3 Ways To Get a Headstart on the Holidays

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Sometimes when I hear Christmas music starting in early November, I’m a little taken aback. Surely I can’t start thinking about December shopping when I haven’t bought my Thanksgiving turkey!

And yet, here I am, writing a post about holiday planning over six months in advance. Am I a Christmas fanatic who leaves the tree up year round? Not quite. I’m just a guy who wants you to set yourself up to have the best holiday possible, without piling up a bunch of debt to deal with in the following year.

The best way to survive the holidays and enjoy them to the fullest is planning ahead and being prepared. I don’t care if it’s warm out and you’re trying to plan your summer vacation, I’m ready to start talking about Christmas and I want you to join me.

1. Identify Your Issues

Another holiday season has come and gone, and if you’re like everyone else, you panicked, overspent, and were thrilled when you finally got to put it all behind you. So what did you learn from that process? Again, if you’re like most people, probably nothing.

Somehow, the holiday season sneaks up on us. It doesn’t make sense, because Christmas is a regularly scheduled event. Nevertheless, people focus on surviving summer, then plan for the start of the school year, then get drained by Thanksgiving and inevitably pummeled at the end of the year. They dust themselves off on New Year’s Day, then rinse and repeat.

You won’t fix this broken cycle unless you engage in some serious planning. If the holiday season has become so much of a time-drain and financial burden that you dread it a little, I don’t expect you to be able to correct your problems in real time. You have to start early (right now!) and be honest about what causes you the most strife when November turns into December.

Holiday planning brings about different struggles for different people, but I find there are three main hurdles the average person faces:

● Gifts

● Travel

● Time off work

Between these issues, almost anyone can find a way to get a holiday headache. If you have a good job and plenty of money, it might be hard to get away from the office for a significant amount of time; if you don’t have a lot of extra funds, it’s hard to get presents for all the lovely people in your life; and whether you work too much or don’t have much money, travel is almost always problematic.

So what holds you up each year? If you can identify the problem, you can focus on how to solve it. Faith, resolve, and a little creativity can conquer all challenges. Identify your obstacles and start taking steps to remove them.


Let’s start here, as many of us think of shopping as the primary holiday hurdle. You can’t change how many people you care about and you can’t ask for prices on all items to be universally lowered, so you have to find another way to buy presents and stay afloat. This is one of the main holiday projects you can tackle in the early going.

A simple solution is to keep an eye out for sales during the offseason. Lots of stores advertise their layaway deals, and you can usually pay far less in May for certain goods than you can in December. For the people on your shopping list who have specific tastes and don’t change up their wish lists every few months, buying early can solve a lot of money problems. This tactic lets you approach Christmas shopping the same way you do a financed purchase - pay it down a little bit at a time, spreading the expenses over several months.

Shopping early doesn’t always help with how much you end up spending. Prices won’t necessarily drop in spring and summer, so you may need to try something else in order to save on gifts. Having received and appreciated plenty of homemade items, I’m always encouraging people to take up a hobby which allows them to create presents. Watercoloring, songwriting, woodworking, website building, you name it. Take a little extra time to make your gifts personal, and you’ll probably get a great reaction from the recipient while keeping your checking account flush.


Unfortunately, shopping in advance for travel doesn’t always work. Sometimes you’ll find a great deal, other times you’ll overpay, and occasionally you’ll book flights on dates that don’t actually work and spend an arm and a leg changing your reservation.

This doesn’t mean holiday travel is hopeless. I’ve written about some of the tricks of flying around the holidays before, and there are steps you can take to reduce your spending. However, none of those steps is waiting until the last minute and hoping against hope you find the one cheap ticket available.

Instead, just like with your gift buying, you need to get a jump on things. If you have a credit card that earns airline points, you can passively pay for your holiday travel all year long. This does require you avoid using those points on summer vacations, but that’s a sacrifice you should be willing to make if you’re the type of person who starts worrying about Christmas plans in mid-June. Depending on where you typically go for the holidays, you can figure out which airline usually has the best rates for that airport and then sign up for the appropriate card.

If you have a big family and it’s impossible to fly around Christmas without breaking the bank, consider a crazy alternative - stay home on Christmas day and have your family gathering around New Year’s. For most of you, this probably sounds like an impossible change of plans, upending years of tradition and potentially breaking your mother’s heart. I get it, Christmas is about family and togetherness. That said, is the stress and expense of holiday travel diminishing how much you enjoy that togetherness? It might sound crazy, but pushing your family gathering by a few days and saving a thousand dollars on airfare could be the beginning of a new, delightful family tradition. It’s at least worth thinking about, right?

Time Off Work

This one might be the toughest. I’m a financial advisor; I want you to work hard, maximize your earning potential, put your money to work, retire early and live your best life. I also want you to live your best life right now and spend time with your family during the most important times of the year.

