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Stuck On a Date - The Deadline Delusion

by Dana Winslow

Has This Ever Happened to You?

Your freelancing business is booming. Or maybe it's not yet – maybe you've just started and just landed your first big project. So you start plugging away – typing up those articles, designing those logos, writing those emails. Or maybe not... maybe you've procrastinated just a little bit (or maybe even a lot) because you know that you have plenty of time.

And before you know it, it seems like every task you finish leads to two or three new tasks. Deadlines are quickly approaching, but instead of feeling uber-confident as you normally feel, you start feeling a little behind. A few days later, the deadline is tomorrow and it feels like there is still so much to do... Now you're overwhelmed and stressed. You forego breaks and meals just trying to get done on time.

And somehow at the last hour, or even last minute, you finish. Maybe you know that this is the best work you've ever done, or maybe you feel a little wonky – like you know that you could have done better if you just had more time. Maybe you find a typo just after sending that article in. Or maybe you've worked and worried yourself into such exhaustion to try to finish that you don't even want to look at another computer for a couple of days.

However you react, it doesn't take long before you're doing it all over again. Tasks are multiplying, problems and delays are happening, deadlines are approaching and your overwhelmed feeling returns for an encore.

Now, you might say that you do some of your best work under pressure. Or you might say that chaos and delays are a part of life that you're able to handle well. Essentially, you find a way to justify everything – the procrastination, the lack of planning, that sensation of overwhelming stress and the fear of missing a deadline. You try to accept it as a strength.

But the truth is that working under pressure – even doing your best work under pressure – is an excuse. This ability is not meant to be a part of your daily freelancing routine. What this ability is supposed to help you through is undue stress or undue pressure brought on through circumstances beyond your control.

It doesn't have to be this way. With some planning and organization, you can meet those deadlines without working in a pressure cooker. In this article, I'm going to show you how.

1. Care About Those Deadlines

First thing's first, and this is probably a given, but you need to care about those deadlines. I mean, you need to really care about the deadlines. These have to be more than dates to you.

To your clients, those deadlines mean more than just money. They mean reputation, prestige, and promises. It's their image on the line, and its an image that they take very seriously. It has to be the same for you. Missing that deadline should mean a small hit to your reputation – and that's something you should care about. As a freelancer, you don't have the backup of a major company or corporation to get your name and reputation out there. All you have is you and your reputation.

So these deadlines, the dates that are at the frontline of your reputation, should be something you care about.

Some of the best freelancers I have met – whether they be writers, SEO experts, site designers or wedding planners – are successful precisely because they take those deadlines seriously. Meeting a deadline is a standard of professionalism that they have set within themselves, not an expectation inherited from their client. And many of them set their own deadlines: if a client wants their project done by Friday, they shoot to have it finished by Thursday.

It's their reputation, their deadline, and their expectations driving them to succeed, and this works the majority of the time.

Work On Your Own Timetable

Of course, if you truly care about your deadline, you're going to also make sure that it's reasonable. No sense in risking your reputation or stressing yourself over an unrealistic deadline. If a client wants it done by Friday but you know it's humanly impossible to be finished before the following Tuesday, well, then it's either time to build a robot or you need to explain to your client why it can't be done before that Tuesday. And then make sure you finish it by Tuesday.

This is my favorite way to set deadlines, personally. I rarely, if ever, accept a deadline from a client. I take their needs very seriously... If they need something by Friday, I will absolutely do everything in my power to get it done before Friday. But even that adds a lot of stress on me. So, before a client even has a chance to tell me, "I need this by..." I let them know...

"I can have this finished by..."

This way, it's my deadline – not the client's. It's my promise and my reputation. I sound that much more confident in my abilities because I set the timeframe, and my clients trust that I know what I'm doing when it comes to my schedule. Plus, there's less pressure on me because I don't have to care about the client's deadline – he already agreed to my deadline. I'm not letting him down or feeling the added pressure of carrying his deadline on my calendar. All I have to worry about is following through with my promise to get something done within the estimated time frame.

