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How to Effectively and Easily Conquer Tight Deadlines and Commitments

“Hi, I’m Lauren, and I’m a freelance copywriter,” she said fabulously, as she handed him a business card, winked knowingly, and took a sip of her super-fancy champagne.

I’ll be honest, sometimes that’s how I feel when I tell a new acquaintance I’m a freelancer. Their eyes get a little wide, they ask 500 questions about health insurance, and they finally walk away thinking, “Woah, she’s like Indiana Jones!”

Alright, so I’m imagining them thinking that, but I’m not entirely exaggerating about the wide eyes and the questions. The freelance life is a mysterious one to many, and can seem fairly glamorous.

The truth? Well, we know the truth, right? Freelancing is fabulous, for the most part, but sometimes it’s frustrating and stressful. On a good day, I’ll leave those conversations feeling pretty cool, but on a bad one, I’ll leave them thinking, “Yeah, it sounds real cool until you think so hard about a job you’ve procrastinated yourself into a corner!”

Freelancers carry a lot of responsibility on their shoulders, and it’s up to them, and only them, to make sure they don’t drop that responsibility on someone’s (or their own) toes. My goal today is to talk about meeting deadlines and commitments in a way that keeps that responsibility at a manageable level from the get-go.

Prepare like a hippie.

My parents are a totally groovy couple of old hippies, and I’ve been fed a steady stream of their self-help literature for most of my life. I think most of the mantras and advice I’ve heard can be boiled down to this basic philosophy:

“Be honest, set healthy boundaries, and be open to the ways of the universe.”

I would even recommend that you not agree on one you can barely meet. You’re in charge, right? You have the unique opportunity of being able to set yourself up for success. When deciding on deadlines, it’s important to leave yourself a few days of wiggle room. What if your computer dies and is stuck in the shop? What if your pet dies and you can’t see the computer because of all the crying? What if your niece puts laundry soap in the dishwasher and fills your entire house full of bubbles? I’m betting that, in any of these scenarios, it would be nice to have a day to sit back and collect yourself without the worry of letting down one of your clients.

Set healthy boundaries. Freelancers aren’t the only responsible parties in a business agreement. Especially in creative fields such as design or content creation, input from the client is crucial to a successful project. Having to wait three weeks for a client to say “Yeah, I like that shade of green,” or “Can we replace my logo with a photo of my cat?” is not only infuriating, it slows down your project process, interferes with your overall work timeline, negatively impacts your other client work… so on and so forth. Some freelancers even go so far as to set feedback deadlines for their clients and charge fees for the delays. While this might feel extreme for some, the truth is that a freelancer juggling many projects can lose a lot of money on clients who dilly-dally.

How to Effectively and Easily Conquer Tight Deadlines and

Including client deadlines or time limits on feedback in your onboarding process and in your contracts can move some of that shouldered responsibility onto your client. Another thing to consider when setting deadlines is the time zone in which your client resides. That could help or hurt you, depending on where you live. When you set your deadlines, agree on the time zone that gives you the most leeway, so that (although the point is to NOT be scrambling at the end) any last-minute scrambles can be made slightly less-stressful.

Be open to the universe. In this case, we can probably leave the universe out of the equation, but the principle is the same. You’ve got to be as open as possible in your communication with your client. Don’t assume anything. If you think a portion of the project needs more work, tell the client and renegotiate a deadline.

Become an expert in damage control.

We can talk all day and night about preparation, but when you’re drowning in a tar pit of deadlines, hearing “You should have set boundaries in your onboarding!” isn’t terribly helpful.

First of all, you’ve got to learn to tackle the hard stuff first.

You can do all the deep-breathing exercises and stress-relief meditations you can find, but the only thing that will remove your deadlines and commitments is tending to them. Starting each day by knocking out a daunting task will leave you with a feeling of accomplishment antaskd not a feeling of dread. If you need some help, there are plenty of task-management apps out there. My favorite? A totally geeky, totally fun RPG-style app called Habitica.

Treat yo’self.

When you get down to the nitty-gritty crunch-time of tight deadlines, it’s sometimes necessary to bring out the big guns… and by “big guns” I mean rewards. Chocolate from the fancy section. A copy of your favorite Hall & Oates album on vinyl. A big, fat, juicy cheeseburger… whatever floats your boat. If you’ve got something to look forward to, you’ve got a better chance of actually making that phone call/sending that email/ finishing that project you’ve been putting off for weeks.

Phone a friend.

Sometimes your reputation and pride is worth more than the pay. If you’ve run into a rough patch, it can be helpful to hire a fellow freelancer to pick up the slack. There’s no shame in a little friendly outsourcing, and it can build up highly lucrative relationships between freelancers. This can be a delicate situation, though, so it’s important to hire a trustworthy freelancer whose work you respect.

Reflect, rework, recover.

The sweet relief of a finished deadline is always a fleeting one, and it’s okay to relish in that feeling for a little bit. Go grab a high-five from someone, schedule a margarita night, or binge on five episodes of your favorite show… but don’t get too crazy (or lazy). The fact of the matter is that a successful freelancer is a working freelancer, and you don’t ever want to run out of deadlines and commitments.

If you constantly find yourself scrambling to finish those tight deadlines or fending off freelancing nightmares, it’s pretty obvious that you need to make some changes.

After your “deadline freedom” celebration, give yourself the gift of scheduled reflection time. Whether it’s monthly, bi-weekly, or even weekly, a chance to look over your habits and calendar will give you insight into the effectiveness of your process, and provide regular opportunities to improve.

Sure, it’s important to be able to work under pressure. The point, however, is not to make it a regular practice. With thoughtful preparation and a backup plan for emergencies, you’ll be able to significantly lessen that pressure for future projects.

A stressed-out freelancer is easy to spot… and that’s really going to mess up your Indiana Jones-like image.

Success!