#19 The Unconventional Path
Trading Security for Sovereignty
Welcome to issue 19, where I share an honest look at the freelance life and the roadmap I’m using to navigate this path of creative autonomy, from building networks and battling comparison to embracing creative madness and weathering financial storms.
First, an announcement: There are two spots left on my Dolomites Photo Retreat this June 2025.
I built these experiences to be transformative both on a personal and professional level by sharing my playbook for becoming a fulfilled and successful pro photographer. To keep things actionable, we will tackle two different commercial shoots from real clients, all in the incredible setting of the Italian Dolomites.
If you are ready to create standout work and take your career to a new level, please apply here today. I only do one or two retreats per year, so these spots will sell out.
Patagonia For 5 Days
I’m in a cloud of haze as I search for the words for this introduction. The culprit for this groggy feeling? Two words: jet lag. After fighting to keep my eyes open for 10 minutes, I was able to extract myself from bed at 9am, stretch, do some push ups, and walk down to the studio where I find myself now, wondering if I should have remained in the horizontal position instead.
You see, I just got back from Chile where I was making a film with my good friend Isaac for one of the LVMH brands. (They won’t let me say which one yet!) It was one of those assignments you can’t say no to. The kind where you imagine yourself as a grandfather, telling your wide-eyed grandchildren, “Yeah… grandpa did this one day…” Once the project is out, and the people in the Parisian offices with herringbone wooden floors and high ceilings allow me, I’ll give you the backstory in one of these next issues.
“I don’t tell my plumber what to do”
Those were the client’s words, verbatim. Mercifully, it wasn’t one of mine. But still, as a colleague of mine recounted this heated exchange he had last week, it made me reflect on our relationship with our clients.
The client was upset about missing shots — shots they had never requested in the first place. The irony? This wasn't even a paid job; my colleague was doing a favor. I wrote about this approach previously: Either do favors for valued relationships or charge full price, but never discount. That's exactly what he did. When the client complained about "missing crucial shots" after delivery, my colleague responded, "You never mentioned those needs or provided a shot list. How was I supposed to know what you wanted?" That’s when the touchy plumber analogy was put forward by the client.
So… It’s true that I don’t exactly write a detailed plan to my plumber for how he should do his job. I trust him with the gist of the project, like “please install this new sink here.” But if a client tells us, “please photograph my new table here,” are we supposed to be like the plumber and just do what we think is best? I’m not so sure because on the surface, it seems reasonable. But there's a fundamental difference between technical trades and creative services that this analogy misses entirely.
A plumbing job has a clear, objective outcome: the sink works, doesn't leak, and meets code. There's a finite set of "right ways" to install plumbing, all leading to the same functional result. Whether the pipes run slightly left or right behind my wall makes no difference to me as the client.
Photography and filmmaking don’t work this way. When a client says, "Please photograph my new table here," the possible interpretations and executions are virtually infinite:
Is this for e-comm requiring clinical white-background product shots?
Is it for a high-end catalog where lifestyle context matters?
Do we need details of the craftsmanship?
Are we showing the table alone, or styled with accessories?
Will these images be used in print, IG, or both?
etc…
Each of these questions fundamentally changes the approach, and none of them has a universally "correct" answer like plumbing does.
While it would be nice, mind reading is not a service we offer.
As creative professionals, we constantly battle the assumption that we should intuitively know what clients want without adequate briefing. The truth is that even experienced creatives can’t read minds and require some form of direction. Ok… to be completely transparent, I have to admit that often, clients come to me with a “carte blanche” approach where I have a lot of creative freedom. They usually want it to look like the photos I share online, straight out of that universe. It sounds fun, but it can be very exhausting because it takes a lot of empathy for the client to get the balance between what serves me and what serves the client right. But even in these circumstances, there are a set of deliverables, a timeline, and a budget.
The problem with a lack of visual direction is amplified when working for free. My colleague found himself in the awkward position of having donated his time and expertise, only to be criticized for not delivering something he was never asked to provide. It's like giving someone a free ride and having them complain about your choice of route.
The solution
For photographers and clients alike, the solution lies in better communication:
Establish clear expectations upfront - Even for free work, a simple email outlining deliverables protects both parties.
Ask the right questions - As photographers, we need to proactively interview clients about their needs, even when they seem reluctant to provide details. In this case, asking if there any “must have shots” would have been useful.
Sniff test - some clients won’t be worth your time and if you get bad vibes as the conversation advances, you can always send the gig to someone else without creating an enemy but still preserving your sanity
Trading Security for Sovereignty
I sometimes lay awake in the wee hours of the morning. One thought leads to another, and then another. This time I found myself pondering the life choices we all make and where they take us. We often see the highlights of our peers: the big shoots, the dream clients, the incredible locations. But what go unseen are the sacrifices made and the struggles encountered. Let me preface this by saying I am fortunate enough to not have encountered life-threatening hardship in my life — most of the bad things that happened, I was the one who put myself into them.
