Productivity For Creatives

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A few weeks ago, I shared a list of things I got done in a one-month window.

And it generated a lot of conversation. A lot.

The point of that post was to say I’m no different than any other person who hunkers down and “does the work.” We are all capable of getting more done than the average bear when we truly commit to making things happen.

The  word “Pro,” for those who got it, was actually an allusion to Steven Pressfield’s The War of Art, where he speaks about the difference between Pros and Amateurs in the creative world.

As some of you pointed out in the comments, though creating a habit of “doing the work,” though, isn’t quite the entire equation (thanks for keeping me honest).

There’s a pretty mission critical element I left out…

Knowing which work to do.

It’s one thing to sit down and quite another to sit down and know which is the small slice of the work that will yield the majority of the benefit.

So I thought it might be helpful to share the approach of one of the most productive creators I know,’s Charlie Gilkey. Charlie, for those who don’t know him, is a productivity genius who works largely with creative professionals. And he’s become my go-to person when I’m having trouble figuring out which way is up.

So, here’s how our conversation unfolded…


JF: What do you find to be the biggest obstacles for creatives/entrepreneurs in turning actions and outcomes.

CG: Before I answer that question, I wanted to say thanks for the interview. I appreciate the conversation and I hope it helps some of our peeps start building some momentum rather than spinning those creative wheels.

If I had to say what the top three challenges are, I’d say they’re

  1. trying to do too much at once,
  2. trying to get results too quickly, and
  3. not quite having enough of a strategy under what they’re doing. Let’s handle each in turn.

Time and time again, what separates successful entrepreneurs and creative professionals from the struggling ones is that the former ship and get stuff done. One of the best ways to ship and get stuff done is to focus on a few key projects and activities and landing them. The very same hypercreativity that drives small businesses is the hypercreativity that can stifle them if it’s left unchecked.

Trying to get results too quickly fits in here because many creative people can’t tell themselves “Not Now.” There’s a fundamental difference between seeing that not doing something now doesn’t mean you won’t ever get to do it, but that’s hard to understand when you’re first starting out. Every idea has to get developed right now, which means few ideas get developed into fruition.

And here’s where strategy fits in. Knowing which few ideas to work with now, which to do next, and what to do after that helps glue all of this together. This is especially true in a creative small business because a large part of the challenge is balancing all the activities so that there’s enough money coming in the door to support the creative projects and operations you’re working on.

JF: It’s important to work hard. But most people I know have a ton of potential places to focus energy and attention and enough work to keep 5 of them busy, so how do you determine how to allocate your work energies? How do you know what needs loving and what needs shelving?

CG: I love that you brought up energy and attention, as it completes the time, energy, and attention triad that I think we all need to consider more than just time management or energy management. It’s a bit more complex and nuanced than what you could put on a timesheet, but it more accurately represents the life of the creative professional.

Speaking of the life of the creative professional, something we all have to accept is that we’ll never actually finish the list. If we’re in the right environments, they’re not the ones where someone hands us a list of things to do, we do them, and then go home. We tend to have those types of lists that, once one thing gets completed, it spurs three or four more ToDos. Truth be told, we have ToDo hydras rather than ToDo lists.

One of the best frameworks I have for deciding what to do is to look at your activities in terms of Cashflow, Opportunity, and Visibility. When you start thinking about the ends of the different things you might do, it becomes much clearer. For instance, if you need to make your payroll numbers, it’s probably time to reorient your activities so that you focus solely on cashflow generating activities. If you’ve got a bit of margin and know you need to make some key moves in your business so it grows, it’s time to look at new opportunities or new places to get some visibility.

The challenge is that these priorities might shift every few days. A successful visibility campaign might quickly create a new opportunity-making project one day only to become a closing cashflow operation the next. We creatives have the ability to change the world that way, which means we need to be especially agile in the way we process what needs to get done.

JF: Do you use any specific tools or methodologies?

CG: I’ve read and implemented so many different methodologies that it’s hard to point to any single one of them as the one I use. I think most of the well-known frameworks – GTD, 7 Habits, Lean Six Sigma, Pomedoro, etc. – have some key insights, but, when it comes to productivity systems, no one size fits all. We each have to build our own system, although it does help to have someone guide you through the process.

