and account for income in your bookkeeping system
  • Categorize the transactions in your books
  • Reconcile transactions with your bank statements

A bookkeeper can do a lot of this for you, but you might not be ready to hire one yet. If you just did everything on this list without a bookkeeper, take a break for a slow deep breath, stretch your body, and pat yourself on the back!

If you are using a double-entry accounting system such as QuickBooks, that should make it simple for you or your assistant/bookkeeper to pull the reports for this next step:

  • Review your Profit and Loss statements
  • Review your Balance Sheet
  • Review your cash flow statements

Now that you know what’s going on with your business, next comes the part that needs you, the entrepreneur, the most: Make strategic decisions!

  • Create or revise your spending plan/budget for the next quarter or year
  • Plan how much you’re going to spend this month
  • Review your recurring transactions to make sure they are still desired
  • Plan your income — think about how to increase your revenue

Write down: What will I do on my money dates?

Celebrate at the end

Make sure your money date ends on a high note.

Plan your next vacation or day off. Spend a small budgeted amount on a treat for yourself or a friend. What feels like indulgent self-care? Exercise? Rest? A meal with all the colors of the rainbow in it? A delicious dessert?

Another great way to end a meeting is to express appreciation. If your money dates are just you and your money, you can notice how far you’ve come, write down what you got out of the money date, and acknowledge yourself for taking steps to make things change. If you do these money sessions with an assistant, you can close the meeting with each of you taking a moment to express gratitude about something or appreciation for each other.

Write down: How will I make sure I feel good at the end of the money date?

What motivates you?

One of the goals in planning out your money date routine is to ensure that you’ll look forward to your money dates and stay motivated to keep doing them. Reread your plan. Is anything missing that could help you approach your money with more curiosity, eagerness, and tenderness?

Schedule your money dates now

Don’t wait — put your money dates on the calendar for at least the next 12 months.

Getting help

My earlier blog post 3 Steps for Bringing Your Vision to Life explains how to use your inner resources as well as accountability tools to make sure that you stay on track with your plans.

Many business owners need support in order to stay accountable. That’s why we periodically offer mastermind groups & classes — so that you can find a cohort of supportive peers.

If you’re ready to get started with professional bookkeeping services, if you need help with budgeting and planning, or if you need other help such as getting your tax information to your CPA, reach out to Bliss Your Money. Be free to focus on making the best decisions for your business with Bliss!


7 Ways Your Bookkeeper Can Help You Get – and Stay – Profitable.

Your Bookkeeper CAN Help You Make—and Keep—More Money. It’s not as hard a you think. And we can even put the processes in place for you. Sign up to get more details!

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