Top Resources for Freelancers

It was around this time two years ago that I started toying with the idea of making freelance writing my full-time thing. It all started with one $50 blog post I wrote for my roommate’s brother. That blog post turned into another blog post that turned into a weekly blog commitment at a much more professional price. That first client led to another client and soon enough, I was writing blog content before and after my 9-to-5 job most days of the week.

Having some extra cash on hand was awesome, especially at the time — I was living downtown next to lots (and lots) of bars and restaurants. My day-to-day rhythm, however, was pretty stressful. When I wasn’t writing, I was obsessively researching, planning, and networking — desperately trying to figure out how I could make freelancing work logistically and most of all, financially. Mapping it all out was tough, time-consuming work, as was the hustle needed to set things in motion and keep things moving when my situation changed or I changed my mind (this tends to happen).

When I talk about how I made the jump from working full-time office job to freelancing, I typically glaze over the nitty-gritty details. I usually tell people I hit a magical “tipping point” where my income from freelancing was enough for me to say goodbye to the 9-to-5 and dive into freelancing headfirst. This is true, it’s just not the whole truth. The whole truth is ugly and sleep-deprived. It’s obsessive and hungry. It’s scared and pretending to know what’s going on, but more than that it’s determined and hellbent, because that’s what it takes to make the leap.

In the months leading up to going full-time freelance, I toed the fine line between healthy knowledge gains and death by information overload. I’ve used the word “obsessive” twice already in this post and that’s because it’s an accurate description. I was totally, completely, 100% obsessed. Looking back, I can admit I might have stressed myself out more than necessary with excessive media consumption (we all have our vices) but at the end of the day, I learned SO MUCH not just about freelancing but about starting a business. I developed an entrepreneurial mindset and without a doubt, it helped speed up Operation Go Solo which, if you’re wondering, took about six months total.

I’m planning to do a whole series of posts on Freelance Life since I’m frequently asked by friends and Internet folk about the realities of the work (Rule #1: don’t believe everything you see on Instagram). One of the most frequent questions I get is what books or other resources I would recommend to someone looking to get their feet wet, so that’s where I’m starting.

Below you’ll see my top recommendations when it comes to podcasts, books, websites, and apps for freelancers. If you like this type of stuff, I send out similar lists every Friday on my newsletter, which you can sign up for here 🙂 Enjoy!


If you’re wondering whether or not you’re crazy, listen to… 


I plowed through Season 1 of this podcast on my drive to work every morning. It gave me courage in my goals in that it showed me I wasn’t insane for wanting something outside the realm of a traditional job. It opened my eyes to new perspectives on work I hadn’t yet seen and offered tactical advice along the way.

If you want to learn from high-achieving people, listen to… 

The Tim Ferriss Show

Tim Ferris really is an expert interviewer, and the long, in-depth conversations he features on his podcast allows you inside the minds and lives of some very extraordinary individuals. There are some undoubtedly tech-bro topics of discussion that simply comes with the territory of Tim Ferris, but if you can stomach it (or fast-forward through it) you can usually walk away from whatever episode you listen to with new insights and perspectives.

If you want to learn how to make money while you sleep, listen to… 

Smart Passive Income

This podcast is sort of like a combination of Unemployable and The Tim Ferris Show. If you’re interested in figuring out how you can create an information product to sell rather than spend your time working on a service-based business (e.g. freelancing), this show will give you hundreds of examples of people who are doing it and doing it well.

If you’re like, where all the ladies at?! (I feel you.) Listen to… 


A fountain of knowledge for anyone wanting to learn more about business, in general. The podcast features a healthy mix of interviews, coaching tips, financial advice and strategy sessions with successful female entrepreneurs.

If you want to learn how female CEOs, founders, and entrepreneurs are doing it all… 

Girlboss Radio

Sophia Amoruso is not my favorite interviewer, but the guests she brings on to Girlboss Radio have a lot to offer in the way of business advice, startup stories, and tackling topics that are more women’s-specific. In a sea of entrepreneurial content geared toward men, it’s a welcomed change.

Speaking of badass female podcasts, I helped put together an article for Entrepreneur that featured 24 female-hosted podcasts entrepreneurs should listen to in 2017. Check it out here.


These are Amazon affiliate links. That means if you buy one, this blog gets a little somethin’ so thanks! 

If you want to learn what NOT to do, read… 

The E-Myth Revisited by Michael E. Gerber

Although this version of The E-Myth is a little dated (i.e. not geared toward online businesses) it’s still chock-full of timeless business advice that’s helpful to anyone at any stage.

