How to Never Miss a Deadline

deadlinesI’m going to let you in on the secret to keeping clients for years and getting more referral business than ever. Stellar portfolio? Sure, that helps, but no. That’s not it. It’s simpler than that. Here it is:

Never miss a deadline. Ever.

One of the most common complaints that clients have about freelancers is that they’re not reliable. What is this complaint based on? You can bet that missed deadlines had something to do with it. The project took twice as long to complete. Or you met the deadline, but it wasn’t tested for bugs. Perhaps this complaint was due something simple like failing to reply to an email in a timely fashion. These are all variations on the same key element of reliability. That is the ability to deliver a finished product, on time, every time.

I certainly have first-hand experience with this. Over the course of my freelance web design career, I often need to sub-contract other freelancers to help out with time-sensitive pieces of my client projects. The sad truth is that more times than not, the job isn’t done on time. I end up picking up the slack myself, or doing damage control with my client who expected their website to launch a week ago. Will I re-hire a freelancer who missed a sensitive deadline? Chances are, the answer is no.

This Is Your Opportunity

Given the fact that too many freelancers have a lack of regard for deadlines, it’s hard not to see the massive opportunity this creates for you. This your chance to set yourself apart from the crowd. You can spend hours making your portfolio website shine, but the reality is there are tons of beautiful portfolios out there. Yours should be great too, but it won’t guarantee the one thing that every client is really looking for: Reliability.

If there’s one skill you must hone to perfection, regardless of your industry, region, niche, or price range, it’s your reliability. And the best way to prove you’re reliable is to meet every deadline thrown your way. Clients value this a lot more than you might think. Deliver their project on time, and they are much more likely to love the results than if it were late.

Plus, your clients will jump at the opportunity to recommend your services to their friends and colleagues. As we all know, the best way to attract new business is by generating referrals. And the best way to do that, is to be reliable.

How to stay on track and on time

I think I’ve made my point about the importance of meeting deadlines. So how do you go about doing this in your day-to-day work-flow? Here are a few tips that help me stay on track and never miss deadlines:

  1. Set padded time estimates. Don’t give time estimates based on how many work hours it is for you. Set estimates based on your overall schedule, taking into account all your other projects. You also need to take into account extra time for testing, tweaking, and polishing. So if a project will take you two work days to complete, tell the client it will take two weeks. Of course, you need to be reasonable, but if you’re client is professional, they will understand the importance of thoughtful timelines. This brings us to the next tip:
  2. Thoughtful communication. Effective client communication is all about managing expectations. Sometimes it’s best not to be so precise about an upcoming deadline. “I expect to have that ready for you early next week” might be better than “You will have it by Monday, the latest”. The former gives you a bit more flexibility, while offering a reasonable expectation for the client.
  3. Break large projects into bite-sized milestones. Many of my projects can last several months. So how I do make sure things stay on track? Split them up into short-term milestones, each with their own deadline. Whether or not these deadlines are internal or if they involve a client review, it’s good to set clearly defined calendar goals for yourself (or your team). Don’t make your project revolve around one final deadline, months down the road. That’s too far ahead and will likely result in cramming everything just before the deadline. Split it into weekly or daily goals, and knock them out one by one.
  4. Use Getting Things Done (GTD) software. I’ve tried several apps before landing and sticking with Things. It’s perfect for visualizing my to-do list, separated by client or project. It fits nicely into my work flow, allowing me to prioritize tasks, and set deadlines for time-sensitive ones. I keep it open during the work day, reveling in the moment I get to place that check next to each task.
  5. things

I even have a backup system for items that are extremely important and time sensitive. That system is Google Calendar. If I know I can’t miss something, I’ll enter it in my GCal and set an email or mobile reminder for it. Since I’m constantly connected, this should keep me covered in case something falls through the cracks.

Do You Meet Your Deadlines?

How do you make sure you’re on top of your deadlines?

Share your tips in the comments!