I use OmniFocus to help capture a lot of tasks, but I don’t actually use it as my productivity dashboard. I use good ol’ pen and paper for that. Sometimes I’ll use the planners I’ve designed, but, mostly, I separate a piece of notebook paper into the main categories represented on those aids and work from that. The separation ensures I’m not fiddling with a todo list on the computer when I need to be writing on the computer.

I also use a lot of microsystems such as TextExpander and 1Password. I’ll not go into too much detail here, but the microsystems fit into the workflow and help speed up a few steps. They save me time indirectly because I’m not always trying to find information or open other applications so I can stay on task.

JF: When you find yourself heading off the productivity rails, what do you do to get back on track?

CG: As counter-intuitive as it sounds, I stop doing a bunch of stuff and get out of my office. I’ll walk around the block, exercise, talk to Angela (my wife and ops manager), take a shower, or play guitar for 10 – 15 minutes. It’s so easy to spend a few hours wheel-spinning or stuck on the Loop, and the best thing (for me) is just to unplug and get some perspective on what needs to be done.

A simple trick, though, is to ask yourself what you really need to do before you check out for a bit so that you let your unconscious mind start working through things. When we too heavily focus our conscious mind on current activities, there’s not enough bandwidth and time for the other parts of our minds to do any of the work, and there’s a lot of processing power that happens in other parts of the brain. Disengaging a bit opens up more capacity, and leaving with that open question has a tendency to anchor that processing power onto something useful.

The more challenging bit is knowing when you are off the productivity rails. A lot of us get stuck doing things without thinking about what we are doing, and this is especially problematic when you don’t have a clear plan for what you should be doing. The simplest way (for me) to not get off track is to visualize and plan out what the track should be every day. The 10/15 Split helps with that.

JF: What are your feelings about what’s become known as the 80/20 rule?

CG: The insight to the rule is that there are a relatively few things that make a big difference to the results we actually get. That part is sound.

The other part of the rule that’s sound is that our work often becomes bloated with non-critical elements if we haven’t evaluated our workflow in a while. When I work with clients on workflow/productivity issues and get into the details, we often find that they’re using tools and processes that over-complicate what they need to do.

I have two concerns about some expressions of the 80/20 rule, though. My major concern is that many people end up cutting the soul and heart out of their work. There comes a point in which a pure efficiency analysis of our activities can lead us to taking out the joy in our workflow. For instance, responding to blog comments may not fall into that core 20%, but it might be something worth doing just because you enjoy it.

The second concern is that many people don’t have a clear idea of what results they want or need. As an example, many small businesses and creative entrepreneurs focus so much on cashflow because their 80/20 analysis is so heavily biased towards cashflow. At a certain point, they find themselves stuck or burnt-out because they haven’t been building opportunities and visibility, and (they think) their only way forward is to keep doing the same thing they’ve been doing better, longer, and harder. You can only do that so long before things fall apart.

JF: What else should I be asking you?

CG: I think you covered it, Jonathan. I’d like to end with a reframe, though.

When it comes to productivity, many people focus on what they aren’t doing, what they’re not getting done, or what they won’t be able to do. That’s a natural negativity bias that most of us carry with us.

I’d like to encourage you to focus on what they have done. Sure, you might not hit every pitch thrown your way, but at least you’re swinging and hitting a few. So many people have ideas and never actually step up to the plate.

Focus on the hits and homeruns. The more you do that, the more you’ll see what’s working – and then build on your successes. Focusing on the strikes is a great way to underplay your own power.


Charlie Gilkey shares strategies for thriving in life and business at Productive Flourishing. Follow him on Twitter to get bite-sized slices of mojo and inspiration.

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34 responses

34 responses to “Productivity For Creatives”

  1. gerry suchy says:

    Great stuff. Enjoyed reading it and I must say, it doesn’t get any more true than this.


  2. Mark says:

    1. trying to do too much at once,
    2. trying to get results too quickly, and
    3. not quite having enough of a strategy under what they’re doing. Let’s handle each in turn.

    Great rule of three…I’d add the whole day-job/creative lifestyle quagmire. Then again, I can remember 3 things.

    • There *is* something about 3 things that makes it so easy to remember, isn’t there? That one additional thing often is the straw that breaks our memory’s back.

