8 Side Hustle Roadblocks And How To Overcome Them

I want to admit something to you – I’m not perfect.

Yup, if you are a regular reader or someone who found me in some Google search you might be thinking that I have this great website and that I don’t make mistakes, or run into roadblocks.

Nothing could be further from the truth.  Since starting my first side hustle in 2004 I’ve encounters many failures, pitfalls, and roadblocks.  In this article I’m going to share the roadblocks that I’ve dealt with over the last 11 years running my side hustle.

However I don’t want to share these to scare you, that is not my goal here.  My goal is to show that their will be some tough times in your business and that it’s not all velvet ropes and big money.


Rather starting a side hustle is just that, a hustle, and you will have to work hard for what you want.  Their are going to be frustrating moments in your business but it’s all in how you deal with these moments that determines your success.

So in this article I’m not only going to share the roadblocks I’ve been through but I’m also going to show you how to overcome them and get back on track.  Also at the end of this article feel free to share the roadblocks you’ve dealt with in the comments below.

#1 Things Take Longer To Complete

One of the first roadblocks I noticed when I was first getting started online was how long it took to complete something.  Just as a good example, when I started my first website it took me just over a year till I earned my first $100 in one month online.

Now even though I’ve been doing this for several years I’m still experiencing this problem. Currently I’m in the process of creating my first online course and it’s taking me a lot longer to get done than I thought.  I originally planned to have this course done mid June but it’s looking more like mid July.

How To Overcome This:  First don’t beat yourself up because it’s taking you longer in the beginning.  When you start anything new it’s almost always going to take you longer.

My suggestion is to take the amount of time you think it should logically take you to get something done and double it, at least in the beginning.  Until you get systems in place and learn the processes you need to complete to do something it’s almost always going to take longer.

#2 Beating The Learning Curve

Another issue that’s going to get in your way is knowledge.  I’m not talking about the knowledge of your topic but the knowledge to create your product or service.  For example, when I was first getting started I didn’t even know how to set up my website, load plugins, or set up my website theme.

However over time I’ve learned a thing or two and those things are second hand to me now.  However when it comes to online business their is almost always something new to learn.  Currently I’m learning everything from setting up sales funnels, landing pages, sales pages, to running ads on Facebook.

How To Overcome This:  To overcome this you really have two choices you could sit there and try to do everything yourself which takes forever or you could pay to join a course that will teach you a particular skill.  Since I’ve started online I’ve joined nearly 20 courses.

These courses taught me everything from how to write better content, outsource stuff, run Facebook ads, and even how to create courses.   If you’re looking to increase your knowledge check out this list of places I put together to help you get started, and best of all they’re free.

#3 Not Enough Time In The Day

Time is another big issue that you’ll be dealing with as well.  If you’re like me time is your most important asset.  With 3 kids and a wife it can be hard to find the time get things done in your side hustle.  I put an entire article on how to deal with this which you can check out here.

With so many things fighting for our attention these days from family, to your iphone it can be hard to get even just 30 minutes in a day to work on your business.  I know this because I still deal with this problem.

How To Overcome This:  First off don’t let time be the excuse.  I’ve found that if their is something you really want to do you’ll find the time to do it.  It all comes down to priorities, and watching reruns of of your favorite TV show don’t count.

For me I try to find the the times of day where I’m the most energized to work on stuff from answering emails and writing content on my breaks and my lunch hour at work.

Then in my evenings I focus on the more important activities in my business such as creating products, setting up sales funnels, and pretty much anything that grows my business.

#4 Fearing What Others Think

Fourth is the fear of what others think.  This may or may not be a big deal for you but I know it was for me.  For some reason humans have this huge fear that we might look bad in front of others.  I think this has to do with the fact that we don’t want people to judge us.

I get that because when I tried to explain to my parents what I do and they didn’t really understand it.  The same goes for my wife, she didn’t really understand my business in the early days but once I started to earn the extra side income she supported 100%.

How To Overcome This:  The way I deal with this is to just realize that their are things I can control and things I can’t.  I can’t make someone understand and like my business that has to come from them.

