Entrepreneur's Handbook
Sep 22
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Over the last five years, I’ve fallen into my fair share of trap situations with my photography side hustle — eleventh-hour cancellations, delayed payments, massive disappointments, etc.
And it wasn’t a pleasant feeling.
Sure, you can say I’ve gotten wiser through the lessons learned. And after I confronted the people who got me in there, you could say I’ve earned their respect.
But I wish I didn’t fall into them in the first place. If only someone had warned me to be wary of them. That’s the thing with traps; you don’t see them from afar. Or even if you do, they look harmless. You follow the bait, and in the excitement, you land in a deep hole.
That’s why I’m warning others to watch out for these unsuspecting scenarios that could spell trouble if not spotted earlier.
On some assignments, you’ll have to go up against a team. It’s hard to find a well-coordinated one. Many teams are an incoherent mess. Among the few great ones, every teammate wants to stamp their authority on proceedings.
And you could become a victim of a brutal power play if you don’t sort out some issues at the start.
For example, I once did a shoot for a client. When I presented the work, they were happy. But they told me they had to run it by other colleagues, then their higher-ups.
Some colleagues had their unique inputs. They couldn’t even agree on one thing that suited them. Their bosses were also unhappy. Worse yet, their specifications differed from what the liaison officer asked me to do.
Long story short, all the inputs from the various voices and stages of the chain of command led to multiple revisions and unjustified delays. With little extra payment. It was really frustrating.
From the off, ask who approves the completed work. Where possible, find out if you can get direct communication with them. Or at least get their input before submitting the final work.
It could be hard to get these requests, but it’ll save you time, headaches, and multiple revisions.
Also, get clarity on who gives the orders for your fees to be paid. Is it an accountant, the CFO, or the board? And to whom do you address your invoice? And what processes does it follow?
Takeaway insight: Beware of dysfunctional teams. Or at least teams with uber-competitive members with unclear communication systems. Trace the lines of communication ASAP before you begin work.
Especially in creative assignments, some clients will like to have you do one extra task too many. You agree on what they want you, but in the thick of affairs, they come up with a minor request they forgot all about at the start.
Sometimes, it’s hard to say no, as you’re already built that relationship with them. That may be true, but it’s still extra work. And the hours and effort add up.
Once, a friend booked me to take some pictures of her sister, a model, in some new dresses they’d sewn together. While at it, the model’s husband came home, and she asked him to join.
The couple pleaded for a few minutes to find matching outfits. Before I knew it, I had twice as many pictures to sort through and edit. For no extra pay.
Thankfully, my friend understood my frustrations and added a slight raise to my fees. Not quite enough, but at least she understood it. Others would expect you to let things slide. I’ve faced such situations, and it wasn’t pretty.
Ask clients to repeat their requests. That way, you’ll get them to commit themselves. Also — and more crucially — remind them some clients spring surprise tasks on you mid-assignment, and you’ve since learned to charge extra should that happen.
With those reassurances, you’re setting the ground rules, and you can easily fall on those commitments should that happen.
Takeaway insight: Some clients can come up with extra work outside the approved task and budget. Prepare for that and plan how you’ll deal with that.
Some tasks flirt with legal trouble. But sadly, some clients will make no commitment to helping you deal with those issues. And if you don’t press for clarity, you’ll be in trouble if something goes wrong.
Watch out for clients who disregard — or remain silent on — crucial issues like copyright violations, permit acquisition, and trespass fines, especially if the work touches on those items.
If you need to use images, get clarity on who pays for the right to use them. If your client presents them to you, ask if they have the rights. Need to use a location? Who gets the permit — or pays for it? Not all clients love you well enough to bear those burdens. Address those concerns from the start.
For example, on two occasions, I shot at locations where professional photography was not allowed without permission — one in a high-end residential area, another on the premises of a shopping mall.
On both occasions, I questioned the client; both times, they told me, “Nothing will happen. People do it all the time with no issues.”
Except in my case, something happened: security seized my camera. I got it back after days and a stern warning. I should have been proactive enough to do my background checks. If I only knew better!
Indemnify yourself, folks. Get things in writing, at least some clauses to spell out what happens if trouble arises. Don’t merely take clients’ words for it. Those words may change at any time.
Also, do your independent background checks. Your due diligence could save you from trouble.
Takeaway insight: If an assignment requires permitting or has legal angles, get a concrete commitment from clients. Even better, do your own checks.
As a one-person freelancer/side hustler, you’ll likely have a weaker hand against some clients. Also, some individual clients may not regard you nearly as high as they would a more established brand.
And that manifests in the tricky everyday scenarios you have to navigate.
You need to keep your eyes open for these pitfalls. They may not be noticeable at the start. Or they may look normal even if you spot them. But if you don’t handle them right, they’ll harm you down the line.
I’ve lived many scenarios, and I don’t want you to go through same. Things are stressful as is, and you’re better off without the extra stress.
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