4 Ways to Overcome Side Hustle Obstacles

Have you ever been working hard at something, only to encounter one problem after another?  This seems to be the norm for the average side hustler!!!  Obstacles can be frustrating and defeating, and if you have enough of them, they may lead you to consider scrapping your whole idea.  But don’t forget, you’re here because YOU ARE A HUSTLER!


If you read my very first blog post then you know that this website/blog is ONE of my many side hustle attempts.  Again, I started out with ZERO knowledge of building websites and automating email systems and customizing my MX (I’m still not sure what this means, but apparently its important!)  And trying to go from zero to something, has been incredibly challenging!  

I have discovered that my website/blog is a little unusual as it is both a website, offering physical products for sale and digital products to download, as well as a blog, including thoughts, ideas, and updates.  I have been told that setting up a blog is easy…and it seems to be so.  I have also been told that setting up an ecommerce site is easy…and it seems to be so as well.  Marrying the two together however, creates quite the challenge.  

And if that wasn’t difficult enough, finding an email management company for a website that seeks to help others make money from home and celebrate their entrepreneurial success is apparently an impossibility.  When we first sought to automate our emails, we chose a reputable email marketing service (not gonna throw anyone under the bus here) who offered a free trial.  We created an account and after spending hours making all the necessary connections, setting up templates, and running tests to make sure it all worked, I received notification that our business model didn’t meet their compliance standards.  This resulted in our account being terminated.  ARGH!!!! Those are hours of my life I’ll never get back!

So, we then signed up with another reputable email marketing service who also offered a free trial.  I got smarter this time and learned to speak with a sales rep to see if I would encounter the same problem as before.  And sure enough, our business model (sharing ideas on how to make money from home) didn’t meet their compliance standards either.  But wait, there’s more…  The next day I received a phone call from that company stating that they had looked through our website and were excited about what we’re doing and are glad to help out!  WOOHOO!!!  I signed up for their $20/month basic service and got to work getting our emails set up and automated.  We would finally be past that obstacle!

HOWEVER, the next day I received notification that my account had been shut down because…yep, compliance.  That didn’t make any sense, I had already asked this question, and our initial denial had been reviewed and approved.  I called the company back to make sure everybody could see the notes on our account that we had been approved, only to discover that our approval was apparently premature.  Our account was again terminated.  More hours lost.  

It is these types of obstacles that side hustlers will encounter.  For us, emails are a pretty important piece of a website trying to offer content to help people. (If you’ve subscribed to our site and have experienced any issues with receiving our emails, we offer our sincerest apologies!!!  I assure you that it is not for lack of trying!) 

How to Overcome Side Hustle Obstacles

So what do you do when your hustle hits one obstacle after another?  


    Starting a side hustle can be overwhelming enough.  You’re trying to make something from nothing.  You’re trying to figure out every small detail in order to make your hustle successful, and every one of those details has the potential of becoming an obstacle.  BUT keep plowing through!  Take a step back, take a break, take a nap, take in an extra chocolate chip cookie…remember why you’re doing what you’re doing, and get back to it!  


    Maybe you’re hitting an obstacle because the specific road you’re attempting to travel isn’t the right one.  Is there an easier way, a different way, a better way?  What lesson is the obstacle teaching you?  What shift might you need to make?  Be honest with yourself.  Don’t be too blinded by ambition to not re-evaluate.   Keep plugging ahead, but maybe do it differently.  As the odd saying goes, “There’s more than one way to skin a cat.”  That’s just weird and gross!  Let’s go with “There’s more than one way to build a burger!”


    Sometimes we simply lack the knowledge on how to overcome a certain obstacle, especially if it is something technical.  Use “Help” features online.  Find a forum and ask some questions.  Talk to others you know that might have the information you need to help guide your through the obstacle.  Realize that others have faced this problem before you, let their experience help guide you to success.


    Obstacles are part of the journey.  You didn’t start your hustle simply to quit.  Yes, you can listen to any number of voices that simply tell you that “Doing nothing is so much easier than doing something.”  Some may tell you that your idea is stupid…or it is a waste of time…or doesn’t fit their compliance model.  I can tell you that ALL of my side hustle endeavors have worked…not because I am awesome, but because I simply wouldn’t let them fail (though truthfully, some I probably should have abandon sooner than I did).  The road ahead may be all up hill, but as long as you know where it leads, you can keep hustling!

Our Email Outcome

By the end of the day today, we MAY have our email automation figured out.  I can’t remember if this is our fourth or fifth attempt, but we don’t quit. We keep learning and re-evaluating, getting lots of help from various sources, and keeping our eyes on the prize because I want you to get as many ideas as possible to help your side hustle journey.  As for you, whatever your journey looks like…keep hustling!!

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