The 3 Biggest “Side Hustle” Mistakes Parents Make

Side hustles are sexy. 

If the boss sends you packing on a Monday, you can rest assured there’s an alternative in place that doesn’t require you and your family to rely on anyone but yourself, right? 

Why wouldn’t you want your own side hustle?

While there’s a ton of reasons why you should, there’s an even greater number of non-sexy, overlooked reasons why some of you shouldn’t, especially if you’re a parent. 

If you’re toying with the idea of starting a side hustle or if you’re already on it, I’d like to offer the three biggest mistakes, guaranteed to crush your side hustle productivity. 


Mistake #1 - Your “Why” is All About You

If your #1 motivation is to tell your Company to pack sand, you’re not ready for a side hustle.  

When I began my side hustle experience almost six years ago, my most difficult task was to answer my “why."

Why do you want to break away from your job?  Are you unhappy and unfulfilled?  Is your answer to start a side hustle or to find a new job?

Too risky?  Ok.


Is it that you’re unwilling to move outside your comfort zone? 

What kind of job would give you fulfillment?  Does your fulfillment need to come from your job, or do you just need to pick up a hobby?

Maybe it’s about the money. 

Side hustles can be great for side money…yet, if you’re a parent, there’s real consequences with such a motivator.

What part of your life are you willing to sacrifice for the money? 

Your marriage?  Your relationship with the kids?

How long before your children finally stop asking to spend time with you when you’re always unavailable?  What do you do with your time after you’ve solved your money issues?

Maybe it’s about the time. 

You’re working too hard…I get it.

What can you do to stop working so hard?  What uncomfortable conversations do you need to have with your boss?  With your wife?  With yourself?

What are you afraid of?

Painfully difficult questions to answer I know; but if your intentions for starting a side hustle are all focused inward, your fire will eventually burn out. 

Inward-focused hustles don’t rally support from people either. 

People rally around causes.

If your cause is you…well, don’t ask me to invest any time or energy into your hustle.

Instead, focus outward.

How will your side hustle help people?  How can you develop a cause your family believes in?  

photo by   Niall Brown

photo by Niall Brown

I spun my wheels for five years focused primarily on myself. 

It was a toxic undertaking that left me tired, sick, and distant.  It wasn’t until started focusing on helping people that I was able to turn my side hustle into my full-time hustle. 


Mistake #2 - You Sacrifice Family Time

Are you planning to work all night to hustle?  When will you do it?  From 10PM to 12AM?  5AM to 8AM?  During lunch break?    

What does this look like for you and your family?

What sacrifices will you be making to your health, your energy, your temperament?

The biggest detriment to my success as a side hustler came in the form of my secret expectations - the ones I never communicated with my wife.

I expected she knew I would be working on my side hustle after the kids went down.

She expected I would spend quality time with her and watch a movie.

What agreements need to be made with your spouse?  With your kids?

How can you negotiate the right time and place to work on your side hustle?

How can you gain support, instead of friction, from those closest to you?

The only healthy way to work on your hustle guilt-free and laser-focused is to create clear agreements as to when you’ll be working on it, and more importantly, when you’ll be available for your family.  

If you’re too scared or lazy to have this conversation, you’re not ready for a side hustle.

Don’t steal time from your family; it’s not worth it.


Mistake #3 - No Deadlines

If done with good intentions and a solid plan, starting a side hustle is smart! 

You have an opportunity to test a business concept while simultaneously funding it from your full-time income. 

It’s a beautiful thing!  Beautifully comfortable.

I let my side hustle go on for five years. 

I didn’t treat it like my job, I just worked intensely, allowing the perfectionist in me to take full reign and scare me into not taking action.

I refused to do anything to make me vulnerable.

The never-ending side hustle, the one that gets worked on tirelessly without ever showing results has a name...


There’s a mammoth difference between a side hustle and a side hobby.  There’s nothing wrong with a side hobby whatsoever.  I have several!  Just don’t fool yourself into thinking you’ll someday quit your job when the stars align and someone stumbles upon your hobby and offers you enough money to support your family for it.

Never gonna happen.

If you want to hustle to the point of generating any income whatsoever, setup firm deadlines with high stakes.

Establish key checkpoints along the way to know when it’s time to pivot; get an accountability partner or pay a coach to ask you tough questions.

If you refuse, you’re just a risk-averse dreamer with an expensive hobby.  

Just being real (because I’ve been there).


So Should We Side Hustle After All?

I didn’t write this article to deter people from starting a side hustle.  Side hustle’s are a really smart way to test ideas and concepts before we go all in and bet the farm. 

Before we quit our jobs and start a business there absolutely needs to be an element of side hustle.  Nevertheless, there’s a right way and a severely detrimental way to go about it, both with life-altering consequences that stem from polar opposite directions. 

If you’re scared, it’s ok.  Examine your fear closely. 

What is it your afraid of?  What chances can you take now that you haven’t because you’re comfortable?

What’s holding you back? 

Be brave, but be calculated.  Remember there’s a difference between bravery and recklessness. 

I’m not saying a side hustle isn’t worth going after with excitement and vigor either; just recognize everything comes at a cost.  If you’re a parent, your mission isn’t yours anymore.  It’s your family’s. 

There’s not a lot of people out there who’ll shoot it to you straight these days.  There’s far too many who want you to believe you can do it all so they can sell you something.

Just remember, you can do ANYTHING, but you can’t do everything. 

As parents, we need to be relentless about understanding what’s important, and what we’re saying “no” to, in exchange for the side hustle.

What's your side hustle?

Leave a comment below and let us know what you're up to these days.