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I won a trip! (Now what?)

| by Alyssa
Last updated on November 12, 2024
Alyssa and Michael with friends and Brad Paisley

You know how we all have our little digital “escapes?” Maybe it’s mindlessly watching an hour of TikTok videos, sifting through resale sites for pieces of fashion treasure, playing video games, or doom-scrolling threads on online forums.

Here’s mine *whispers*: I enter sweepstakes.

Yep, online contests and giveaways.

And I do so daily. Well, on the days I’m home, at least.

Every morning I wake up, make a cup of coffee, and sit down on the couch with my cat Meow to enter contests (she has come to expect this every morning, and starts meowing at me if my coffee-making takes too long).

It’s a process that only takes ten to fifteen minutes but has unexpectedly added more value to our lives than it would initially seem. Over the years, I’ve won prizes large and small, like gift cards, jewelry, branded swag, hotel stays, free meals, event tickets, and more. Not unlike the moment before scratching off a lottery ticket, there’s a little thrill in imagining winning a prize – but the odds of winning an online contest are generally a little better.

And as I recently won my biggest prize ever (or hopefully, my biggest prize so far) – a four-day trip to Dallas-Fort Worth, Texas – I thought it would make for a fun blog post. Today I’m sharing a little about what happens after your name is drawn as the winner, what it’s like to travel as a prize winner, expectations for filing taxes, and some best practices and tips to better your chances of winning.

But before I get into that, I should make a quick disclaimer: I am not a lawyer, so none of this information should be taken as legal advice, and I am only sharing my personal experiences with winning sweepstakes here in the United States (other countries may have different rules and regulations). And though I’ll be using contest and sweepstakes interchangeably here, I’m really referring to no-purchase-necessary, random-draw sweepstakes – not the lottery or judged contests.

Cool? Cool. Let’s dive in:

WHAT HAPPENS AFTER YOUR NAME IS DRAWN AS A WINNER IN A SWEEPSTAKES?

Well, it depends on the prize administrator.

Sometimes you’ll receive an email, sometimes you’ll receive a phone call, and sometimes you’ll receive a message on social media – depending on the contest.

In the case of my most recent big win, it was a phone call and an email – for which I am grateful because I’ve gotten in the habit of not answering phone calls from unknown numbers – but for the most part, all communications are sent via email (love having things in writing). Typically these messages contain a congratulations, a list of the prize winnings, and an attachment or link to an affidavit to complete if necessary (along with a deadline). If you didn’t enter your shipping address when submitting your sweepstakes entry, you may be asked for it now to complete fulfillment.

At this point, you should be feeling pretty excited – free things are great, right?!

But I want you to approach this situation cautiously, and make sure you perform a little due diligence before responding. First of all, do you remember entering this contest? You might be thinking, “What? Of course I remember entering this contest!” But if you’re in it as deep as I apparently am, you might not remember submitting your email address. Regardless of the answer, though, I still want you to dig a little further before responding with (potentially) a W-9 containing your social security number.

Now it’s time to pull up the official rules for the sweepstakes (they should be easily accessible). Give them a thorough review to make sure the message you received was sent around the drawing date specified in the rules. Way too early or late? That’s a red flag. The rules may also helpfully indicate who will be administering the contest, which will be easy to compare to the information you receive.

If not, review the email you received carefully for misspellings, grammatical errors, or vagueness – all signs it could be a scam. Perhaps most importantly, look carefully at the domain in the email address. Is it from the legitimate company sponsoring the contest? That’s a great sign! But frequently, large companies hire marketing firms to handle their contests. If this is the case, time to do some sleuthing on both the company’s website and the prize administrator’s website.

To provide a real-life example, our trip to DFW was a prize sponsored by Lipton, but the prize administrator was a marketing firm that handled all aspects of the drawing and prize distribution. My first stop was the contest entry page (which I firmly remembered entering), and then the official rules. Things seemed to check out, so I switched over to Instagram, scouring the marketing firm’s page and Lipton for connections. Only once I felt satisfied with the evidence of collaboration did I respond.

The affidavit and other documents for this prize were a bit more intensive than other prizes I’ve won in the past (even, yes – another trip back in 2016, to New York City). Because this prize included a celebrity meet-and-greet and COVID waivers, I was asked to have my document notarized and my guests also had to sign separate documents. We also were all required to submit a copy of our government-issued IDs, I believe to verify eligibility and to make it easier to purchase plane tickets.

