The Habits of Highly Effective Side Hustling Moms: Habit #1- Be Proactive (So You Don't Go Down the Wrong Path)

Habits of Highly Effective Side Hustling Moms

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Don’t be like me.

After working at my corporate job for 20 years, I was searching for something more.  My career was as dull, gray, and windowless as my office, and I was feeling stifled, suffocated, and trapped.  So at 40 years old, I decided I wanted to be a makeup artist.  I love makeup, so I thought this was a great idea. I had big dreams of eventually living a life of freedom and creativity and making women all over the world feel beautiful.

I have to say—I was pretty good.  At one of my very first fashion shows, I was doing the makeup for a runway model and as soon as I was done, I had another model waiting for me.  She told me that she walked around, surveyed the 10+ artists at the show, and came back to wait for me.

Turns out, she was a local swimsuit model and we began a symbiotic relationship; I did her makeup and she gave me the pictures from her shoots so I could build my portfolio.  I was busy— I did pageants, proms, fashion shows, and model photo shoots.  

One day, I was taken under the wing of a successful local makeup artist.  She was the go-to makeup artist for major movies shot in Hawaii and had been flying back and forth to LA to work for a national TV network. 

This was five years ago, and I still remember it clearly.  I was standing in the stairwell at my 9-5 when my mentor called.  She asked me to go with her to LA to take a special effects makeup class for movies and TV.  Going to LA would unquestionably help my makeup career.  

I said no.

I said no because I had been internally wrestling with this whole makeup artist thing for a while.  I’d been taking off a lot of time from my 9-5 to work on fashion shoots, TV commercials, and movies.  In addition, pageants, proms, weddings, and fashion shows usually take place on the weekends, and I was missing out on a lot of my kids’ games, potlucks, and team and family dinners.  

 So although it wasn’t easy, I said no.  That was a crossroads moment, and my decision was based on one of my strongest values….that I want to be around, as much as possible, for my kids and family. 

My experience perfectly illustrates why you need to adopt Habit #1 of the Habits of Highly Effective Side Hustling Moms (based on, and adapted from Steven Covey’s 7 Habits of Highly Effective People).

Define Your Outcomes From The Outset

Habit #1 is to be proactive.  Steven Covey says that in order to be proactive, you must “define outcomes before you act”.  In terms of side hustling, being proactive means doing your research up front.  It means not jumping into something without doing some up front work.  

Had I done my research about what was involved in becoming a successful makeup artist, I probably wouldn’t have done it!  I ended up spending a ton of money on makeup and supplies and wasted a lot of time going down a path that wasn’t consistent with one of my core values.  

I get it.  We love to skip this proactive part because it’s not as fun as jumping in when we’re super excited about something.  But as working moms, doing the upfront research is super important.  Our time is so precious and limited that you don’t want to waste time going down the wrong path.  This is not to say, of course, that unexpected stuff won’t come up and you’ll never make mistakes or you’ll never have to course correct and pivot.  But if you can avoid making a mistake by simply doing some investigation on the front end, why wouldn’t you?

On the other hand, I’m not suggesting you get caught up in analysis paralysis, where you never make a decision because you’re always researching.  At some point, you have to go for it. The trick is knowing when to feel comfortable that you’ve done enough research to move forward.

Again, doing some background research should be standard operating procedure for any part of your side hustle.  For example, if you’re trying to figure out what type of side business to start, find out—what types of businesses are most compatible with your existing skill set and experience?  What do you want to do and how can you parlay it into a business?  Is there a market for your business or will you trail blaze the way in an entirely new market?  How long will it take to get set up?  What kinds of skills will you need to develop to get started?  Will this side business fit into your lifestyle?

The Niche Finder Workbook

Whether it’s deciding on what type of business to launch, what type of product or service to offer, developing a marketing strategy, what type of website to build, or who to hire to coach you through the process, you should adopt Habit #1 to be proactive and define outcomes before you act—in order to save you time, effort and potential heartache.  


So, get going and start researching the viability of your side hustle idea! Be sure to read the next article in this series of the Habits of Effective Side Hustling Moms!  If you found this post helpful, please share it with a friend or pin it to your Pinterest boards!  Aloha!

Jennifer Wilson