I also wrote a blog post about the book that got quite a bit of buzz on LinkedIn in 2015. Check it out here.

If you need a confidence boost, read… 

You Are a Badass by Jen Sincero

This was a transformative book for me when I read it last year and I’m planning to read it again this year for a little extra oomph. If you’re having trouble believing in your own badassery or struggling to see that anything is possible, give this one a go.

I also wrote a brief review of the book on a roundup blog post from last year. Check it out here.

If you want to redefine the way you network, read..

Build your Dream Network by J. Kelly Hoey

The number one piece of advice I give aspiring freelancers is network, network, network. My network is what truly made getting started in freelancing possible. But, as in all things, we can always be better. Which is why I’m reading this book right now with the hope of giving my networking skills a refresh in 2017.

If you need some guiding principles on how to get started, read… 

The Consulting Bible by Alan Weiss

This book was recommended to me by a wiser, more experienced copywriter when I first started my business. Unless you’re well into your career, I’d say it’s one to skim and look at from a big-picture point of view. Despite parts of it being unrelatable, there were even more sections that helped shape my attitude around communication, image, money and advocating for myself in the moments that matter.

If you want to be inspired by an unlikely success story, read… 

#GIRLBOSS by Sophia Amoruso

This might have been the book that got my wheels turning when I think back to it. Again, Sophia’s story isn’t all that relatable to someone who (mostly) followed all the rules when I was in school and focused on GPA in college. That said, the book is a swift “you can do it” kick in the ass that might be just what you need to get started.

If you want to change the way you think about work forever, read… 

The Four Hour Workweek by Tim Ferriss

This was another book that was truly transformative in my freelancer/entrepreneurial journey. Is that cliche? It might be at this point but I can’t lie about it. As an English major who wandered into content marketing, the concepts Tim introduced in this book were totally new to me, but totally made sense on so many levels. It was almost as if Tim put into words what I knew I’d been wanting to hear. If nothing else, check out the chapter on dreamlining (I think you can read it online) and use the philosophies in The Four Hour Workweek to help yourself get clear on what it is you really want.

Websites + Blogs

If you need free stock photos that don’t look like crap, check out… 


On to more tactical resources … once you actually start freelancing you might need some stock photos, for your clients or for your own projects. Pexels is great and the photos (most of them) don’t make me wanna gag.

If you want a community, check out…

Admittedly, I am bad at using this website, but that doesn’t mean it’s not full of value for freelancers. There are lots of great threads about how much people charge for different types of projects, how to approach different inbound marketing challenges (that you’ll inevitably face once you start booking clients), and occasionally there are threads with actual job leads which is always nice.

If you want long-winded, detailed tactical advice, check out… 

Kopywriting Kourse

I used to subscribe to these emails. They got a little bit overwhelming after awhile, but they always offered in-depth advice on topics like how to start a consulting side hustle and how to self-publish books. It was worth the subscribe when I was first starting out, and now I just check out the Free Copywriting Guides page when I’m looking for something specific.

If you want a catch-all freelancer blog, check out… 

The Freelancer by Contently

This blog covers a little bit of everything in the world of freelance. Tax questions, contract questions, pricing questions, time management questions, how-to-get-client questions … if you got ’em, this is the blog for you. They also occasionally post industry-specific jobs for writers for their own site. Win-win!



If you like free invoicing software, download… 


Really that’s all there is to it. This is an easy-to-use, free invoicing platform that makes getting paid simple and straightforward. It continues to amaze me how many people “forget” to invoice their clients. I just don’t get it. No invoice = no money = big problem for everyone but especially freelancers.

If you want to grow your number of followers, download… 


I got to 1,000+ Twitter followers largely thanks to this app. It helps you batch follow/unfollow users who are inactive, no longer following you, or following other specific users or hashtags you can type directly into their platform. As long as you go about using the app intentionally, it should work in your favor.

If you need a better way to get shit done, download… 


I’ve recently switched over to a pen-and-paper planner (I like making physical lists), but prior to that I used Trello to manage all of my to-do’s. There are lots of ways you can design Trello to work for you, but I’ve found it best to use it intuitively based on how you think about your tasks. Here’s a guide that might help you get started.

Oy! That was a long list. Hopefully, a helpful one.

Let me know which of these resources you check out and which ones you enjoy. And keep me posted on your freelancer journey here or on Twitter! I’d love to help out.

Thanks for reading,