Experience with Windows Operating Systems

Posted Mar 5, 2026 Updated Mar 28, 2026

By Jay Song

1 min read

My Windows history

My journey began in 1995 at the age of five with MS-DOS. Since my father ran a computer shop, I naturally learned how to assemble hardware and install software even before I started school. Since then, I have transitioned through Windows 95, 98, 2000, ME, XP, 7, 8, 10, and I currently use Windows 11 alongside macOS and a Synology Linux server. Although the most dramatic change I experienced was the transition from Windows 95 to 98, Windows XP remains my personal favorite. It holds a special place in my heart because it reminds me of my happiest and most carefree years as a student.

Legendary Windows Games

I still vividly remember my first MS-DOS games: a card-flipping memory game, a skiing game (SkiFree) where you flee from an abominable snowman, and a game where a cat (Neko) chases your mouse pointer. Later came Minesweeper, and Windows XP featured the masterpiece known as 3D Pinball: Space Cadet. Microsoft eventually stopped including Pinball because the original code lacked proper documentation. This made it nearly impossible for later engineers to fix bugs or update the game for 64-bit systems.

OS Installation Challenges of the Past

Installing software back then wasn’t as simple as a few clicks. To install Windows, we had to go through these steps:

Prepare a Windows CD
Enter the BIOS settings.
Set the CD-ROM as the primary boot source.
Reboot and start the installation.
Configure drive partitions.
Continue the installation process.
If prompted, insert the second CD into the drive.
Enter the product key (Serial number).
Go to bed while waiting.
Install various drivers and reboot at least 10 times.

If you missed the graphics driver, the screen would default to a low 800x600 resolution, making the icons look massive and the computer feel primitive.

Nowadays, Microsoft officially supports creating a bootable USB drive. You simply need to download an .exe file and find a spare USB stick with at least 32GB of storage in your drawer. The installation takes only about 10 minutes, as most computers now use SSDs instead of slow HDDs.