Moonlighting Millennials Part II

Moonlighting, or having a second job in addition to one’s regular employment, has become the norm for the Millennial generation.

In Moonlighting Millennials Part I, my last post, I noted why Millennials are jumping at opportunities to generate additional income and gain experience.

If you too what to build your own hybrid career, here are seven advised strategies:


Your first idea might not be the best one, but you’ll find it generates a steady stream of other ideas. By just getting started and saying “yes” to opportunities that present themselves, the evolution the project will surprise you and you can start generating some side-income as well as buzz.

Many of the best side-gig ideas happen by accident: a friend asks for a favor then refers your services to others, or maybe you’ll come across a simple every-day problem and create a new or more efficient solution. For example, I’m just dying for someone to engineer a clasp-less necklace chain so I don’t have to consciously rotate mine around anymore (have at it, folks!).


Side projects can almost always be launched on little or no budget. You may start selling handmade goods you already make, start freelance blogging for a company online, or offer consulting services to local small businesses.

Take advantage of free tools and resources, including websites like,,,, and, where you can create an online portfolio, offer services and sell products. Use free social media channels to start spreading the word, or post a Craigslist ad offering your services. Once you build your client base, then you can upgrade to a professional website, order new business cards and other investments.

Unless you’re planning on starting a much larger business and truly transitioning into self-employment, don’t look for financial investors. Initial investments is a no-no; there is much more work involved in calculating revenue and writing business plans, and you will most likely have to give up some of your profits to the investors. If you do need money to launch a project, look to crowd funding. Crowd funding campaigns like Kickstarter allow you to generate buzz about your project or business while raising money to get it going.


Just because your Etsy shop only earns $50 a month, or you only do enough work to invoice a freelance client every other month for few hundred dollars, doesn’t mean the initiative is a failure. Earning even a small amount on the side gives you extra income that you wouldn’t have anyway—it covers your monthly phone bill; pays for your gas or groceries—and it can quickly add up over time. Even $3,000 a year equals around $40,000 after ten years if it’s in an account earning five percent interest.

In the event of an life-change—a move or a lay-off—this type of work can be scaled up. Pick up more hours at a part-time job, increase marketing efforts to sell your services, pick up another farmers’ market if they have a vendor cancellation, increase time you allot for crafts and in turn offer a larger variety of handmade items on your online retail store.

Bartering, which is not taxable, is also a great way to measure your success. If the barter benefits both parties—for example, gives you access to free fitness classes rather than paying for a gym and brings your hourly pay rate down—both parties benefit in offering their services.


Avoid conflicts with your main gig. Some jobs are stricter than others when it comes to allowing outside activities—exclusive agreements or anti-competitive contracts—but there is usually a way to work around even the most severe regulations by getting explicit approval of agency lawyers. Going through this process is well worth the time and effort if it means protecting your primary form of employment.


It’s hard to market yourself and your products or services if you’re not used to it, but it’s a skill that will serve you well throughout your career. Plan an elevator pitch and be able to talk about what you do in under a minute—be concise and don’t be humble. Emphasize how your offerings help people and improves their lives, then differentiate yourself from your competitors.


"Entrepreneurship is living a few years of your life how most people won’t so you can spend the rest of your life how most people can’t."

You may be burning the midnight oil to get your work done, but remember to schedule some R&R (rest and relaxation) to keep your work ethic strong and mind clear. By getting stressed or overworked, you are eating in to your own capacity to perform two jobs to the best of your ability.

Schedule time for friends and family—you need to maintain a healthy relationship with your primary support team, too. Dedication to work is admirable, but friends and family will resent you for picking career over them.


The more advice and guidance you have, the better off you’ll be.

College organizations, like Champlain College BYOBiz for example, offer free business advising to students and alumni to help advance that business forward.

Government-funded organizations (like CT SBDC) and independent associations (like SCORE) offer free small business advising. Business incubators are also springing up within co-working spaces across the nation. Consultants and advisors can't tell you what to do, but can give you advise of where to take your business or side-hustle.

Many tools and individuals online offer free resources for marketing, templates for legal documents and more. Google Drive offers templates for documents, spreadsheets, invoices, and more. Some professionals offer PDF downloads of forms on their websites in exchange for your email. Even contact forms and pop-up chat boxes on websites open the door for some free advice.

So here’s to launching a successful side-business and to building a more meaningful career.


Anything I’m missing? Why have you started a side business or taken on another part-time job? Leave a note in the comments.

Moonlighting Millennials series idea inspired by Lindsey Pollak and Kimberly Palmer’s post Why Millennials Need Side Businesses. For more about the trends of the Millennial generation, look no further than the world’s leading expert on Millennials, Lindsey Pollak.

Check out Moonlighting Millennials Part I for reasons why Millennials start their own hybrid careers.

#freelance #millennials

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