I Wish That I Knew What I Know Now: Career advice from people more successful than me

We like to think we have a master plan. We like to think life is linear. We like to think we know what we’re doing while we’re doing it. But we also know that pretty much none of this is true. The number of times we look back on our lives and think “If I’d only…” or “I should have…” or even “What in the name of God was I thinking…?” are, unfortunately, more than we would like to admit to.

So when a journalist asked me “What’s the one piece of career advice you wish you’d gotten when you were first starting out?”, I was certain I would be able to regale her with memories, aphorisms, witticisms and other bon mots that would make me the Oscar Wilde of our age.

I was wrong. I had nothing.

Oh sure, there were things like “Buy Google when it IPOs at $85 in 2004.” Or “Your good relationship with the client does not extend to telling him what you think of his karaoke.” Or even “The flight for the big presentation is at 4, not 430.” But nothing I could really use, nothing I wanted to affix my name to in public (like I’ve just done here. Ahem. Oh well…).

So I passed the buck. I reached out to some of my closest friends — and to some folks I wished were my closest friends — for their two cents. What career advice did they wish they’d had way back when we were all young and firm and comparatively debt-free and able to bounce back from all-nighters with a staggering effortlessness?

What I got was a lot more than I bargained for. Apparently my friends have lots of opinions. And they’re not shy about sharing them. And while the journalist seems to have disappeared as effectively as a late inning lead by my beloved White Sox, the advice I ended up with still remains. And it’s still valuable. And a lot of it had to do with warning their young selves about the future.

“Plan on the inevitability of middle age and age-related obsolescence” said my buddy the designer Gary Hudson, who was not alone in this admonition. And while few were complaining (okay, some were complaining — this is advertising, after all), they were still making it clear that they would have liked to have been made aware of what the future looked like so they could have planned for it. Because you know how good people in advertising are at planning.

And speaking of planning, it was also interesting how many talked about relationships, about how they wished they had made more of an effort to stay connected to people. Not purely from a business networking standpoint (although to be sure there was a lot of that. Like Contagious’s Paul Kemp-Robertson who explained “I must have applied for 500 jobs via the usual listings and recruiters, but I got my first break because I freelanced with someone who just happened to know someone who was setting up a new venture and needed eager young fools to work for free.”) but from a quality-of-life standpoint. MUH-TAY-ZIK | HOF-FER’s John Matejcyzk said “I’ve met so many great people along the way who I’m no longer in touch with. Kinda sad.” And Co:Collective’s Tiffany Rolfe echoed that sentiment, saying “I wished I had done even more of this rather than only focusing on my work and being too busy.”

Of course, “focusing on the work” came in for a large does of career advice, to be sure. The idea that there’s a lot to do, a lot of competition to do it, and a lot of opportunity to piss it all away. “Persistence creates luck and put the fucking time in” was what illustrator Hal Mayforth advised. Leo Burnett’s Director of Talent Acquisition Debbie Bougdanous expressed a similar sentiment, but put it in a way that perhaps is more befitting her position: “Always be the last person to leave. Ask anyone if they need help before you leave at night. Those people always seem to do well.”

Where exactly you put in that effort, however, was also extremely important, and there were a number of people who echoed McCann’s Rob Reilly’s career advice (“Don’t chase the titles or money. Chase the work. The title and money follow.”). And while I completely understood the sentiment — cash is fleeting, but the Alex Bogusky-Rob Reilly-Dan Weiden seal of approval on your resume lasts a lifetime — as someone who has taught literally hundreds of kids who are emerging from universities under mountains of debt, I wondered how realistic it was for anyone starting out today. Because it’s not about telling these kids to suck it up and eat ramen noodles for a couple of years while forgoing the flat for your parents’ basement. It’s about them literally not being able to afford to take the job at the better shop, unless someone is subsidizing them.

And maybe that sounds a little harsh, but honestly, the career advice itself was full of hard — and valuable — truths like that. Like Miami Ad School’s Hillary Lannan, who reminded me that we’re not as precious as we think we are and that the sooner we understand it, the better our careers will be. “We’re all replaceable” she said. “No one cares about you having your job as much as you do.” Oh, if I’d only known that when I was in my twenties…

And still the advice pours in. From people I emailed months ago. From people who already gave me advice and are giving me more. From friends of people who heard about my question and want to weigh in. Good advice. Great advice. Weird advice. Terrible advice.

And, perhaps the best career advice of all, which came from Ogilvy’s George Tannenbaum — “The advice should be, don’t listen to advice.”

Thanks to everyone who took time out of their busy days to provide me with valuable input and insight. And stay tuned, as invariably more career advice is on the way.

Rumours of My Demise: Some thoughts on the value of an ad campaign

My buddy Mark Dimassimo was pissed. He’d been watching an inordinate amount of tennis and he’d reached his limit with the constant repetition of ads. Not that the ads were bad the first five, ten or twenty times he saw them. But around the hundredth time he was subjected to the same, singular “tennis” ad that each company had deigned to produce in order to be “relevant” during the tournament, he was, as I could tell form his tweets, texts and messages, about ready to hurl something toxic and large at his television machine.

