When does travel become a business expense?

A CPA and a full-time travel writer's guide to understanding travel during tax season

Travel and taxes don’t usually belong in the same sentence—until you run a business. As tax season fast approaches, questions start to surface: can you deduct that flight? What about the hotel? Does a brand trip count?

Instead of guessing, we’re breaking it down from both sides in today’s letter:

• Ariel LaFond of dumb rich. is a CPA and Fractional CFO advising business owners, high-net-worth individuals, creatives, and influencers.

• Tori Simokov of Window Seat is a travel writer and founder covering the art of flying well, standout hotels, and the business of travel.

This is your no-gray-area guide to travel and tax season: what W-2 employees need to know, what actually changes when you’re self-employed, how to document trips properly, and what actual business travel has looked like behind the scenes.

The Reality of Work Travel as a W-2 Employee

Let’s start simple. Are you a W-2 employee going on a cute little work trip? I hate to say it, but the IRS does not care. You don’t get a write-off. I’m sorry. I don’t make the rules.

Flights, hotels, meals, Ubers, conference fees, etc. all became non-deductible because of the 2018 tax law changes. Even if your job literally requires you to hop on planes weekly. Even if you’re fronting thousands of dollars and getting reimbursed later. From a tax standpoint, that travel is simply part of having a job. And yes, it’s annoying.

But there’s good news. While you can’t deduct work travel anymore, you can still turn it into one of the biggest financial perks of being a corporate employee.

The first thing every W-2 traveler should ask (or politely email HR about) is who actually gets the rewards from company travel. The answer varies wildly by employer and the difference can be worth thousands of dollars per year.

Some companies allow employees to book flights and hotels on their personal credit cards and get fully reimbursed. When that’s the case, you’re not just getting your money back — you’re also keeping the airline miles, hotel points, and credit card rewards. The reimbursement itself isn’t taxable income because it’s a business expense your employer is covering. Meanwhile, you’re stacking free points on the side. This is the holy grail scenario, and if you have it, never take it for granted.

Other companies require a corporate card but still allow employees to attach their personal frequent flyer and hotel loyalty numbers to each booking. Even though the company pays for the trip, you’re earning miles toward free flights and nights toward elite status. There is even a chance your employer allows you to transfer the points to your own account for a fee.

I’ve seen people hit airline status tiers and luxury hotel tiers entirely through work travel. They didn’t spend a dollar of personal money to get there, yet they reap the benefits every time they travel for fun. That’s not a tax deduction, but it is very real money saved.

Elite airline status can mean free checked bags (which add up shockingly fast), priority boarding, complimentary seat upgrades, and lounge access that saves you from $22 airport salads. Hotel status can translate into room upgrades, free breakfasts, late checkout, and entire free nights on personal trips.

Over a year or two, this can easily turn into thousands of dollars in value. All funded by your employer’s travel budget. And none of this is taxable. Yay.

What Changes When You Travel for Your Own Business

When you’re self-employed, travel stops being a perk and starts being a strategy. As a W-2 employee, your company owns the deduction. You might optimize points and status, but from a tax perspective, the story ends there.

When you run your own business, everything shifts.

Now the tax treatment hinges on one deceptively simple concept in the IRS code. The trip must be “ordinary and necessary” for generating income. Not inspirational. Not aesthetic. Not “good for the brand.” It needs a real business purpose.

The IRS doesn’t care if your hotel is five stars or a roadside motel. It doesn’t care that the trip sparked creativity. It cares whether the primary reason you went was to make money.

That primary purpose is usually determined by time. If more than half of your days are legitimate business days (meetings, content production, client work, conferences, deliverables) the transportation to and from the destination is generally fully deductible. Flights, trains, rental cars to get there can qualify. That doesn’t magically turn the entire trip into a write-off, though.

Your hotel is deductible for the business days. Meals connected to business activity are generally 50% deductible. Ground transportation between work obligations counts. The personal days you tack on afterward don’t. The spa appointment doesn’t. The cute excursion you booked because you were already there doesn’t.

Business and personal travel can live in the same trip—you just have to split it cleanly.

This is where a lot of people can get sloppy, and I highly advise against it. Posting one Instagram story doesn’t convert a vacation into a business expense. But producing sponsored content, filming contracted deliverables, meeting with partners, scouting locations for monetized projects, or attending revenue-generating events can absolutely qualify. The difference isn’t intention. It’s documentation and income connection.

Points and rewards generally follow a simple logic. If you pay for business travel and earn points, those points usually aren’t taxable. If you redeem points for business travel, there’s no deduction because you didn’t spend cash. If you buy miles specifically for a business trip, that cost can typically be included as part of travel.

A good gut-check is simple: would you have spent this money if it weren’t tied to income production? If the answer is no, it’s likely a business expense. If the answer is “kind of,” it probably isn’t.

And none of this works without recordkeeping. The IRS technically wants you to keep a diary. Little do they know, my diary is a dark, dark place (jk). They mean more of a calendar. Dates matter. Notes about business purpose matter. A dedicated business credit card helps. A calendar trail helps. If someone unfamiliar with your life looked at your records, the business story of the trip should be obvious without explanation.

The difference between aesthetic and income-producing

Tori here–I’ll be taking over from here on! As someone who travels for a living, I think the “income connection” is where most people get confused. A trip isn’t deductible just because it fits into your brand, it’s deductible because it directly ties to your revenue production.

For example, last year I traveled to Portugal. Portions of that trip qualified as business expenses because I had a signed contract with a brand that required on-site deliverables, and I was producing a review for my newsletter tied to publishing revenue.

Those specific days were business days. They were documented, contracted, and connected to income production.

However, the primary purpose of the overall trip was personal. Because of that, the round-trip flight and lodging didn’t qualify as deductible travel expenses. What did qualify were the expenses directly tied to the business activity: transportation to and from what I was contracted to review, and meals associated with those business days.

How I plan trips differently as a business owner

So much changed when I left my corporate job last year to take Window Seat full-time, but a big one is that I stopped planning travel purely around inspo and more around income alignment. Not to force business into every trip, but to be more intentional about when travel serves my business.

For example, I know I want to get out of these frigid New York temps and visit some friends in LA. Now that I have a destination in mind, from there I can ask myself:

• Do I have a brand partnership opportunity there? If not, should I begin outreach?

• Can I schedule meetings with hospitality partners while I’m in town?

• Is there content I can monetize from this trip? Can I turn my flight or hotel experience into interesting social or newsletter content or a future brand partnership?

Sometimes the answer is yes, and the trip becomes primarily about business. And sometimes it’s no, and it’ll just be personal–which is totally okay. The big difference is that I’m being strategic about this before I book anything.

The Bottom Line

There’s nothing wrong with loving beautiful hotels and great flights. Lord knows I do. There’s also nothing wrong with wanting to be smart about your money. It just comes down to knowing whether the trip serves your life or your revenue.

When you respect that line (and document it properly!) travel goes much further than an expense—it becomes part of a real, sustainable business model.

And take it from me: that’s a much better long-term strategy than hoping the IRS loves a good view as much as you do.

---

Tori Simokov is a Travel Writer and Graphic Designer/Strategist based in New York. To get in touch, email tori@v1projects.com. Want more? Check out Instagram, TikTok, or shop her curated favorites.