Based in Noblesville, Indiana, Curtis writes the syndicated humor column, Grammar Guy. He also likes to write for startups.

Give Your Dream Job an Audition as a Side Hustle

Give Your Dream Job an Audition as a Side Hustle

One of the worst things I could do right now is to quit my day job. I've got a great job with benefits, work for a great organization on a great team. And the whole writing thing isn't exactly paying the bills yet. But, I'm hoping to transition into being a full-time freelance writer by January 2019. This started as a 2-year goal back in January 2017.

It can be scary to cannonball yourself into the deep end of chasing your dream, especially if you have kids or a spouse's well-being to also consider. Now that I've hedged my bets, it would also be foolish not to pursue something that falls into any category of calling/dream job/passion.

Because you don't want to be that guy who lets his dreams die with him.

Sorry for being so heavy. It just kind of snuck up on me.

I can think of tons of benefits of pursuing your dream job as a side hustle:

  • You get to keep your health insurance from your 9 to 5 employer until you're ready to walk away from it.
  • You get to test the waters. What if you actually hate the thing you think is your dream job? If you try it on the side, at least you'll know, and there will be few (if any) negative consequences.
  • You get time to build it. I don't have much of a freelance writing portfolio yet. By starting on the side, I can be relatively low-key and slowly build up a steady client base of monthly contracts to ensure guaranteed money will be coming in when it is time to go full-time as a writer. If you were expecting it to just happen overnight, it doesn't. You've got to keep at it and stay at it.
  • Working on freelance writing as a side hustle has helped me approach my day job from a fresh perspective. I don't always have the best attitude at work, but writing for clients truly scratches my creative itch, which makes for a happier me.
  • The biggest thing I'm loving right now--you get to be picky about which projects you agree to work on, as well as with whom you are going to work. Because I've been pursuing freelance writing on the side, like writing an automated phone script for a new pretzel business in New Jersey. Seriously. Call 908.349.8316 and listen to the menu. I wrote the script. I've started writing content for a boutique children's clothing company. I'm even working with a successful Silicon Valley startup on some really fun content. And that's really the tip of the ol' iceberg.

So, the benefits of pursuing your dream on the side until it grows into something bigger are nice, and, to me, they outweigh the drawbacks, which include, but are not limited to, there's never enough time to devote to the thing you love to do the most, you feel like you're either cheating on your day job or your family when you're working on the side, and sometimes I miss out on what's happening on an old episode of Project Runway and Carrie has to explain everything to me because I'm only half watching.

My biggest piece of advice if you have not yet taken the first step to pursuing your dream job is--do it! Do some research, talk to someone else who does a similar job, create an Upwork profile and start with a few small projects. You can do it, but you will never get there if you don't start.

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