The Problem with Always Learning on the Job

You’ve mastered learning by doing—but at some point, reacting to every challenge in real time starts to wear you down. In this post, we’re talking about why constant on-the-job learning can stall your growth, and how the Squire Book Club helps you shift from survival mode to strategy with business books that actually apply to real vendor life.

Just because you can figure it out as you go… doesn’t mean you should.

Most of us didn’t start our wedding businesses with a degree in entrepreneurship or a trust fund to cush the trial-and-error. We learned by doing—on the job, in the middle of chaos, while wrangling flower girls or Googling tax tips between editing sessions.

And honestly? That kind of hustle deserves a standing ovation.

But here’s the thing no one tells you: if you’re always reacting, there’s no time to grow.

I’m going to say that again for those in the back… If you’re always reacting, there’s no time to grow.


Wedding Vendor = CEO, CFO, CMO… and Also Therapist to the Drunken Bridesmaid

You’re not just showing up with a camera, bouquet, or binder.

You’re running a real business with systems (or… system-like things), pricing structures (hopefully), and customer experience (plus last-minute Pinterest curveballs).

If you’re constantly learning in survival mode, you’re putting duct tape on things that need blueprints.


What Learning on the Job Really Looks Like 

Sure, you gain experience. But you also:

  • Undercharge because you don’t know how to price with profit in mind
  • Burn out because boundaries are hard to set mid-panic
  • Stay stuck in cycles that feel “normal” just because they’re familiar
  • Waste time reinventing the wheel when a better system already exists

And most importantly?

You miss out on the ease that comes from learning before the fire starts.

**I recommend you read the above one more time**


Enter: Intentional Learning

That’s what we’re doing at Squire Book Club.

Not learning after the breakdown, but building the business brain before the chaos.

Each month we tackle one book with practical, vendor-relevant insights—books like:

  • Profit First – so your money isn’t vanishing by October
  • Atomic Habits – because tiny changes = massive results
  • You’re a Badass at Making Money – to rewrite that pesky “starving artist” mindset

You don’t need more to-do lists. You need lightbulb moments you can actually use.


We’re Done Scrambling. We’re Ready to Strategize.

And if you’re reading this thinking “okay wow, this is me,” you’re not alone.

Most vendors we talk to are doing amazing creative work—and quietly wondering how to make the backend of their business feel less like a mystery novel.

This is your invitation to stop winging it and start learning with intention.

(With a supportive crew behind you, too.)


Let’s grow your business with purpose—not just panic.

Hi! I'm Jessica

Here to cheer you on and remind you that you’ve got what it takes to build a business as powerful as your talent.

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**Your zip helps us let you know when in-person meetups are happening near you, and your vendor type lets us send content tailored to your inbox—because a florist and a DJ don’t need the same tips (but they both deserve great ones)

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