Sometimes, it’s all about a good mug shot: A recap of the @MeetingBoy debates

Last week I held debates on which was better or worse– working for The Man or working for yourself. I had three opponents – Lauren from ARoundTuit Organizing & Productivity, Patrick from The Sunshine Initiative and Andy from his own blog, While they all did well, let’s be honest– they had the easy job. I had to somehow defend the advantages of working for a company and a boss.

They all painted a pretty rosy picture, though Andy was willing to concede that when you start out on your own it isn’t easy. As he said:

Don’t go out on your own….

Without the support of your spouse.

A service you know people want.

A pool of clients.

And some cash reserves.

And a good mug shot.

I think right there– cash reserves and pool of clients— is why most people don’t go out on their own, and may never have the chance to. Something else that came up is that while you may be working for yourself, you may need others to help too, especially to do the tedious chores. Andy mentioned that he had a virtual assistant:

Andy: I have a VIRTUAL ASSISTANT that does a lot of work for me too. He’s in the Phillipines.

MeetingBoy: So you’re his boss! You’ve just passed the hassle down to him. Or by virtual do you mean he’s some sort of robot butler? TO BE CLEAR: MY JOB WOULD BE A LOT BETTER WITH A ROBOT BUTLER!

Andy: No, he’s a great human being. Name is Jeff, speaks great English and loves working for $6.50 an hour.

MeetingBoy: Maggie, tell your engineers at to get to work on the ROBOT BUTLER. I’ll be in the test group.

All three scored a lot of points in three areas that I can’t possibly best them in:

1. Less meetings. Because they are billing people by the hour, they find that their clients are more productive in meetings and that there are fewer of them. I remain skeptical on this point, because my boss has brought a number of consultants in, and if anything he wastes more time bragging and trying to impress them with how much he doesn’t need their help and knows everything anyways than he does on internal meetings.

2. Not as many fools to suffer. The big point they all made is that they (mostly) get to pick who they want to work with, rather than being stuck with whatever idiot boss or coworkers I’m paired up with. It seemed like the longer they’d been on their own, the more freedom they had to fire a bad client. However, Andy painted quite a rosy picture on this one, to the point where it sounded like he was the boss of his clients, to which I responded: You sound like the really hot girl in high school who can see everyone on her own terms, and they just drop everything for her. Certainly that can’t work for everyone.

3. Less micromanaging. Since most micromanaging occurs because the person can come over and harass you while you’re working, the opportunity for people like my boss to stick their nose into every little detail is greatly reduced.

However, I still think that they lost in a two key areas near and dear to my heart:

1. They are taking client calls at any time, even weekends and vacation. They claim they don’t have to, that they love their job, but the only time I answer my boss’s call on vacation is when he’s left at least 200 messages in a panic, and my calling in makes me the hero and him the fool. Otherwise, “I was in the mountains. No cell service. What did I miss?” People at work think I take really exotic vacations, when really I just refuse to answer the phone.

2. Money magically appears in my account every week, no matter how lazy, sick, surly or distracted I may be. And if my laptop or cellphone breaks, gets a virus, or is lost, well, they just issue me a new one.

In the end, going out on your own is a personal decision, and of course one which I could never do myself. After all, if MeetingBoy ceased to work in an office for a boss and with a bunch of lazy, stupid idiots, then he would cease to exist. Sadly for me, happiness is an existential threat.

If you’d like to read more, check out a few of my favorite excerpts:

And Patrick has already posted his take on our debates in two parts, the great debate 1 and the great debate 2.

And since he had a little fun with it, as did I, you should check it out because there’s some funny parts, as well as frank discussion. A favorite bit is how working from home might be too quiet for him:

“ALL I have is privacy. Like, J.D. Salinger privacy. …We have a new rule that I’m not allowed to talk to my wife for an hour after she gets home because at first I was talking her head off.” – Patrick

Till next time…


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Maggie Hibma is a member of the product team.