Know Your Strengths and Limitations

Having a good sense of your limitations and available resources will help with setting deadlines in this way. This may require you to perform a few reality checks before you're able to accurately map out your strengths and limitations. I usually estimate a little long to give room unexpected problems. When a client tells me, "This is what I want and this is how I want it to work," I'm thinking to myself, "This is going to take me at least 3 weeks," and I'm telling my client, "I can have this done in 3 1/2 weeks."

Regardless of whether you set the deadline or if your client sets the deadline, it's a date that should matter to you. Once the deadline is set, you should have it ranked up there with your anniversary, spouse's birthday and your kid's soccer game. It is something you do not miss, and something that you will regret if you forget.

I know I sound a little pushy right now with this – especially equating your client's logo to your wedding anniversary. But yes, it's that important.

2. Break Up Your Deadlines

Each of your deadlines should actually be made up of three different mini-deadlines. Call them whatever you want:

  • Milestones
  • Proposal, Submission, Review
  • Stages
  • Stooges... ?

Hopefully you get my point. If you want to get your project completed on time with 100% satisfaction, you've got to break down those deadlines.

The absolute deadline, the one that's circled on your calendar in bright red marker to match your spouse's birthday, is the day by which the project absolutely needs to be finished and completed. This is the deadline that you and the client agreed on (whether it came about as a request from the client or as a promise from you). This is the day that the client expects to get to his site to see the new design working as promised; the store should be working, credit card payments processing, and images popping-up very nicely in that shadowbox.

That is the deadline that both you and the client care about the most. After that deadline, you can cross the project off your to-do list and get paid.

But before you can reach that deadline, you have to first submit a draft to your client, allow that client to review the project and request any revisions or fixes, and then you can cross that finish line. I mean, really, if your client needs a project done by Friday, what good does it do for you or the client if you submit it on Friday, only to then be emailed on Monday because it wasn't quite right? Did you really make the deadline then? No. You finished on Monday, not Friday. You were three days late, and you're already behind on starting your next project.

So, as you set up your important deadline, break it down and make sure you include enough time for those other two additional deadlines. Be sure to discuss all three deadlines with your client, and follow through on every one. Give both you and your client enough time to take necessary actions between each one.

Deadline A / Milstone #1 / Stage 1 / Proposal / Draft / Moe – This is when you will initially send the project to your client, and it should be as close to finished as possible. It's sort of like a progress report; it allows the client to see how far you've come. If there have been any unexpected problems or delays, it also allows you to demonstrate those problems to your client and explain how you plan on overcoming those problems while still meeting the deadline. Finally, this allows your client to review what's going on with the project and ensure that it's what they had asked for. If something isn't working quite the way they expected, this gives them the chance to make adjustments to their plans.

Deadline B / Milestone #2 / Stage 2 / Review / Critique / Larry – This is one of my favorite deadlines because it's not mine – this one belongs to the client. For this deadline, after you have submitted your project's draft, you wait for the client to contact you with his or her thoughts, questions, reviews and any possible requests. Of course, just because it's the client's turn to contact you doesn't relieve you of all responsibility. If it's getting close to this deadline and you're still awaiting the review from your client, you need to email or call to follow up. This will help ensure that you still have time to review any questions and address any revisions requested by the client. Additionally, this will let your client know that you care about your deadlines and about his or her project.

Deadline C / Milestone #3 / Stage 3 / Completed / Revisions / Curly – As we've already discussed, this is the final stage of your project. This is delivery of the project with all the finishing touches. Everything works exactly as requested and expected, and the project is complete as originally contracted. From here, if there is more work to be done, it should be as part of a new project – which may even require a new contract. But the original needs of the client are fulfilled and the client is happy with your work.

Of course, if you're doing everything right – listening to and anticipating your client's needs, following through on your communications throughout the project – then when the review comes back, the client will already be satisfied with your work and may even say, "This is it! You've done it!" This is a great feeling, because you haven't only finished early, but you've guaranteed a happy client and can now add this spectacular project to your portfolio with pride.

