How to Be a Dream-Chasing Realist: Consider a Side Hustle While Keeping Your Day Job


Welcome back to the 
How to Be a Dream-Chasing Realist blog series. So far we’ve explored several actionable steps to help you pursue your dream or make a major life transition. If your dream involves a professional change, you may want to consider a side business or “side hustle” to supplement your 9 to 5 job. According to LinkedIn, the number of professionals that freelance while working full-time has more than doubled in the past five years.

The benefits of a side gig are twofold. Not only can the additional income allow you the financial freedom and saving potential we discussed in Step 1: Get Your Financial House in Order, but it can also give you the fulfillment you crave, doing something you love while using your unique skills. A side hustle is a great way to build your self-employed income on the path to becoming your own boss, without losing the safety and security of your day job.

This article from Forbes discusses the financial flexibility and freedom that come with a side hustle, making it a smart investment for many. The article features author and entrepreneur Chris Guillebeau, who has been studying the concept of the side hustle for years and has found that nearly anyone can take an idea and make it profitable if they are thoughtful, strategic and realistic enough. You just need an idea, some extra time, and a lot of hard work and determination.

According to Guillebeau, “A side hustle is more than just another stream of income, it’s also the new job security. When you receive paychecks from different sources, it allows you to take more chances in your regular career. More income means more options. More options equals freedom.”

Here are some things to consider along with actionable steps for pursuing a side hustle while juggling a full-time career.

Be prepared for the time commitment.
Your full-time job is likely only one of many commitments that consume your time. Managing your home, spending time with family and friends, self-care and/or volunteering on top of a 40-hour work week can be overwhelming enough, and adding another “thing” on top of it all may seem impossible. But I challenge you to really think about where you’re spending your time, and consider where you might be able to free up some space for something as important as chasing your dream. Make time for self-assessment and decide whether this is something you’re willing to make sacrifices to achieve. This is consistent with ithrive31 core principle #2: Be deliberate with your time and resources.  

Develop the skills you need to succeed.
In Step 3, Broadening Your Knowledge, Skills and Network, we talked about the many ways you can build on your current knowledge and abilities and establish the credibility you’ll need to be successful. If you haven’t already, visit that post for some actionable ways to develop your skill set.  Creating a side hustle is also a great way to develop your business skills and learn more about what brings you energy. In addition to refining your skills, exploring a business idea in a safe environment will give you the personal confidence needed to take the next step.  

Create a business plan.
Spend some serious time thinking about your business and the products or services you’ll provide your customers. Do market research to determine who is offering similar services in your area, clearly define what your differentiators are, and be prepared to sell consumers on that unique experience. Think about a pricing model that will make you profitable; will you charge by the hour, bill customers a flat fee, or sell existing products for a commission? Having a solid plan in place before launching your new business is a critical step in ensuring your success.

Seek input from others.
So, maybe you’re sold on the idea of a side hustle, but you’re not sure what service or product you can provide that creates value for the marketplace. Don’t pursue this new opportunity in a vacuum. Get objective feedback from potential customers to validate whether your idea will gain traction (and turn a profit!) in the real world. You may need to explore multiple options before you find one that sticks.

In closing I wanted to share some real-life examples of women I know who have successfully started their own side hustle. In their own words, they explain what made them pursue a side gig, why they chose the business they did, and what the business provides them in terms of financial freedom and pursuit of their long-term goals.

Kandi Nissen

My side hustle:  I am a Rodan + Fields consultant which means I own my own skin care business.

What made me consider a side gig? Iwanted to be able to say yes to more things that I wanted to, rather than saying no because I had to.

Why this one? I research everything. The Doctors are world renowned female dermatologists. They created Proactiv. Guaranteed results. I don’t have to carry an inventory. I don’t have to have parties. I don’t have to punch a time clock. I can work from anywhere as long as I have my phone or Wi-Fi. I use the products and they work. My earning potential is unlimited. You don’t age out of this business.

My goal: I want to earn enough to be able to retire early and volunteer with Hospice an organization that is near and dear to my heart. My mother is in good health now but I hope that when the time comes I am able to be retired and spend time with her and take care of her.

My greatest discovery: This isn’t just a paycheck. That is the icing on the cake. There’s been so much personal development. I have grown beyond my wildest dreams. I know I can do anything I set my mind to and I never would have believed that a year and a half ago. This business is truly a gift and I love sharing it with everyone. I’m a badass and never knew it!

Lisa Loftus

My side hustle: Loft Design Co, An interior design consulting, home remodeling and handmade décor business.

What made me consider a side gig? I’ve been working corporate jobs for more than 13 years. While I’m good at what I do, my “day job” doesn’t bring me joy. I don’t feel fulfilled, or that I’m using my skills and talents to my greatest ability. My time at work is time spent away from my family, so I want it to be meaningful. I’m also driven and independent, and have always wanted to be my own boss.

Why this one? For as long as I can remember, I’ve had an eye for design, and sincerely enjoy creating beautiful spaces for families to live and enjoy each other. My husband and I have been tackling home improvement projects years, and every time I posted a before and after photo, friends and family would encourage me to design professionally. I finally listened!

My goal: Eventually, I’d love for this side gig to become my full-time gig. I’m 35, and will be working for years and years to come. I want that work to be something that makes me happy, so it doesn’t feel like “work”. I also want to set an amazing example for my kids that if you work hard enough, you can do anything!

My greatest discovery: For a long time, I took my interest and skills in the area of interior design for granted. I thought everyone loved HGTV and couldn’t wait to redesign their home – ha! This gig has taught me that those skills and interests are actually very unique. I work with a variety of clients; some have the skills but don’t have the time…others have a general ideal of what they want, but no idea on how to execute….and others are so intimidated and overwhelmed, they want to write a check and let someone else deal with it. I’ve loved bringing my unique perspective to each experience.


Whether it helps generate the extra income you need to make a professional transition, or gives you the experience and client base you need to pursue the work full time, a side gig is a great tool to help you along your path to chasing your dream. So roll up your sleeves, get creative, and start hustling!

Dorene MacVey is the owner of ithrive31, LLC A Coaching and Personal Development Company.  ithrive31 offers leadership and professional coaching along with personal development programs to help people live a thriving life in the workplace and in their homes.