Ok, this collection is definitely tech-biased and when mentioning “digital life” it does not mean reading an ebook but getting in touch with the technology in the background.
Disclaimer: There is no claim for completeness, independent assessment, or anything else. It’s just a collection of tools that I found useful sometime.

smtp4dev

http://smtp4dev.codeplex.com/
https://github.com/rnwood/smtp4dev
A very useful small tool for windows simulating an SMTP server on localhost. If your application sends an email to a localhost hosted port 25 SMTP server, this email is received and can be viewed or saved. The tool runs in the tray and can be opened to see the emails send.

fakeSMTP

http://nilhcem.com/FakeSMTP/index.html
I faced issues on some Windows 10 machines with running .NET Framework 3.5 which is required by smtp4dev. Since then I switched to fakeSMTP as an easy to alternative written in Java.

Fiddler Web Debugger

http://www.telerik.com/fiddler
A very useful tool for sending web requests and debug what’s going on. For example, to test REST APIs as done in this video introducing the Elastic Search REST API: https://www.youtube.com/watch?v=60UsHHsKyN4

WinMerge

You need to merge text files or just compare their content and don’t want to rely on GNU Diff? Go and give it a try: http://winmerge.org/

Notepad++

A very powerful text editor with a plugin system, language support, and column-based editing. Did you use the CrimsonEditor in the past? You will love Notepad++: https://notepad-plus-plus.org/

HeidiSQL

A free and lightweight SQL client supporting many different SQL databases: http://www.heidisql.com/

WinRAR

A recommendation for handling a wide range of archives from tar balls to zips: http://www.winrar.de/

Windows Image Resizer

If you need to resize images, it’s just one right click (and another left one 😉 ) away with this nice little tool: http://www.bricelam.net/ImageResizer/

GoW GNU on Windows

As I am used to live in both worlds (windows and *nix), I like to have handy *nix command line tools on windows as well. While Cygwin etc. comes with a big overhead, this set of precompiled *nix tools for windows is pretty useful and lightweight to install on your windows machine.  https://github.com/bmatzelle/gow

GnuWin32

Gnu tools such as wget or diff for the windows command line. I preffer to use the GoW set, but these tools are a reasonable alternative as well:  http://gnuwin32.sourceforge.net/packages.html

FileZilla

A probably well known open source (S)FTP client: https://filezilla-project.org/

Eclipse Plugins

Eclipse is not the latest (and maybe not hippest ?) platform and development environment, but it is powerful and even Microsoft recognized this and started investing in it.

EasyShell

Simple and straight forward context menu to open files and folders in a shell or system file explorer: https://marketplace.eclipse.org/content/easyshell

Plugin Homepage: https://github.com/anb0s/EasyShell

Tools for Hacking your Everyday Digital Life

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