How Winging It Was My Life Strategy (And Why It’s a Terrible Idea)

By: Manji Cheto

4 October 2024


Spoiler alert: upskhill coaching can fix this!

So, once upon a time, I did what any overconfident, slightly underprepared person would do: I invested all my savings into a packaged drinking water business in Nigeria aka “pure water”. My logic then was this: everybody drinks water and there's a lot of money to be made from the business otherwise there wouldn't be so many people doing it, so what could possibly go wrong, right?—well, the answer is a lot. Turns out, running a water business - or any business for that matter - is a lot more complicated (duh). So long story short, my dreams of water-world domination fizzled faster than you can say “oops.” Yep, I lost my savings.

What happened next? Well, I did what most people would do after watching their savings go poof - I decided to wing it in my career, of course! I thought, "How bad can it be?" And let me tell you, it was bad. I landed a job I quickly came to hate - duh again. Turns out, “winging it” might get you a job, but it won’t get you a job you actually like. Who knew, right?

The Problem with Freestyling Through Life

Look, I’ve done it all - winged it through business ventures (remember the water debacle?) and even winged it through a career pivot. And spoiler alert: it rarely works out the way you think it will. Sure, you might get lucky now and then (hey, even a broken clock is right twice a day), but when it comes to major life decisions - like your career or business - improvising isn’t the winning strategy you think it is.

Winging it feels like fun and games until you’re knee-deep in emails from recruiters who ghosted you, or in a pitch meeting, trying to explain why your business idea isn’t just a glorified lemonade stand. And don’t get me started on “networking” without a plan - turns out it’s just a lot of awkward small talk over stale pastries. Delicious. 🙄

That’s where upskhill comes in.

Enter: The Coaches of upskhill – Your Personal Career/Business GPS

Think of us as your life’s GPS. We’re the ones who stop you from taking unnecessary detours like, say, “investing all your money in a doomed water business” or “accepting a job you’ll hate within two months.” (Not that I would know anything about that. Ahem.)

Whether you’re:

  • Trying to figure out if your CV is why recruiters are treating you like a ghost (hint: it might be),
  • Desperately trying to convince investors that your business idea is more than just fancy buzzwords and big dreams, or
  • Wondering if “networking” just means collecting business cards you’ll never look at again (been there),

We’ve got your back. We know how to help you go from winging it to winning it (Yes, I went there. Deal with it).

What’s In It for You?

Let’s break it down. Here’s why you NEED upskhill coaching, like yesterday:

1. No More Guesswork

Are you tired of Googling “how to write a cover letter” and ending up with results from 2003? Our coaches know what employers actually want to see. We’ll get you past the generic template stage and into the standout candidate stage.

2. Business Plans That Don’t Rely on Vibes

Your business plan can’t just be, “Let’s see what happens!” We’ll help you think through a real plan that gets investors interested and doesn’t sound like, “I dunno, let’s wing it.”

3. Interview Prep That Doesn’t Involve You Sweating Buckets

Don’t walk into your next interview praying they don’t ask you something difficult. We’ll do mock interviews, give you feedback, and make sure you’re not answering every question with, “Uhh… good question?”

4. Negotiation Skills So Good You’ll Feel Like a Jedi

Seriously, you’ll be mind-tricking your way into higher salaries and better business deals in no time. (“This is the raise you’re looking for.”)

5. A Coach Who Won’t Let You Panic-Google Your Way Through Life

We’ve all been there: something goes wrong at work, and suddenly, you’re Googling “how to fix my life in 24 hours.” Don’t worry, we’ll be your go-to before you start spiraling.

But Seriously, Do I Really Need a Coach?

Short answer: Yes. Unless you’ve somehow hacked the system of life and know how to avoid all the wrong turns (in which case, please share your secrets with the rest of us), you’re going to need a coach. A coach helps you:

  • Save time: Who’s got time to waste figuring this stuff out on their own? I sure didn’t. And guess what? Neither do you.
  • Save money: A business coach will save you from expensive mistakes—like, say, investing all your savings into water pipes that no one will buy. (Don’t ask.)
  • Avoid Burnout: Because who wants to burn out before they’ve even hit their stride? (Hint: no one.)

And the Best Part?

We’re running a special offer: be one of the first 50 people to sign up for a coaching session, and you’ll get a bonus session for free. That’s right, free. We like you that much.

How to Get Started

It’s simple. Just click here to book your coaching session, and let’s get you on the path to actual success, instead of “crossing your fingers and hoping for the best.” Trust me, it’s time to stop winging it - your future self will thank you.

Final Thoughts

Listen, if you’re ready to stop relying on luck and start relying on expert guidance, upskhill coaching is for you. We’ve got the experience, the strategy, and yes, the humor to help you navigate every challenge that comes your way. Let’s turn your career chaos into a career comeback. No winging it required.


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Winging it might work for karaoke, but it’s a terrible strategy for your career or business.
Stop guessing your way through life - let upskhill coaching help you go from winging it to winning it.

When it comes to your career or business, winging it isn’t the move. It’s time to start thriving with expert guidance.

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