The worst thing about being self employed


Oh for the days of the corporate I.T. department! Photo by Jon Chevreau.

There are many great things about being self-employed. On the other hand, the two biggest things I miss about salaried employment is paid vacations and in-house tech support from the much-aligned “IT department.” Guys, I miss you!

As I am rapidly discovering in this my second incarnation as an “independent writer” (sounds so much better than freelance, doesn’t it?), when it comes to technology, a small business is pretty much left on its own.

In the bad old days of robber baron capitalism, most workers depended on a big well-capitalized employer to provide the so-called “means of production.” Here in the 21st century, technology has become so pervasive and affordable that anyone who hangs out a shingle now has the means of production at hand.

Life without the I.T department

Only problem is, when something doesn’t work out the gate – usually soon after purchase – there’s no corporate I.T. department to deal with technical SNAFUs. When you have to deal with a technology issue involving computers, the Internet, peripherals and all the rest of it, you’re either going to have to do it yourself or pay someone to help you. In the first case, you’ll need time and expertise; in the second, you’ll need money.

Last Saturday, I wandered first into Future Shop and then into Best Buy in search of an affordable monitor to hook up to my MacBook Air. I had the wireless mouse running and the split keyboard, and life was going to be just grand if I could just find a reasonably priced large monitor. They have an Apple department embedded within Best Buy and I was assured an Acer or HP monitor would do the trick: Apple’s own dedicated monitors are prohibitively expensive. The part of me that is an Apple shareowner likes that, but as a consumer? Not so much.

So I talk to a Best Buy salesperson. I don’t think they are paid commissions because he wandered off half way through the sale. I hunkered down with my iPhone and waited for his return. When he finally rematerialized, he assured me that an HP Pavilion monitor would do the trick. Just to make sure, I went back to the Apple booth to double check.

No problem from Apple’s perspective, but by then my friendly salesperson is again nowhere to be seen. I go to checkout and buy it anyway. I unbox it at home and discover the CD-ROM is only for Windows, not Mac. Doesn’t matter, I’m later told. I hook it up as best I can but just can’t get the Mac display to correspond precisely to the HP monitor. I put up with this for a few days, constantly having to switch my gaze between the laptop display and the HP monitor, since the latter isn’t quite picking up the top inch and the left-side half-inch of what appears on the Mac. This pretty much defeats the purpose of having the bigger monitor so I go back to Best Buy and ask for a solution. Just resize the Resolution, the Geek Squad guy tells me, although he’s not quite sure it’s to be set higher or lower. I go home and try every which way to make this work but get no satisfaction. My day is being consumed and I decide to make it my top priority for what’s left of it.

Service? Sure, but it’s going to cost you

Remember, I bought the monitor on Saturday and it’s now Tuesday as write these words. I go to and dial phone support. A not overly friendly woman at the end of the line tells me they’re a paid service and it’s going to cost me $60. The monitor only cost $200 in the first place but it appears the price just went up 30% if I actually want it to work. I’m pretty certain this is a simple fix if I can just find out what it is. I argue that the equipment is not doing what the salespeople told me it would do three days earlier, so why should I pay? Sorry, I’m reminded, it’s a paid service. I don’t play the media card but do mention social media, which fazes her not a bit.  I hang up, getting frustrated.

Same attitude at Apple

“Ah ha,” says I to myself, “I’ll try Apple.” Over to the Apple site and it’s looking promising. I go to the Display part of the Help section and am told to enter the serial number of my Apple device. It even tells me how to find it. I enter it, anticipating the imminent delights of a large monitor that shows everything my computer does. But no, apparently my two-year old Mac Book Air is no longer supported, based on the serial number I entered, and that will be $60 if I wish support. I don’t wish it and go back to the drawing board, making repeated calls to the Best Buy store from which I bought the monitor.

No one answers from the Geek Squad so I try the Sales department. Now it’s getting a bit better. I get a partial answer that still doesn’t work, so finally I’m told to bring both laptop and the monitor in. Problem is the Apple guy isn’t working that day. By now, I’m determined to fix this problem TODAY, even if I accomplish nothing else. Besides, I think, I can at least get a blog out of it, which you’re now reading. Oh, I’ve also fired up an angry tweet about this experience, which has gotten a bit of traction, including from Best Buy Support.