  3. Lori says:

    It’s -35°C here, looking like the middle of January with all the snow, and my brain is as frozen as my front door. But your post has interrupted my morning with some insight and encouragement. Thank you!

  4. Sukhi says:

    Thanks again for the awesome value.

    Got it! For me it’s all about… No more strikes, focusing on the hits and homeruns.

    • You’re welcome! Careful about the “no more strikes” mentality, though – it’s an impossible goal. How about more hits than strikes? :p

  5. Tom Meitner says:

    I agree especially with his first point about wanting results too quickly. It is really hard to remember the steps that are needed to be taken to be successful. When you look at the people that inspire you, you are already looking at success, so when you do what they do (or what you think they do), you expect to come out the other end with the same measure of success. But missing from that equation is time, and it’s important to remember how much time it took for someone to become a success. It doesn’t happen overnight, and it’s hard to remember that, especially when you are starting out.

    • This is a wonderful point, Tom! Thanks for the contribution. It’s interesting that we don’t look at conditioned athletes and think we should perform at their level, yet we do look at seasoned creatives and think we should be able to do what they do.

  6. I also enjoy Charlie’s blog—it’s got some great stuff.

    Thanks for the interview!

  7. Karin Olsen says:

    Loved this. Perfect timing. I’m trying to get my blog going while I juggle my PR and merchant services work. I was sitting here wondering where to start when I read this and promptly ordered his planners.

  8. oh goodness, i needed this today. time to slay my to-do hydra!! thanks for sharing.

  9. Karen says:

    You’re bang on with the top 3 challenges. I often find myself with too much to do, not enough time to do it in and no way to figure it all out. Often when I’m able to strategize and lay the road for what I want to do, I can do so much more because I have a clear path!

    Thanks Jonathan and Charlie for a great interview!

  10. wendy says:

    I LOVE the “ToDo Hydra!” Wow, that expresses my creative experience EXACTLY. Great interview. Thanks!

  11. One tool that everyone here might enjoy that I just recently found out about is a piece of inexpensive software called “The Action Machine” actionmachinedotcom.

    This software helps you easily implement a kick ass productivity framework system that consists of three simple steps:

    1. Write down all the things you want to get done for the day. Everything from writing, creating content, or planning your next project to answering your email and balancing your checkbook.
    2. Assign a specific time to each task or group of tasks. Anything from 15 minutes to 2 hours. Chunks of 50 minutes or less work best for me.
    3. Select a task, start a timer within the software (like an egg time), and focus on nothing but accomplishing that task. This means you don’t answer the phone, you don’t get up for a drink, you don’t log onto Facebook – none of that. You remain focused on the task-at-hand!

    This software helps you implement this framework that I actually learned about from Eben Pagan and I love it.

  12. Rob says:

    Great points GC.
    Most baseball fans recognize Reggie Jackson as, ‘Mr. October’. He also been struckout more than anyone else in baseball history (2597). That is just over 26% of the time.
    We can be sure that when it counted most that he was not focusing on the strikeouts.

  13. Thanks Jonathan and Charlie! I love the idea that productivity is a fluid, morphing space. Yes, aim for tangible results, but sometimes results aren’t so concrete: like taking time to do things which are just plain highly enjoyable work, even if they don’t show direct results in a measurable way. I like to aim for my own personal “satisfaction meter”–how satisfied do I feel with how I am using my time for whatever payoff, tangible or not.
    Great topic–thanks!

    • Thanks, Kristen. Our productivity systems have to handle the fluid of our lives – the goal of them should be to help us live our (fluid) lives, not fit our lives into the system.

  14. Lisa says:

    It’s first about setting priorities… if you don’t know what is important everything is! And then once you know what matters most, it’s all about discipline!

    • Right on, Lisa! It could also be the contrary: if you don’t know what’s important, nothing is. (At least, as far as your intentions go.)

  15. I want to add on a bit to one of Charlie’s closing comments, “That’s a natural negativity bias that most of us carry with us.”

    One important “life lesson” is the value of understanding your strengths and working to play in that space. Often we focus on what went wrong, where we need to improve, the what-ifs that might have made things “better”.

    We all need to expend energy on focusing on what went right and WHY it went right, what we did well and HOW TO DO IT AGAIN, as well as a “what-if I hadn’t done that” that shows a crash and burn situation. You averted disaster and should pat yourself on the back.

