WTF moments

Let’s cut to the chase. It’s not easy being an entrepreneur. The internet is overflowing with tales of billion-dollar startups springing up overnight and rags to riches stories that bring tears to the eyes. But what you don’t hear much about are the WTF moments every entrepreneur has survived on their way to the top.

Call it a rite of passage, but I’m willing to bet that before Elon Musk and Jeff Bezos reached the dizzying heights of entrepreneurial royalty, they wished the floor would swallow them whole on at least one occasion.

Running a successful startup isn’t all glitz and glamour. The road to success is more of a minefield than a red carpet, laden with WTF moments to make or break your career. Or, serve as an entertaining anecdote later on, when the horror and shame have passed.

So, here goes: 7 WTF moments every entrepreneur has survived, in no particular order.

1. Sending Out A Client Pitch (To The Wrong Client)

Ever stayed up all night working on the perfect pitch? Writing and rewriting your proposal, adding fancy graphics, including impressive data and underscoring the special discount other clients don’t receive?

It’s one impressive package guaranteed to bowl them over… Except, you sent it to the wrong client. There’s no way to press the back button. And now you’ll have an angry phone call to contend with demanding a renegotiation on your your pricing. Ouch.

2. Not Remembering The Smiling Guy’s Name

It happens to the best of us. You’re at a dinner, networking event or conference, and you see a friendly face bounding towards you. They greet hello with the kind of enthusiasm usually reserved for old college buddies and… You can’t remember their name.

In fact, you haven’t a clue who they are. The situation is cringeworthy. The only thing more awkward is being with someone else who’s waiting to be introduced. Or perhaps the sentence, “I did not have sexual relations with that woman.”

3. Having Your Kids Barge In On You In The Middle Of A Meeting

Is there anyone who hasn’t seen the Robert Kelly interview? A political analyst eloquently explaining the North / South Korea situation when all of a sudden his toddler and baby burst into the room. Followed by his wife. On all fours. Desperately trying to avoid the camera.

This is one of those WTF moments that shall forever be preserved in internet fame. The video received more than 26 million visits on YouTube and struck a chord with every entrepreneur who’s ever worked from home.

4. Taking A Client Out For Lunch And Forgetting Your Credit Card

The lunch is going well. The conversation is flowing and you’ve got a good feeling about this one. The client is clearly interested in what you have to say. You’ll continue the discussion more formally at his office, of course, but for now you’re feeling pretty great, until…

You ask for the check.

You reach into your pocket, dive into your purse and that sinking feeling in your stomach hits you. You’ve left your wallet at home.


5. Flipping Someone Off – Then Following Them To Their Office

How could that A-hole cut you up like that on the road? What a jerk. That douchebag isn’t even fit to drive a car. Why should someone who doesn’t know how to handle a stick be allowed behind the wheel of a Mercedes S-Class?

You flash your lights at him, toot your horn and flip him off to boot…

Then follow him as he drives all the way in the same direction as you and pulls into the company where your afternoon meeting is, parking in the C-suite zone. Oops.

6. Investing At An ATH Then Watching The Value Drop

Is there an entrepreneur alive who hasn’t experienced this WTF moment at some point in their life? Maybe you heard about the hype accumulating over Bitcoin. If you’d bought a year ago, you’d be a millionaire by now.

But it’s risky and your friends say you can mine it. And it’s banned by the Chinese. But f*** it! You decide to invest anyway just as the market reaches an ATH. Then you watch as its value drops like a stone. Plunk… plunk… plunk…

You’ll survive WTF moments like these. Think of them as life lessons.

7. Sharing Content That Only Your Mom Likes

Sharing an article on LinkedIn and getting no comments or likes sucks. But what’s actually worse than that is having no comments and likes except for your mom. And it’s usually something totally unrelated.

You’re interviewing the CEO of large multinational and all she has to say is “your hair looks great, honey!”

WTF Moments Are Part Of Life

Most things worth having in life are pretty darn hard to obtain. So, if you’re plagued with WTF moments, remember you’re in good company. And as they say in the acting world, never work with children or animals. Perhaps you should extend that rule to your office.

Christina is a copywriter, MBA, marketer, columnist and general life enthusiast with a love/hate relationship with monkeys.


Leave a Reply

Your email address will not be published. Required fields are marked *