Career & Side Hustle Coaching For High Achievers

4 Costly Mistakes to Avoid When Starting a Side Business

Many people have great ideas that either fall to the wayside or never get executed (myself included!). 

This article is a part 3 out of 3 part series on the blog. If you haven’t started your side business yet, make sure to read this article about how to get started (with my TNT framework) and how to balance a side business with a full-time job.

Statistically speaking, 20% of small businesses fail in their first year. And I’m not saying this to be discouraging, I’m saying this so that your side business isn’t a part of this statistic. 

That’s why in this article I want to focus on the 4 costly mistakes you need to avoid when starting a side business (and how to overcome them!).

Let’s get started.

1. Prioritizing Outdated Strategies Over Mindset

When you first begin starting a side business, it can be so easy to be pulled into the shiny new promises of every course that will teach you the mind-blowing strategy. However, as someone who has taken so many courses, I can’t even count the number of courses I’ve bought. I used to buy those course bundles that would have like 80 courses for the price of one because that was all I thought I needed. That’s why the first costly mistake you need to avoid when starting a side business is prioritizing outdated strategies over mindset. 

But instead of focusing on strategies, it’s more important to leverage the free content out there and then work on your personal growth in being consistent and actually implementing those strategies.  There is a lot of free content out there but most people struggle to implement those strategies because they don’t have the right mindset.

For example: When I first started what Work Life Money Co is today in 2018, I took a blogging/group coaching course where not only did I learn the basics of blogging, I really learned how to be consistent and persist through it. I really enjoy writing so I knew this was the pathway for me and I’m so glad I focused on utilizing the free tools out there (like just getting a free website domain) and then easing into buying a course that taught me more and a group coaching program to continue and develop my self-confidence in marketing myself.

On the other hand, I know a lot of people that bought an extremely popular (and expensive!) blogging course that taught you every little bit about blogging but realized it wasn’t for them. 

One of the things I always try to remind myself is that courses will always be out there. But when you work on your mindset first, it’s so much easier to execute the courses well. Buying lots of courses and procrasti-learning will not cost you a lot of money, but also time because strategies change!

On that note, if you are looking to create a successful side business alongside your 9-5, I invite you to join me inside my 1:1 Coaching Program. One of the things I wish someone told me when I was starting a side business was that I could be successful in both my career and side business at the same time. A lot, and I mean A LOT of people who I was following and who I heard talk about creating a side business was doing it because they wanted to take it full-time and they villainized their 9-5s.

But I truly believe and have seen there is a way to be successful in both. In this program, we will be not only working through the mindset blocks of you build a business, but also the ones in your 9-5 so you can have the choice to either stay full-time in a career path you love or work towards building a full-time job in your side business. Yes, it can happen both ways. Make sure you book your free Career Consultation Call for 1:1 Coaching at

2. Having An Entry-Level Employee Mindset

When you come from the corporate world, it’s so easy to take on the mindset and actually desire to have someone tell you what to do. That’s why so many people flock to courses at the beginning and then don’t end up finishing them (myself included!).

That’s why the 2nd costly mistake you need to avoid when starting a side business is having an entry-level employee mindset. Most people stay in entry-level jobs in their careers and then begin to resent their 9-5 because they don’t learn that as you move into the middle phase of your career, doing what you are told is not enough. You have to take greater initiatives and truly become a leader even if you don’t have all the answers at the time. And that mindset is actually what allows people (including myself) to get promoted and jobs I don’t feel qualified for while having a successful career, because the mindset shift is the same.

To add to the first point: I would not recommend buying a ton of different courses to try to find the perfect strategy. As someone who has seen literally hundreds of courses, I can tell you that 99% of them are very beginner. I’ve been shocked with how simple some courses have been and not just in the information because I think there is definitely value in having things in the first step, but so many courses consist of videos that are 2-3 minutes long and that’s it.

I have also taken super amazing courses that really taught me so much about my business but the problem is that if you are learning from a lot of different creators, it is so confusing. There are a lot of methodologies out there that definitely work, but to take advice from 12 different people is more counterproductive than helpful. 

So if you are looking to be successful in your career while you are building your 9-5 so you can get paid and make an impact in both areas, make sure to book your free consultation call for 1:1 coaching here.

3. Relying On Conditional Courage

Starting a side business takes courage. It takes courage to put yourself out there and courage to overcome the self-doubt if this will actually work if it’s for you, and what other people will think about you. That’s why the 3rd costly mistake you need to avoid when starting a side business is relying on conditional courage.

However, a lot of us are used to only acting upon conditional courage. Conditional Courage is when you act upon knowing that you will get a certain outcome. For example, I have a lot of courage when it comes to high adrenaline activities like scuba diving or sky diving. However, I’m taking that action out of the condition that I don’t die. 

Similarly, you might be used to taking courageous action based on a known result like you will have the courage to raise your hand in class or in a meeting if you already know the answer and will be praised for it. 

However, when it comes to business, you have to take true courage with is taking action without knowing or even having the full result planned out. It’s so important to understand the difference and learn how to act upon true courage or it will cost you a lot of opportunities. 

I remember the first time I pitched myself to a media company to publish my writing (and pay me for it!) and it was terrifying because I had no idea what the result would be. Fast forward 3 years, I now get paid regularly for my writing and the relationships I have built with organizations have opened me up to opportunities I didn’t even know could exist for me.


4. All or Nothing Mindset and Fear of Wasted Effort 

And the 4th costly mistake you need to avoid when starting a side business is actually the fear of wasting effort, money, and time itself. When it comes to starting a side business, the fear of wasting effort and the all-or-nothing mindset can truly hold you back because it causes a lot of overthinking regarding scenarios that haven’t even happened.

Both the fear of wasted effort and all or nothing mindset tie in together but let’s start with the fear of wasted effort. 

When you first start your side business, it’s easy to be driven by fear. School has taught us that we have to know what we are doing, and to do as much as possible not to “waste time.”  However, when you are looking at starting a side business it’s important to remember that there will be times when things don’t work out. You can put your time and energy into something and it might not sell or in creating a piece of content and it doesn’t become as popular as you hoped…and that’s okay. 

Starting a side business is really learning about what works and what doesn’t. There will be things, no matter how much you try to research and plan out, that won’t work out the way you thought it was and it can feel tempting to want to avoid that feeling of wasting time or money. Instead, reframe it as a learning lesson. 

This ties into the all-or-nothing mindset. The all-or-nothing mindset is when we constantly try to act and control all aspects of our lives. It can be enticing and even normal to feel like if you just learned enough, if you just planned enough, then everything will work out as planned but it’s more important to move into a growth mindset where not everything is a learning experience instead of having it mean something about you. 

Lastly, creating a side business can be a long game, and even if it’s not that specific business (I’ve switched up many times too), the lessons will last a lifetime. 


Looking to start a side business and have it be successful alongside your 9-5? Make sure to book your free 1:1 Coaching Discovery Call here

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