3. Burn the Candle Where It's Meant to be Burned

Of course, this is just my silly way of reminding you not to burn the candle at both ends. Stop and take regular breaks when you need to. Yes, your deadlines are important, but so is your sanity!

All too often, new freelancers work crazy hours. When I first started freelancing, I was working close to 18 hours a day, 7 days a week. As you can probably guess, it took me about 2 days to get completely burnt out and want to quit.

It is not healthy, mentally or physically, to sit tied to a computer for three quarters of your life pounding away at deadlines – but it is really easy to get sucked in to thinking that you have to, just to meet your deadlines. Unfortunately, your work will start to suffer before you even realize that you've burnt yourself out.

Take regular breaks, schedule your hours of operation at reasonable times, and stick to those schedules. Yes, there will be days when a paricular project may need some extra attention that will force you to work a little later than normal – but that should not be a daily event. Schedule breaks, birthday parties, and take your spouse out for that anniversary. Go watch your kids play soccer or take some friends out to lunch.

Find a schedule that works for you and stay with it. Some people work better doing 4 days a week at 10-15 hours a day and then taking 3 days off... Others work better in 5- or 6-hour shifts for 6 days.

Personally, I do the majority of my work at the beginning of my week, then take a break and finish out the week with lighter work:

  • Monday through Wednesday: New clients, site development, major upgrades, graphic work.
  • Thursday: My day with my husband – no phone, no people, no work for either of us.
  • Friday: Follow up with clients, emails and schedules, minor upgrades
  • Saturday: Day off with contact; I usually have friends or family over, but my clients know that I will have my phone with me if they need me.
  • Sunday: Finish up any loose ends, module and / or database upgrades, progress reports and billing.

Having my weeks scheduled out this way allows me to track everything that is going on with each of my clients. They also know and understand which days I am available for them and which days I am not. I know it's a common thing to think that a client doesn't care about your schedule – and that's a little true. They really only care about your schedule if it interferes with their schedule. But if you can make your schedule work with them, they'll be flexible.

4. Get Your To-Do Lists in Order

I am a huge fan of ToodleDo... so much so that I was actually a little jealous when I found that site, and realized I hadn't thought of or built it.

ToodleDo is a task management site. It's free to sign up for and offers applications for most of your mobile devices as well – including tablets. This site makes it very easy for me to organize my tasks into easy-to-manage lists. You can set up categories for your lists and tag each task with a priority level. The best part for me is that you can add as many tasks at the same time as you need, setting them up to repeat as often or as rarely as you like. Quite often, I even copy-paste items and requests directly from emails that my clients send me into new tasks, which takes less than 5 seconds to do... So come Monday morning when I sit down at the computer, I can see exactly what my goals are for that day and can check them off one by one as I go through them.

Since my mornings usually start around 6 AM and I don't get my first tea until around 9 AM, I usually need the extra organization that lists can provide to get started right away....

I got into the habit of writing down each task for a simple reason – perspective. Have you ever had a feeling that there is just too much going on around you? Like you had so much to do and you just weren't going to have enough hours in the day to get them all done? And yet, if you write down everything that you have to do... it never looks like it's all that much.

So, I keep everything in lists. I get a weird sense of accomplishment every time I can cross something off that list, too. And when I start feeling like I have more tasks to do than time to do them, I look at the list and it helps me to remember how small some of these tasks really are – which gives me a sense of renewed hope and lowers my stress just enough to get it all done.

5. Evaluate Your Progress

Every night, just before I finish at the computer for the day, I take a look at my to-do lists and see which tasks I've finished and, if applicable, which tasks I was not able to complete. If I was unable to finish something that I had intended to get through that day, I start to analyze why. Were there problems? Was it within my skill set? Were the problems something that I had anticipated or were they surprises? Was I distracted? How did I spend my time?

