I’m currently sleeping in a shed in Kenai, Alaska.
Tomorrow I’m taking a boat to a remote island homestead to spend the next month fishing salmon. The homestead is only accessible by boat, there’s no running water or wifi and I have never fished before in my life. This is my Paris Hilton in MTV’s The Simple Life era of the trip.
Also my friends Leah and Emily are joining me so it’s officially salmon girl summer.
First let me tell you more about this shed.
This is a fixed up tweaker shed owned by our host David. He calls it “Jabba the Hutt” which I’m told is a Star Wars thing.
David is a commercial net fisherman who lives off of the Kenai peninsula. He lives on an island with his wife where they fish, garden and generally live off the land. He has a rotating crew of volunteers who come stay with him every summer to help out with all the work.
David has a few properties on the mainland in Kenai and the one we’re currently staying in is a compound consisting of Jabba the Hutt, three camper vans, and an assortment of strategically placed Conex shipping containers which he calls the Conex Fort.
You might be wondering “wow I really want my own complex of shipping containers how do I get that”. Well it turns out the previous owner died and left all of his possessions, including the land and containers, to the NRA. Yep, apparently you can leave land to the NRA. And the NRA turned around and put it on the market so David purchased it.


The number one question I keep getting about this whole Alaskan adventure is “how on earth did you find this random homestead in Alaska to fish on”?
And I’m going to answer that question and also take this as an opportunity to impart on you some of the knowledge I’ve acquired over the past year about a good quarter life crisis.
If you decide to quit your job and spend a year traveling, or just generally you want to fuck off and leave society behind, you have one best friend. And that friend is the almighty work exchange. Sometimes referred to as work trades, labor exchanges, or volunteering, a work exchange program allows you to trade your labor for free room and board. These programs help you save money on a long trip, provide structure, and give you new life skills like net fishing salmon!
Over the past ten months I’ve met many people who have also done work exchanges while living out their quarter life crises and I’m going to share with you the top apps and websites where you can find such arrangements.
WorldPackers
WorldPackers is an app and website that has a ton of work exchanges of all types. It’s been my tried and true all year long.
This homestead is my sixth work exchange program of the year. The previous five have been hostels. Four out of the five hostels I found on WorldPackers. The fifth I just walked in and asked the owner to volunteer and she said yes. I also found this Alaskan homestead on WorldPackers.
WorldPackers has all kinds of exchanges. There’s hostels, farms, schools, meditation retreats, homesteads, and surf camps. I even remember seeing a listing for a motorcycle shop where you could learn to fix up motorcycles for free. There’s also this listing I saw for a nudist RV resort.
Whatever you want you can find on WorldPackers.
WorkAway
WorkAway is very similar to WorldPackers. They are both essentially a catch-all for work trades containing a wide range of listings.
All of these apps more or less work the same. They have listings of places you can work and every listing has reviews so you can see if previous volunteers liked the experience or not. You can even message previous volunteers to make sure that the owner or manager of wherever you’re going isn’t a total weirdo. Volunteers also get reviews and then future hosts can verify if the volunteer they’re getting is trustworthy.
WorldPackers and WorkAway are both free to browse but when you want to apply you have to get a membership. The membership is $60 for the year which in my case has been totally worth it.
WWOOF
WWOOF stands for World Wide Opportunities on Organic Farms. It’s a registry of organic farms offering free homestays in exchange for farm work. I haven’t done it but I’ve heard amazing things from the people who have and if you’re interesting in spending a lot of time outdoors this is definitely a good option.
CrewBay
CrewBay is a website that allows you to find sailboats and yachts looking for crew. The crazy thing is that you don’t need any boating experience so if you want to learn to sail on a five day trip for free this is 100% the way to go.
I will say I’ve only met one guy who did this and his boat sank and had to be rescued by the coast guard. He was totally fine but he lost all his stuff so if you choose this one you might want to verify that your captain actually knows how to sail.
Trusted House Sitters
Trusted House Sitters is by far the easiest work trade. It’s a website that pairs volunteers up with people who are looking for house sitters. You get to stay in someone else’s (often bougie) house for free. All you have to do in return is take care of their house. A lot of these do include taking care of cats or dogs but if you like pets this is a super easy way to stay in a nice house for free.
The great thing about all of the apps above is you can find exactly the right work trade experience for you. You can party in New Orleans or you can go to remote Alaska. You can choose city or rural, social or introverted, and go to almost any country in the world. You can also learn a variety of new skills for free.
While I’ve branded this as a quarter life crisis I will clarify that my primary motivator for this trip was to work in hostels. It’s just something that I’d always wanted to do. I love hostel work but I realize it’s not for everyone. When choosing a work trade it’s always good to remember the age old saying “wherever you go, there you are”. Or as summarized by this 10/10 SNL sketch.
Like I mentioned above, there’s no wifi on the island and the cell service is limited so you likely won’t hear from me for a bit. I’m in Alaska for a month but then I’m flying home to Chicago to end my trip how it started - bartending at Lollapalooza.
Can’t wait to see you all in August!