The greatest hits (freelance edition)

Hello and welcome to issue number 20 of Rough Draft! (*Picture me gently waving at you through the screen*)

There are quite a few new readers here thanks to my friend Kara Detwiller who mentioned Rough Draft in not one, but TWO of her recent Wishful Working issues. Grateful for pals like Kara and the rest of the freelancing community I’ve had the opportunity to connect with thanks to this newsletter 🥹 

Rough Draft began as a way to share my unconventional career story and has turned into a bi-weekly newsletter where I share tips and musings on creating a freelance career from scratch (and get to hear your stories and experiences in return!).

So today, in honor of my 20th issue and as a welcome to anyone who’s new here, I thought I’d re-share some of my favorite Rough Draft issues. Bonus: I’ve also included some of my favorite recent issues from other newsletter writers bc sharing is caring 💛

My Rocky Freelancing Journey

I’m 6+ years into full-time freelancing, and I’m still figuring it out! These issues share my freelancing origin story and highlight the ups and downs I’ve encountered along the way. Read these to be reassured that whatever freelancing challenge you’re going through, you’re not alone!

• Freelancing is a form of rebellion

• Every freelance gig I’ve ever had

• Finding my freelance niche

• My 2024 Year in Review

• I’ve lost 3 clients this year — now what?

Quick Tips

Read these if you’re looking for actionable tips about getting started with freelancing, finding clients, and understanding the costs of running a freelance business:

• How to start freelancing in 2025

• The Venn diagram I live by 

• How I cold DM clients 

• How much it costs to run a freelance business

Get to Know Me

A glimpse behind the scenes (open if you want to know my Zodiac sign, see pictures of my office, and get a link to my Desk Toolbox™️)

• A realistic day in my life as a freelance writer

• Freelancing = running

• What’s in your bliss station?

• Fake it ‘til you make it

Other Newsletters I Like

Newsletter issues from fellow freelancers that had me instantly nodding my head or eagerly replying with multiple —> !!!

• The Simple Freelancer: I Tried LinkedIn Premium for 2 Months. Here's What I Thought (I love Steph’s practical and transparent storytelling. She also shared an interesting experiment on LinkedIn about the results she got from doing cold outreach via connection requests and DMs)

• Wishful Working: “Someday” is a dangerous word (Love when a newsletter inspires me to take action, which is what I did immediately after reading this one from Kara)

• The Lunch Break: The power of a palate cleanser (Maria shares quick, actionable tips for posting on LinkedIn and honestly makes the platform seem less intimidating)

• Time Intentional: Flights, fears, and family (This personal essay from Alyssa resonated deeply with me, but I encourage you to read all of her issues for tips and prompts about being more intentional about life and time 😌)

Enjoying this issue? Share it with a friend or subscribe below if you aren’t already subscribed.

• Recently saved this Reel from an OG newsletter creator, Austin Kleon, where he shares 3 tips for writing a newsletter people actually want to read (I’ve been doing the third tip from the start and it does wonders for my mental health 🥲)

• You may or may not have seen the “Most Days” essay pop up in your corner of the internet, but if you haven’t read it yet, I highly recommend doing so. It’s basically about having the mindset that you can try your best most days, but not every single day (idk about you, but this is something I needed to hear!)

• A couple weekends ago, my friend and I went to this Tiny Farmer’s Market here in Austin and I’m still thinking about it! It was like a community yard sale with homemade art, jams, coffee, and live music. A great reminder to just do things — lean into your creativity and joys and don’t be afraid to share it with others 💫

I’ll be back in your inboxes on September 2nd 💌 In the meantime, let me know what you’re working on and how I can help!

Rough Draft is a bi-weekly newsletter where I share tips and musings on creating a freelance career from scratch. Subscribe here. You can also find me on LinkedIn, Twitter, Threads, or my website. 👋 Have a question about freelancing? Submit it here!