“Why don’t you do some work?”

Gotta tell ya… I’m getting pretty tired of hearing that.

Was having a conversation the other day with someone via IM. She asked me where I was, and I told her I was talking from the lobby of the W hotel in Times Square, waiting to have a drink with someone who runs a marketing firm.

“The W Hotel?! What a tough life! Will you please do some work?!” she IM’d back. It was around 3pm. She didn’t know I’d closed two deals, brought three new advertisers to HARO, and gotten one client onto CNN. Not bad for someone who, according to my friend, had to be nagged to “do some work.”

It’s not the first time I’ve heard that from her, or for that matter, from countless other people. One of the sub-hazards of having several status updates on various devices, I assume. In the past, I’ve heard virtually identical comments resulting from Facebook or Twitter updates that have included “Driving from LA to SF, stopped to get gas outside some wind farm,” “Sitting in the lounge at Gatwick, munching on a bagel,” “Singapore–>EWR flight delayed, hitting Duty Free, anyone want anything?” “Sitting on the hood of my rental car, watching the sunset from the desert outside of Eloy, Arizona,” and of course, “working from the Ranch, waiting for them to fuel the plane,” which is code for “handling a client issue via conference call, with my skydiving rig on my back, hoping I’ll finish the call so I can be on the next load that goes up in the air.”

To my detractors (who I should say, I don’t believe are saying “do some work” to be mean,) I respond simply with “On any given day I’m working twice as hard as you if not more so, and if you’re hating, you’re simply not as adept at playing the game.” And I mean that with absolute respect, and no insult intended.

Look, I talk all the time about how I have ADHD, how I use it to my advantage, blah, blah, blah, but let’s seriously consider this for a second: What does that actually mean?

I don’t do well in offices, I don’t do well in a structured environment, I sure as hell don’t do well in a cubicle, and the last time I had a “job” with a “boss,” I quit within three months of starting. I’m very fortunate to have realized it as early as I did, because what it tells me is that I’m simply not designed for working the way you work, but I’ve been smart enough to learn from it, and adapt my lifestyle to not only meet my needs, but exceed them, all while having fun.

I can work from anywhere. With the technology available to me, I’ve worked from a forest, an airplane (as I’m doing now) the back of a Taxi, or a beach in Phuket. I’ve sent out the HARO while waiting to board a plane, on a Metro North Railroad, or poolside from a conference in California.

I’ve also closed deals at nightclubs, in bars, or while running through Central Park at 11:30am on a Tuesday. I’ve taken client calls while taxiing down the runway while in the plane out of which I’ll skydive nine minutes later. I’ve gone on TV to talk about marketing with 27 minutes notice, stopping in a Nordstrom to buy a button down shirt and jacket, because I was wearing a t-shirt at the time, and it was soaked with sweat after a run. With logic suggesting that I’ll be placed at a desk where the camera won’t see the lower half of my body, I walked into the newsroom in a button-down shirt, blazer, Nike shorts, and New Balance sneakers. I washed my face in the bathroom, they applied foundation and pancake makeup two minutes to air, and 15 seconds before we came back from commercial, a production assistant ran on set to pull off the tag from the sleeve of my jacket. The interview went flawlessly.

Best part? One of my greatest accomplishments is that I have NEVER, EVER had a client say I wasn’t paying enough attention to them, or a colleague tell me that I missed a meeting, or wasn’t focused. In fact, 90% of the time, I don’t tell people where I am, and they naturally assume I’m in an office, at a desk. Good. That’s what they should be thinking!

But before you tell me to screw-off as you read this from your desk, know that it’s not anywhere near as free-and-clear as it might seem. With this freedom, comes the inevitable other side of the coin. And this flip-side is for my friends who shout “do some work” in all caps in the window of an IM.

Sure, I might try and tack on a half-day of skydiving or a few hours of beach time after a business trip before flying home, but the last time I took an honest-to-G-d vacation, without a laptop or cell phone? July of 2001. Last time you did? Probably a few months ago, if not sooner. Every year, I’m invited to view photos from my friend Karen, as she comes back from Africa, or Australia, or some other wonderful place, where she’s toured for the previous two weeks, totally off the grid. My friend Cheryl heads to Fiji, or the Galapagos Islands, or Brazil, or Portugal for a week after the NYC Marathon, every year.

While I try to explore at least one new place every time I travel, the concept of “off the grid” is virtually foreign to me. I never know where the next deal is going to come from, or who’s going to present it. My plane seat-mate? (Who on this flight, works in oil and gas in Houston, and has fallen asleep) Not this trip, but next time, maybe. At the supermarket? Always carry a business card or two, just keep a few in every pocket, you never know. At a step-cousin’s Bar Mitzvah? Why not. It’s happened. Watching the Mets? Who knows what the guy next to me does for a living when he’s not trash-talking the Pirates?

