STONY POINT, NY — If you’ve recently purchased a new computer, the excitement of unboxing a sleek, faster device is likely fresh in your mind. But before you begin copying over every file, photo, and program from your old machine, take a moment to consider the advice of Rockland-based entrepreneur and IT expert Tom Ossa. In a recent reboot of his Work Smarter, Not Harder podcast, Ossa shared three key reasons why transferring everything from your old computer to your new one might be a bad idea.
As Ossa puts it, “In the words of Bob Seger, you’ve got to figure out what to to take (with you), and what to leave behind.” Here’s why.
1. Avoid Technical Debt to Your Older Devices
Think of your new computer as a fresh start—not just in hardware, but in performance. Copying over every application, document, and background process from your old system clutters that clean slate. This clutter is often referred to in the tech world as technical debt—the accumulation of unnecessary files and outdated programs that slow down your device over time. This term was recently coined by Matt Mullenweg of Automattic, the founder of WordPress.
The more bloated your new computer becomes, the faster it will degrade in performance. “I saw my other laptop starting to slow down just a hair,” Ossa explained, “and because we’re in a very technical field, we have to stay on top of things.”
Bottom line: only transfer the tools and files you actively use. Treat this moment as an opportunity to “cherry pick” the essentials, while leaving outdated, redundant, or rarely-used content behind.
2. Reduce Digital Clutter, Reduce Personal Stress
Just as a messy room can weigh on your mental well-being, so too can digital clutter. Ossa likens a full, disorganized computer to a pile of unsorted paper: “It becomes very, very difficult to manage… and it could lead to increased levels of stress, as you accumulate more and more.”
Transferring everything means you’ll need to manage and sort everything—again. That’s not only time-consuming, it’s mentally draining. Instead, Ossa recommends a more mindful migration: move only what you need, leave the rest safely on an old device or backup drive. “Remember, it doesn’t mean that you’re deleting it completely,” he says. “It just means that you’re leaving it on another device.”
3. Make Room to Innovate
Perhaps the most forward-thinking reason to avoid full migration is the freedom it creates for what’s next. Too often, holding onto outdated programs or even something as simple as rarely-visited website bookmarks – becomes a subconscious anchor, slowing your ability to adapt and evolve.
“When you keep too much of that stuff from the past, you don’t have the ability to accelerate into the future,” Ossa said. By keeping your device streamlined, you’ll have more resources—RAM, storage, and processing power—for tools that actually move your work and creativity forward.
Whether you’re exploring AI applications, editing video, working remotely, or simply navigating today’s productivity tools, your system needs to be responsive and flexible. That’s hard to do when it’s weighed down by yesterday’s data.
Final Thoughts
Before you drag and drop your old computer’s entire hard drive onto your new one, pause. Ask yourself what’s really necessary to keep—and what can be left behind. By reducing technical bloat, minimizing digital stress, and creating space for innovation, you’re not just saving your new computer—you’re setting yourself up to work smarter, not harder.
As Ossa puts it, “You want to make sure your new device is optimized so that it’s not only retaining the necessary elements of what you had in the past, but having enough firepower to propel you into the future.”
For more tech tips and productivity strategies, follow the Work Smarter, Not Harder podcast—now streaming again from Rockland County.