A couple of years ago, I took everything I had learned in my brief freelance career and put it into an article, Lessons Learned from A Year of Freelancing: rb.gy/95yhlx It was one of the most liked, shared and commented-on pieces I’ve ever done, and a lot of people mentioned how helpful they found it.
Now that I’m a couple more years in, I’ve learned some additional things along the way. With a sudden onslaught of new, Corona-caused freelancers hitting the market, I thought it could be of assistance. So here goes round two.
Always say yes
When someone approaches you about a job, say yes. Don’t say probably, or that you have a slight conflict you can probably work out. I know. I’ve lost gigs because I said “yes but” instead of “yes”.
When recruiters reach out to freelancers, they’re usually frazzled, stressed, maybe even a little panicked. They don’t care that you have a conflict with your daughter’s ballet recital. Or that it’s a holiday weekend and you had planned to take the family out of town. All they’re looking for is a solution. Someone who can come in and take something off their plate that still has 15 other things piled on it. And the person who says yes instead of “yes but” is going to get the job.
So repeat after me: Yes. But of course. Without a doubt. How high?
You will lose jobs
Even if you do everything right—say yes to everything, have category experience, agree to cut your rate just this once—you will still lose jobs. It’s not personal. There’s no rhyme or reason to it. It just happens.
Some people get really affected by this and they carry around the losses like personal slights. Don’t do this. Chalk it up to fate and move on. There’s a reason why it didn’t happen. Sometimes I have actually found out the reason, sometimes I haven’t. But I am confident there is one and it’s probably not me.
You’re not booked until you have paperwork
You think you have the gig. They may have promised you repeatedly that the job is happening. They might have even made sure you’re free for a kickoff briefing. But guess what? You’re not actually booked. None of that stuff is binding. It’s not official until you have signatures on documents. And if you turn down other gigs because of a verbal commitment, you’re taking a chance. (See the next topic.) Unlike the exit row of an airplane, a verbal ‘yes’ doesn’t count.
The Trap Door
Sometimes, while you’re waiting for the aforementioned paperwork, another gig will come calling. You’ll probably do the right thing and say you’re already committed to the other gig. (Even though you have signed nothing and really shouldn’t say that.) Then invariably, you hear a faint ping. It’s a “there’s a been a change” email and the paperwork for the first gig ain’t coming.
Now flop sweat droplets appear on your forehead. You panic and pivot back to the second gig. But it’s too late. They already found somebody. Then you find yourself on the couch, watching The View, polishing off a box of Fudge Grahams and making no money.
Juggling a couple of potential gigs is the toughest part of freelancing. And I’ve “done the right thing” and wound up taking the hit more than once. So I’ll say it again (mostly for me). You’re not booked until you’re booked.
Buckle up. You’re going in.
No one hires you because things are going great. No one looks around and says “You know what? Things are going so smoothly right now, let’s spend hundreds—no wait, thousands—of dollars on some freelancers.” No, you’re brought it because something has hit the fan. Maybe there’s a rush pitch and the agency is shorthanded. Or people are burned out on an account and they need fresh eyes on it. Or the client is pissed and wants to see new work ASAP. Either way, it’s going to be a hairy, intense one, so suit up and strap in. Like a freelance smokejumper, you’re going in.
Briefs never are.
They say writing is easy, but editing is hard. That seems especially true when it comes to creative briefs. I’ve worked at a lot of agencies over the past few years. Like Tolstoy’s unhappy families, briefs are all different in their own ways. However, I’ve rarely seen one that lives up to its name. So the first part of your job is sift through the ‘brief’ and find the nuggets that will lead to great work. They’re in there somewhere, buried among the targeting landscape and tertiary considerations. Take the time to find them. The rest will go much easier.
I worked at one place that actually had brief briefs, and I wound up staying there almost 10 years.
The faster they want rounds, the less likely you are to hear from them.
It’s some kind of weird law of nature. There are agencies who ask for insane turnarounds or want the work in three hours when you were originally promised two days. By some weird law of nature, they’re also the ones who go radio silent and you don’t hear from for days. It’s like an inverse mathematical relationship y = f −1(x) with y being feedback delivery and x being turnaround expectancy by… On second thought, it’s more like chaos theory: the crazier the schedule, the slower they get back to you.
No one wants your opinion.
Seriously. No matter what you used to do or how lofty your title once was, people really don’t want to hear it. So when they kill an idea, don’t defend it. If they don’t love a direction you love, don’t reexplain it. Maybe they have some criteria you don’t know about. Maybe they have no taste. Either way, they don’t care what you think.
This took me a while to get my head around. Fortunately, I had friends who beat this one into me until I finally relented. Sometimes, I still think people would do well to listen to me. But then like Luke hearing the echo of Obi Wan, I remember the truth “No one wants your opinion” and I stand down.
The truth is, you could have the wisdom of Socrates combined with the intellect of Einstein and they still wouldn’t be interested. Just send in those rich media banner ideas by 3 pm, ok?
You will whiff occasionally.
Casey at the bat. The sidekick in every romcom. You.
SFX: GAME SHOW BUZZER “What are ‘people that strike out’?” SFX: DING DING DING
Sometimes, you miss the mark. Sure, sometimes it’s not your fault. The brief changed along the way. Or they didn’t brief you properly. But sometimes it’s you.
Just hope it’s not your first time working for them. Otherwise, you have no track record or goodwill to fall back on. I try hard to rebound strong in round two, or I can chalk it up to the law of averages, but it hurts. I can still name the ones I whiffed on and I beat myself up about every single one. But you shouldn’t.
Never Be a Dead End.
If I can’t take a gig, I ALWAYS recommend somebody else. There are a couple of reasons why I’ll invest time trying to find what they’re looking for. First, it means I helped them instead of leaving them hanging. Second, it gets me good will from a fellow freelancer. And that stuff definitely comes back to you in a good way. It’s like freelancer karma. Then, I can count on them to return the favor. And in case you’re wondering, (as I worried about in the beginning) I have never lost a recurring gig when I’ve recommended somebody else. When the next project comes around, they always come back to the mothership.
Lead with the ask.
When people are on the hunt for work, most of them have a standard email template they use. It tends to start with some nicety, usually geography related. “Hey (person), how are things in (your city here). I hope it’s not too (whatever the city is known for) there.” I used to do it too. But I was starting to have doubts, and when a fellow freelancer rattled off his version of the same spiel, that was it for me.
Just go direct. Don’t hide behind a bunch of trite goodwill inquiries. Just get to the ask. They know you’re going to ask for something—coffee, a referral, “pick your brain”. You wouldn’t email them otherwise. So save everybody some awkwardness and get right to it. Once you’ve gotten the business out of the way, you can end with a more personal, and hopefully sincere, wrap up. Possibly even geography related.
Send the Email To Yourself.
Here’s an addendum to the previous topic. Want to be objective about your cold call email? Write one and send it to yourself. Open it in a day or two and take a good hard look. And I bet you will tell yourself “Why yes, it has been very windy in my city. Please get to the ask.”
Redacted
Sorry. I can’t give you all my secrets. I hoped these helped, but I have to keep some for myself. I was going to include a couple of them in this article and it hit me, “Am I crazy? That’s my go-to move. I can’t have everybody using that move.” Maybe I’ll include them in “What I learned in Year Six of Freelance.”
Good luck. And stay safe out there.