Home Advice For The Young At Heart Dancing In The Moonlight: Keeping Options Open While Holding A Steady Job

Dancing In The Moonlight: Keeping Options Open While Holding A Steady Job



‘Moonlighting’ is a term that often means you’re working a secondary job (usually at night, hence the name), but now it’s sort of shifted toward this idea of seeking the type of work that defines your lifestyle.

I did this for a good while to a good degree.

While holding my full-time position working at an e-commerce company, I spent my afternoons blogging, writing, producing video, graphic design, and doing everything I could to bring in additional income. All the while, I knew one day I’d run my own online business.

When assessing the value of moonlighting, people like to start with pros and cons like:

  • Pros – Extra money, security, new skills
  • Cons – Stress, lack of time, conflict with employers

It’s that last one that usually gets people to put their moonlighting on hold. They’re often too afraid to start something on the side because they don’t want to cause any trouble with their comfy position at their current job.

Well remember this: what you do in your free time is your own business.

As I take you through some of the possibilities and opportunities inherent in moonlighting, I want you to keep an open mind about starting one of these side hustles. These are the concepts I picked up along the way – I feel you’ll find them valuable for the cause:

Start small (but with a big goal).

I’m a firm believer in lifestyle design. It may sound like something romantic but I think it’s a good mindset to get into because it forces you to make decisions and take actions that ultimately leads you to the type of life you want to live … not the type of life you settle into.

My first suggestion is to find one skill you feel is your best and start small.

  • See if you can find a small business that could use a helping hand
  • Offer your skill to someone you know through Facebook
  • Put up some flyers around the neighborhood

It’s basically taking the same actions you would when you were younger trying to find a summer job, but the difference here is that the dream (and goal) needs to be BIG. Look beyond those tough starting months and project yourself as being a success from enough hard work. That should give you the inspiration and drive to keep up with your goal(s).

Work the right angles.

Once you get comfortable with your job, it’s easy to stick around and eventually go through a slump if you don’t happen to get a whole lot of promotions. There are other factors, such as being close to the people you work with or the mindset that you’ve already put in so much time that “why ruin a good thing?”

When you get comfortable you begin to forget those necessary skills (and resources) for finding new opportunities – skills and resources like:

  • Knowing how to create a solid portfolio, resume, and cover letter for applications
  • Negotiation skills and people skills to help get your foot in the door
  • Networking and business connections to grow your expertise

Over time, you may forget these skills because you haven’t had to use them in such a long time.

When you’re stuck, remember you can turn elsewhere:

  • Temp services can help you find positions uniquely tailored to your skills, desirable position, pay range, and window of opportunity.
  • Start attending local business meet ups or conferences where you can mingle with other professionals in your desired field to gain some insight and connections.
  • Online educational courses can help hone your skills and put them into practice (which is great for building your portfolio and skill sets).

Be ready for the push.

There will be a time when you’ve hit a tipping point – this is the moment where you’ve done enough provisional work and with a little nudge you can then ride the rest of the way to success.

There will be two options:

1 – Stay at the job and hit a stagnation point with your moonlighting

2 – Make the jump and go all out with the side hustle

Many people get fearful at this point and let their moonlighting fizzle–so they go back to the comfort zone. Others make that push and find themselves in a whole new world of opportunity.

From that point out there will be times when things get rough (especially with finances), but since you’ve overcome the hardest, uphill battle of going alone you’re now ready to keep at it because you’ve honed the skills, you’ve developed great resources, you’ve made great connections, and you’ve got the drive.


I can’t say moonlighting is for everyone. Sometimes it’s nice to just have a comfortable job because some of us just want the security and peace of mind. But for others … those who have the “itch” to do something more – to change their lifestyle – PROGRESS is always possible.