Our morning was the start to a perfect Alaskan day. The sun was out and a cool breeze from the Arctic Ocean kept the fog away as we commuted across Kachemak Bay. Stepping off The Far Side, a two story boat, onto Stillpoint Lodge’s dock in Halibut Cove, Alaska where we were greeted by the staff – they already knew our names – and escorted us to the main lodge. We enjoyed any drink of our choice and a charcuterie board as we learned about the float plane flights, glacial kayaking, and wildlife tours in store for us this week. A quick tour of the grounds, ending at our private cabin overlooking the cove. My girlfriend, Kristin, and I were out of place. A single night at the lodge cost more than I make in a month, yet we were here for a week and it wouldn’t cost us a dime. So, how is that possible?

Pros of work trades

• You get to be creative! You can extend your trip

• You feel appreciated and wanted, as your collaborator is investing in you as well

• You might build a side hustle to fuel your passions

 CONS of work trades

• You might have to take work home from vacation

• It’s possible everyone will say no, but that rarely happens

Connecting with Potential Clients

Flash back one month. I had just gotten off Denali, where I was making a mini-documentary on a climber attempting to summit North America’s tallest peak, and was beginning to sort through the footage in my van, in a grocery parking lot, waiting for Kristin to land in Anchorage. Our plan was simple: a road trip around the Kenai Peninsula for a month, then begin the 3,200 mile drive back to California. 

For the past seven years, I had been building a sustainable career in the outdoor space as a content creator focused mainly on adventure sports, like surfing and mountaineering. During these seven years, I had been dreaming of visiting Alaska, but the cost was always far too great for me to afford on my own. With a bit of luck, I landed the job to film on Denali, but I knew I wanted to stay longer. I wanted to explore the vastness of Alaska and I wanted to expand my work into the tourism industry. I mean, come on, who doesn’t want to be paid to go around the world and do fun things?! So, before our road trip began, I gave myself the goal of building a portfolio for tourism, specifically adventure tourism. But, I kept asking myself, “Where do I start?” 

Thinking back to when I started creating content, I recalled starting with speculation work. Work that you do for free, to build the thing you want, in hopes of making money later. Once this memory popped into my head, I realized I just needed to accept Alaska is big and full of more opportunities than I can do in a single trip, so I should just reach out to potential clients and see who is open to an exchange.

Tips for connecting with clients:

• Reach out three different ways; social media, email, phone call

• This is a numbers game, so reach out to anyone that interests you

• Follow up, several times if needed, people are busy and forget easily

• Connecting and getting a yes takes time, so begin this process 2-3 months in advance

• I’ve found showing up, in person, and asking it’s likely to be a yes

Shifting gears from sorting footage, I pulled out my phone and layed on the bed in the back of my van to start hunting for tourism clients. Starting on Google with a simple search, “must do adventures near anchorage” I found a few lists that linked to touristy things to do. At first, wildlife tours seemed to pop up most, so I started to copy and paste a template pitch to every company that would be along our route via Instagram DM’s, but I really wanted to get on a float plane ride and see some glaciers. Eventually, I found a company and started to send a message, but… buzz, buzz, buzz, my phone was ringing.

“Hey! We landed a bit early. I am headed to grab my bags now. How far away are you?” Kristin asked.

“Not far, I’ll be there in 20 minutes.”

Our adventure was about to begin.

Playing the Long Game

During our first week on the road, we did a multi-pitch rock climb, surfed the bore tide, went on several hikes, sought out waterfalls, and filmed everything along the way. Why? I’m playing the long game and investing in my future. What do I mean?

Kristin and I are both on this road trip to have fun, but it is also work. Alaska isn’t cheap and paying for the gas to drive the 3,200 miles home is going to hurt the bank account. Additionally, I don’t want this trip to end once I get back to California. So, I have to think about the long term and the sellability of most things we are doing. This means staging photo shoots, hiking to drastic landscapes to snap photographs that could sell as prints, finding wildlife, filming everything to make Youtube videos in the future, and taking notes in my journal at the end of everyday so I can reference them later for blogs like this.

Before coming to Alaska, I pitched over 150 companies the idea of an adventurous road trip around Alaska. By the numbers, roughly 15 responded asking for me details, two wanted to create something together after Alaska, and one said yes. Overall, I would say this is the standard response rate for outdoor content creation. That job I secured was a glacial kayaking trip on Portage Lake. 

