The Best Moonlighting Jobs As An Entrepreneur

Published by Mike Michalowicz (Google+)

How To Become An Entrepreneur

1. Rental Real Estate ROCKS

Rental Real Estate is the BEST moonlighting entrepreneur business that is available. While there is some time required up front to acquire the properties, if you buy the right houses and screen renters properly there is very little work to do after they're rented. So this is truly a part-time business that I can comfortably handle outside of my day job hours. And besides, what other business can you start that will be CASH FLOW POSITIVE on Day 1 and also give you incredible tax benefits?
Thanks to: Dennis Fassett of Cash Flow Mercenary, LLC.

2. Combining eBooks with Software

The best moonlighting job has got to be as an eBook author or software developer, or -- what I did -- combine the two. I have a day job as a .NET developer, but after the wife and kids go to bed, I work on my job resource kit for software developers, which contains an eBook, software, and a sample resume template. It's definitely a niche market, but the number of potential customers is high enough that it's a worthwhile project.
Thanks to: Dave Haynes of Shove It, FizzBuzz.

3. Seek Flexibility

I was a 9-5er at a publishing company and requested that I be placed on 100% commission and move to my home office(Scary!). It is still full-time work but allows me 24hr access to my budding company. Now the lines between my day job, my mom job and my dream job are somewhat blurred, but the schedule flexibility is what allows me to do each of those jobs better than ever.
Thanks to: Jennifer Marshall of Happy Mama Gifts.

4. Setting A Goal Sticking To It

I know firsthand the value and the rewards that can come from doing what you have to in order to pay the bills and still pursue your dream. I set a ten year goal of working in the hotel business as a manager. It was a job that gave me a company vehicle, lodging and the flexibility to build my brand around it. In the process I developed contacts that would be valuable to me after I left the industry. Today I am able to devote all of my time to being my own boss and helping others do the same.
Thanks to: Cyrus Webb of Shadow Play Entertainment.

5. Create A Job

The ideal solution is to create a job in your own startup. Identify what in your business can help you bring a positive cash-flow. Consulting & coaching the clients with your expertise can be a good start that will keep you afloat in your own business without the distraction of a traditional job.

If that doesn't suit your business model then take an entry level/ part time position that you know would have least after work stress, so that you still have enough time & energy for your business.
Thanks to: Devesh Dwivedi of Entrepreneur In Making.

6. Do What You Love

Do what you love and you will love what you do. I am an entrepreneur, a writer, producer, actor, comedian, speaker, teacher, son, husband and Daddy to 3. I've moonlighted on Broadway. I did my thing during the day and other than Wed. Matinee's, all shows were in the evening and weekends. I now Coach & Teach adults and kids a few evenings a week. I also volunteer my time as the Drama Adviser to local schools. I bring in some extra income while giving back to my community.
Thanks to: Adam Sietz of Big Hug Productions-A Div. of SEM.

7. Tell Your Story With Pictures

Where passion meets passion. I believe the best second job to have to support your startup is one that complements your startup. I own Blue Rooster Photography and specialize in commercial, event and marketing photography. My other job is as an Internet Strategist working with businesses and non-profits helping them connect with their audience. My "second" job provides me with introductions and leads for my startup - my "second boss" even sends me leads as my services (images) help his clients!
Thanks to: Jonathan Mast of Blue Rooster Photography.

8. T-Shirt Entrepreneur!

Best night job = T-shirt entrepreneur! With some saved money, I was able to set up my funny t-shirt company, build its social media presence and sales, and most everything related to its launch and operation was and is handled at night. It's an eCommerce site - no store, no face-to-face interaction. The idea here was not to avoid people, but rather to make the moonlighting gig manageable and able to fit into my schedule. Frankly, any eCommerce site is perfect for a moonlighting biz.
Thanks to: Chris Reimer of Scorch Agency.

9. Dressing Men For Life

As an image consultant, you'll give clients makeovers to help them land better jobs, find a mate, shine at weddings or just feel better about themselves. You'll coach them on the right wardrobe style for the image they want to project and even weed out closets or go on shopping expeditions. The advantages to the image consulting business are that you can work at home, you can start part time with low costs, and it's creative and satisfying. It’s a great opportunity for budding entrepreneurs.
Thanks to: Grant Harris of Image Granted, LLC.

10. Web Design / Computer Repair

I work full-time as an IT manager, and last year I realized I could make a little extra money doing web design during the evenings while I'm not working (web design is what I really enjoy). I started my own web design business, shortly added a friend who does computer repair, and now we have a successful business working on websites and computers during evenings and weekends. It serves as a great additional source of income.
Thanks to: Jared Murphy of Murphy & Smith.

11. Moonlighting & Loving It!

My moonlighting job was on my bucket list. As Exec Dir of the charitable foundation for a west coast construction co. I coach & mentor the chairs of our 4 grant committees. We give grants to orgs that benefit Children & Families, the Environment & Animals. We have an employee match prog. for giving & volunteering. My flexible schedule allows me to speak, train, consult, learn, & market my business. The steady income provides a consistent base. In business 1 year. I am in the black & growing.
Thanks to: Susan Bender Phelps of Odyssey Mentoring.


Compiled by Mike Michalowicz, Author of The Toilet Paper Entrepreneur

Category: Managing Focus, Money & Equity, Recommendations
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  • Josh Chandler

    At the beginning, something has the pay the bills.

    For me, it was a tough choice on how I would make a little extra whilst I built up my business. I currently own a website which generates passive income, but I really want to expand on this.

    I think that if you choose to moonlight it should be something which will have transferable skills to your full time job. This way, you will experience a win-win across both jobs.

    • Mike Michalowicz

      @Josh – thanks for sharing that tip. The key is definitely the “transferability” of the skills. To work a job that doesn’t build skill, knowledge or a network that will support your ultimate full time entrepreneurial endeavor, will simply stretch out the time before you start… maybe indefinitely.

  • Josh Chandler

    @Mike – No problem. :)