Image by wwarby


  1. says

    Thank you Brian for the well informed article on project collaboration relating to the system development life cycle. I agree being reliable and maintaining professionalism is key to freelance success.

  2. says

    Great writeup! Thanks! I would add another one to the list which is to prioritize your projects making sure you’re getting the most important stuff done first. It’s easy to piddle around on the smaller things for hours because it’s ‘too much effort’ to dive into the big stuff. And then when the deadline is looming you’ve got all these small things done but the big kahuna is still staring at you in the face.

  3. says

    I ussually let the client know that the project will take 4-6 weeks to complete, that way I have a lot of time to finish it up.
    I agree with the tip in this article that you should never say that you will finish up by that day. Rather early in that week works bettter.

  4. says

    @Chris – Yes prioritizing is key. In fact, I find it’s the lower paying clients that often eat up the most time because they tend to require so much hand-holding (phone calls, emails, etc.).

    @Lucian – Indeed. Always pad your time estimates to allow flexibility in scheduling and also for unforeseen set backs.

  5. says

    Hey Brian, thanks for this useful post! I totally agree. My clients are blown away when all I’ve done is stick to the agreed schedule. Apparently, freelancers who complete projects on time are a minority.

    My problem with padding deadlines is, I tend to procrastinate until the deadline is near. Which makes the padding virtually useless.

    I will definitely check out Things. I’ve been looking for something like this for the longest time.

  6. says

    Well said and nice points are clubbed here. Prioriting the project and broken into parts will save your time and helps you to manage the project and you will be able to complete it on time.
    today i receive the project and working on it to be completed before time. Hope i could finish it tonight

  7. says

    @Lexi – I must admit. I tend to keep things until the last minute. But sometimes I mark it due ahead of what I promised the client so that I’m all set when the deadline arrives.

  8. says

    Great article, Brian. Missed deadlines are the bane of any client’s existence, and you don’t want to be the one facing the wrath when you’ve missed it. I find many clients are flexible enough and provide a rough time estimate themselves of when things need to be completed, but it makes it all the more important to keep to dates when they are specific about when something is due (given it is reasonable of course).

    However – I find that in most cases where deadlines aren’t met the client hasn’t provided the necessary information, content, feedback, etc. to complete the job. So, may I suggest one more point, which probably fits in well with your Thoughtful Communication section, is that you have to effectively communicate that timelines are also based on the client doing their part in order to complete the project. If they are going to set a date for you, you have to do the same for them. Get me X by this date, or timelines will be pushed back by Y amount, for example.

  9. says

    @Carlos – great point. I have had many deadlines pushed as a result of delays from the client’s end. For the most part, my clients have been 100% understanding of this.

    I also recommend adding a note about this in your contract and/or proposals — that various things can affect the final delivery of a project, including the client delaying materials, feedback, etc.

    It also ties into the way I communicate timelines to the client. Instead of saying “This will be done three weeks from today”, I might say “This will be done three weeks from the time I receive all materials from you”, or something to that effect.

  10. says

    Of course, I’m going to be bias, but I definitely think that Clutterpad is one of the best ways of not missing deadlines and getting your projects done on time. That’s why we created it – so we can organize our own projects and not miss deadlines.

  11. says

    Great post and comments!

    I would add that time management and knowing who you are and your skill level is key to being reliable.

    From my experience, we can all say we would like or need to be reliable, but actually knowing how to be reliable is at the core.

    The 4 that are mentioned are excellent starting points.

    Looking forward to the next post.

  12. says

    Brian, you are so right about making deadlines! I’ve also found that making deadlines (every time) also makes a huge difference in holding clients to their commitments. If you don’t make the deadlines you set, then why should the client? I know a few freelancers who tie their billing to deliverables–they do it to help motivate themselves to make timelines. It’s extreme, but at least these creatives discovered their own secrets to never missing deadlines.

  13. says

    Thank you for the great article/tips! I immediately clicked on “Things” to check it out and was sad when I saw that it is only for Mac. Does anyone have tips on such tools for PC’s?