The budget was small, but that didn’t matter. We loaded up the van with two kayaks from Anchorage and made our way to Portage Lake to enjoy ourselves and create a couple pieces of content for Dermatone, a sunscreen company. The skies were a clear blue, unusual for Alaska, and we paddled on calm water for half a day to reach the glacier. Hooting and hollering to each other, Kristin and I splashed around, ate iceberg ice, and attempted taking in the glacier view. This single day of creating content would yield the start to the portfolio I had been hoping to build on this trip.

 What was the best part of this day? Ending it with a charcuterie board and drinking tea with the back doors to the van open, allowing us to drink in the midnight sunset that occurs during the Alaskan Summers.

How Long Does it Take to Land a Client? But wait, do you even need a client?

Returning the kayaks to Anchorage felt like a metaphor for a new beginning as we officially had no more clients to offset the costs of the trip. Meaning, it was time to bootstrap. Yes, I have money, but I am not made of money. This trip is an investment in my future, but I didn’t want to tap into my savings unless I had to. Which meant I needed to come up with a way to go for flightseeing tours, get on fishing boats, and see wildlife without it costing me my savings. So, I was back on social media hunting for clients, but that wasn’t going to be enough.

We had roughly three more weeks before summer would turn to fall, signaling it was time for Kristin and I to head home. With a burning desire to share rad experiences, we committed three full days at a cafe to shop ideas to potential companies. Thankfully, we had the time as we were fully committed to Alaska at this point. So, we drank our coffees and searched google for wildlife excursions, flightseeing tours, and unique stays – the van was getting stinky and a house would be nice – to refresh ourselves. However, on the third day, we had no responses, which is expected, so we loaded up the van and headed for Homer, Alaska to go on a week-long backpacking trip we had been planning. 

We tossed our backpacking bags into a Mako’s Water Taxi and met our captain, Lance. A friendly soul who pulled out a map and genuinely wanted to learn about our trip, as well as share his local knowledge of the area. There seemed to be a recurring theme I had noticed during my Alaskan experience, everyone looked out for each other. Lance was a talker and loved to share anything you had an interest in. During the hour-long taxi across Kachemak Bay, Lance stopped several times for me to snap images of sea otters, told us about the history behind peak names, pointed out ski lines that we needed to come back for in the winter, and rerouted us to see a few whales.

Walking up the dock, we looked over our shoulders as Lance motored away. Then it hit, we had no quick way of getting back if something were to happen. Kristin and I wandered into the woods for our week of walking, getting scared by bears, getting soaked by the rain, finding a remote cabin with a sauna, attempting to summit peaks in high winds, and cooking a gifted salmon filet over a propane stove. Needless to say, this trip was what we were looking for out of our Alaskan Adventure. But, a week goes quick!

Becoming VIP Guests

To our surprise, Lance picked us up. Sitting down inside the cabin of the Mulligan, his boat, Lance offered us a beer in exchange for stories. Laughing and smiling, we recapped our week in the woods, away from our computers, and our attempt to stay dry during the storm which rolled through.

Once back in Homer, Alaska, we checked our emails for the first time in a week. A couple of no’s and thankfully one email that read:

Hey Dalton!

Thank you for reaching out. We would love to hear more about your ideas. Can you hop on a call soon?

Best,

Beka

A maybe, yes! Excited to share this potential with Kristin, I quickly responded to the email to set up a call. Within 10 minutes, I was chatting with Beka and setting dates for us to visit in just a few days. Kristin was excited, she wanted a week of pampering after our last week in the woods. Turns out, we would have to stay in their only room available during our stay, the VIP cabin, which rents between $10-15,000 a night per person. Yup, if you did that mental math, that means it would have cost $20-30,000 a night for both Kristin and I to stay there. I don’t have that kind of money, but I do have the skill to create content for them. So, a few days later, Kristin and I were stepping off The Far Side and being escorted to our cabin.

Conclusion:

With trips like this, you don’t know how the trip will end. Are you broke, or did you make out ahead? What I have come to realize is that it doesn’t totally matter. I went to Alaska to make a documentary about an athlete climbing Denali, then took a chance by spending all the money I had made into a personal trip adventuring Alaska’s Kenai Peninsula in my van. Yes, I did come back with a portfolio that I am happy to share, once I edit it. Yes, I did get to experience things I never thought would be possible, like staying at Stillpoint Lodge. And yes, I was given the opportunity to do it all with the love of my life. But, after five months on the road, I returned with terabytes of content to edit and $200 richer. Depending on your priorities, this might not be okay for you. For me, this was a good way to spend five months of my life.