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How to Overcome Mental Roadblocks When Starting a Side Hustle

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Last Updated on July 11, 2022 by Daniella

You’ve decided to start a side hustle.

First, congratulations. This is such a great step in diversifying your income and designing your dream life.

You could be starting a side hustle to save for your next car, to pay off debt, save up for your next big trip, start investing, or build a business to eventually do full-time. No matter what your motive, it’s important that you have a clear idea of what you want to do.

If you don’t, you might hit mental roadblocks keeping you from starting. 

To get a clearer idea, our free side hustle quiz can help:

What are the most common mental roadblocks when starting a side hustle?

Every project I start begins with apprehension. I’m not sure if I’m going to be able to pull it off.

I say this to tell you that it’s okay if you feel unqualified to start a side hustle. I felt unqualified when I started freelance writing, and now it’s my full-time gig. Everyone has roadblocks that they have to work through in order to be a successful entrepreneur.

Here are the six most common roadblocks I encounter when helping people get a side hustle started. 

You Don’t Know Where to Start

When you first have an idea, it can feel so large that you don’t know where to start. Side hustles like printable shops can especially lead themselves to that. You can design effectively anything, and then sell it to the world. 

I always recommend brainstorming. Write down every possible thing that you could do with the project. Start with every possible angle laid out on paper. If it’s a good idea, you’ll probably still be overwhelmed by avenues that you could take it. That’s okay. The goal is to figure out what is possible. 

Next, find the easiest section of the project. Rate it with a 1. And then rate each other section in difficulty starting from 2 and continuing. 

You now have a scalable action plan for your goal. 

You Don’t Think You’ll Be Good Enough

Imposter Syndrome is a bear. But anytime you think you aren’t good enough, you need to ask yourself why.

Usually, the answer is pretty obvious. When I first started doing side hustles, I felt like I wasn’t good enough because I wasn’t experienced. The funny thing about that though is that I knew I was only going to get more experienced with practice. 

Another common reason I hear about not being good enough is that no one is going to buy your product because they’ll buy it from someone else who is better. This is negative self-talk. It’s a thinking trap called seeing the future. You can’t actually know what’s going to happen.

You Don’t Have Marketing Experience 

Fun fact! You don’t need marketing experience in order to sell your product effectively. A lot you can learn on your own. You can sell your services to friends and ask them to pass the word along. You can post on community bulletins offering your services. If you run an online business, spend a little time learning about SEO to optimize your posts for Google and other search engines to find you. 

If your lack of marketing experience is still bugging you, there are plenty of marketing books you can read to brush up on the subject. One of my favorites is the Launch by Jeff Walker. He has some brilliant points on marketing and his writing is highly accessible to consumers. 

You Don’t Have Customers or a Client Base

This is another concern of a lot of new side hustlers, especially those who make products. You can start by selling to your friends and family. A lot of people like to support new endeavors. You can also consider signing up for a booth at a fair if you have a product-based business. 

If you have an Etsy shop or something like that, take it to social media. That’s one of the best ways to market your product. Come up with some cute captions and use organic traffic to build your business. 

If you’re a writer, LinkedIn is your tool of choice! Message editors and ask if they need freelancers. 

Most importantly, you just need to get yourself out there into the world. You’ll have to be proactive, but the more time and energy you spend finding clients, the better return on your efforts you’ll have. 

You Find Yourself Lacking Necessarily Organizational Skills

I personally struggled with this for quite a long time. But organizational skills are necessary for solid entrepreneurship. Sometimes you just need a system in place. 

Take time trying out different systems. I found that a paper planner works the best. But some people like spreadsheets, bullet journals, or online to-do lists. 

Creating a system will give you the sense of organization that you need in order to complete projects in a timely manner. And when you’re more organized, you’ll drop fewer balls and keep your clients happier.  

You Don’t Have Enough Hours to Complete Your Project 

Time is a huge deterrent to a profitable side hustle. If you find yourself always running out of time for your projects, consider rescaling your operation. If you don’t work remotely, your time can be even more packed. Maybe what you’re working on is too big for your current lifestyle. That’s okay. Change your expectations to meet what is actually feasible for this side hustle. 

Alternatively, you need to look at your schedule and determine what you can cut out. Before I was a full-time freelancer, I decided to watch one less movie a week to make time for writing. I wrote an article or two a week during that time, and still had a great quality of life and did things that I enjoy.

Now that I work full time at my side hustle, I work four to five hours a day and then have the rest of the day for entertainment, household chores, and hanging out with friends. 

Start a Side Hustle

Want to start a side hustle but are overwhelmed with what to do?

Learn all the basics of launching your side business with my Launch Your Side Hustle online program and start earning money doing what you love. 


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