There’s no easy fix if you don’t get much paid time off, or you work a job where December is the busiest month for your company. If getting away from work is a huge burden for you around the holidays, you may have to take bold action: ask for more time off, consider a career change, or give in to your long-term goals and look forward to future Christmas Days when you have more freedom. I’m not going to pretend there’s a simple solution where one doesn’t exist; this may take some serious personal analysis on your part.

Nevertheless, there may be options and opportunities you haven’t thought of. Perhaps you have a coworker who celebrates different holidays and an arrangement can be worked out for how your time off is divided. You may also be able to work from home for a few days, enabling you to travel without using PTO.

Today’s work environment offers more flexibility than you may expect. Every company is different, but a little creative thinking might help you free up your schedule without hurting your paycheck or costing you your position.

2. Budget All Year

As I said earlier, you can’t let the holidays catch you off guard. You know when Christmas is, you’ve always known, and you can rest assured the date isn’t going to change. On December 26 of each year, you know you have 364 days to prepare for the next round of holiday madness, and you should make the most of each of those days.

Naturally, I don’t expect you to start plotting out the next Christmas before you’re out of the current year - you need at least five days to recuperate and get your life back in order. But starting in January, you should absolutely be siphoning off some funds to cover the spending you know will happen in 11 months.

Budgeting this far in advance confounds some people, as the variables make it hard to decide how much should be put aside, and the need to buy other things makes long-term savings goals difficult. You have to put some extra thought into your holiday budgeting, targeting a specific amount you’ll need based on spending from previous years. If you think in terms of the people you shop for and the things you want to buy, it becomes much easier to put aside $50 each month without feeling the urge to spend that money on other things.

If you’ve embraced step 1 above and identified your issues, you’ve hopefully looked over your spending to see where your dollars went. With an 11-month budget goal in place, you can decide which spending was necessary and where some corners can be cut. Be realistic with your expectations for the coming Christmas and then start setting aside your monthly allotment.

Plus, there’s a budgeting bonus that comes with this type of planning. Say you’re setting aside $50 a month, planning on spending $25 per family member and friend when December rolls around. Because you have that money stashed for Christmas spending, it’ll be ready to go when you come across the perfect sale. You might find the ultimate gift for your father for just $18; not only is that money available to be spent, but you’ve just cushioned your holiday spending by seven big ones. How rich does that make you feel?!?

Have fun with budgeting. It might not sound like a great time, but saving money and planning ahead can be very rewarding and enjoyable when done right. All it takes is one Christmas where you don’t feel strapped for cash to show you how helpful a holiday budget can be.

3. Find Your Shortcuts

I bet you can’t find two families who celebrate the holidays in the exact same way. There are so many variables that dictate how people go about their business over the holidays, there’s no chance any two households have the exact same Christmas routine.

This makes each person’s planning unique and ensures I won’t be able to tell you exactly what steps to take for your holiday planning. You have to navigate your own finances and family matters to figure out how your end-of-year strategy will play out.

Still, you can learn from people who have come before you and charted their own course to holiday savings. I make a point of learning from friends and family who seem unphased by holiday hoopla, and it’s usually tricks they’ve learned from relatives that help them keep calm and carry on. Some friends started a potluck tradition years back, which blossomed into a month long thing with friends and family making and sharing food throughout December. In the end, everyone saves money on dining out and spends more time together. It’s a nontraditional way to save and it’s turned into an awesome tradition.

The more thoroughly you analyze your spending, the more shortcuts you’ll find. Have you gotten into the habit of driving to a mall two hours away and buying both lunch and dinner on your way to and from said shopping center? That might be a fun day in the moment, but if you’re driving up your credit card bills over the holidays, this is the type of outing you should skip for a year. Order more stuff online or save money on gas by shopping locally. “This is how I’ve always done it” isn’t a good excuse for driving too far and spending too much.

If it’s the presents that get you every year, you’ve got a few options to consider. Secret Santa and White Elephant exchanges help people set price limits while making sure everyone in a large group gets a nice gift. Enjoy a night of merriment, get and give something, and do it all for $20 if that’s the price you opt for. People get caught up wanting to get the newest and the fanciest, when that kind of spending never matches the value of quality time with friends and family. If you can believe that and resist the urge to splurge, cutting back will be a piece of cake.

You might also save money with semi-bulk buying, getting five of an item at a discounted rate and spreading that gift among friends, family and coworkers. Five matching phone cases might not work for the members of a nuclear family, but that gift could be perfect for your boss, your uncle, your nephew, your mechanic and your buddy Rob from college. When you stay open to opportunities to save, those opportunities will appear much more frequently.

I love the holidays, and I do my best to keep money and travel and stress from getting in the way during that time of year. If you put forth the effort and focus on correcting issues that have plagued you in the past, you can make your holiday season a whole lot merrier.

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