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I convinced my agency to let me start shooting/directing small things and worked my way up beyond just organic social stuff. Eventually you kind of hit an impasse where the agency needs to profit and look creatively relevant but your cost is sunk in payroll and you don't sound as exciting as the hot production company so you have to choose between easy staff agency life but meh work or the really hard freelance game but potentially amazing work.
I have zero regrets about leaving my agency career but this is neither a poor man's sport nor for the faint of heart.
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Thanks for taking the time to answer. Really interesting. Wish you all the best with it.
Not from the creative department, but I was an editor internally at an agency who became a director (well, director / editor technically. I do both now). I was shooting lots of smaller stuff as a DP and expressed interest in it. Eventually the opportunity just showed up through various circumstances. The first one went well and I started doing broadcast spots pretty much monthly, at bigger and bigger budgets, all while still in-house. (Generally in the range of 200k-400k so not huge but also not nothing.) The problem becomes no agency knows how to pay a person like this fairly, and, in my experience, seems totally uninterested in trying to figure out the math. So you just get totally fucked monetarily for a while and suddenly you’re writing treatments bidding against other directors who will get a huge payout if it gets awarded to them and while you, the salaried employee, just gets the same shitty salary no what matter what happens - that becomes kinda a tough and complicated battle. So I ended up just continuing to use it as a reel builder while preparing to go off and do it on my own. I think if you express an interest in it, the opportunity may arise but once it becomes a regular thing, be careful to not get exploited. It can turn into mountains of work for very little pay - so be a little careful what you wish for in a way. Make sure you know this is the life you want before diving in. It’s definitely an unsustainable position to have salaried internally at an ad agency long term (unless it’s independent and run by some real cutting edge and clever folks).
One typical route (albeit apparently deemed illegal and recently investigated by the Department of Justice, but it still happens fairly frequently) is for agency creatives to build their reels and careers directing internally at their agency, and then “level up” by bidding against other outside vendors in a triple bid, getting awarded the job, and shooting it for their salary, not a director’s fee.
https://www.aarmusa.com/2018/10/19/advertisers-department-justice-know-dont/