personal finance

Your Post-Vacation Guide to Getting Your Finances Under Control

Photo-Illustration: by The Cut; Photo: Getty Images

Forget January; September is the best time of year to make new resolutions. It has the same clean-slate feeling of the new year but without the depressing, sober quality of midwinter. It’s full of promise and clarity and action; it’s time to get your shit together. In France, where it’s normal to spend all of August en vacances, the beginning of September is known as la rentrée: a point of reentry where you take stock and organize yourself for the year ahead.

Of course, September and January do share one negative element — the dull hangover that comes from spending the previous month like you have an indestructible liver and bank account. Late summer is a free-for-all, a space to float away from rules and pressures and emails. There are trips to take, sales to shop, lobster rolls to eat and martinis to drink. I hope you did all of that and enjoyed it! But nothing negates relaxation quite like knowing you’ll have to pay for it later.

Luckily, September is the perfect opportunity for a fresh start. I spoke to several financial experts about what they do every fall, and how to dig out of a post-vacation money slump.

1. Do an inventory of the next three months — including the people you want to spend time with.

“During the summer, I always know I’m going to be more loose with my funds,” says Jasmine Ramirez, a financial therapist based in New Jersey. “Come September, I ask myself, ‘Okay, how can I get my life back in order after spending this extra money, so that I can finish the year strong and hit my bills?’”

This involves planning for the holidays now. “I know it might sound ridiculous, but if you think ahead, you can avoid repeating the same cycle of guilt or debt in December,” she says. “Then, you won’t start January feeling depleted, digging yourself out yet again. And that will put you in a much better position for all of next year.”

To do so, Ramirez doesn’t just look at her calendar for the next few months; she also considers individual people in her life. “Write down all of the loved ones that you want to visit, celebrate with, or get gifts for during the holidays, and then decide your spending range for each of them,” she says. “That way, you can see how much money you’ll need to set aside and you won’t feel overwhelmed.”

This list exercise not only helps you plan ahead; it also gives you something to look at when you need a reminder of the relationships that you value and want to focus on. It’s a lot easier to cut back on smaller nonessentials when you have a clear view of the expenses that are most important to you.

2. Wait to buy anything new. 

Sure, it’s September and there are lots of cute fall things to buy! But it’s also 94 degrees today and I’m wearing running shorts. This is the weirdest season to dress for — stores are pushing soft sweaters and snuggly coats, but in reality, you won’t need that stuff for a while. “I usually don’t buy anything for myself or my kids in September,” says Farnoosh Torabi, host of the So Money podcast and author of the forthcoming book A Healthy State of Panic. “I’ve learned that we can continue to wear summer clothes well into October and by then, all the fall styles are on sale.” It also gives you enough time to realize that you do not, in fact, need a third puffy coat.

3. Imagine you had an extra $5,000. What would you do with it?

Instead of making goals that require cutting back, think about what you wish you could spend more money on. “This is a good thought experiment to try with a friend or a loved one,” says Megan McCoy, a professor of personal financial planning at Kansas State University. “Pretend you got a small windfall. Not a life-changing, lottery-winning amount, but more like an extra $5,000. What debt would you pay off, what trip would you plan, what treat would you spoil yourself with?”

Then, once you’ve talked it through, reflect on how your life would look different after that money was gone. “Maybe you would be less stressed or tired. Maybe you would have more memories with a loved one. Or maybe things would be about the same,” says McCoy. The exercise can help you identify your priorities more clearly — if that money would really alleviate your stress, then this could motivate you to make a plan to save it up. Or, if you realize that you’d spend it on something like travel, you could brainstorm more affordable ways to see new places or people. “Even if you realize that an extra $5,000 wouldn’t actually change your life that much, then that allows you to be grateful for where you are,” says McCoy.

4. Break down your goals into bite-size pieces.

Anyone can get carried away with goal-setting and envision a shiny, frugal, debt-free version of themselves. But before you do that, remember the difference between a goal and an aspiration, says McCoy. The latter is big, lofty, and often requires sheer motivation and self-control — which almost no one can keep up. To actually reach a goal, you have to cut it into small, easy steps.

“These steps should be something you can do right now,” McCoy adds. They should also be repeatable. “Examples could be opening a savings account and automating a regular transfer into it, downloading a spending tracker, checking your accounts every day, making a pact to not eat out on Tuesdays,” she says. “Fall is a great time to think of both your larger aspirations and those little behaviors you can use to get there.”

5. Gather a team. 

Most people have the best intentions with their finances but get overwhelmed when it comes to putting their plans into practice. “If it comes to making an important financial decision or making dinner, most people will go and make dinner,” says Elana Feinsmith, a certified financial planner and financial therapist based in California. “The reality is that most people get very triggered when it comes to money.”

To get past this, pick some people you can call on. This doesn’t mean you need to hire an accountant or a financial advisor (although you could if you think you need one); rather, start by wrangling a couple of trusted friends, loved ones, or family members who know at least little more about money than you do and can act as accountability partners and financial mentors. These are the people you can call when you need someone to walk you through a healthcare bill, taxes, or a 401(K) plan, or just to vent about how much plane tickets cost right now.

6. If a financial decision or conversation gets overwhelming, walk away for 20 minutes.

In my personal experience, financial decisions can also be confusing. Most banking and investing websites are hard to navigate and full of jargon; dealing with paperwork and accounting records makes my eyeballs dry up and fall out. It’s hard to stick to when there are so many other things that need doing, too.

It might sound counter-intuitive, but the trick to plowing through the annoying, uncomfortable parts of financial planning is knowing when to walk away — and when to come back. “Whether you’re triggered by a person, or even by your own frustration, it takes at least 20 minutes for that stress response to shut off,” says Feinsmith. “Instead of giving up entirely, put the uncomfortable task or conversation on hold for an hour, and then come back to it. Go get yourself a cup of tea, cut your toenails, watch a YouTube video, whatever. And then, once the hour is up and you’ve calmed down, you’re better equipped to readdress the issue.”

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Your Post-Vacation Guide to Cleaning Up Your Finances