When you are first starting a new habit, the key is to first get the motions right. For example, when I started writing these posts Monday-Friday, the goal wasn't to write perfectly, it was just to write every Monday-Friday.
Similarly, when you first get a new brand identity, you should follow your style guide to a "T." Why? Because you are learning to walk within your brand and if you start running you will fall, chip your teeth and look stupid.
Think about it, the kid who can consistently walk at a steady pace will get further than the one who pushes himself too far.
What's more? The kid who walks will get faster with time and practice, naturally.
Treat the design of your brand the same way, walk before you run.
Before we jump into details, we gotta get one thing straight:
A brand is the gut-feeling has toward a business. By definition, being "on brand" would mean that the feeling you want people to have is being felt by your target consumer. Being off brand would mean they feel the opposite or something unrelated. For example, if I want people to feel "rebellious," then similar feelings like edgy, badass, and cool are right up my alley. What I'm looking to avoid is the opposite; safe, quaint, pretty, timid, etc. With me so far? Cool, here are the three steps:
Define your brand
This is done through a brand discovery workshop, it's borderline therapy for business owners. Founders sit in a room with an objective third-party and tell everything they can about their business. Their customers, their dreams and goals, the culture they desire, all of it is put on the table. In doing so, nuggets of information can be pulled that show what someone should feel about the business. The goal is to create a definition of the brand that can be used as a yardstick.
Review all marketing collateral
Social posts, brochures, swag, websites, the name, logo, identity systems, business cards, email templates, everything that comes into contact with a customer is put up for review. It goes without saying that if you're jumping into a rebrand, you are probably not happy with all of these assets anyway, but you need to clarify why that's the case. If you don't you open the door to repeat the same mistakes in recreating them.
Make a game plan
Using the items in the review, make a plan of action prioritizing the elements that would have the greatest impact on the brand. Then, get to work updating them and getting them on brand.
This will be simple.
If you want people to love your brand, don't give a half-assed effort into the design of it.
If you don't care, carry on as you have been.
A minor effort into a major problem is a recipe for disappointment.