How to Get Out of the Side Hustler Mindset

To all my Side Hustler friends out there, I love you, but get ready for some real talk:

A lot of you are never going to change that side hustle into a full-time job.

Ouch. I know. Is it because I don’t believe in you? Hardly.

It’s because you don’t believe in yourself. Let me lay it out for you.


First, here’s the Side Hustler Mindset:

  1. You believe your dreams or interests are unimportant enough to be a priority in your life, hence the side hustle position.
  2. Why do you do #1? Because while you believe your creative pursuits make a great hobby, but there is no way you can make a “real living” at it.
  3. As such, you believe you are supposed to pay yourself with the leftovers. This is either leftover time in the day to work on your side hustle or leftover money to pay yourself once all of your expenses are covered.


Now, the kicker is that you will make choices and decisions, likely subconsciously, to reinforce #1 and #2 so that #3 will never be enough to do anything with.

Then we create a self-fulfilling prophecy that helps us continue to deny our deepest wishes & passions. Why? Because we were taught to turn off our inner voice and signals by others as we were growing up. Deep down, we believe the things we really love are “silly” and not “practical.”

So, when we start side hustles, it’s us trying to let our dreams and true selves finally break through.  But then, many of us experience not knowing how to create a side hustle that will give us the financial resources to do it exclusively.

Is the reason we don’t know how because we don’t know math? No.

It’s because many of us don’t know how to put our passions first. If we acted independently as children, we could have had our dreams squashed by well-meaning adults. Or maybe our role in the family was to take care of other people, put our needs & wants second, or risk being punished, shamed, and called “selfish.” There is even a good chance that some of you have people around you who still belittle your dreams, which doesn’t help.

The point is that most people are stuck in the “Forever a Side Hustle” rut because they don’t know how to recognize when they’ve fallen prey to these self-defeating thoughts. So, let’s go through some questions you can use to see if your side hustle is being held back by these limiting beliefs.


Self-Coaching Questions

  1. When I think of doing my side-hustle full-time, what feelings and thoughts immediately come to mind? Do I come up with all the reasons it won’t or can’t work? Do I feel excited or doubtful?
  2. When I talk to others about my idea, what are they telling me? And how do I respond? Do people tell me I am very gifted at my side-hustle and encourage me? Do I believe them? Or do I have people who discourage me?
  3. When I think about re-working my financials and adding in a salary, what does my body do? Do I feel tense and uneasy? Do I even look at my money numbers, or do I ignore them altogether?
  4. If I had to be honest with myself, is my side-hustle actually my number one choice? Or is it my runner-up?

I think the last question could be pretty telling for some of you reading this. That is because creativity is expressed in many different outlets, from crafts to writing to music. And some of us creative types play with a lot of different mediums.  For example, maybe you’re spending time making jewelry because you love to work with your hands. But perhaps your first love is designing and building furniture. Unfortunately, you’ve convinced yourself that it’s unrealistic to pursue. So your side hustle of making and selling jewelry is actually your second choice because your real passion seems too big. In other words, you are playing small, hoping it is enough to satisfy the itch you have to let your creativity out.


Final step – Go Find The Truth

The truth is that people are doing what you want to do and making a living at it. But what happens when we go looking for the truth? We don’t like what we see.  In this case, when it comes to seeing that we might actually be able to do what we really want to do and see others being successful at it, we don’t feel relieved. Or excited. Or inspired.

No, our initial feelings are fear. Shame. Inadequacy. Envy. And we use those feelings as evidence we can’t or shouldn’t do what we really want to do.

But those feelings are just memories. Not facts. They are the terrible things we were taught to feel and believe about ourselves whenever we tried to be and express who we really were while growing up. And the shame we learned to feel towards our inner impulses continues to haunt our entrepreneurial aspirations.



Chronic side hustlers have a mindset that keeps them trapped into playing small because they are trapped by self-limiting beliefs. These limiting beliefs are based on the fact that side hustlers haven’t learned how to put their own desires first and be okay with choosing their own dreams. But, with the self-coaching questions in this post, you can finally get honest with what is holding you back from being successful once and for all. We all deserve to do what we love and make money doing it!



Share :