Some weeks ago, I got a message on LinkedIn from a connection I don't really know, though we've been "linked" for over five years and we, apparently, worked at Ogilvy during the same time.
Brett asked if he could write a guest post in this space. A lot of people ask--and I almost always say yes. Partly because most people intend to write and then lethargy-out when they realize it's hard.
Brett, however, sent me this and I was sold.
Like 97-percent of the cognitive world, I love a good origin story, and Brett's seem interesting and off the beaten bivouac. In just a few days, Brett was back in my mailbox with the post below. It's good.
Read it, Maggot.
Fire and Maneuver:
Becoming a Caddy and Rediscovering the Art of Client Service
By Brett Jones, a MadMan/Caddy for hire
Growing up I watched my father do very well for himself working in advertising. As a rebellious teenaged youth I wanted no part of corporate America but after some reflection I decided to follow in his footsteps, both into the United States Marine Corps and then into Advertising. After swinging with the Air Wing for almost 5 years I spent the better part of a decade working at places like McCann and Ogilvy learning the ins and outs of client service.
I’ve met a lot of smart people and studied the art of client service next to some of the best in the business. I take notes from great account leaders like Adam Tucker who says, “Clients don’t care how much you know until they know how much you care,” and creative leaders like George Tannenbaum who has 15 great pearls of wisdom on how to be a good account person like number three, “Be curious. Question everything and everyone. Get out of the office and look around. Learn from others.”
I’m constantly on the lookout for how to transfer knowledge from one domain to another. See my book, “Shock and Awe, RECRUIT! (or how I learned the fundamentals of advertising in Marine Corps Basic Training) for more on that front. Advertising has a lot of similarities to the military, filled with challenging campaigns, exciting projects or missions, and glimpse of top brass like the Secretary of the Navy or the occasional A-list celebrity.
It’s not all ponies and rainbows though. Life threw me and my family a curveball when I was laid off from Comcast in March of last year. It felt like the wind had been knocked out of me. I had never been laid off before. I knew I could bounce back.
I had already done a stint as an entrepreneur when I helped an A-lister launch a global lifestyle brand just before COVID broke. After going through the turmoil of being a business owner and living through COVID with two young kids my wife and I both agreed a steady W-2 for my next gig was the right path. So I hit the job boards and applied to scores of agency account gigs and marketing roles on the ‘client side.’ I got a few looks from HR and even a handful of first and second round interviews, but no offers were coming.
It seemed the entrepreneurial path beckoned once again. I launched my own agency last summer when I met a prospective client sitting across the aisle on a plane back from a family reunion in Utah. Semper Ads came about later that week and before I knew it I was sitting in rooms with futurists and AI luminaries by helping promote the NYU Intellibus AI Masterclass and filming content for an AI initiative concerning World Digital Governance.
From there I built out a client base and have been helping with building websites, helping with SEO, and developing go-to-market strategies whenever the opportunity comes up. The work is rewarding, but also stressful. Running your own business, you quickly learn it’s a feast-or-famine lifestyle. Some months are amazing; others leave you wondering if you’re in the right game. That’s when I realized I needed another stream of income to steady the ship.
Enter caddying, a gig where you carry a golfer's clubs, read their putts, and polish their balls.
Yeah, I became a caddy—a move I never would have imagined for myself back when I was leading big advertising campaigns. At first glance, it might seem like a drastic step down. But trust me, the job’s not just about lugging clubs and cleaning balls for a tip. It’s about reading the course, analyzing the situation, and giving real-time guidance—skills I honed in the Marines and in the world of client-service.
Just like in advertising, being a caddy is all about strategy and support. You’re there to make the client (or golfer) look good, help them achieve their goals, and manage expectations. There’s a lot of prep work involved. Before a round, I study the course, think through the conditions of the day, and figure out where the traps are. Just like pitching a campaign, you’ve got to know the landscape before you offer guidance. On the green, when reading a putt, I have to size up the terrain, think about the speed, and give my golfer the best advice I can. And it’s not always perfect, but it’s my job to help them navigate and improve their game, just like it was my job to help clients improve their business.
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