On top of that people who want to buy my product or service will buy it if they feel they are the right fit for my business.  That’s the great thing about going online with business, I never have to force someone to go to my website or buy my products because when they come there on their own free will they want to read and buy what I have.

#5 Not Enough Money

One roadblock that has been tough on me over the years is not having enough money.  The great thing is though getting started with a side hustle does not take much money to get started.  In my early days I didn’t have a need to buy much but as things have progressed I’ve been investing more in my business.

This could be anything from buying courses to learn new skills to paying for things like Facebook ads.  Money is the life blood of any business and when you’re just getting started money is always hard to come by.

How to Overcome This:  In the beginning it’s OK to go the cheap route but once you start to earn some income in your business think about how you could reinvest that money in your business.  Also make sure you spend your money on things that either grow your business or free up more of your time.

Like I mentioned before I invest in things likes courses that help me beat the learning curve, such as Facebook ads so I can reach a bigger audience, and even outsource small things in my business so I can free up more of my time.

#6 Shiny Object Syndrome

Another area I’ve gotten stuck in is overwhelming myself with to many things also known as shiny object syndrome.  Since starting my online side hustle I’ve started numerous websites from personal finance sites to life insurance training, and link removal.

For me it seems like an idea pops into my head and think I need to act on it.  I don’t know if you can relate to this but I’ve found I like to start a million projects and finish none of them.  Then before I know it I have so many things going on I give up on all of them.

How To Overcome This:  If this a major roadblock for you the best way I’ve found to overcome it is to focus one thing.  I found if I shut everything else out and just focus on one thing I tend to do a lot better.

To do this you have to eliminate things.  For now just pick one project you want to work on and complete it.  On top of that eliminate all the other distractions.  Things like checking my email and Facebook need to be limited to specific times of the day.

Also you need to eliminate sources of information that may be causing you to fall into this trap.  For me this meant unsubscribing from mailing list and not listening to certain podcast.  I’ve found these two areas to be my biggest culprits to throwing me off course.

#7 Being A Perfectionist

The opposite of shiny object syndrome is being a perfectionist.  This isn’t a particular problem for me but I know a few people who do deal with this, and what I’ve noticed from them is that they can create some really great stuff but don’t feel it’s never good enough.

My brother is a prime example of this.  Currently he’s in the process of creating a brand new site and I have to constantly keep telling him just put it out and let your audience decide.  I’ve also found perfectionist tend to want to make everything they do the best that the best may not always be what everyone needs right now.  So how do you deal with this roadblock?

How To Overcome This:  The simple answer would be to just get it out there.  Whether it’s a product, or a service, you can weigh all the pros and cons but until you get it out in the marketplace you’ll really never know what the right answer is going to be.

When it comes to being a perfectionist you might feel like you never want to be wrong and that everything has to be perfect.  Well I’m giving you full permission that everything does not have to be perfect.  Just put something out there and improve it from there.

#8 Failure

The final roadblock is failure.  Since I’ve started my first side hustle way back in 2004 I’ve failed numerous times. My first side hustle ended up being a huge failure, which was a business opportunity doing financial services that a few of my friends had gotten me into.

Another failure I dealt with a few year back was the Google Panda updates.  These update literally took two thirds of my traffic from my first site overnight, not to mention my income.  Ouch!

How To Overcome This:  First off, don’t let failure beat you up to much, all businesses encounter failure at one point or another.  When you fail at something it just means it doesn’t work and that you need to adjust your plan.

Instead of getting upset or depressed look at your plan and ask yourself what you learned from this and move on.  I know this can be hard to do in the eyes of defeat but it’s the quickest way to getting back on track.

After I failed at my first side hustle doing financial services I came to the realization that I didn’t like doing direct sale and I decided to take a more passive approach and started my first website shortly after.

When my website lost a whole bunch of traffic I ask myself that same question again and realized that if I would have had a mailing list my situation would have been much better off.

In the end just remember when you fail at something that doesn’t make you a quitter it just means you need to try again.

Have You Faced Any Of These Roadblocks

So now that I’ve shared several of the roadblocks I’ve dealt with how about you, have you dealt with any of these roadblocks.  Share your thoughts and comments below.


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