Time Management is Pain Management
Find Motivation in What Matters
We all have the same 24 hours in a day; nobody can “manage” their way to more. The ocean of time continues to flow regardless of our wishes to stem the tide. There is one difference between those who successfully surf the waves and those who wipeout under its tidal force. They learn to minimize the pain of doing what matters, and maximize the pain of deferring what matters.
Deadlines: Turning Pain into Productivity
When I landed my first job as a game designer on the Marvel vs. DC trading card game, I had no idea what I was doing. I had never designed a game before. In fact, I had never done anything I would have considered remotely “creative.”
But I did have one thing in my favor: if I didn’t get the job done, I’d be fired. I had three months to prepare the game for printing, or I’d be heading back to the snow-covered streets of New York, pursuing a miserable career as a lawyer. Even though I lived in sunny San Diego, I still kept an ice scraper and shovel in my trunk for three years—reminders of the trauma from digging my car out of New England snowstorms.
The fear of losing my job and returning to a career I despised drove me to push through the pain and discomfort of tackling unfamiliar, difficult tasks. That is the power I want to bestow upon you—the magic of deadlines.
Maximize the Pain of Procrastination
High performers learn to push past the discomfort of doing the things that are most important to them. But there is another side to this coin. By increasing the pain of not doing what matters to you, you can motivate yourself to accomplish almost anything. The best tool for that is deadlines—clear, short, and consequential deadlines transform procrastination into action.
These steps show you how to use deadlines to turn vague goals into actionable tasks, breaking them down and adding stakes to ensure that you follow through:
Clear Deadlines: A goal without a deadline is just a wish. Define a specific date and action for each goal.
Short Deadlines: Shrink large tasks into smaller, manageable chunks with shorter deadlines to avoid last-minute scrambles. The shorter the deadline, the more powerful the motivation and the less likely you are to get off track.
Consequential Deadlines: Hold yourself accountable by setting up real consequences including social pressure, financial stakes, or public commitments. Different people are motivated by different pressures (social, monetary, etc.) so find something meaningful for you. The more scared you are by the suggestion, the better it is for you—some experimentation is required!
Exercise: Pick a project, set a clear, short deadline, and add consequences to increase your motivation.
Minimize the Pain of Meaningful Work
To stay productive in the long run, in addition to increasing the pain of not doing work that matters, you also need to reduce the pain of doing meaningful work. Here are two ways to do that:
Pay Attention: Recognize the discomfort when it arises. Instead of avoiding it, pause and acknowledge how it feels. After a few deep breaths, the resistance often becomes manageable.
Start Small with Focus Blocks: Begin with just 5 minutes of focused work to overcome initial resistance. Set a timer for this short period, which makes starting less overwhelming. As you continue, gradually extend the duration of each session. This approach helps you build momentum, making it easier to stay engaged and productive over time.
Think Big
When tasks feel tedious, reconnect with your bigger "Why." Parents may be annoyed at having to take care of their children, but almost all do it without hesitation. This is because they care about their child’s wellbeing and the relationship is a meaningful part of their life. In other words, the more meaningful the task is to you, the easier it will be to push through discomfort. Stay clear on your goals, set aggressive deadlines, and keep learning from your mistakes until you reach success.
If you need a quick power-up, here’s a cheat sheet to keep you focused:
Pick something you care about and get clear on what you want.
Be clear on why it matters to you.
Set aggressively short but achievable deadlines.
Find a way to hold yourself accountable.
When discomfort comes: take a breath, embrace it, and keep going.
Reconnect with a powerful why to stay motivated.
Repeat until you achieve your goals.
Need an Extra Boost?
The Level-Up Journal is my personal, gamified companion for building habits and achieving goals. By treating life like an epic game, you’ll earn rewards for completing tasks, tracking your progress, and creating positive daily routines. With just 5 minutes a day, you can automate important actions, improve your mindset, and level up your life! Check it out here.