Trip #3 to Best Buy

I trundle up the gear in my car – not even using the original and by-now soggy packaging – and go back to the Best Buy outlet for the second time that day. Finally, a long-suffering Geek Squadder deals with it. At first, he’s a bit baffled too but after five minutes he finally figures it out.  That’s me done and he instantly switches his attention to the next frustrated customer.  I carry the stuff back to the car, set it up again in my home office and bang out the first draft of this blog.

Now I’m doing a final edit on the big screen and you know what? After all, I’m happy, plus I got this blog out of it. The lesson? I should have gotten the original salesperson’s card and hounded him. Don’t cave in at the first request for extra money to support a product sold less than a week before. And for the vendors, how about a little post-sales followup to make sure the promises you made to customers actually materialized? If they didn’t, don’t be so quick to demand more money to fix what should be a simple problem.


Embracing Change

1838 Mark Venning Low Res copy

Mark Venning, Change Rangers, courtesy Mark Venning

As noted last week in my MoneySense Financial Independence blog, I intend to write a series of posts on the mass migration of almost-retired baby boomers moving from large corporations to free agency.

I recently attended a full-day workshop on this topic put on by Mark Venning of Venning knows well of what he speaks: He has spent more than a decade and a half working with mature (55+ generally) clients who have migrated from corporate employment to self-employment. A big part of his perspective is extended life expectancy and longevity: he prepares clients to continue working at some level well into their 60s, 70s and even 80s. The slogan on his business card and website is Envision the Promise of Longevity.

Claiming your place at the fire

As I argued on the MoneySense blog, 40 years is a long time to go without a paycheque, which is how long someone leaving the paid workforce might have to plan for if they leave paid employment in their early 60s. Add the type of extended longevity that Venning and others envisage (I’m thinking of Lee Anne Davies and her Agenomics blog, or Moses Znaimer of Zoomer Media), and “retired” boomers need to start preparing for this next great stage of their lives. There are of course many books on this topic: we looked at one last week and another I’m currently reading on my Kindle is Claiming Your Place at the Fire: Living the Second Half of Your Life on Purpose.

Leaving the Corporate Womb

But back to Mark Venning and Change Rangers. I can’t possibly summarize his content in a short blog but suffice it to say that in this economy there are many talented people who are either voluntarily or involuntarily being motivated to consider alternatives to employment in large corporations.  One is self-employment, an option that “more and more people 50+ are exploring,” he says.

Compared to 50 years ago, these mature people are in better physical condition, so can expect an extended lifetime. “They’re living longer than they typically used to so they have to plan for a longer period of time,” he told me in an interview, “This is why the word ‘Retirement’ doesn’t work for me. It’s about longevity planning. My core message is plan for your longevity, not for retirement.”

A Portfolio Career

As I see it, there are at least three ways to go when you decide to set up your own shop. One, you may see this as an opportunity to test out clients (and them you) with a view to possible full-time reemployment down the road. Second, you may decide such a “portfolio career” is a more attractive route at this stage of life: when you think about it, a single “job” means just a single client, which is less secure than having several clients. And of course, you don’t have a traditional “boss,” although being your own boss has challenges of its own. And third, while many choose to start such enterprises tentatively as a one-person shop working from a home office, there’s always the possibility of growing the enterprise down the road so that one day you are an emploYER, rather than an emploYEE. And that in turn offers the potential to sell a business.

Free Agent Nation and other books

As I warned, this blog doesn’t even begin to scratch the surface but for now, I’ll leave you with a few book suggestions from a list Venning hands out. One I just read on the Kindle is Dan Pink’s Free Agent Nation: The Future of Working for Yourself. Another I’ve just begun is Peter Block’s Flawless Consulting: a Guide to Getting Your Expertise Used. And a third I’ve put on hold at the library is Alan Weiss’s Value-Based Fees: How to Charge and Get What You’re Worth.


When a million isn’t enough

Here’s my latest “Financial Independence” blog entry published at

When a million dollars isn’t “enough” to retire on.

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