Episode 034: Build Your Freelance Career With Confidence (And Fun!)

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Episode 034: Build Your Freelance Career With Confidence (And Fun!)

freelance writer

Who said work couldn’t be fun? 

Well, if truth be told, so freaking many of go to work with anything from “boredom” to “terror and dread.”  

What if there’s another way to use your skills, experience and interests that didn’t involve the New York City subway at rush hour (I just got the chills)? 

On this week’s episode, “Build Your Freelance Career with Confidence (And Fun!),” we’re talking with freelance writer Elana Lyn Gross, Founder of Elana Lyn on how she got started and how she’s growing her business. There are SO many goodies in this show, and if you’re thinking of starting something on the side or have recently started a side project, this is a great episode to tune into.  

Because taking what you’re doing as a hobby (or thinking of doing as a hobby) and turning it into a career – whether as a freelance writer or something else – is a HUGE decision and one Elana didn’t take lightly. We get to dig in with her about her thought process behind leaving her comfortable, stable job and making this leap to becoming a freelance writer. And, we also get to see a lot of the heart behind this writing powerhouse.  

You see, Elana didn’t mind what she was doing. She loved her colleagues and enjoyed collaborating with them daily. And she also liked the idea of going into an office each day with other people working toward a common goal.  

Although it kept her hooked for awhile, ultimately It wasn’t enough. And she started to make the transition. Maybe you see some of you in this example. Maybe there’s something inexplicable drawing you to do something different, and maybe you even already do it as a hobby. But the pull of the known, the comfortable and a fun workplace keeps you motionless. This episode will help you find your footing and decide what to do, rather than stay in limbo between two opposing forces.  

This is a pretty well-rounded episode, so you get a peek into it all, including: 

  • Getting comfortable with the concept of building something brick by brick, rather than expecting an overnight sensation 
  • Decision making process to make this a full time career move 
  • Defining success as an entrepreneur 
  • Breaking down walls about money as a taboo topic 
  • Learning how a freelance writer gets #inspo 
  • Creating goals and learning how to either follow through with them….or not. 

So grab a listen with the big buttons in this post- the episode will go right to your inbox- and let’s get you moving! 

And if you have any other questions about this topic, post them in the comments and I’ll get your question answered! 

 freelance writer



Show Notes (Timings are Approximate):  


Key piece that made the transition stick: 5:12 

Thinking about your career development plan as an entrepreneur: 8:15 

Getting out of her comfort zone: 9:21 

Measuring success when you have your own biz 10:55 

Getting financially savvy 13:55 

What’s a freelance writer do? 16:50 

Getting comfortable with rejection 21:30 

Pitch Perfect – Building your Freelance Biz Course 22:40 

Goals for 2018 – and tips and tools for how to go get those goals: 25:00 

What happens when you DON’T achieve a goal 30:57 

Rapid Fire Travel Question: 35:45 


Resources Mentioned on the Show:  

Elana’s Website- Stay in Touch!  


Elana’s Instagram – Follow her! 


Pitch Perfect Online Course – Elana’s tools and project plan to start your freelance career  


Dreamers//Doers: A community of female entrepreneurs (and entrepreneurially minded women too!)  


Social Comparison Theory