This might seem like I am beating myself up, but what I'm really doing is reviewing my strengths and limitations. I'm trying to identify whether or not that incomplete task wasn't finished because I couldn't finish it or if it was something else entirely. Perhaps I was just distracted that day (every one's entitled to a bad day here and there, including freelancers) or maybe a family emergency came up that took me away from work. Or maybe I just scheduled too many tasks and I wasn't able to meet my own demand.

These are important things to track if you want to accurately set your limitations and be able to consistently meet your expectations. Yes, you always want to strive to do and be better – but you also need to reach your goals if you're ever going to feel accomplishment. What sense is there in setting unreasonable goals, and then feeling like you've failed completely when you can't reach any of them?

This also lets me evaluate how I've spent my time that day, and whether or not my time was spent efficiently. If I was not working efficiently, how could I have done better?

And at the end of the day, if I did my absolute best, made the best possible use of my time, and still couldn't get that one task done, well then – now I know that I scheduled too much for me. Of course, it will get added to the next day's task list (which also takes about 3.2 seconds, thank you ToodleDo!).

The other thing that this regular evaluation will allow you to do is measure how well your are making progress toward your deadline. If any possible problems start popping up that might delay you from meeting your deadline, you'll still be able to make adjustments as necessary so that your deadline can be met without issue. And if it's starting to look like you might have to miss that deadline, it's vital that you contact your client and let them know as soon as possible. Daily evaluation of your progress and performance is a great way to tell early on whether that deadline remains reasonable, or if enough problems have popped up to necessitate changes. Again, no client wants to hear that you can no longer deliver on what you promised. But most clients can handle that news much better if you're able to tell them 2 weeks ahead of time that, because of their server issues and buggy plugins, you may need another day or so to complete everything.

And last but not least, if you want to ensure that you make your deadlines...

6. Kick Your Family Out

Okay, don't kick them out of the house – that's rude and probably illegal! But you definitely need to talk with them and make sure that they understand you're working.

Working out of the home is tough, especially if you have a family. Spouses, kids, parents... they all see you as being at home – and if you're home then that means you're available for their questions, stories, requests, and package deliveries.

My father happens to live in my house right now, and he is notorious for this. Whenever he has something being delivered, he just tells them, "Oh, my daughter is home, she can sign for it." Though small, this 5 or 6 minute distraction can completely wreck whatever track I'm on. He's always coming around to ask a question or tell me about something. Despite multiple conversations with him on this topic, he unfortunately continues to be my primary problem area when it comes to working from home.

Sometimes, these little distractions from your family will be welcome. After all, who wants to miss it when your kid does something adorable across the room? Or who doesn't want to hear about how great their spouse's day went? But you need to keep them under control. And this means setting up limits from day one – when you're in front of the computer you are not home... you're at work. And your family should respect that time just as if you were out of the house and in an office.

On this, my father is a lost cause. I have even gone so far as to move my computer into a spare room near the attic, and still he comes. I just think that he's slightly more dependent on me than he cares to admit, and he doesn't quite understand the concept of working at home just yet. And that's okay – to him this is home, not an office. But for you... for you there's hope! Talk to your family and set up those ground rules. There will be times when they forget that you're not really there; but use occasional gentle reminders and you'll see fewer and fewer interruptions.

Ready... Set... Be Productive!

Follow this advice and you'll see a decrease in pressure while working to meet your deadlines. You may still have a couple of problems on ocassion – especially if a deadline is unreasonable or if unforeseen circumstances delay your results. But the endless feeling of anxiety over your deadlines will begin to relax, and you'll soon notice just how much better your work is and how much more you're able to accomplish!

No one works well if the pressure never lets up. Sure, you can last months at a time – maybe even years. But eventually, if there's never a break in the pressure, you will crack. And when that happens your work will suffer. That's bad for any professional, but for a freelancer it can be disastrous.

Have you successfully implemented some of these ideas in your own freelancing career? Have stories to share? Please let us know in the comments below!

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