Open Thread: What's Your Web Working Pain Point?


ScreenshotMost of us are web workers because we enjoy it. Whether it’s the feel of being on the cutting edge of technology, the joy of working anywhere, or the contribution to saving the planet by not commuting physically, there are a lot of good things to be said for our chosen way of working.

But we all know it’s not all strawberries and cream. There are days that staying home instead of mixing with peers in the workplace is the most boring thing in the world. There are hotspots that won’t connect, computers that break down, privacy and security worries. And of course there are all the joys that come of dealing with computers, the machines we love to hate.Presumably, the good outweighs the bad for most of us. But it’s OK to grouse to your peers once in a while. So, today’s question: where are your worst pain points in web working? What areas would you desperately like to find help with? What parts of your life make you long for a “regular” job?

Photo credit: stock.xchng user ForwardCom


Little Shiva

PS to pam: the reason career office workers get stuff like benefits and savings plans is to compensate them for all the CRAP they have to put up with being office workers! Not worth it in my book. But yeah, I do wish there were better benefit options for freelancers. That’s definitely a valid point.

Little Shiva

I’ve worked from home for most of my so-called career, and LOVE it! I can work on my own rhythm, whenever I want, as long as I want or in short bursts if I want. I love the peace and quiet of it –very zen. The only thing is finding clients, but that’s the key to biz anywhere, whether you work from home or not. I also love being able to travel and still work. Of course, I need to go where there’s hi-speed internet…


One word only: Benefits. It’s still effed up that the independent worker gets a bad deal on things like health insurance and easy retirement savings plan. Almost everything else – the isolation, the lack of support, the annoying technical details – I can deal with that stuff, but the benefits, I just can’t seem to wrap my head around how to make it better.

Marcin Grodzicki

@Mike: Well, construction is not really a web business :) Besides the company I currently work with is REALLY low tech. I’m implementing some of the tools (Google Apps, Highrise, Mail (!), Google Alerts) but it’s taking me loads of energy and time. And of course whenever we do two steps forward we also do one step back…


I have issues with phone calls vs voicemail vs customer service.

I’m a solopreneur who is elbow deep in projects a lot. I can’t er WON’T answer the phone most of my work day.

I get a LOAD of jabs and complaints from my biz network because people always get sent to my voice mail.

I research this topic online all the time and see constantly that “you must answer your phones live” to provide “good” customer service. And you see complaints all over about how “impossible” a company is to reach because they had to leave a message.

I do block times of my day to return calls but Programming is not something you can start and stop every 15 minutes every time the phone rings.

I’ve looked into answering services…but I’m pretty nervous about letting somebody be my front line…and have yet to find a pricing model that makes sense. Per minute calls would seem to encourage keeping the caller on the line longer. Per call pricing would seem to encourage RUSHING the caller off the line.

Outsourced call centers are -outrageously- priced and simply not an option.

This has been my Pain Point for YEARS. And the ridicule has come close to being the very thing that frustrates me out of this business….because I DO provide excellent customer service…even if they have to wait a couple of hours for me to call back.

Mike Gunderloy

@Tim: I might try running the VPN client in a 32-bit VM – though I wouldn’t necessarily expect it to work.

@Marcin: Sounds like the flip side of the managerial complaint that telecommuters can’t be managed because they’re not around. Can you employ some of the tools for tracking web workers’ work in reverse, so to speak?

Marcin Grodzicki

The inability to properly manage people that are office-bound. This is actually something that continuously makes full homeworking impossible for me.


I started contracting, bought a laptop with 64-bit Vista, and subsequently discovered that Nortel’s VPN client (which I require to connect to my No. 1 customer) is not available in x64. Arrrggghhh!!! I’ve had to solve this one by remote desktopping to other machines running XP or 32bit Vista to connect to my client.


The loneliness of working on your own all day long! Luckily all you need to do is schedule lunch with a friend, duck out a little early for a round of golf, or have a meeting with a client to fix the problem.

It isn’t a big deal in the summer time, but during the winter months it can wear thin at times. On the bright side, during the winter months it sure feels good not to have to bundle up at 6am for an hour to an hour and a half of commuting in the cold, rainy weather!

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