  14. says

    I personally make it a statement to clients that deadlines are deadlines and I will never miss one. Now, some clients tend to need lots of changes and hand holding, and they push the deadline back through this, so I have missed deadlines because of client insecurities, but great article and tips anyway! I am curious as to how padding the deadline works when most clients I have had want a hard deadline…

  15. says

    @Matt – Padding the deadline is my normal practice. Of course, a freelancer’s padded deadline should be a faster turnaround time than that of a larger agency. Agencies always deal with pointless meetings, bureaucracy, etc. So if the client is used to dealing with agencies and they hire me (a freelancer), they should be pleasantly surprised with my turnaround time.

    If they require an extremely tight deadline, then you can explain it will require an expedited fee. If they accept, great, more $$. If they reject the fee, you’re probably better off passing on the project.

  16. Jim says

    As someone who occasionally hires freelancers and does a good deal of writing (and proofreading) myself, I’m as put off by sloppy writing as by missed deadlines. For example, the use of an apostrophe to form the plural of “client” would quickly make me a former client.

  17. says

    Good post. I, too, got excited reading about “Things”–my old time/project mgt tools just not working for me–only to have my hopes dashed, discovering Things looks to be Apple only. Moi? “I’m a PC” + “Droid does.” Will dig further, hoping to find PC version in the works…? Meanwhile, might you recommend your 2nd or 3rd fave GTD software/apps that might be PC-friendly? And I will def look into Google calendar. Thanks for the “timely” tips! :)

  18. says

    @Christine – Pretty sure Things is Mac + iPhone only.

    Other GTD apps to look into:

    – Remember the Milk
    – Teux Deux
    – Ta Da List

    These are good because they’re all web-based, which is a downfall of Things.

  19. says

    its really true its difficult for a freelancer to get jobs, the major reason for that is some says freelancers are not reliable they are not ready to keep their promises, they will never finish work on time, these things are to be changed. It can changed only if the freelancers can finish the work on time and make sure u take a work only if you are sure that the work can be finished….

  20. says

    Excellent points. Reliability is absolutely the #1 concern of clients. The true kiss of death is missing your *first* deadline with someone. As a former editor, I simply wouldn’t trust you if you did that to me. (Sort of like in court: Once a liar, always a liar.)

    There is, however, a slight corollary to the never-miss-deadlines rule: The person who ALWAYS makes deadlines will receive a lot more latitude from loyal clients on those rare occasions when something happens to make a deadline impossible. The client who has experienced your excellent track record will know you’re not messing around, and will accommodate your request.

  21. harry says

    For GTD software, have you tried GoalsOnTrack? It’s a goal setting and task management app and has worked very well for me. It saves me a lot of time in keeping track of my goals and most importantly it helps me better organize my daily todos towards achieving my goals.

  22. says

    Never missed a deadline, and I hope I never will. This is way too important to mess around with…
    These tips are very helpful, especially for large and complicated projects. Thank you for this great article!

  23. says

    Brian, I looked at the web-based GTD you recommended and they’re great. But I was wondering if you knew any desktop apps with the same functionality. Things looks great but unfortunately I’m on a PC.

  24. says

    A very thought provoking article Brian. You are right that we freelancers are thought as guys who never meet the deadlines. I have been freelancing full time for 6 years from my home since I left my regular job and thank god for that day when I took that decision. Generally, in 95% of cases I have met the deadlines. In some case clients are slow in organizing pictures or text for their website and are busy in their business. Only in those rare cases project is delayed.

    I believe in the power of communication. A perfect communication can help you even beat the deadline. I find my Blackberry very very useful for that. Clients demand quick assurance than quick work at some stages of the projects. Moreover if you have discussed the project fully in advance with proper inputs in the beginning things hardly get struck.

    And to quote Tears for Fears “Break it down again” is my Mantra when I work for slightly big projects. So when it is all mixed up, better break it down :)

  25. says

    @Paul – Sorry, I don’t know of any for PC (I’m a mac). However, I know many people strongly rely on Microsoft Outlook to keep track of calendars, to-dos, email-reminders, etc.

