As you read this, I’m being induced, going into labor, and giving birth to a baby boy. As I write this, there are less than 24 hours left to the big event. How can I possibly get through my seemingly never-ending to-do list with so little time to spare? It’s not a new problem, though; as the clock’s ticked down to D-day over the past two months, trying to accomplish a mountain of work in a minimal amount of time has been an all-consuming theme for me. I just keep plugging away, hoping to get as much done as possible before the baby arrives.

My to-do list started and proliferated in the same manner that most daunting to-do lists begin; I wrote down projects and set unrealistic deadlines. As a result, the to-do list created stress for me that lingered in the back of my head long enough to start causing guilt trips. I had things on my to-do list that were fossils from 2 years ago—items I didn’t have the courage to delete, but that made my list akin to a pack rat’s collection. I felt I couldn’t afford to discard any to-do actions, in hopes that I would get to them one day. This statement Douglas Adams made described my feelings about my overwhelming to-do list accurately: “I love deadlines. I like the whooshing sound they make as they fly by.”

As the baby deadline approached, I suddenly found myself getting exponentially more productive. Just as my self-imposed deadlines to get stuff off the list didn’t motivate me to chip away at it, this new deadline inspired me and gave me the strength to grapple with my former procrastination. I turned into a task completion machine—and I intend to milk it to the very last minute until I have to go to the hospital tonight.

Specifically, I found that two techniques, in particular, were driving me to be more productive suddenly:

  1. Emotionally amplify a “flexible” deadline that’s not self-imposed. See, it’s easy to blow off your own self-generated deadlines, because you know they’re movable and that you won’t have to deal with another person’s disappointment or irritation if you miss them. I’ve found that deadlines have to be real, honest, and emotionally compelling to be effective; otherwise, I know I won’t have any problem missing them. When I’m feeling that way, I use a technique to amplify the emotional state compelling me to get the work finished. Sometimes the deadline is so undeniable that I feel driven and on fire, and I practically levitate off my chair to get it done. But other times, I have to play a bit of a mind game to make progress. For instance, I have two projects that I really need to get done today, but these thoughts of procrastination have been circling through my head: ‘Sure, I don’t need to have the new OST capabilities statement done and timesheets submitted by tonight. It’s not like I’m planning to retire tomorrow.’ Fortunately, I’ve thought up some compelling reasons to fight that desire to procrastinate. I’ve mentally amplified just how much the new baby will take my attention off business for at least a week or two, or three, and I’ve gathered up the memories of how I felt when I had my daughter Julia. These thoughts and the desire to enjoy being a new mom again with a clear conscience and without the hindrance of work-related guilt and stress have given me the push I needed to get my work done now rather than postponing it to a point when it would taint those special early weeks with my new baby and family. This conscious amplification of a real deadline really does the trick!
  2. Use “baby steps” to minimize the pain of meeting a deadline. Planning actions in tiny next steps is another technique to trick my mind out of procrastination and into action. Essentially, instead of thinking of monumental tasks such as “I need to redo our capabilities statement”, which daunted me into postponement for a good year, I broke it up into teeny steps that I could actually tackle so I felt like I was making progress all along. For instance, ‘I will put it on the agenda to brainstorm about it with the team while taking notes. After the meeting, I will open the old file and save it as a new file. Then, I will start organizing the deck and brainstorming on the main graphic…’ and so on. I did the same to motivate myself to start making calls I’ve been putting off: ‘First I will look up the number, then I will dial it, then I will say hi…’ and so on. I have taken decision-making out of the process, which has reduced my propensity to attach emotional baggage to tasks—such as a lack of confidence in being able to complete the task in the time allotted.

Using these two techniques, I’ve blown through huge tasks recently, such as developing a new business plan (we are about to roll out a new identity for OST, so be on the lookout for ways we can help you), launching new initiatives, and even getting back into painting—a hobby I love that I haven’t touched for 20 years—by doing a piece for our newly-built wine cellar (shown above). And yes, for all the wine snobs out there, I did immortalize the J. Lohr bottle of Cab—a bottle my dad gave me with a dinner he cooked for me. This is the best I could do, being unable to drink it.

I’d like to wrap this up by sharing a quote from Nolan Bushnell, the godfather of video gaming and founder of Atari and Chuck E. Cheese (the dreadful place my son will certainly drag us to in celebration of his friends’ birthdays): “The ultimate inspiration is the deadline.” So what are you procrastinating? Can you find natural deadlines, make them more compelling, and take small steps to get your tasks finished now?

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