From My 'Boring' Bookshelf: 6 Game-Changing Questions

My bookshelf tells an embarrassing truth about me.

I keep telling myself I should lose myself in fiction or at least read about history or something. Isn't studying World War II battles appropriate for someone over 50? But no, the books that litter my side of the bed are all about getting things done, focusing, systems, mental models, and productivity. They're my guilty pleasure, or as my wife calls them, her "natural sleep aids." Sometimes when she can't sleep, she asks me to read from one of my "boring books." A few pages about workflow optimization, and she's out like a light. Works better than melatonin.

But I find these different perspectives fascinating. While most people are turning pages of John Grisham thrillers, I'm getting lost in concepts like the "bike shed effect" (more on that in a future newsletter). Give me a deep dive into why meetings always expand to fill their scheduled time, and I'm hooked.

So this week, I'm leaning into my productivity nerdom. I've pulled insights from six of my favorite authors: incredible minds who've spent years studying how we work, why we work, and how we can work better.

Each one offers a powerful question that can help us break free from the busy trap and focus on what really matters. You know the busy trap: that exhausting cycle where you're constantly doing things but never feeling like you're getting anywhere. Your calendar is packed, your to-do list is endless, and at the end of each day you're left wondering "What the hell did I actually accomplish?" It's the hamster wheel of modern life, where motion gets mistaken for progress.

Think of the following 6 questions as a greatest hits album from my "boring books." I promise it won't put you to sleep, but it might just help you escape that busy trap and start making real progress on what matters most.

1. What Can I Stop Doing?

The Book: Essentialism 
The Author: Greg McKeown

McKeown challenges the "more equals better" mindset with a radical concept: what if the secret to getting more done is actually doing less?

My entire life is in Google Calendar. I have one for work and one for personal life. Recently, Google introduced this "helpful" feature called Time Insights. And yes, those are definitely air quotes you're hearing in my voice, accompanied by some eye-rolling.

This little demon of a feature gives you a rollup of how much of your life is spent in meetings. When I turned it on, I discovered I was averaging 3.25 hours a day in meetings (with Tuesday being my personal circle of calendar hell). I quickly turned it off because who needs that much reality in their life?

But despite my denial, it forced me to ask an uncomfortable question: do I really need to be in all these meetings? Don't get me wrong, in our digital world, meetings can be what makes the world go round. But I realized I was still attending meetings I'd set up months ago that could have been handed off. What's more, I was getting added to meetings simply because people assumed I wanted to be there. (Spoiler alert: I didn't.)

One of McKeown's core lessons in Essentialism is to stop and ask yourself: If I stopped doing this, would it really matter?

With that in mind, consider:
✔️ Are there meetings, tasks, or habits that add little value?
✔️ Am I holding onto responsibilities that could be delegated or eliminated?
✔️ What's draining my time and energy without meaningful results?

Productivity isn't just about what you do—it's about what you don't do. Let go of what doesn't serve your bigger goals. Because sometimes, saying "no" is your secret superpower.

2. Is This Moving Me Forward—or Just Keeping Me Busy?

The Book: The 12-Week Year
The Authors: Brian Moran & Michael Lennington

Brian Moran and Michael Lennington make a bold claim: thinking in 12-month cycles is slowing you down. Instead of planning for an entire year, what if you treated every 12 weeks like its own year, with a clear goal, focused priorities, and no time to waste?

Think about early January. You start the year energized, setting bold goals and making detailed plans. But because you think you have plenty of time, it's easy to procrastinate. The real work often gets delayed until later in the year, if it happens at all.

A 12-week mindset forces urgency. It strips away the fluff and makes every action count.

Ask yourself:
✔️ Does this directly contribute to my most important goal?
✔️ If I had to accomplish my goal in 12 weeks instead of 12 months, would I still prioritize this?
✔️ Am I spending time on things that feel productive but don't actually matter?

Stop confusing motion with progress. A shorter timeline forces better choices.

3. What's the One Thing That Makes Everything Else Easier?

The Book: The One Thing 
The Author: Gary Keller

Gary Keller asks a pretty great question: "What's the ONE thing you can do, such that by doing it, everything else becomes easier or unnecessary?" It's deceptively simple, like most brilliant ideas.

To be honest, I struggle with this one. So many things vie for attention, and it can be so very hard to narrow down to one single thing to focus on – let alone stick to it. Take this newsletter for instance. In my finer moments, I block out a few focused hours mid-week for writing. That's it. No email, no Slack, no "quick meetings." Just me, my keyboard, and enough ZipFizz to worry my doctor.

