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, ProductiveFlourishing.com’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…

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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

trying to do too much at once, trying to get results too quickly, and 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.

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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.