In both of my travel-related prizes, I was able to have a say in some portions of the itinerary – in the case of the Dallas trip, I could indicate flight availability and managed to convince them to provide a stipend for a rental car instead of a rideshare service gift card. If your prize is a trip, there may be a little flexibility – it doesn’t hurt to ask!

If your prize is a physical item, you may be able to request a specific style or color – or you might just be locked into whatever stock is on hand. Delivery is typically much easier to coordinate; for the most part, things will simply be shipped to your home (unless you’ve won some sort of experience, which will require a bit more effort on your part to obtain).

Now onto the fun part:

WHAT IT’S LIKE TO TRAVEL AS A PRIZE WINNER

Depending on the prize, your prize travel experience will likely be similar to that of your regular travel but with a few extra perks. If airfare and/or lodging is part of your prize, you probably won’t have to worry about making those bookings – that will likely be taken care of for you. The same goes for any experiences you receive, which may very well be more VIP than you’re used to (or at least, what I’m used to). Some real-life examples of these experiences:

1. Sitting in the second row of a Broadway show

Part of my NYC prize back in 2016 included tickets to an “event” of my choosing. This seemed like the perfect opportunity to finally attend a Broadway show, so I requested tickets for The Book of Mormon and didn’t for a moment consider where our seats might be. Imagine my delight when the usher steered us toward the stage, directly behind the first row (or as Michael refers to it, “the splash zone”). At $400+ per ticket, this was something I’d likely never consider purchasing – truly a once-in-a-lifetime experience.

2. A private celebrity meet-and-greet

Full disclosure: I don’t place much stock in celebrity. We’re all just people at the end of the day, and I don’t feel that tingle or sense of awe at being in the same room as someone famous – and doubly so if it’s not a celebrity I know much about. So admittedly, our meet-and-greet with Brad Paisley was a tad awkward as we’re not big country music fans, but a fun story to share nonetheless.

3. Courtside seats at an NBA game

Although I didn’t have to travel for this prize – four tickets to a Charlotte Hornets game – it was yet another incredible experience-based prize I would never have purchased myself. Sitting courtside and watching the players’ athleticism (and whoa, they really are so tall) was certainly a pinch-me moment – but I was honestly just as excited for the massive free buffet in the club (you can see this prize in action on TikTok!).

WHAT TO EXPECT AT TAX TIME AFTER YOU WIN A SWEEPSTAKES

From the highs to the lows, right? Let’s chat about a subject we simply can’t ignore when discussing sweepstakes winnings: taxes.

(I know I already made a disclaimer, but I’m just going to say it again anyway: I’m not a lawyer and I’m not a tax advisor – I’m just a gal who has won a lot of sweepstakes and paid the taxes on them. Consult those experts if you have any questions on the nitty-gritty of prize taxes).

A free trip is great – but according to the IRS, its value is considered income.

You and I both know you can’t pay your rent or grocery bill with a free hotel stay or concert tickets, but the IRS doesn’t see it that way. To them, a prize is a prize is a prize – and all of them are treated the same. So, whether you win $5,000 cash or a trip to Jamaica valued at $5,000 – the IRS doesn’t care. All they want is to get their share of that $5,000 value.

If you win a prize that’s valued at over $600, by law the company administering the giveaway is supposed to request a W-9 and report your winnings to the IRS by using form 1099-MISC. But even if you don’t receive a 1099-MISC, you are still required to report the fair market value of all prize winnings on your tax return. I highly recommend keeping a spreadsheet to record your winnings.

But that’s not all – depending on the prize value and your personal income situation, you may need to pay estimated taxes quarterly (a tax advisor is a great resource here!). And if you’re “lucky” enough, it’s possible that your winnings could bump you into the next tax bracket, and you’d owe a higher amount on that additional income.

BEST PRACTICES FOR ENTERING SWEEPSTAKES, AND TIPS FOR INCREASING YOUR ODDS OF WINNING

The misconception among both friends and acquaintances is that I am somehow luckier than other people, but that, naturally, is not true. The reality is that I only win things because I enter. You have a 0% chance of winning a contest you don’t enter, as I always say.

