Creative workflow management

Lately I've been thinking about how I manage my work. I'm curious how other designers and self-employed folks tackle it, but haven't found any detailed conversations along these lines. Since so many of us work in isolation, maybe it's helpful to share our approaches and how they've evolved over the years. Some of you in larger corporate and agency settings may also find it just as interesting. So I'll go first. Here's a fairly detailed description of how I manage my workload, with a few recommendations at the end.

Level 1: It's all in my head

We all have some capacity to simply remember what we're working on, especially if it's just a handful of things. I faintly recall working at this level when starting a new job and then again when I launched my freelance business, but I quickly move on to the next stage. 

Level 2: To-do

When the workload grows beyond my cranial capacity, it's time for a list. To-do list apps are ubiquitous these days, but I prefer analog methods because I also have a thing for pens. The big win with a list is the way it frees up brain space for actual work. Sometimes my list is a simple first-in-first-out queue, where I just work on what's next and keep digging through it until quittin' time. More typically, I have some flexibility to choose what I want to work on given my current mood, capacity, or mindset (also true at Level 1). I work in whatever sequence is best for that day or block of time. If I'm feeling energized and creative, I'll work on concepts or explore big ideas. If not, I'll grind through some edits, refinements, correspondence, and other office work.

An urgent item, when it pops up, can jump to the front of the line (I usually just circle it) or even take precedence over the whole list. When I'm busy and it's super-urgent, I just remember it (Level 1) and the to-do list is there to remind me what I was working on before the alarm sounded. 

Level 3: Traffic board

Simple to-do lists can be unwieldy, and lose their helpfulness the longer they get. Plus, there isn't a way to see work on the horizon or track what's in other stages of completion. This calls for a centralized job board, and for this I use Trello, a free, web-based system. There are lots of other platforms/services out there (I've used Basecamp and 5pm), made for teams managing large projects. They are full-featured, but that feature set comes with a price — because they aren't simple, they can require a lot of time and maintenance. That leaves less time for the fun part: doing the actual work. I much prefer the simplicity of Trello, even though it has some limitations. Trello lets me define stacks (mine are: proposal, needs attention, out for review, to be invoiced, and so on) and then create cards (projects or discrete tasks) I can drag from one stack to another as creative work proceeds to completion and billing. I can always see the full set of cards for an instant snapshot of my workload. Each card can contain notes, checklists, PDFs, and more (I don't use Trello to anywhere near its fullest capability), but in essence it's a virtual traffic board. There's also a Trello app, but I don't use it much, since I really only manage my workload when I'm at the office. I do use the app occasionally, to get my bearings. Level 3 is definitely my preferred setup and I function in this mode way more than half of the time. It still allows me the flexibility to work on whatever feels right at the moment, but has the added benefit of visibility to the entire workflow.

The focal point of my Trello setup is the "needs attention" stack, which can contain a lot of cards. I typically sort them vertically just so I have a plan for what I'm working on today and what needs to be done in the near future (1-2 days out). Longer-term or "when I get to it" items hover at the bottom.  

Level 4: The Red Zone

Sometimes I over-promise on multiple deadlines, or urgent needs interrupt an otherwise well-managed workflow. The "needs attention" stack gets too many oh-crap-I-have-to-do-that-too items near the top. Clients are expecting work, and I don't specifically know when I'll be working on their stuff, so the delivery dates I promise are based on conjecture. That's a problem and a major source of stress. Time for the big guns: scheduling.

Creative types don't like to be constrained. Design constraints  can feed creativity, but when it comes to constraining how we work, most of us get uncomfortable. We don't want to promise, "at 11:45 I'll have an idea, and sell it to the client at lunch." There is an ebb and flow to this type of work. But. Sometimes it just needs to get done, and a professional is someone who gets the job done. So there are times when I need to literally (yes, I know) plan out my work in 15-minute increments. I give myself an exact window to get something done and out the door, and then I have to move on to the next one. (As Lorne Michaels has famously said of being ready for SNL each week, "We don't go on because we're ready. We go on because it's 11:30 on Saturday night." That's Level 4.)

To do this, I use Trello in conjunction with my calendar, and I plan the work just like it's a meeting (using a different color). I usually plan a full work week, with Trello as a reference for what needs attention, what's coming in, and what's likely to come back. I also leave some margin -- perhaps the last 90 minutes of the work day -- for overflow and cleaning up any correspondence I missed with my head down. But most of the day is booked solid. When a client asks, "when will I see it?" I can give a definite answer. And when a new opportunity pops up, I can honestly tell them how long it will be before we can get started. 

I don't love working in this mode. It's high-pressure and requires relentless focus. But I often find relief in moving from the stress of a jammed "needs attention" list to a scheduled, planned week with windows of time set aside for each. There is some sanity in the structure, and most of all (as with the other level-up transitions) it frees up my mind to think about the project instead of the whole workload. Frankly, some of my best work over the years was stuff I had to produce on-demand; I had to dig in, trust my process and get it done. 

Working the System

Simply monitoring which level I'm in and adjusting up/down as needed keeps me moving forward and reduces friction. I've found fluidity more effective than locking into one and staying with it.

I know there are other approaches and I'm sure many are better than this one. Every time I hear Merlin Mann talk about productivity or David Sparks explain OmniFocus I realize I'm in the stone age (bronze if I'm lucky). Getting Things Done (David Allen) has appeal as a comprehensive alternative, but I'm uncomfortable putting a life-encompassing system between me and a finished project. Collating the grocery list, my parents' anniversary, vacation planning and freelance design work in one massive system feels way too complex and fiddly. (And I don't think OmniFocus has a job-board view.) I fully acknowledge that's an irrational stance since I haven't tried it. 

One key for me is turning off email notifications. I check it as infrequently as I can get away with. And when I do, I process it once and never use it as a to-do list. I put the project-related bits into Trello and file the email. Non-work stuff is easy... read it and put it in one massive archive. Search/sorting makes this a lot safer than it used to be, and you need old emails a lot less than you think you do. 

Also, I try to take great notes in one place. Because I'm a pen guy, I'm also a notebook guy, so I take my book with me everywhere and use it to capture meeting notes, phone calls, random thoughts, and so on. It's purely chronological, which works really well for my brain. And it's centralized, which means I don't have to search through text files, Evernote, 3x5 cards and loose scraps of paper to remember what the client said... and I can keep working.  

Advice

First, regardless of the system you use, do EVERYTHING YOU CAN to remain focused on the part of the work you love to do. My workflow management takes exactly as much time as necessary and not a second more. (Usually about a second less.) This means you're in control, and you're working on what you've chosen to do — based on who you are and what's important, not the most recent item in your inbox or some external force. 

Second, avoid extended time in Level 4. While useful, good for revenue and sometimes necessary, if I work for more than two weeks in this mode I get toasty around the edges. You'll get through a glut of work, but (for me) the burnout requires down time for recovery so I'm not really winning. Reward yourself for getting through it — see a movie, buy a new pen —  and then go back to a reasonable pace you can sustain for the long term. The sweet spot is when the work itself is energizing. It's always effort, but if it's draining, something's wrong.

Third, make occasional visits to Level 1 (or even better, Level 0). Rest is important, especially for our minds, and it's where we do our best introspection, reflection and decision-making.