Remember the scene in Beverly Hills Cop II, (I doubt you would, normal people wouldn’t, it’s just how my brain works) where Eddie Murphy, undercover, says to the guy with the fake credit cards, “If you can’t handle this, I’ll just go to someone else. I’m a bizness man. I’m doin’ bizness. I’m makin’ moves. I’m movin’!” He’s snapping all around, moving in a million different directions to make his point. That’s how I live – Spinning ten plates at any given time – and thoroughly enjoying it! And that’s the key – when you enjoy what you do, it’s not work. That’s why the part about not going off the grid or taking a vacation isn’t a plea for sympathy – quite the opposite, it’s saying “hey, if you want this, can you handle doing things a lot differently than what you’re used to?”

“Why don’t you do some work?” This is work! This is what I do! I meet people, I put people together, I make deals, I make two and two equal five. I don’t sit behind a desk and create spreadsheets. I don’t move numbers from category A to category B. I don’t take phone calls asking where the TPS report is from a boss who hovers over me all the time, and I certainly don’t send an email, then go out for a donut, hoping that when I get back to my desk, I have a response. Wherever I am, that’s work. Whatever I’m doing, that’s work. And no, it’s not at a desk, and no, it’s not in a cubicle, and yes, I’m probably having a hell of a lot of fun doing it.

So Let’s translate “why don’t you do some work” into what it really is: “How come your job lets you fly all over the place, and have meetings in really cool places, and why can’t mine? Your job certainly doesn’t seem like work, why does mine?”

My answer to them? Because you don’t want it badly enough. If you really did, you’d have it. You’d take the risk, and play the game. (In actuality, that’s all it ever is – one giant game.) Face it – Having a job where you’re not the boss is, well, safe. You might hate it, you might think you can do it better, and you might want to firebomb your cubicle, but in the end, it’s safe. Your direct deposit comes in every other Friday, and you know it’ll be there. Going out on your own isn’t that simple. You’d worry every single day that this is the day you’re going to screw it all up, and lose it all. And when you woke up at 4:30am the next morning, (not because you can’t sleep, but because 4:30am to 5:30am is the only time you can work out without having to carry your phone with you) you’d smile that you kept it going another day, and actually look forward to working. You’ll wake up smiling, no matter how early it is. So you’d be scared on a regular basis. The paycheck wouldn’t be guaranteed, but the excitement damn well would be.

In the end, it comes down to boundaries, be them self-imposed or imposed by your own environment, either of which you feel you can’t fight. Boundaries that say “I have to work at a job and make a living so I can provide for my family and not be risky.” That’s fine! There’s nothing wrong with that. But that boundary comes at a cost, and it can be expensive at times, and I’m sorry, but those boundaries that lock you into your desk job aren’t my fault. See, I just never understood the boundaries. (Hell, I never understood a lot of things.) I never got that there were these man-made boundaries between working and playing that said the two shouldn’t ever meet, and because I never understood them, I couldn’t understand how to respect them. That definitely got me fired from the “I Can’t Believe It’s Not Yogurt” store when I was 17, no question. After college, I worked in several jobs early in my career, and they were always fun. When they weren’t, I simply left, and found something that was fun. And let’s not confuse “hard work” with fun – hard work, if you like the work, is fun. I’ve never left a job because the work was hard. I’ve left because I wasn’t enjoying it. And that’s two different beasts, entirely. The best New Yorker Cartoon I ever saw showed a man on a beach on his laptop, talking to his wife. The caption read “I’m not a workaholic. I work to relax.”

As I said above, I absolutely LOVE what I do. I didn’t get into PR and marketing because I thought it would be easy, or because I thought it was a party job. I honestly do like telling a story, and I’ve been blessed with an ability to do it well. The entrepreneurial aspect of all of it has come from, well, from not caring what other people thought, really. The same brain that got me beaten up in junior high is finally able to express these ideas that, shock of shocks, are actually worth something! How freakin’ cool is that?? If you go out and interview 10 entrepreneurs, I guarantee that almost every single one will say that they got teased as a kid, they were different, etc. And where are the kids who teased me? I’ve got no idea – but I’d be willing to bet they’re in a cubicle somewhere. And again, that’s cool – if they’re happy.

The problem though, comes when “do some work!” really translates into “I hate that you get to do that and I don’t.” Because if that’s the case, then don’t waste your time telling me to “do some work,” but rather, do some work on your own, and figure out why you’re unhappy. Once you figure that out, I guarantee, you won’t call it “work” a second longer.

Want to try it? I encourage it! Why wouldn’t you? Figure out what you do, figure out how to do it on your own, and go to town! It’s not for everyone – no doubt – just like I couldn’t handle a cubicle, there are people who can’t handle the doubt and fear that occasionally comes with doing it on your own. And that’s totally cool! That doesn’t make you any the less of anything! This isn’t a competition, which is what my “do some work!” friends don’t seem to get. The only people we have to compete with in this life are ourselves. If we’re happy with what we’ve done at the end of the day, whether that’s working for someone else, for ourselves, or somewhere in the middle, then I think we’ve won.

“Do some work?” October 28th, 2008 will be 10-years since I incorporated my first company. For the past 3,650 days, I’ve done nothing but work. But you know what? It’s never once felt like it.