In 2005 I won two trips worth about $5,000 each. I went on one. The other expired without me, and I paid tax on it anyway, because a prize you accept counts as income whether or not you use it. It was non-transferrable, so it didn’t reach anyone else either. Letting it go cost me a tax bill and gave nobody a trip.
Both wins landed the same year. I can’t tell you which came first, since my records from that era are pieced together from an old blog and the dates are approximate. Same year, same value, opposite endings. The difference between them is the only useful thing I have to hand you.
What made one trip possible and the other impossible?
The NASCAR trip came with a schedule somebody else had already built, and the Sports Dream Package came with a blank page. In 2005 I could follow a plan, but I couldn’t make one.
The one I took was a NASCAR trip to Atlanta. I was one of ten finalists at a Jeff Gordon key-turn event, and I didn’t win the Tahoe. What I got was VIP race access, airfare, a hotel, and $500 to spend.
Getting there was the hard part. The airport, the flight, the leaving-my-house part. Once I’d arrived, somebody else’s schedule ran the day. I didn’t have to decide where to be or when. That’s the piece I’d underrate for years afterward.
I was in a bad place mentally in 2005 and I struggled to even leave the house. When I won the second trip, I felt nothing but guilt. Not delight, not luck. Guilt. I wrote more about why a win can feel that way in why it’s so hard to accept wins.
The other prize was a Sports Dream Package: a trip to anywhere in the United States, for any major sporting event I wanted. On paper it’s the better prize. On paper it’s the dream. In practice it handed me a blank page and asked me to fill it in, and a blank page was exactly what I couldn’t do that year.
I tried. I kept meaning to work up the nerve. I kept coming up with reasons it wasn’t the right month, and there were real limits attached too, on timing and location, which gave the excuses somewhere to live. Then it expired. I’m not proud of this at all.
| NASCAR trip to Atlanta | Sports Dream Package | |
|---|---|---|
| What came with it | VIP race access, airfare, hotel, $500 | A trip anywhere in the US to any major sporting event |
| What it asked of me | Get on a plane, then follow a set schedule | Pick the event, city and dates, with limits on timing and location |
| What happened | I went, anxious the whole time | It expired unused |
| Taxed? | Yes | Yes |
Do you pay taxes on a prize you never claimed?
Yes, if you accepted it. I got a 1099 covering both trips, on a combined value of about $10,000, including the one I never set foot on. The IRS says a prize you refuse to accept stays out of your income, so the time to say no is before you accept, not after the form shows up.
So the trip didn’t just disappear. It cost me money, and “I’ll just let it go” sounds free when it isn’t.
It gets worse in a way I didn’t think about until much later. The prize was non-transferrable. I couldn’t hand it to a friend, couldn’t pass it to my sister, couldn’t give it to anyone who would have been thrilled by it. Somebody out there entered that sweepstakes and didn’t win, and what they lost to was me, and then I didn’t use it. It went nowhere. That feels crappy.
The Admin Arcade tax document checklist lists the 1099-MISC that prizes come on, plus the January 31 date it’s due to you.
Is wanting a prize enough reason to enter?
For a long time I told myself the lesson was to only enter for things I want. It’s a decent rule and it’s not the real one, because I did want that trip. I thought I wanted it a lot.
The real variable was how much each prize asked of me compared to what I had to give that season.
Atlanta asked me to get on a plane and then follow a schedule someone else had already built. Hard, and possible. I was an anxious traveler the entire time I was there, and I’m not telling you to only enter for easy things. I did the hard thing while anxious, and it counted.
The Sports Dream Package asked me to plan a trip from scratch, pick the event, pick the city, pick the dates, and make a dozen decisions in a year when I couldn’t reliably make one. Fewer decisions meant fewer places to get stuck. That sentence explains more of my life than I’m comfortable with.
Capacity means knowing what this season of your life can carry. That changes, it can include hard things, and it has nothing to do with how badly you want the thing.
What I do about it now, twenty years later
I don’t enter for trips. Or concerts. Or anything requiring an outing.
That filter runs before a sweepstakes ever reaches my tracker. I use SweepSheet, a subscription service I’ve paid for for years to find and vet sweeps (not my product, not sponsored, no affiliate deal, I’m just a customer), and I screen those categories out there. They never become records. They never get entered.
It isn’t a sad rule and I’m not writing it wistfully. It’s protection, and it works. I still enter a couple hundred sweeps a month and I still get a real kick out of a $10 gift card showing up. I wrote about exactly what that returns in my real sweepstakes win rate, and the full log of what I’ve won since 2005 is on my winnings page.
One prize I couldn’t claim in 2005 rewrote what I let myself want from this hobby for two decades. I’m fine with the trade.
How do you know what your capacity is?
Look at what you actually managed last month, then ask one question before you enter: could I claim this if I won it tomorrow? A trip with set dates and a schedule asks a lot less of you than one you have to plan from scratch.
If you want a real read on your own capacity instead of a guess, I built Energy Battery to log your energy a few times a day and show you what drained it.
Today’s action
Before your next entry, ask one question: if I won this tomorrow, could I actually claim it in the season I’m in right now?
Not the season you’re heading toward. Not the version of you who has more energy. Today’s season. If the answer is no, skip it, and don’t treat that as wasting your luck. It’s aim.
Planting seeds is the whole idea here, and I’ll keep saying it. But a seed you can’t tend turns into a chore with a deadline. Growing your own luck includes knowing which ground you can actually water this year.
Frequently asked questions
Do you have to pay taxes on a prize you never claimed?
Yes, if you accepted it. Prizes count as income, and the IRS says a prize you refuse to accept stays out of it. I was 1099’d on the combined value of two trips, including one I never took, because I’d accepted both. If a big win arrives and you know you can’t use it, talk to whoever does your taxes before you accept it.
Can you give away a sweepstakes prize you can’t use?
Only if the official rules allow it. Mine was non-transferrable, and the rules said so. Read the transfer line before you accept. Declining before you accept is a different thing, and it’s the cleaner move if you already know the prize is unusable.
What happens if you don’t claim a sweepstakes prize?
The official rules decide. Some sweeps draw an alternate winner if you don’t respond in time, and some let the prize simply expire and reach nobody. That second outcome is what happened to mine, and it’s the reason I stopped treating an unused prize as harmless.
Should I enter sweepstakes for trips?
Only if you could claim one in the season you’re in. Trips carry the most friction of any prize category: dates, travel, time off, and taxes on a large value. I’ve cut them completely and I don’t miss them. If your life has room for a trip right now, enter away.
How do I figure out my own capacity?
Look at what you managed in the last month, not what you managed in your best month ever. Capacity is a moving number and it responds to what’s happening in your life. Mine in 2005 could handle a scheduled trip and could not handle an open-ended one, and knowing that difference would have saved me a lot.
The short version
Prizes you can’t claim aren’t free to walk away from. You can still owe tax on them, and if they’re non-transferrable, nobody else gets them either. Enter for the capacity you have this season instead of the capacity you wish you had, and you’ll plant fewer seeds you can’t tend.
I still enter almost every day. I just aim differently now. Pick one thing you could genuinely say yes to tomorrow, and enter that one.
A book I made
Postmark By
A mail-in sweepstakes log book that puts the postmark-by date first, so every entry you mail gets stamped in time to count.
Log your next sweep →I run an affiliate program on the tools I build. Approved affiliates earn 20% on what their referrals pay, for up to a year. US only for now. See the program →
