The Executive's Bucket List
Samer Taher
Board Director | Editor-at-large | But most of all, I write The Elephant in the Office newsletter.
If you think being an executive is all about strategic planning and quarterly earnings calls, think again. There's an unwritten checklist of experiences that separate the truly seasoned corporate titans from the mere corner-office occupants. If you haven't ticked these boxes, are you even really in the game?
The Million-Dollar John Hancock
Nothing says "I've made it" quite like signing a check that could buy a small island. That moment when your hand trembles slightly, not because of the amount, but because you're worried your signature might look like a seismograph reading. Pro tip: Practice your signature beforehand – this isn't the time for your doctor's prescription handwriting.
The Marathon Masquerade
Because apparently, running a multinational corporation isn't enough cardio. Whether it's a 10K, half, or full marathon, there's something about executives and their need to prove they can outrun their administrative assistants. Bonus points if you close a deal while passing the 20-mile mark. Double points if you're still wearing your "power socks."
The Marquee Motor Show-Off
The unspoken rule: your car should cost more than your first round of venture funding. It's not about getting from A to B; it's about arriving at the board meeting in something that makes the valet drop their keys. Just remember: choosing between "midlife crisis red" and "corporate takeover black" is part of the experience.
The Timepiece Testament (No Rolexes or APs)
Rolex? Audemars Piguet? Please. That's so middle management. We're talking about watches that require an art historian, three authenticators, and a small down payment to acquire. If you can pronounce the watchmaker's name without practice, it's not exclusive enough. Points deducted if another executive at the charity gala has the same model.
The Face-to-Face Farewell
Until you've looked someone in the eye and said, "We're restructuring your position out of existence" while your own position feels increasingly unstable, you haven't truly led. It's like a corporate bar mitzvah – the moment you truly become an adult in the business world. Extra credit if you avoid using the phrase "It's not you, it's the market conditions."
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The Town Hall Tightrope
Picture this: standing under harsh lighting, facing hundreds of employees armed with questions ranging from "What's our five-year strategy?" to "Why did the cafeteria switch coffee brands?" It's your chance to demonstrate that yes, you can dodge questions with the agility of a political candidate while still sounding somewhat sincere.
The Private Jet Jaunt
Nothing says "I've arrived" quite like arriving in an actual private jet. It's the ultimate humble brag: "Oh, sorry I missed your call – was at 40,000 feet over the Atlantic." Just remember: posting about it on LinkedIn is considered gauche. Unless, of course, it's a "business strategy meeting in the clouds" post.
The Philanthropic Flex
Donating a sizable chunk of your disposable income to charity isn't just good karma – it's good business. The trick is finding that sweet spot between "genuinely helpful" and "still able to maintain your lifestyle of artisanal water and bespoke suits." Bonus points if you can announce it without someone muttering "tax deduction" under their breath.
The M&A Marathon Meeting
You haven't truly made it until you've sat through a board meeting discussing mergers or acquisitions that lasts longer than a Lord of the Rings marathon. Extra points if you manage to stay awake through all the due diligence presentations. Double points if you can explain synergy without using the word "synergy."
Remember, this list isn't about achievement – it's about survival. Because at the end of the day, being an executive isn't just about leading a company; it's about collecting enough war stories to make your eventual memoir worth reading. If you haven't checked all these boxes yet, don't worry. There's always another quarter, another board meeting, and another chance to perfect that million-dollar signature.
Just remember: the real measure of executive success isn't completing this list – it's being able to laugh about it at your retirement party. Assuming, of course, that your vintage watch collection hasn't depreciated too much to afford one.
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