Dear Outlook, you still suck! … or not?

Ole-Olook 210There is a saying in German “Man trifft sich zwei mal im Leben”, which means so much as “You always meet twice”. I don’t know what your first thoughts are when you read these words. I always took them as true advice to treat every person you ever meet well because you’ll never know in what situation you’ll meet them again. For meeting them, you will. In other words, in the sense of never burn any bridges. Karma is a bitch. I absolutely believe that. What goes around, comes around, eventually.

However, just a month ago I met an old friend (not), who I thought I would never ever see again: Outlook

I can remember for my first job that involved a lot of email communication, coming from clunky webmail, I was out of my mind happy to use Outlook. I could finally write emails just like I wrote a letter in Word. I would have a calendar and task reminders, and…
Well, yes and an ever-growing archive file that included all my saved emails (*.pst). To save valuable hard disk space (the olden days…) you had to be brave and delete the ones you didn’t deem important. And because it was impossible to find even the ones you kept ever again, you had to print out important emails and file them at physical locations. Well, then Gmail came around with the promise you’d never have to delete an email again, with filters, labels, the possibility to use Gmail with your company’s email address (Send via Gmail), with plugins like active inbox , and so much more. Life was good.

After almost a decade without it, I was sure I would never have to use Outlook again. In fact, I didn’t know Outlook was still around. But you know, you always meet twice.

One new job later and there it sits on my computer. And not much has changed.

And as much as I am not happy about it, I totally get why it is still here. It makes sense because Outlook doesn’t do what is ‘wrong’ with Gmail. Wrong from a corporate point of view. It doesn’t go through your emails and it doesn’t give you the creepy feeling that it may you screw you over in one form or the other. That may even go less for Gmail itself but for the fact that it is just too convenient to use Gmail within Chrome. You now work in an entirely Google-controlled environment and giving up control should always concern you (Why I am leaving Gmail) .

There are of course other reasons. As a private person or small business, it may not bother you much, but the more people are involved, the more sense it makes to go with the entire Office package. Especially when most if not all computers run on Windows. Don’t mess with a working system when hundreds of people are part of it.

I also wouldn’t want to write 20,000-word reports in Google docs. And so I happily put up with Outlook instead.

Doesn’t mean I am not struggling. For the last four weeks, I tried to treat Outlook like Gmail and I see it is not working. I just cannot add hundred different categories to emails just to keep all of them in one folder. I am now back to the one folder per client/project structure, which makes finding emails really difficult if I cannot remember in which folder to search. There are no “undo send” or “forgot attachment” tools, which prevented me from sending emails too early or without attachments. There are a lot of things that are not there anymore and I have yet to find what is great about Outlook.

Do you struggle with Outlook as well or is it just me? Please leave a comment about what you love or can’t stand about working with Outlook.