Jonathan Barwood of Portland had just graduated from college with a degree in ceramic sculpture when his mom asked him to carve a pumpkin for the front porch. Since his parents paid for his art school education, he took the request very seriously.

After that, he started entering contests — and the rest was history.

Jonathan’s side hustle as a professional pumpkin carver has been paying his rent or mortgage every October for 20+ years.

Q: How did you transition from pumpkin carving contests to paid commissions?

A: I realized I could enter a contest for somebody who's going to give a $100 prize or I could get paid $100 to do it. Yeah, so it's like, why not just get paid? I was doing up to 16 to 30 pumpkins a season — I was doing like four a weekend or so and then a couple during the week — so it was paying the rent.

And then a friend of mine works in the television industry and the company that was doing her shows was also casting for pumpkin carvers for a pumpkin carving show, which was “Halloween Wars.” She was like, “You should apply for the show.” I was like, “Oh, well I gotta do something better than what I’m doing," so I switched it up and started doing faces [and auditioned for the show]. I was always a face sculptor when I was doing clay, but to actually try and make things look like real faces. And all my stuff is cartoony because my style was cartoony. But I started doing things with more teeth, and more scary stuff.

Jonathan (far right) on Season 4 of "Halloween Wars." | Photo via Jonathan Barwood

Q: How long does it take you to carve a pumpkin?

A: I think the longest I carve now is about eight hours.

Q: Who do you carve pumpkins for?

A: I would carve mostly for restaurants and people's front porches, and I did some raffles and some other things like that. I've done a lot of corporate stuff, like for Brew Dr. Kombucha.

Q: How much do you generally charge?

A: If it's corporate, and they're doing a big event, I’ve charged up to $500. I think my friends and I did one event and charged them for the pumpkins as well, because pumpkins were expensive. And we had 250-lb pumpkins at $2 a pound.

Q: Let’s talk about the babies in pumpkins.

A: My cousin — I gave him a pumpkin because it was Halloween when I was visiting — and I just went and bought a pumpkin and carved it real fast and then gave it to them because they just had a baby. I'm like, “Hey, here's a pumpkin, I do these things and they're silly.” And then my cousin's husband just stuck their kid in it and took a picture, which I thought was great. And then I'm like, “Oh, man, babies and pumpkins — I gotta do that again.”

One of my favorites is the changeling, which is the one with the really creepy goblin about to snatch the baby. It was really fun because that was a friend of mine. And then the spider pumpkin — the one with the big Shelob — is my son and he's little Frodo all wrapped up.

Jonathan's son sleeps inside a pumpkin carved to look like J.R.R. Tolkien's Shelob. | Photo via Jonathan Barwood

Q: What’s your favorite part of the carving process?

A: The sketch. I do a bunch of sketches usually in a sketchbook and then I'll actually draw right on the pumpkin. That's always kind of this moment when you're trying to figure out what it wants to be or what it could be. Teeth are my favorite thing to carve.

Q: What kind of tools do you use?

A: I have a zillion different tools. The one I use the most is called a fettling knife — it’s a knife that you would normally use for ceramics. The second knife that I use the most is a Thai fruit carving knife, which you can buy from Asian restaurant supply stores, and they're very inexpensive. I also use a bunch of loop tools. (Check out this timelapse.)

Q: Do you carve pumpkins any other time of the year?

A: At the end of my season, I usually have a couple extra [pumpkins] left over, and I'll put them in my basement and then I carve an Easter Bunny pumpkin every year. Pumpkins were originally a winter squash and the whole idea behind them was that if you put them in a nice cool dry place, they don't go bad and so you can eat fresh fruit in the winter.

Q: Do you have any pro tips on how to make a pumpkin last longer once it's carved?

A: Okay, so there are a couple of different things. You can hit it with a can of Lysol, but that means you can no longer compost it. Now it's a toxic sponge and I personally don't like that. So I let them just dry. It's really fun to let your pumpkins rot and watch the squirrels, you know?

Part of the joy for me is it's a very ephemeral artwork. So just like sand sculptures or ice carvings, all of that is like you're making something really pretty, but it's not going to last.