But struggles are struggles. Like with anyone, there are highs and lows in my career. Some days you feel like you’re on top of the world with endless momentum and enough strength to tow a freight train. Then, there is an off month, and you find yourself covered in doubt, wondering how you’re supposed to keep doing this for 30 more years. To be honest, I have never thought about quitting. But I sometimes wonder what it would be like to have a real job. You know, one with a steady paycheck and built-in vacation time.
Here’s my humble roadmap to navigating this unconventional career path.
Building a career without a roadmap
Obviously, no one really knows what they want to do when they leave high school. I didn’t either. There are, however, very respectable careers that offer a predictable path such as law, doctoring, accounting… But what do you do if those don’t sound like you? I was bad at math and I couldn’t imagine spending 10 years studying. I wanted to go out and “see the world,” but counselors couldn’t really help me find a job that did that. Ok, I could be a pilot, but again, I’m bad at math. The thing is that the world changes so quickly that my job didn’t exist when I left school. I somehow invented it by following my intuition, and doing what other people whom I looked up to were doing. So when people ask me how they can do what I do, I tell them the following.
Never stop building your network and meet people (college is a great way to do that) — opportunities are attached to people.
Develop a strong discipline by training you to do hard things.
Create, constantly. You never know who will see the work and what is going to happen.
Comparison to others
This is a tricky one I struggle with. What helps me is remembering that the world is not a zero-sum game. It’s not because someone has been handed a very good opportunity that anything has been taken away from me. Of course, as there are more and more people in one specific field, then at some point we all are competing for the same opportunities, at least on the surface. That’s hard, of course, and frustrating. In this case, you want to diversify and build your own identity outside of that niche by doing things in new ways, or adding new services, for example:
Developing communications skills to be invited as a keynote speaker.
Positioning yourself as a full service production studio.
Bringing two different aesthetics together: ie. fashion and running ( What Satisfy and Salomon Sportstyle did).
Learning how to fly FPV drones.
Building a recurrent model with your clients vs. one off projects
Tackling other aspects of the marketing puzzle for your clients: art direction, styling…
Once you have your own thing going, you will find it easier to not be comparing yourself to your peers as much because you are doing different things. The key is to see yourself and what you do as completely unique and irreplaceable. That is a lifelong struggle, of course.
Saying no to a safe but uninspiring job
The universe favors the bold, and the rewards you reap are only proportional to the risks you take. That’s the equation, at least. But some of us are not innate risk takers, so what to do? To me, a steady job was never in the equation. I’d be a terrible bus driver because I’d want to finish the trip as fast as possible to go for a run. Cook in a restaurant? Can’t do that very well either… The only thing I was good at was looking at the landscape and realizing what bits of it would make a good picture. I don’t think anyone is hiring for that job. But I somehow, miraculously, found a way to turn it into a career. And you can too if you truly believe it’s the life you want. If you are OK with the stress of creating original work day-in and day-out, getting paid on other people’s schedules, having your schedule change at the last minute. I know it’s the life that suits me most, but make sure you really weigh the pros and cons according to what you value.
Consistent output: If I do something, something will happen.
To do this job, you need a certain level of madness. You need to be able to pour tens hundreds of hours of work into something and hope anyone cares enough to consume it. And often, those are self-funded personal projects, so no one is there to reimburse you for your fuel or mileage. But deep inside, you have to believe whenever you have an output of work, something will happen. Someone, somewhere, will notice it. Maybe they will forward it to a friend, or show it to their partner, or boss. Most of the work I get is through that. So if I don’t put anything out, then less work comes in. Seems simple, but it’s easy to forget.
So freelance life is full of horrible hurdles and it’s not worth pursuing — or is it? Yes, freelancing is a never-ending circle of chasing payments from clients who treat invoices as optional reading, getting no replies to emails, then too many at once, and producing work that's often consumed and forgotten faster than a Big Mac. The freelance existence isn't so much a career as a pathological condition, a madness that compels sensible people to trade security for sovereignty. Yet there remains something stubbornly empowering about crafting a life outside the norms of conventional employment. The freelance journey simply offers a different landscape for life — sometimes breathtaking, sometimes barren, but always, unmistakably, our own.
Outtakes
This newsletter is edited by Danny Smith
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The Dolomites Photography Retreat 2025: Experience the still-authentic side of the Dolomites with a group of like-minded photographers led by Alex Strohl
Strohl x Moment 45L ultralight camera pack: “You no longer need to choose between a mountain pack and a camera bag. With this bag, you get both” — Moment
Adventure Photography Pro Workshop: Learn what it takes to make iconic work.
Incredible newsletter Alex! I will be attending your Summer 2025 Dolomites Retreat! Really excited to experience the magic of the Dolomites and learn from a PRO such as yourself!
Loved this issue very much. One we photographers should all resonate with. Thanks mister A.