The Truth About Deadlines

April 4th, 2007 | Posted in Freelancing

Good news! I’m not dead and I’m done with that MAD job. I’ll share the art on the blog upon publication next month. That may have been the shortest deadline I’ve gotten so far from them.

Ahhhh deadlines… the bane of the freelancer’s existence. Every freelancer wrestles with deadlines, and we all complain about them. We complain about how short they are or how they are not flexible or not realistic. They are imposed on us and stress us out. How they eat into our time and brains and creativity, or make us compromise on aspects of our work to meet them. Deadlines are the enemy we are always railing against… or are they?

The ugly truth about deadlines is that they are almost always our choice and fault as freelancers. Yes, occasionally real life catastrophes get in the way, but really those are few and far between. I can’t ask a client to extend a deadline because one of my kids has a choir concert I forgot about, or some other job becomes more complicated than I thought it would be. Those aren’t valid reasons to blow a deadline. On the other hand, if some emergency really does happen then I would expect a client to understand… for example if I was to unexpectedly die during a job, I’d would expect my client to extend the deadline by several days at least.

Occasionally (The Lovely Anna might say more than occasionally) deadlines issues are a result of procrastination. I’m not the best at getting a head start on things, and I seem to need a little pressure to keep myself focused and on task for a job. I think when my parents gave the “never put off until tomorrow what you can do today” lesson I was busy trying to finish something I was supposed to do the day before and wasn’t listening. Most of the real deadline problems aren’t a result of that, though… that’s just self inflicted drama.

Most of the problems with deadlines are result of a taking on too many jobs at once, or one with a ridiculous deadline. Both of those issues are directly within my control. I should turn down jobs like that, but I very seldom do. Few freelancers I know have the wherewithal to refuse work no matter how short the deadline or how much they currently have on their plate. This is true even if taking on the job means hardship, lack of sleep and being generally miserable for several days in order to get it all done. Why do we do this to ourselves? It’s all about fear.

When talking to someone with a 9 to 5 job about freelancing and deadlines, I invariably am asked why I take on jobs that cause me to pull all nighters and miss opening day ballgames. Unless you freelance for a living, it’s almost impossible to explain. Personally I can’t remember the last time I had a real job, where I punched in and out at specific times, did my work and then went home. If I didn’t get my work done on Monday, then I just resumed on Tuesday and my paycheck still arrived in full regardless. I try to tell my 9 to 5 friends what it’s like to not have a paycheck that arrives every other Friday in the exact, expected amount. I try to get them to understand that when I do have a job to get done by Monday and it isn’t done, I don’t get paid for it. It’s hard for them to comprehend that when that telephone rings with another job I will take that job, within reason, because there is always an underlying fear that this will be the last time the telephone rings for a month or more. It’s that fear that makes freelancers accept the short deadlines and the multiple jobs.

I have gotten much better over the years at turning down jobs. Certainly I have no problems at all turning down a job that doesn’t pay well enough no matter the deadline or my present workload. I got a call not too long ago from a daytime TV soap opera magazine which shall remain nameless wanting me to do a full page illustration for an article… for $250.00. At the time I had virtually no jobs on the board, but I turned that one down without a thought. I also turn down jobs regularly that ask me to do something that is not what I normally do. For example I get a few calls a year to design logos or do an illustration of a building or something. I don’t feel the need to do something alien to my focus like that. That said, when the job and the pay is within my usual spectrum, I still find it very hard to say no even when the deadline and/or my current workload is an issue. When I do turn down a perfectly good job like that, I always feel like I just dropped a touchdown pass or struck out with the bases loaded. Maybe that was going to end up being a long term client, and they’ll never call me again. You can’t do it all… but you want to.

With MAD, almost no deadline is too short. I let them know long ago that they could count on me to pull off impossible jobs and be the go-to guy in an emergency. They took my word for it. I’ve only turned down one MAD job since I started with them in the fall of 2000. I got that phone call when I was driving on my way to Massachusetts with a trailer full of theme park concession equipment and fixtures to spend two weeks setting up a new caricature and airbrush tattoo operation. No way could I do that job. There are only a few other clients who I will not say no to. The rest I’ll weigh the job against the pain and suffering before deciding to take it on… then I usually do it anyway. Fear. It’s powerful.

In all fairness, my theme park/retail concession operations provide a financial foundation so I don’t need to be as concerned as your typical freelancer about the house payment or my kid’s braces. Still, my freelance income is a big part of my overall income and there is still that nervousness about finding myself in a dry spell with no jobs and a dwindling bank account. The funny thing is that the fear of such a spell is not abated by the knowledge that the telephone always rings again in short order and that there is very seldom ever a time when I do not have jobs on the board. Yesterday I got assigned a new poster job only hours before I finished the MAD parody.

That reluctance to say no is still there no matter what. Sometimes it makes for a hectic week, but no matter how bad it gets it’s always better than sitting there looking at the telephone waiting for it to ring.