    I’d also highly recommend Google Calendar, although that of course is web-based.

    I rely on Things, but I’d much prefer on a web-based solution so that I can sync with my iPhone and other computers.

  26. says

    @Jay – Indeed. I very much rely on my iPhone to keep in touch when I’m out of the home office. I’d add that I intentionally keep the “sent from my iPhone” message in the signature. I want my clients to know that I’m staying on top of it, even from the road. Every extra bit of reassurance that they’ve hired a reliable freelancer always helps.

  27. says

    As someone who’s been on both sides of the deadline (the one assigning and the one writing), I’ve become a deadline fanatic. Yes, there’s usually some wiggle room on the assigner’s end (if she’s a smart assigner), and yes, you should still do everything in your power to meet said deadline. Or, better yet, be early!
    I follow the same tips you listed, but I rely more heavily on calendar reminders (Google and iCal) than on a software program. Things looks interesting, though, so I may give it a whirl. Thanks for the tips!

  28. says

    Thanks Brian for your article. You’re really on target with this. Some of us who are not used to seeing things from the buyer’s point of view need to be reminded of these things. Being late or not getting the job right is like having to wait a long time in McDonald’s drive thru or go back because the order wasn’t right. We might put up with it once or twice but after that we won’t be back.

    About “Things,” I was teetering on the fence about buying it but your recommendation may just help me over the fence.

  29. says

    Here’s a suggestion for people new to freelancing who have trouble estimating how long a task will take:

    All engineers keep a log book, which is like a diary of the work they do, as they’re doing it. They religiously jot down information as they’re figuring things out, and they record the time at the beginning and end of major tasks.

    Taking notes this way is a hard habit to get into, but it’s one worth acquiring. If you’re constantly jotting down your problem-solving ideas and results–and recording the time (all in one book, so you don’t lose your notes)–soon you will develop a very good “feel” for how long particular tasks will take. Then you’ll be able to give more accurate estimates for how long a job will take to complete.

  30. says

    @jjdebenedictis – I like this idea a lot!

    I’d suggest going the extra step and keep a public personal blog. Web developers do this a lot as they are constantly solving technical problems and posting their solutions (with code snippets) on their personal blogs. Not only do these types of posts receive great search engine traffic (“how to I solve [enter specific problem here]?”), your own blog archives can be a fantastic resource for your own reference.

  31. says

    I have always found that if you pad your lead times you need to remember why you did. don’t get comfortable and slack because you gave yourself and extra few days.



  32. soulshock99 says

    Thanks for the excellent article! I was wondering what other freelancers do when clients miss deadlines and this further delays the project. In my contract, I have a clause that basically says that I can charge an additional fee to the client in the instances where their delays drag it out and/or begin impacting our other clients. With that said, is there a standard fee or project % that is recognized as fair? Or how do you all deal with client delays in terms of billing? Thanks everyone!

  33. anamika says

    Hi , its a great post but saddly I miss too many of my deadlines though my work is good and due to that I do get grace time and my clients are very flexible , but I havent to improve this habit of mine I always rush my work on last moment but thats because I love my work and i put every detail in it but in last everything falls on my head . I dont know how to manage 2 to 3 projects at a time as I am a flash animator hence you can imagine the work I get is not small they are quite big . Please help I tried to find a solution but every time same thing happens . :(

  34. says

    great article i have ever seen in my seo 5th year of career, sometime clients are so much worried about these kind of useless movement but everyone should aware from this
    article sounds great buddy

  35. John Doe says

    Being reliable is the HARDEST THING EVER. I’m not even reliable to myself: I don’t achieve the self-improvement goals I set for myself. I am a coder and I have caused pain to multiple clients by goofing off. I am a monster.

  36. says

    Hi! I’m at work browsing your blog from my new apple iphone! Just wanted to say I love reading through your blog and look forward to all your posts! Keep up the fantastic work!


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