5 Ways to Dig Into Dreaded Deep Work

Photo by  Emre Gencer  on  Unsplash

Photo by Emre Gencer on Unsplash

I’m a person who kind of relishes deep work. I like having solitary, long(-ish)-term projects that I’m working on, and I hate the feeling that I’m in an endless cycle of sending and answering emails, working on quick and discrete tasks, spinning my wheels in the mud of the daily grind.

Don’t get me wrong, though. It’s still often extremely difficult to get myself to dive into my deep work projects.

It’s like with many people and exercise – I know I’ll enjoy it once I get going and definitely after I’m done. But still, the barrier to getting started can prove insurmountable some days.

Part of it is that many of our work environments are physically and structurally designed to constantly distract us from getting into the deep work. There’s the constant urgent-and-important, “putting out fires” kind of work that pulls at us. There are demands on our time – from other people, systems we work within, and emails – that are urgent-but-not-truly-important. And then there are the other insidious factors that play on our tendency to procrastinate in moments of weakness – social media, push notifications, so many spam-y emails (not-important-and-not-urgent).

It’s much easier to allow ourselves to be distracted by these than to do the harder thing, which is to pay attention to the important-but-not-urgent work.

The projects that will really be meaningful in the long run. The ones that will push us to grow. The ones to which we often attach so many unnecessary emotions – to the point that we really can’t get started.

Photo by  Samantha Sophia  on  Unsplash

Recently, I’ve had to battle my procrastination demons in order to work on creating an online version of my Stop Settling in Your Career workshop. I’d known I had wanted to put together an online workshop like this for a while and had been collecting the footage in order to create a workshop with the best parts from my live workshops. I was excited about it, theoretically. I talked about it enthusiastically and couldn’t wait for it to be done and ready to share with people.

But when it came time to actually start working on it, I can’t tell you how many weeks I pushed it off for. I could not seem to get started!

Much of the problem was that I had attached so many extra emotions to it: dread, shame, fear, anxiety.

I was afraid to watch the footage I had collected. I was anxious about how I’d look, my nervous tics, my awkward movements. More than that, I dreaded hearing my voice. For many years I’ve had a serious aversion to hearing my voice on tape, which was mostly why I could not bring myself to review the video and audio for the longest time.

Finally, I realized that I’d be way off my target deadline if I didn’t get started soon. So I had to apply a bunch of different strategies all at once in order to simply start. Here’s what I did, in case it’s ever helpful to any of you too!

Photo by  Marvin Ronsdorf  on  Unsplash

Scheduling it into my calendar

First, I scheduled working on the online workshop into my calendar in two different ways. I made it a several-weeks-long event so that there was a bright banner across multiple weeks of my calendar reminding me that I needed to be working on the workshop. I also scheduled in 2-hour blocks of time each day to work on it and I did my best not to book anything else during or close to those hours (more on this strategy here).

Scheduling it in strategically

I also scheduled these blocks during the mornings, when, based on my circadian rhythm (more on this on this podcast, at the 1:05:00 marker), I have the greatest mental energy and capacity to do focused work.

Breaking it down

I also broke down what I’d need to do into much smaller tasks and chunks. Instead of: Make Online Workshop, I created a laundry list of bite-sized tasks like, Transfer videos from iPad to computer; Upload video files into iMovie; Find audio files; Transfer audio files into iMovie; Open notes documents from each live workshop, etc.

Putting all the tasks into a sensible order

Then I put them into some kind of a feasible order and put one or two onto my daily To Do list, sometimes broken down even further into micro tasks.

Photo by  rawpixel  on  Unsplash

Photo by rawpixel on Unsplash

Clearing my physical and electronic work space

I also tried to remove visible distractions. I cleared things from my workspace so that I wouldn't be tempted to work on other things during my protected time. I would have to close my email tab on my browser sometimes (or even the entire browser). And I put my phone away from me and face down so that any notifications that did come up wouldn’t derail my work.

Troubleshooting obstacles

One of the hardest things about doing the video editing was that I couldn’t use one of my main go-to tools for focusing on deep work: listening to classical music. Whenever I have to do serious work, I stream my classical station, which plays random pieces of music (in a big loop; I’ve been listening to it for years, but it kind of helps that it’s often the same pieces over and over because it doesn’t distract me). But with the video editing, I had to listen to the audio – OF MY OWN VOICE. So I couldn’t use the trigger of the classical music to send me into a mental place of focus.

Another challenge was the tedium. It was high-level brain work, in a sense, because I had to figure out how to combine the variations of what I’ve presented at live workshops into one cohesive, sensible, “best of” workshop. But on the other hand, the actual manipulating of video and audio files and combining them with slides got extremely boring after a while. For this, I had nothing to rely on except my longstanding tendency to attack things with brute force. My work motto used to be: “Just do it till it’s done.” (Yikes.)

So to counter balance these obstacles, I told myself I’d be allowed to do something fun after, as an incentive and reward.

I’d give myself 15 minutes to send personal emails, 15 minutes to waste on the internet, let myself work on my puzzle later that day, or spend some time doing a mindless administrative task that I found at least a little fun. (Go ahead, judge me on how I define fun lol!)

Predictably, just like with the exercise dread, once I dove into the video editing and hit a groove, I started to enjoy it – even the most tedious parts!

All I had to do was get started.

Photo by  Samuel Clara  on  Unsplash

Photo by Samuel Clara on Unsplash