Financial-advice columnist Charlotte Cowles answers readers’ personal questions about personal finance.
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 not 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 downside — the dull hangover that follows a period of behaving like you have an indestructible liver and bank account. Late summer is a free-for-all, a liminal space to float away from rules, emails, and news alerts about tariffs and economic doom. There are trips to take, sales to shop, lobster rolls to eat and martinis to drink. Escape reality while you can! But nothing cancels out relaxation quite like having to pay for it later.
No matter; September is a great 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.
“During the summer, I always know I’m going to be more loose with my funds,” says Jasmine Ramirez, a certified financial social worker 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?’”
First, Ramirez plans out her calendar for the rest of the year and makes a list of the people she wants to prioritize. “I write down all the loved ones I want to visit, spend time with, or get gifts for during the holidays, and decide my spending range for those relationships,” she says. She even makes her holiday shopping list now, so that she can buy things gradually and when they’re on sale, instead of leaving it all for the last minute.
This list exercise helps Ramirez plan ahead and find things to look forward to; it also gives her something to look at when she needs a reminder of what — and who — she values. “It’s a lot easier to skip smaller nonessentials when you have a clear view of the expenses that are most important to you,” she says.
Plus, it sets her up to skip the January scaries. “I know it might sound ridiculous, but if you start planning for the holidays now, you can avoid repeating the same cycle of guilt or debt in December,” says Ramirez. “That will put you in a much better position for all of next year.”
Sure, it’s September and there are lots of cute fall things in stores. But it’s also 94 degrees today and I’m wearing 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 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.
Here’s a thought exercise: Instead of making goals that require cutting back, imagine what you wish you could spend more money on. “This is a good experiment to try with a friend,” 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, 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. “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.
Sure, it’s nice to aspire to a shiny, perfect, debt-free version of yourself. But it’s more useful to write down a few steps that you’ll actually complete. “These steps should be something you can do right now,” McCoy says. 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 or certain days of the week,” she says. “Fall is a great time to think of both your larger aspirations and those little behaviors you can use to get there.”
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 or loved ones 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 talk to when you need help understanding a healthcare bill, taxes, or a 401(K) plan, or just want to vent about how much plane tickets cost right now. (They can also provide good recommendations when you do need to hire a professional.)
Financial chores and decisions can be mind-numbing. Most banking and investing websites are full of jargon; dealing with paperwork and fine print has a way of stuffing your brain full of cotton. It’s particularly hard to plan at a time like this, when the economy feels so precarious and no one knows what to expect.
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 return. “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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