    Even when formal evaluations have both strengths and areas for improvement (I personally avoid the term “weakenesses”) time is predominately spent on the improvement areas. Spend more time on the strength areas and how to leverage, grow, build those out further.

    Nobody is perfect…at least no one I’ve met. But there are an awful lot of great people out there that while they see it in others, struggle to see it in themselves.


    • Great points, Faith. The funny thing about flipping “weaknesses” for “areas of improvement” is that I’ve found it often leads people to focus on “improving” those areas rather than focusing on their strengths. Language is a funny thing that way.

      I also think in terms of “challenges” rather than “problems.” It helps reinforce that there will always be challenges of one form or the other, but they’re not “bad” per se – they’re just a fact of life.

  16. I love that Charlie encourages us to build our own productivity systems. It’s been a long road to figure that out for myself but since we are all individually unique it makes sense that we all have our own unique systems.

    Pinching a bit from the ones that work well and emulating the best to come up with your own effective system is just beautifully simple and smart.

    Thanks for the probing questions as always Jonathan


    • With complete respect to my productivity colleagues, one thing we often forget is that we each have a particular frame that may not fit all perspectives. For instance, one system might be great in reactive environments and less so for proactive environments.

      At the same time, there are a few principles that just need to be tweaked for our context. There are a lot of brilliant folks helping people be more effective, so, rather than assume one is right, why not start with something that works pretty well for us and then embrace the pieces from other minds and experiences that work for us?

  17. Connie says:

    great post! thanks.

  18. Excellent insights. I will definitely put this info to good use. Working from home, productivity is a huge challenge. Thanks for sharing!

  19. TomC says:

    This must have been specifically written for me. Even Charlie’s replies are great.

    My biggest challenge is when the planning “stops” and I have to actually do the grunt work. I can start it but eventually it seems like there is a mountain of dull, uninspiring work in front of me. Starting things has never been my problem, the grunt work always has. I am getting better at delegating thanks to eLance.

    Much of this is due to a lack of focus and the hyper-focus on other ideas. I’ve stayed up nights thinking about all these cool business ideas that have little bearing on what my present business is. But I love it. If I could monetize developing business ideas and just make enough to cover my modest bills, then I would have a dream job. I’m sure many people feel this way.

    I think this post is brilliant. I wish I had known this years ago and been wise enough to know it’s importance.

  20. […] Productivity For Creatives ( […]

  21. Marie davis says:

    Guilty! My business partner spend tons of time juggling a variety of projects. We frequently remark that we are so lucky to always have new exciting projects to work on. And I must say we are good at the juggle, although I think, as this article points out, we need to focus more on one or two projects at a time. Thanks for this article.

  22. Mark Freddy Farrell says:

    All makes sense to me. I think I have concentrared to much in the one area, – continued to Develop New Products and Processes instead of selling more of what I already had Developed, Endorsed, and Implemented. My Business after 6 years now has Demand, But I am struggling to Deliver.
    Will take all on Board, and try to Disect, and Digest a Little more.

    Cheers Charlie,

    Mark F.

  23. […] Pro­duc­tiv­ity for Cre­atives with Jonathan Fields inter­view­ing Char­lie Gilkey is really, really good.  I’m a sucker for strat­egy, and Char­lie is able to mix pro­duc­tiv­ity tac­tics with long term strate­gic frame­works to consider. […]

  24. William King says:

    Sometimes I think the rules and methods of getting successful and producing creativity varies from person to person and changes from conditions to conditions. If something becomes the reason of the success of one than the same thing can become a reason of someone loss. We need to learn how to change such keys of success according to our situations to produce more creativity or in other words to fully utilize life changing things by modifying them according to our own conditions. But, one thing is common in all scenarios don’t pressurize your self if you are not able to produces something good. Relax mind is the first requirement of producing the creativity and this is what I think you were focusing on the your post.

  25. Thanks Jonathan and Charlie,
    You’ve made me realise that I work like a creative – even though I don’t think of myself as one. Challenged in all the areas you describe Charlie – thank you for the first step to recovery – normalising my behaviour – as in “you’re not completely disorganised or absolutely hopeless -your behaviour is normal for a creative who is eager to develop new things”
    Heading on over to buy those planners.