  1. mengblom says:

    “If I didn?¬¢‚Äö√ᬮ‚Äö√묢t get my work done on Monday, then I just resumed on Tuesday and my paycheck still arrived in full regardless.”

    Time out. Even us 9-to-5’ers have deadlines we’ve gotta hit no matter what. Blow enough of ’em, and you won’t be collecting a full paycheck…or ANY paycheck for that matter. Sure…some jobs don’t have much of sense of urgency (been to the local post office, bank or Department of Motor Vehicles lately?), but plenty more of ’em have all kinds of pressures, weird hours and impossible deadlines. The next time you’re up at 3:00 burning the midnight oil, I might be across town somewhere at a printing press inspecting a print job….or in to the office three hours early to hit a deadline for a big Target presentation. Or staying late into the evening to finish up a display for a show. Etc, etc, etc.

    I completely understand and respect the rigors of freelancing…and fully acknowledge there are unique pressures that you face that I don’t have to. But, at the same time, life in the 9-to-5 world isn’t quite as peachy and carefree as freelancers might imagine it to be.

  2. Tom says:

    Yikes, no offense intended, Mark. I would expect that anyone reading my post would understand that all jobs are different and OF COURSE there are plenty of pressures involved with 9 to 5 jobs and OF COURSE you can get fired if you don’t do your job properly or meet your employers expectations. That’s true of virtually any job, even the DMV. Give me a break and a little credit.

    However there is no question that having a 9 to 5 provides a security that you never have as a freelancer. You don’t get up every morning wondering if you still have your job that day or not, or if next month’s bill payments are going to be a breeze or a nightmare. I was endeavoring to describe what it’s like to have no job security whatsoever while trying to raise a family in today’s economy, and how that insecurity is the driving force behind accepting work under difficult circumstances.

    With all that said, I’ll take my freelancing job over almost anything. I love it and it keeps life interesting.

  3. mengblom says:

    No offense taken, Tom.

    “I would expect that anyone reading my post would understand that all jobs are different and OF COURSE there are plenty of pressures involved with 9 to 5 jobs and OF COURSE you can get fired if you don?¬¢‚Äö√ᬮ‚Äö√묢t do your job properly or meet your employers expectations. That?¬¢‚Äö√ᬮ‚Äö√묢s true of virtually any job, even the DMV. Give me a break and a little credit.”

    Woah. Sorry.

    I guess I misunderstood when you wrote about talking to various people who couldn’t possibly comprehend why you would have to work so hard and so dilligently. But…I guess there ARE some pretty dense people out there.

    My bad.

  4. shawn says:

    Your post really rang true.

    Before going freelance a few years ago, I knew some people who had been doing it forever, and I always cringed when thinking about the uncertainty of the next paycheck or paid vacations. I was a happy worker bee, then gradually got into the position to change that and traded in my 9-5er for the freelance world and I couldn’t be happier. Some of my clients are places I worked for full time, so in way it feels like I still work there, but without the inner office politics and daily grind. (and health benefits…)

    9-5 security and benefits are great, the flexibility isn’t. I like being able to catch an afternoon matinee before having to work into the night or do the grocery shopping while everyone else is working.

    There’s so many arguments for either side. I personally find that I’m more satisfied and work harder for myself at home than in an office environment for a company. The trick is time and money management.

  5. Lar says:

    Another superb article, Tom! Saying ‘no’ to a job always ignites the fear that that may be the last phone call for a job you ever get. As you point out, the phone will ring again and the few times I’ve been strong enough to turn down a job, inevitably another, better one, comes along (although not always without a little work on my part).

    One of the real struggles with being a freelancer is finding those new clients. You are in the enviable position of having regular clients like MAD, as well as a professional reputation that preceeds you. I bet you still self-promote regularly though, and that is undboubtedly a big part of your success.

    Thanks again. Later!

  6. cedricstudio says:

    Great article Tom. You are dead on when you say that ultimately we as freelancers bear a large part of the burden because of the jobs we decide to take on.

    I too find it difficult to turn down work, but I’ve learned that if I am *really* busy it is better for me to be honest and tell the client how busy I am rather than take on a project and make a promise I can’t keep. Sometimes I can negotiate a deadline extension, and if not I think clients (at least the good ones) respect me for saying no rather than missing a deadline or turning in sub-quality work. They’ve been burned by enough freelancers that they will often respect my professionalism and eventually call me back.

    But like you, I have a very difficult time saying No. “Hey, I’ll give you X dollars to sit at home in your pajamas and do something you love” is always a hard offer to turn down.

    I’ve recently started carving out 30-45 minutes each morning to work on self-promotion (i.e. updating my website or sending e-mails to specific clients I’d love to get). Making this a habit has gone a long way towards alleviating my fears of work drying up.

  7. totopo says:

    “I guess there ARE some pretty dense people out there.”

    Now hold on just one minute! I take personal offense to that. I am a dense preson and I am in no way pretty!

    Deadlines suck… noow, back to mine!


New profile pic courtesy of my self-caricature for the Scott Maiko penned article “Gotcha! Mug Shots of Common (but Despicable) Criminals” from MAD 550

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