My tax return is complicated for a lot of reasons. First, I run several different businesses which all have their own set of accounting. WDS, our annual gathering, has its own legal structure, including a foundation that is completely separate from all my other projects. Last year we started an all-new event that also has its own legal structure.
So yeah, it’s complicated. It takes about 20 hours just to prepare all the info for my accountant, and as with most tax-prep tasks, it’s not usually a fun process. But I do enjoy seeing some of the charges on my statements from the previous year. They remind me of the crazy life I have, and the many fun experiences that I’m fortunate to participate in.
– 800 custom-branded yoga mats
In 2014, we set a Guinness World Record on Pioneer Courthouse Square in downtown Portland, Oregon. Making this happen required a herculean effort—from our Adventure Czar, our production team, many, many volunteers, and 800+ participants.
It also required 800+ custom-branded mats, which we purchased in bulk and then screen-printed at a local shop. (And for everyone who’s asked, no, we don’t have any extra. We used 100% of them for the event. But yes, there will be another world record attempt this year — you should join us!)
– One legit log cabin, interior-only
After announcing our new event, Pioneer Nation, we decided to have some fun with the set. There was only one real choice: naturally, an event focused on the modern-day Oregon Trail would have a legit log cabin.
You can’t just go to Ikea and pick up a ready-to-assemble log cabin (we tried). We commissioned it from the same local craftsman we’ve used for WDS installations, and as you can see—it was pretty awesome.
Uh, just one problem: where to put it after the event is over? Yeah. I really should have thought about that.
– The best bathroom sign ever (and lots of other signs)
We spent thousands (and thousands) of dollars on signage for the two events. It sounds crazy, but we need way-finding signs, banners, wall signs, and just all kinds of “here’s where stuff is” signs.
My favorite, though, is now installed in my guest bathroom.
– Scholarships for Real Life: Initial Grants
After WDS 2013 (i.e. two WDS’s ago), we established a foundation to provide microgrants for people doing interesting work that doesn’t usually qualify for other funding.
Our initial grantees were:
We’ll have some updates on these projects soon, and—just as exciting—a new round of applications for this year’s awards.
– One dream machine
For last year’s WDS, we had a special sendoff—but before we could have the sendoff, we had to select a few special people. To do that, we created a “Dream Machine” (AKA video booth) that would whisk attendees into the future and ask them what their life was like five years into the future.
The video below tells what happened next, from the perspective of one of the attendees who was selected.
Cost: hard to estimate. The physical costs for the Dream Machine were around $2,000, but producing the whole project was approximately $10,000.
– Whole bunch of wooden nickels
At this year’s event, we ordered some special tokens that could be used in place of drink tickets (so boring!) at the Portland Experience, an afternoon at the park blocks that featured dozens of vendors and showed off our city to all the visitors.
(Side note: We ordered these from Wooden-Nickel.net, which is obviously not an affiliate link. Wooden Nickel, Inc. has been around since 1945, and it looks like their website has, too.)
– Web hosting and internet services for far too many sites
I have a huge category in my tax return for “Internet Services,” which consists of everything from web hosting to internet access (at home, at my office, on the go, GoGo, paid internet elsewhere, etc.).
We also use a ton of different services for managing newsletters and all kinds of other stuff that I don’t understand, at least for the technical side. But it’s important!
Cost: $28,000+ (no joke!)
– Lots of pizza
When I say a lot, I mean a lot. I love the old story of Mailchimp determining their company’s growth by the number of pizzas required per meeting.
Over at World Domination HQ, we don’t have pizza for every meeting—sometimes our resident Voice of Reason will make a nice crockpot of delicious soup (always vegan and gluten-free). But pizza is a go-to when I’m in charge of catering, so we tend to order a lot of it.
– Lots of travel
For many years, travel has always been my greatest business and personal expense. I’ve gladly chosen to make travel a priority, choosing it instead of buying a car (at least for many years), going into debt for more higher education, and really ahead of just about anything else. If I had to cut costs, travel would be the last thing I’d cut.
Last year I went to fewer places than usual, but I still went a lot of places, relatively speaking. (In the 2014 Annual Review I published a full list.) Of particular interest for the tax return was my 40-city book tour, most of which is a strict business expense as I was doing nothing but meeting with readers and talking about the book during the entire time.
Cost: a bajillion dollars. Well, that’s not quite the precise number, but it was a lot. And it was all worth it and I’d do it all again.
I’m actually pretty conservative in my tax return. I don’t write off travel that isn’t specifically for “business,” even though my “business” is 100% integrated with my life. I don’t deduct clothing purchases or haircuts, even though supposedly public speakers can do that. (My haircuts cost $12 each, so I’m not too worried about it.)
No one likes paying taxes, but I’m grateful for the chance to do interesting work.
Will you have any fun or interesting deductions this year?