5 Key Small Business Mistakes and What to Learn From Them

You’ve packed up your cubicle in pursuit of your dream, your real one.

You’re done working toward someone else’s

Even if it means losing the security and stability of a regular job. And as you make your way out of the drabby office, you smile and decide it upon yourself to never make the same mistakes you’ve seen firsthand here…

Fast forward a few months, maybe even years, and you find yourself making some pretty common mistakes after all. Sure, you’re working for yourself, toward what you believe in, and that feels so good! But at the same time, you can’t escape the… genuine, deep-rooted, painful sense of doubt that makes you look back at your mistakes, and wonder if it’s time to wave the white flag.

Well, it’s not.

Business owners make many mistakes, whether they’re starting out or not, whether they’re running a small business or a big one, etc. It’s all part of the process.

So, perhaps avoiding these mistakes shouldn’t be the goal. You can have control over whether or not you learn from those mistakes, and use those lessons to guide you forward. That should be the main focus.

To illustrate that point, let’s dive a little deeper today, and highlight five of the mistakes most all small business owners make, and what you can learn from each one.

#1 Investing Too Much Upfront

Suppose there’s a man, let’s call him Bill.

Bill started his record store and he’s very excited about the whole thing. He’s picked out a venue, had genre signs printed and hung in their respective corners, and even stocked up on plenty of product for people to sift through.

In fact, he’s hired on a full team of 15 people already, and he’s debating on hiring local artists to play a set on the weekends.

Bill is so excited that he’s what you would call “too proactive.” Everything in business comes in due time. But if all you do is invest everything you earn upfront, you’ll find yourself in dire straits sooner than later.

Businesses take a bit before they earn a profit. Until you’re back in the green, there’s no reason to go overboard on investments that, although helpful for the business, are putting serious stress on your financial situation.

Instead, you can draft up a list of the exciting things you want to complete for your business, and set a time frame for each. Try to prioritize the things that you know you can do quickly, for far less money than the alternatives.

#2 Outsourcing Before You’re Ready

Let’s imagine a freelance content marketer. She’s busy every weekday drafting up content for clients, editing people’s work, designing brands, and handling assessments. In fact, she’s so busy, she’s not actually working on her own brand.

So, what does this entrepreneur do? Hire someone to handle it for her. Surely, another professional with more time for another client can take on her brand.

Well, that could work, but only if there’s a clear cut, defined sense of branding in mind already. Otherwise, it’s just the blind leading the blind.

Here’s what I mean: anytime you outsource people to do your branding, or complete your content marketing, you need to try to have a few things in place first. Among them, you should try to know who you are, who your customers are, and what your business is all about. This will dictate everything you do as a business, including your style, and who you work with.

#3 Not Taking the Initiative

Suppose a freelance copywriter is having trouble making ends meet. She has two clients, both of whom pay her well enough, but it’s still not enough to cover most living expenses without living paycheck to paycheck.

Her problem? She doesn’t reach out to people. She doesn’t put herself out there to cold pitch to people she genuinely wants to work with. Instead, she casually looks through hiring boards, applies to maybe 1-2 per month, and wonders why she’s not getting anywhere.

Business won’t just fall into your lap. People won’t just fall over each other, clamoring to be able to work with you. No, you need to try to show potential clients that you have something that they need.

And that means messaging people, putting in the effort into your message, and linking to your digital portfolio. It means putting in the effort into every query letter and email you send out.

#4 Expecting Results Too Quickly

This one is a hard pill to swallow, so let’s get right to the point: it will take you a while to see any level of profit. Remember, we learned this thanks to Bill, our first example.

That means anything you do is basically a planted seed. It will grow, but not overnight. And that means you may need to work a day job while things kick off. Or maybe it means saving up for a year before jumping ship.

Whatever it means to you personally, whatever sacrifice, you can’t give up because it’s been two years and you “have nothing to show for it.” You can’t give up because all of your friends are doing these amazing things, landing impressive jobs, while you’re struggling to see your dreams flourish.

A successful entrepreneur knows that the struggle period eventually ends.

#5 Procrastination Is a Tool

That’s right, procrastination isn’t always a bad character trait to have. It’s actually a tool, when used correctly.

For example, deciding to hold off on re-branding until you’ve reached a point where you have solid revenue coming in, and you’re more secure in who you are as a person and a business makes sense. It guarantees that whatever decisions you make, branding-wise, will not go to waste.

There is no shame in waiting for things that could change for the better, or for things that would benefit from being put off a while longer. It’s all about being selective with where your time is better suited at any given moment.


As you can probably tell, these issues, although common for most small business owners, aren’t the ones people write about, or even talk about all of the time. These are the mistakes that never really get the spotlight, so to speak, but they’re equally as important as the rest, if not more.

And most entrepreneurs make them, but that’s okay. Avoiding mistakes isn’t the name of the game, it’s the lessons learned from them that matter. If you can learn even one valuable lesson from every mishap, then you’ve gained something worthwhile.

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