Somebody has to win these random drawings – so it may as well be you. Here are some of my favorite tips for staying safe while entering sweepstakes (scams abound on the internet!) and bettering your odds:

1. Use a reliable source to find sweepstakes

There are many sweepstakes forums out there – some with easy-to-navigate sites and others that feel like you’re walking in a minefield. Here’s where I source the vast majority of contests I enter – users on this active forum are quick to share if something seems fishy.

2. Protect yourself

As always, never trust everything you read on the internet (just a reminder, you’re entering these sweepstakes at your own risk!). Before entering, do a little digging: is this contest hosted on a brand’s actual website? Are they promoting it on their social media pages? Is the form put together well, with correct spelling and grammar?

Use this information to decide whether or not it’s safe to enter your information. And speaking of your info, never use your primary email address or phone number – it’s easy and free to sign up for a secondary Gmail account and Google Voice number (just make sure to check them frequently!). You’ll thank me later.

3. Know your tendencies

Entering sweepstakes is kind of thrilling – how fun is it to imagine yourself as the grand prize winner? Although there’s no cost to enter these sweepstakes, it does feel related to gambling. If you struggle with addictive tendencies, it’s probably best to skip this hobby. But some advice for everyone: set time limits. My max is fifteen minutes (or about the amount of time I’d otherwise be scrolling Instagram while trying to wake up).

4. Read the rules carefully

In the U.S., sweepstakes are required to be no purchase necessary – if the contest is requesting you make a purchase or enter a product code, it’s time to open up the rules and search for the AMOE (that’s short for “alternate method of entry”). Some may ask you to submit your entry over email, via a second form, or by mail (personally, I skip the mailed entries because of the postage costs).

While you’re reviewing the rules, note the entry deadline, the total number of entries per person and frequency that a person can enter, and whether or not you are eligible to enter based on your age, location, student status, etc. To better your chances of winning, look for contests that have a small barrier to entry.

Think about it, how many people are going to write an essay or upload a photo? Those requirements at entry are definitely going to deter people – increasing your odds of winning. Contests with a shorter run time will generally have fewer entrants (again, that’s better for you!), as will contests that are only available for target markets (a smaller number of competitors!).

And make sure you’re entering as often as the rules allow – if you can enter once a day, you’ll have better odds than the person who only entered once.

5. Only enter contests that have prizes you actually want

Remember those taxes? Do you want to be paying taxes on junk you don’t want? My guess is going to be no. So if the prize is a set of skis and you live in Florida and rarely ski, chances are you might save money and space by renting a pair of skis every couple of years [here’s where I should mention that you shouldn’t just focus on the grand prize – you’re ultimately entering for those second and third prizes as well].

But money is really only half of it – your time is incredibly precious. If there are things in your life that are more deserving of your time than the slight chance you’ll win something (say, your family or your job), that’s where you should be devoting your time instead. I promise you’ll be much happier, and dare I say it? A guaranteed winner.

FINAL THOUGHTS ON ENTERING SWEEPSTAKES

I still feel like this is such a weird hobby to divulge online, but it’s added so much value to our lives that it feels “worth it” to me. That being said, if it ever stops feeling worth it – if it ever consumes too much of my time, or occupies too much of my headspace during a critical period – I’m happy to walk away. But for now? Well, wish me luck!

Questions for you

What’s the biggest prize you’ve ever won?

What is the last contest you entered?

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5 Comments on “I won a trip! (Now what?)”

  1. I’ve always wondered how the winners in contests were notified. Having the worst luck when it comes to lottery and drawings, I’ve never had the experience.

    Great read. Thanks for posting it.

    Reply

  2. Just came across your post. Congrats on your win. I started entering sweepstakes in 2006 and have won tons of prizes over the years. My biggest wins were a Superbowl trip in 2014 and an Acapulco trip in 2006. I also love to get my coffee first thing and then sit down to enter sweeps. This is my favorite hobby. Sending you good luck if you are still entering.

    Reply

  4. I appreciate the breakdown of the different taxes you might encounter when winning a trip. It’s eye-opening to see how it can vary depending on the prize value and your own tax situation. Definitely something to keep in mind before getting too excited about winning.

    Reply

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