Take a Tax-Deductible Vacation


Next time you’re on the beach, or skydiving, or visiting some bougie restaurant in Tulum, don’t forget to count it as a business expense. I’m not being facetious; there are tangible, legitimate steps to take to make your vacations tax-deductible.

Why do corporations have their “executive summits” in fun locations? They didn’t need to host the meeting in Miami when company is headquartered in Milwaukee.

If those executives took that vacation on their own, they couldn’t write it off. But if the business organizes the excursion, suddenly it’s all above board with the IRS.

So why can’t you do the same?

Here’s how.

  1. Start generating content for your business or as a content creator
  2. Go on vacation
  3. Turn your vacation into content for your business

Tax-Deductible Content For Your Business

If you’re not running a business yet, seriously start thinking about it. It’s the best and most consistent way people end up rich.

Even if you’re not confident about what your business will be, think about how you can elevate your social media presence. Stop thinking about it as vanity and start thinking about it as your most useful marketing asset you will ever own.

Not sure what you’re selling yet? That’s fine. Just make sure it’s one with your face on it. You need to show who you are and that you’re a real person. That way, when you’re showing off vacations, it’s still in line with the brand you’ve already established. The brand needs to be human.

A good basic rhythm can be (1) half or 2/3 of your posts are thoughtful content around your subject matter expertise, and (2) half or 1/3 are personality-based (jokes, interactions, vacations).

For any of this, just make you’ve wrapped all this activity in an LLC you own (and you alone).

RELATED: Start a Business: Learn, Own, Scale

Could you do it with a sole proprietorship? Maybe. I don’t know what the laws are around that in every state. In fact, I don’t know any law, so none of this is legal advice. But in general, I’d say an LLC is safer for tax-deductible expenses.

Become a Content Creator

“Influencer” is a pretty loose term. It’s really just someone with an online following. Do you have social media? Start thinking of yourself as an influencer (because we all kind of are).

If you are selling anything (and all of us are) you must know something. If you know something, why not talk about it? It’s free marketing.

Even if you’re not trying to become someone who makes money from their social media following, it’s still worth it for you to act as if that’s what you’re doing.


Because then you can show the IRS you’re legitimately trying and not scamming them, which will allow you to mark your expenses as tax-deductible.

If you’re doing the activity, you’re already passionate about it. Just put your passion out into the world. Make a blog if nothing else.

Tax-Deductible Degeneracy in Vegas

I watch a handful of people on YouTube.

One of them plays video games. Then one day, he puts up a skydiving vlog. Then it’s back to games. A year later he takes a random trip to Mexico. Then back to games. Why would he do that when his core audience is giving millions of views to gaming content? Because then he gets to write off the $2000 he spent on skydiving as a tax-deductible expense against his income that year.

Another guy just tells funny stories about his life, so more like actual vlogging. And then he posts a okay-ish video about a fan meetup in Las Vegas. Why? So he can write off his Vegas vacation (and it still counts as legit content since he’s spotlighting fans).

And it’s decent content anyway. Win-win.

Find Where Your Followers Are

Where are your current followers? Where are your potential followers?

  • If you’re funny and attractive, Tiktok
  • Just funny (or at least clever)? Stick to Twitter
  • Just attractive? Instagram
  • Are you milquetoast and love meaningless platitudes? Go to LinkedIn

If you’re neither funny nor attractive, then you better be incredibly entertaining in some other way. Then just pick any video platform (YouTube, Tiktok) and go for it.

If you’re simply lacking in talent, I don’t know what to tell you. Fix that, because you are a media asset.

Don’t Overthink It. Just Start.

You don’t have to be a content creator to use this method. Meeting with a potential client on your trip (depending on the trip) can be enough to write it off. But why not just put out some content? It’s way easier, works anywhere, and fun things like vacations are exactly what work on social media.

You don’t need to be a pro. You just need to start.

This post is the entire reason I even wanted to start this blog. It’s the most basic thing any single content creator can do to start living on a different level.

I can’t say it enough. Don’t overthink it.

Just start.

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