Sitting here on my couch, feeling excited and a bit bummed, I’m reflecting on why I keep trying to make this failing side hustle work. Again and again and again and again and again, it has failed in one way or another. Yet, I keep iterating and grinding away hoping to make this side hustle a reality.
So, what they heck is this side hustle? I’ll give you a hint, my childhood goal has always been to travel the world and tell stories. In short, that’s the side hustle, but how it takes shape is now on its sixth iteration. Here are my previous five failures and what I learned from them.
Before I dive in, I want to quickly acknowledge my main career is commercial and editorial photography & filmmaking. I love the career, the access it provides, that I’m good at it, and the creativity, yet, I’ve always been a bit disenchanted with financial security being tied to clients whose needs vary year to year. The ups and downs of a photo/filmmaking career is why I have put time and effort into this side hustle.
A selfie of me ashamed to admit these failures, so I hope they help some of you.
Failed Attempt 1 of 5:
In 2015/16, I started an IG account ( seekshangrila - terrible name, I know, but it meant something to me) to share my travels and adventures in one place, meanwhile connect with other people doing the same thing as me. In just a few months, that account grew from 0 to 10k by posting iPhone snaps while cycling around New Zealand and backpacking in Yosemite National Park. The images are cringe worthy now, but the growth in followers confidence I should invest in a camera.
I bought the Sony a6000 and started focusing on creating images.
At some point, I realized I could make money from snapping images and sharing them to social media. So, I changed the focus of the account over time from iPhone snaps for people to enjoy with a longer caption about the adventures to “I’m a professional photographer, look how amazing my photography is! Hire me!”
Then, that account hit a plateau around 12k, I had renamed the account daltonjohnsonmedia, and just went all in on sharing photos like other professional photographers. And guess what, I faded into oblivion like all the other people who just push how great they are at using a camera.
So, I did what any logical millennial would do, I started a blog.
I didn't know anything about blogs, or blogging as a business, so these "blogs" were really just IG captions with a few photos. So, looking back I'm not surprised it didn't work, but I tried and I learned.
Writing daily to see what would happen. Nothing. But, my writing did get better. At times I had a few articles perform, most of them never did anything.
Secretly, I thought I was the best writer on planet earth and just didn't understand why nobody was reading. It must have been Google's fault (eye roll), but, I chugged along. Cranking out articles. I even started to submit article ideas to magazines, but they didn’t respond.
At some point, I realized blogging was not working, so I decided to educate myself and started reading blogs. Turns out, I had everything wrong.
I tossed in the towel, turned that site into my portfolio, and let it sit. Eventually, a few articles ranked on Google, providing some traffic and job leads for photo and video work.
What I Learned Looking Back:
An audience doesn’t care how you make money (as long as it is ethical) and surely don't want to hear about it, unless that is the content you share
Leaving your core audience behind because you feel like doing something different isn’t helpful
Ego destroys all good things
You need a business model to make something sustainable, but that also means you need to know what a business model means
Diversity of outlets only works if you spend time nurturing them all
Failed Attempt 2 of 5:
Roughly 2017 till 2020, I continued pushing on with the writing and posting to IG, there wasn't really a business model (I didn't have the vocabulary at the time) but I was landing clients off and on for photo/video as well as editorial work. So, I figured I would just go all in. That IG account grew to 17k, I started a newsletter (a recommendation of a college buddy), and kept the website chugging along. The newsletter grew to about 1k, maybe 1500, but then I fell off the map because commercial and editorial camera work exploded. Then, COVID hit, and well I recouped at my parents place for month to reset, learn, and figure out what I was going to do because everything stopped.
Failed Attempt 3 of 5:
2021, I spent a year learning more about business, business models, marketing, etc. I still had the IG account, the blog, and the newsletter, but I had no momentum. The IG account was going backwards, starting the year roughly at 15k and losing followers daily. The blog wasn't really getting any traffic and I wasn't sharing my newsletter because I just didn't care. I was licensing images and selling prints, but nothing was really popping. No growth, just meh.
But, Jan 2022 I got a call to produce/DP a documentary on Denali, accepted the job and road tripped from Baja to Denali. Recorded the film and booked a few photo gigs that paid well enough to linger around Alaska for a few months.
During that time, I figured I would give YT a shot, but why not, right? Well, that was an epic fail. YT travel videos take a ton of work (more than making a documentary), have a cadence that isn't for a sane person, and make no money LOL until you have a massive catalog of footage that generates income via ads and brand deals. But, at least I tried, right?
The YT dream went on for about a year with almost nothing to show for it.
Failed Attempt 4 of 5:
2023 - 24: I got a random DM on LinkedIn, "Can you write as well as you photograph?"
"Yup, I've been published in national magazines like Men's Journal (sent link of story)"
"Cool, meeting tomorrow, what time works for you?"
sent time and booked a call
A few months later, I was running a vertical of Men's Journal (turns out the random DM was a VP at MJ's parent company) and was looking to expand MJ into adventure travel.
I was their guy.
I went hard and built that site from nothing to roughly 450 articles and 170k UMV in just 8 months (it took 4 to launch).
I literally went to every continent, above the arctic circle, and below the antarctic circle for assignments.
Then, the parent company got into trouble, VPs moved companies, and the program I was running got axed.
Ironically, they couldn't even quote my contract correctly during my termination email LOL
Failed Attempt 5 of 5:
mid/late 2024: For some reason, every article that was published was "given back to me", the IG account (now totally destroyed) was handed back to me, and I started The Adventure Travel Network.
At first, it did really well and grew quickly online. Traffic skyrocketed to roughly 500k in a matter of months, it was epic.
Then a Google update hit and I went from making $2,000-3,000 a month of passive ad income to $300/mo. Then $200/mo. Then $100/mo.
Dead.
In early 2025, I pushed for about two months will affilates and trying to figure things out, but the writing was on the wall. This wasn't going to work, so I integrated the site into my portfolio website and continued my work with photo and video.
Attempt 6, Will It Finally Work?
The call to share great stories can't be shaken.
A few weeks ago, while I was swimming in Lake Tahoe and beating myself up mentally, the phrase “unbound” popped into my head. A mantra of sorts that showcased, in a single word, a life not attached to the status quo. In fact, it would be the opposite, a life full unbound and willing to give a middle a finger to accepting the chains of societal norms.
Aggressive? Yes, but that chip on my shoulder is unavoidable and who doesn’t like that movie scene in Top Gun of Maverick giving the Mig pilot the middle finger? I have loved that scene since I was a wee-little-lad.
So, I rebranded the newsletter, mapped out a list of stories that have been denied through magazine submissions, and just decided I would try this thing myself.
And, that’s how UnBound was born.
But, I’ll be honest, right now it makes $100/mo and I don’t have much of a business model to figure out how and where it should go. Yet, I am taking it slow enough that I don’t fully have to worry about that, for right now, as $100/mo covers the costs of doing business for now.