Remember when your office phone was a solidly built multi-line key system with push buttons for the different extensions? And you had a secretary who would answer all of your calls? It seems so quaint now, like something out of a Tracy/Hepburn movie like the “Desk Set.” (Which for those of you that haven’t seen it, features a plot about a room-sized computer that replaces human workers at the TV station. Amazingly, 50 years ago too.)

The biggest change for office telephony these days is the separating of incoming and outgoing calling plans and how we will use computers instead of an actual phone instrument. Maybe, if we all can get our softphones to work properly.

I am not talking about some Claes Oldenburg sculpture, but the software running on your PC that enables you to make and receive calls. Softphones aren’t new – I recall writing about them in the early 1990s. Sadly, the quality of software development is still akin more to this era than the modern day.

Voice over IP has made calling almost too cheap to meter, to recall a phrase from the 1950s (then it was about nuclear power, and we know what happened to that). That’s why many vendors currently offer unlimited monthly calling plans for their VOIP Service – Vonage ($25), Skype ($3), Google Voice (Free!). What is important to note is that these are all outgoing calling plans. Anyone can call you without any plan, you just need a phone number. Here is where things get tricky.

I have been a happy customer of Vonage since around 2002 or so, using their phone service in three different states and for both home and work. The best part about using Vonage (or any other VOIP phone with a reasonable feature set) is that I can set up what happens when someone calls my number. Right now I have it ring both office and cell numbers simultaneously. This way I just have to give you one number to call me, and I can change cell numbers, or add a new location if I am working someplace for an extended period of time. The next best part about Vonage is that I can do all of this with just a couple of mouse clicks, without having to wait on hold for a Bell business office service rep to try to upsell me with services that I don’t want.

But I don’t really get that many calls anymore, not that I am complaining. Most of the time when I am on the phone it is to interview someone for an article I am writing or to listen to a conference call briefing. Those are calls that I initiate and I don’t really need a physical phone anyway – I much prefer to use a headset connected to my computer, to free my shoulder so I can type in my notes. (Yes, I could use a Bluetooth headset for my phone, too.)

I started thinking that perhaps I could eliminate my office phone line, and swap it for a Vonage softphone, and perhaps save some money in the process. That led me to searching for a softphone that will run on my Mac, connect to my Vonage account, and be reliable. Getting all three criteria has turned into A Project over the past week.

The softphone costs $10 a month. A call to Vonage customer support set up things, and moved my office number over to the softphone account. I thought I was doing well.

Alas, it wasn’t so easy. First of all, while Vonage has its softphone app on both Windows and Mac, the Mac version is a poor cousin and I couldn’t get it to work properly. After spending some time with Vonage tech support, I found out that there are “issues” with it running on Intel-based Macs (which are all recent Macs for the past several years).

Vonage does have a softphone for the iPhone (and Blackberry too), but you need to set up another $25 a month subscription plan. It really is designed to call internationally from your phone and save you on these charges. So it really isn’t the softphone that I am looking for.

There are numerous softphone VOIP software companies, and some even have Mac clients. I have tried a few, and tried to get them configured for my Vonage account, but with no success. There is a lot of poor quality information online, and many of these are smaller companies with no tech support.

What about Skype? Yes, Skype can be considered a softphone (and more, since it does video calls too). The monthly unlimited calling plan is $3, but you also need to purchase an online number for another $3 a month if you want people to call you. All of a sudden, my expected savings are evaporating. I like Skype and have used it for years, mostly for the IM features, and the voice quality is terrific.

How about MagicJack? This is a pretty cool USB device that you can connect to both Macs and Windows PCs, and it will set up a softphone (or you can use a regular phone and wire it to the USB device directly). All for $40 for the first year, and $20 a year thereafter. My one problem with the Jack is that I keep getting people calling me who are calling wrong numbers. Not sure what that is all about. I do get the occasional Skype from someone I don’t recognize but not as often.

And then there are Google Voice and eVoice, a new service from J2 Communications, the people that are behind eFax and jFax. These aren’t quite softphones, but do offer some interesting communications features to manage your telephony, and if I didn’t keep my Vonage number I would probably be more interested in them. Google has also purchased Gizmo Project, which had a really nice softphone that came with a built-in voice recorder, so who knows what will happen to that.

Not having a traditional land-line phone can be an issue, I will admit. But it isn’t usually a problem. So as I transition to a phone-free desk, I think back to the days when I had one of the old Western Electric phones. Maybe I should buy one and just keep it on my desk for old time’s sake while I keep fooling around with my softphones and headsets. If you are interested, check out this site which has all sorts of great info on the golden era when people had to rent, not own their phones, and they still had dials instead of buttons.