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Navigating the upgrade to Windows 10 after Windows 7 end of life officially arrives

By Julie King |

External drive bay holding the older operating system drive

For many PC users, today marks the official end of an operating system that has been the backbone of businesses for over a decade.

Like it or not, if you are one of the 30% of users who are still on Windows 7, it is time to upgrade. While you will still be able to use Windows 7 after January 14, 2020 Microsoft will no longer release any updates or fixes or offer support for the product from January 15th onward. The security risks are simply too great to remain on Windows 7.

What are your options?

First off, the free upgrade from Windows 7 to Windows 10 is not surprisingly no longer available. You have four main options available to you.

  1. Upgrade existing hardware: You can upgrade your existing Windows 7 license, but there are a couple of drawbacks to this approach. First, chances are good that you have an older traditional harddrive – for optimal performance Windows 10 runs best when installed on a solid state drive. Second, with this approach you have to backup all your files or risk losing data, which is awkward and time consuming.
  2. Install on a new SSD drive: This is actually a very effective solution for desktop and laptop computers. You purchase a new SSD drive, which will cost between $85-$150. If you have a desktop, you should be able to keep both this drive plus your original Windows 7 drive in your computer.

    If you have a laptop, you can purchase a single external drive enclosure for under $25 (pictured above) and use that to mount your existing harddrive. You then install Windows 10 on the new SSD drive, which will be your main drive, and your original Window 7 drive will now become a secondary drive with your files available*. This way you get to keep your old files intact while having a fresh drive for Windows 10.
  3. Purchase a new computer: If you have been looking for a reason to purchase a new computer, the need to upgrade to Windows 10 could help you finalize that decision. However, most laptops sold today come with Windows Home, which may not meet your needs as a small business.
  4. Upgrade and change to a different operating system. Instead of upgrading to Windows 10, switching to Mac or Linux are both viable options. A critical consideration is how this will impact Windows software and whether these programs and their respective licenses will run on a different operating system.

*If you have used a programmer like Bitlocker to encrypt your files on your Windows 7 system you will want to unlock the files before beginning the upgrade, as the new system may see you as a different user after the upgrade and block access to any locked files.

Which version of Windows 10 should you purchase?

Assuming that you plan to sticks with Windows, it is important to make sure you upgrade to the version that best suits the needs of your business. Windows 10 comes in 3 main versions: Home, Pro and Enterprise.

If you are a solo entrepreneur, don’t expect to have employees in the short term and want to save money, the Home version should meet your needs.

If your business has employees, you will probably want to consider either the Pro or Enterprise versions. The Pro version can work well in companies with only a few employees, but as you start to grow the Enterprise version has advantages, such as enabling you to run an active directory to easily control logins regardless of what computer each employee is using. Enterprise also makes it easier to centralize management of your Windows licenses.

What about other software that you use?

As Microsoft officially ends support for Windows 7, so are many other companies that provide business software.

As I learned the hard way during my own upgrade to Windows 10, it is a good idea to not just back-up your files, but also to write down license and product codes for key programs you use. With so many software programs shifting away from computer sold in boxes to cloud based downloads, it is all too easy to accidentally get blocked from being able to re-install your software after an upgrade.

After upgrading my computer to Windows 10 I found myself unable to find my bookkeeping license codes, which were trapped on the older drive inaccessible to me at the time. A ridiculous circular nightmare ensued... I started to install the software, but it asked me for my product and license keys. Since I couldn't access that information, I went online for support. However I was then informed that I must  open the software in order to contact support. But I couldn't open the software, because I needed to get it installed with the missing codes first!

Do yourself a favour and plan for this possibility by making sure you capture your passwords, logins and product keys before you upgrade.

Also, be ready for the possibility that some software and hardware, such niche software or older printers, might not work on Windows 10.

Tip: Before upgrading your OS, take screenshots of all the programs you currently have installed. The easiest way to see all installed programs is to go to Start > Control Panel > Uninstall a Program, which will show you a list of programs you have installed. You can then either use  print screen or the Snipping Tool built into Windows 7 to capture these details. (To the Snipping Tool  go to Start and type Snipping Tool in the search box).  Just remember to move these screenshots to a place off the drive you are upgrading so they will remain accessible!

Re-configuring your new operating system (OS)

One of the most annoying things about any OS upgrade is that you not only have to relearn how to do things that were natural in your old OS, but you also have to re-install and reconfigure your workspace from the default set-up of  the upgraded OS. These are the small yet highly annoying things you have tweaked over time, like how your email is displayed and whether emails are automatically previewed in your main Outlook window.

Also, chances are good that when you upgrade you will not only have to learn the new operating system, but that you will also find yourself forced to upgrade to newer versions of the entire Microsoft Office Suite, which have a very different look and feel from previous versions. This time spent to get things running the way you want is really the biggest cost to an OS upgrade, especially when compounded across many staff members.

All you can really do is brace yourself, understand what to expect and then carefully and systematically navigate your way through the change. Because no matter how frustrating or annoying a system change may be, security and stability are too important to continue running your business on unsupported software.

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