And when this one thing happens, the newsletter flows. No last-minute edits, no panic writing over the weekend, no staring at the send button on Sunday night wondering if it's good enough. This block of time is my one thing that makes everything else easier.

But lordy, it can be hard to stick to the one thing. Even when you know it's for the best. I like to say that the main thing is to keep the main thing the main thing. But there are so many shiny, squeaky, demanding little non-main things that come along, it gets tough to stay on point.

Which is why Keller’s question needs to be front and center and is worth asking yourself pretty much daily.

Also consider:
✔️ Which task, if completed, would make other tasks easier or unnecessary?
✔️ What's the lead domino that will knock down all the others?
✔️ Where am I making things harder by avoiding the crucial first step?

Find your lead domino. Everything else will fall into place.

4. Am I Prioritizing the Important or Just Reacting to the Urgent?

The Book: The 7 Habits of Highly Effective People
The Author: Stephen Covey

Stephen Covey introduced a simple but powerful truth: urgent doesn't mean important. In fact, the most meaningful work (the kind that really moves us forward) rarely comes with a deadline or an "ASAP" tag.

So, what's the difference?

• Urgent tasks demand immediate attention. They're often tied to someone else's priorities: emails, last-minute requests, unexpected meetings. Left unchecked, they create a constant state of reactivity.

• Important tasks contribute to long-term success. They don't always feel pressing in the moment, but they have the greatest impact: deep work, strategic thinking, relationship-building, skill development.

Most of us default to urgency because it feels productive. But if you spend all day responding to messages and putting out fires, you'll never get to the work that actually matters.

With that in mind, ask:
✔️ What important work do you keep pushing aside because of daily urgencies?
✔️ Which of your "urgent" tasks could actually wait 24 hours?
✔️ Where are you letting other people's priorities dictate your best working hours?

Urgency is often just procrastination wearing a fancy watch. Choose importance over urgency and watch what happens... see what I did there?

5. What’s the Simplest Way to Do This?

The Book: Work Clean
The Author: Dan Charnas

In Work Clean, Dan Charnas explores how professional chefs operate with speed and precision, not by working faster, but by removing unnecessary steps. The same principle applies outside the kitchen: simplicity drives productivity.

Our Sporcle content team taught me this lesson when we took a look at our trivia question creation process. Writers would draft in Word, email documents for review, paste sections into Slack for feedback, and then do the whole dance again when changes were needed. It was...a lot.

But then our head of the content team asked a pretty simple question: "Why aren't we just using Google Docs?" One shared document. Real-time collaboration. Comments right where you need them. No more "Sorry, can't open that file" messages. Just one clean, simple process that everyone could follow. The result? The team produced better content faster, with way less hassle.

Start by asking:
✔️ Which of your processes feel more complicated than they need to be?
✔️ What steps are you including just because "that's how we've always done it"?
✔️ If you had to teach your process to someone new, how many times would you have to say "except when..."?

Remember: Simple systems stick. Complex ones break.

6. What Would My Future Self Thank Me for Doing Today?

The Book: Atomic Habits
The Author: James Clear

In Atomic Habits, James Clear shows how tiny, consistent actions compound into remarkable results. The choices you make today don't just affect today; they shape the future version of you.

At the end of each week, I used to leave a messy desk and unfinished tasks for Monday Me to deal with. It was always a terrible way to start the next week. Then I asked myself: What would make Future Derek's life easier? Now, I spend a few minutes at the end of each day setting up for tomorrow's success: tidying my workspace, setting priorities, clearing mental clutter. Small effort, big impact.

Ask yourself:
✔️ What small action today could have a big impact tomorrow?
✔️ Where are you borrowing time from your future self?
✔️ What habits are you grateful that past-you started?

Today's choices shape tomorrow's reality. Make them count.

In Conclusion

So yeah about those "boring books" I mentioned at the start? Their power isn't in complex systems or fancy frameworks. It's in these simple questions that cut through the noise and get us unstuck from the busy trap.

Keep these questions close for those moments when your calendar is packed, your to-do list is endless, and you're wondering "What did I actually accomplish today?" They're your escape route from the hamster wheel of modern life.

Each question serves as a filter, helping you stop mistaking motion for progress:

• Stop doing what doesn't matter

• Work in focused sprints

• Find your lead domino

• Choose importance over urgency

• Keep it simple

• Think about tomorrow

And who knows? Maybe these questions will become your guilty pleasure too. Though I can't guarantee they won't put your spouse to sleep.

As always, thanks for reading,
Derek
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