And brother, I can relate.

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If you Teach a Man to Fish: Why “fishing where the fish are” is not enough

For as long as I’ve been doing this, people have been telling me that the surest path to marketing success was to always be “fishing where the fish are.” That is, put your message where the people you want to reach, are.

And that makes sense, right? If you’re talking to motorcycle riders, advertise where motorcycle riders are. If you’re talking to Moms, put your message where Moms are. And if you’re talking to Moms who ride motorcycles, well, you get the idea.

And this advice has served advertisers and their agencies for centuries. I would bet that if you dug deep enough into Pompeii’s ashes you would find an ancient Roman vellum purporting delivering this aphorism in some Latinate version of corkscrew advertising-ese.

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I Should Have Known Better: The real value of improvement

It’s mindboggling sometimes to think about how much has changed in the advertising industry. And while I’m sure every generation has said the same thing, the simple fact is that they were wrong and we are right. No generation of creatives, account people and clients have had to manage as much disruption as we have in terms of media, demographics, economics… my god, the list is endless. 

In fact it’s so insane that I have been on something of a crusade to find the truisms that our era has NOT rendered obsolete. The ones we can still rely upon – at least until someone invents something new this afternoon. And thankfully, many of them still are true. Like the one about focusing on what the customer needs over what you want to sell them. And a couple of others too. 

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The Madness of the Method: Why process matters

You walk into a meeting with a new client or a new agency, and you’re in that honeymoon phase when everyone is attentive and polite and laughs at each other’s stupid stupid jokes. And you’re there so you can discuss “the process”, the way you’re all going to get the work done. The “great” work done. The great work we’re all going to be proud of. Together.

Whereupon someone, usually mid-level, begins to describe something that has so many damn moving parts, so many checks and balances, so many org charts with dotted lines that seem to lead to other org charts with still more dotted lines, that you can’t imagine yourself actually doing any of it. And you pray to god that no one actually does.

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Keep the Customer Satisfied: The differences between B2B & B2C advertising

Ask a B2B shop about their B2C cousins and invariably you will hear something like this: “B2C agencies are a bunch of undisciplined, overpriced children who should stay away from the serious business of B2B marketing and leave it to the adults before they do some real damage.”

Ask a consumer agency a similar question and they’ll invariably reply: “B2B shops should keep their second-rate versions of ideas that they stole from outdated back issues of B2C awards annuals and leave the creativity to the real agencies – the ones who do the consumer marketing that those B2B shops only wish they could still do.”

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The Kids Are All Right

“[They are] a generation of coddled infants who developed into demanding tyrants.”

I can’t walk into a brainstorm, client meeting, focus group, or marketing conference without hearing people complain about Millennials. “They expect everything now.” I hear again and again. “They want their jobs to revolve around their schedules. They’re not as committed as we were. They don’t know the value of hard work. They’re spoiled babies who refuse to grow up. And they all expect to be paid like millionaires.”

All of which I would be happy to ignore or agree with or whatever in order to still invoice the gig, if it were not for two extremely important facts.

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How to Client

There are literally thousands of books that will tell you how to manage a brand. And there are at least that many that will tell you how to run a company. Put those together and you might have the number that will tell you how to take care of the people you’re leading to do both of those things.

I know this because in addition to making advertising and teaching it, I review books on it at The Agency Review. And every time I think I’ve read all that there are, the mailman shows up with a dumpster full of new ones and drops them on my desk.

But there’s one important part of being successful – especially in the marketing space – that these books are frustratingly silent on and it’s this: How to client.

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Who Are You?: The case for a creative director

We all know what an art director does, right? They make the pictures - and in a society that is as visually obsessed as ours is, that’s clearly a pretty important job.

And we all know what copywriters do too, right? They come up with the words that no one reads except the lawyers and the brand managers.

But creative directors? They don’t write – though they may have once. They don’t design, though they may have once. And they sure as hell don’t code. So just exactly what do they do, and more importantly, why the hell are you paying them?

What they do - and what you are actually paying them to do whether you realize it or not – is to be the bridge between the problem you have and the solution you pray people you don’t understand will come up with.

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Pleased to Meet You, Won't You Guess My Name?

My friend Dave Marinaccio likes to say that even bad advertising works better than no advertising. And he’s right, of course. For as Woody Allen famously said, 80% of success is just showing up – and advertising, in one sense, is simply about showing up when your competitor does not.

What Dave doesn’t mention about bad advertising is that “showing up” is about all it has going for it. It’s sort of like drunk-dialing your x-girlfriend. Yes, you’re making yourself top of mind with her (awareness!) and you’re occupying her thoughts to the exclusion of everyone else (attention!) – but you’re also rambling and mumbling and cursing and vomiting and being fairly incoherent. But hey! You’re showing up!

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Talking ‘bout My Generation: What Demand Generation Means Now

You remember demand generation, right? Born in that first mythical golden advertising age, when Claude C. Hopkins and Albert Lasker strode the earth, demand generation emerged when clients had products found themselves saddled with unsellable products. Products that they brought to agencies, saying, “I don’t know what to do with this. You think you can come up with a reason for humans to buy it?”

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