A growing, curated list of books, articles, mailing lists, tools, and everything else that have helped me in freelancing!
Roughly a year ago I was struggling in my freelance business. I identified that the problem at the time was lack of knowledge. There were best practices and better practices that I had never heard of that, once I started learning about, immediately gave me a leg up.
If you want to be good at something, you don't have to read very many books and other pieces of advice to know more about a subject than 99% of people out there. I have waded through a large pile of it all, and I wanted to compile a list of the very best resources I know of so you can go straight for the good stuff.
A strategy you can use for improving: find a teacher online who is successfully doing what you want to do, and then consume everything they put out. For added potency, hire them as a coach. Join their mailing list. These are some of the voices I've learned the most from:
Kai Davis specializes in helping freelancers get more clients and do marketing. One of the best all-around experts on running a solo freelancing/consulting practice. I consumed most everything of what he has put out, and even hired him as a business coach. A++ would learn from again.
Jonathan Stark's focus is in helping people moving beyond contract hourly billing and moving closer to being a true consultant - someone who focuses more on the strategy and less on the implementation. He also offers coaching and I'd recommend him for someone who wants to consult for larger companies.
A master of teaching business skills to developers and a great communicator. Has years of high quality content. His Twitter @patio11 is also one of the more valuable ones I know of. Patrick was one of the first people who got me excited about building an online business using software.
The expert on "positioning" - the idea of targeting your services to a specific group and "expensive problem" that you are trying to solve. Has a great mailing list and several books.
Simultaneously the funniest but also most valuable podcast I've come across, "Make Money Online" is my top pick for podcast to learn about freelancing. I listened to all 116 episodes and walked away a better freelancer. Co-hosted by Chicago native Nick Disabato who is an amazing storyteller. Also the website has an animated gif of $100 bills exploding and this captures the tone perfectly.
A wide cast of freelance voices including Kai Davis and Jonathan Stark join a rotating panel discussion on a topic related to freelancing. Lots of great content on here.
If you was just starting out again today, the first book I'd read would be Josh Kaufman's The Personal MBA. It's a great 1000 feet view of the entirety of how to run a business, something I was certainly not taught in school. Get 80% of the value from much less than 20% of the cost of business school.
A mashup of 14 consultants' best ideas, including Kai Davis, Philip Morgan, and Jonathan Stark. You can find a lot of the information in this book across all of their websites but this is more concise. If I was starting out again I'd read this right after The Personal MBA.
A book that seriously impacted my overall worldview, especially as it comes to business. Humans do not act rationally in the face of uncertainty and knowing how and why this happens can make you much less likely to explode your business. The only book of it's size I've read a full 4 times all the way through. The rest of the books in the series are also full of value.
Seth Godin is a marketing master, and this is my favorite book by him. In short, every obvious idea has already been done, but definitely not every non-obvious idea. Straight up "be you over the head style" interruption marketing (read, most advertising) doesn't work anymore - you actually have to be "remarkable".
Life is poker, not chess. World Series of Poker champion Annie Duke explains how lessons she learned from poker apply to nearly everything, since most decisions are made without full knowledge. Discusses in depth the problems and strategies for overcoming them.
A wonderful book about the human and emotional side of running a business. How to not destroy your health, relationships, and life while also building a business at the same time.
A nuanced discussion of the importance or lack thereof of "passion" in building your career. Cal Newport suggests that passion is the result, not the cause, of a good career.
A short and delightful read by the founder and later seller of CDBaby.com, one of the first online music stores. Derek describes the idea that "your business is your own private little utopia where you can make the rules." Inspiring in that it emphasizes that you really can do whatever you want in your business.
An online community of freelancers founded by Kai Davis. I've gotten a lot of value from being a part of this community, if for no other reason than it's increased my Luck Surface Area. It's also nice to not feel alone in a job that's often very isolating. Full of wonderful and interesting people.
Started when Courtland Allen began interviewing independent business starters (sometimes called "Bootstrappers" because they take no funding). A forum has grown up around these interviews that has a thriving scene of people building software businesses. Participating here could open up opportunities for leads, clients, or business partners.
Founded by Paul Graham of Y Combinator, one of the largest and oldest tech news and discussion sites on the web. Not specifically about freelancing, but a community of a large number of technically inclined people. Participating in discussions has gotten me a number of leads and clients over the years. Every month on the first Monday at 11am EST there is a "Who's Hiring Freelancers?" thread where you should definitely post your services.
Jonathan Stark lays out the "Pain Dream Fix" style of writing a sales page. I refer to this page often when I write my own sales pages for new services.
Code is worthless if it doesn't solve a business problem.
How do you get people to read your emails? By making the email about the other person, and not you. A classic.
How to negotiate salary as a developer. Not specifically about freelancing but definitely applies.
Clients pay for value, not time.
What to do when you are first starting out on your own.
Adam Wathan's in-depth explanation of how he successfully wrote and sold an ebook about development. Information products can be a great addition to any freelance/consultant product ladder.
If you are going out on your own, you'll have to learn how to communicate. Copywriting is a valuable skill and not exactly the same as writing a literary essay in high school.
Joanna Wiebe's Copy Hackers has extensive information about how to write sales copy.
Often you don't need a fancy website, you just need a clear value proposition that is targeted to your ideal customer. Some great examples include:
One of my favorite examples of great positioning, Elise Fog offers web development and design websites for beekeepers so they can sell more honey. Elise is so easy to refer because her target customer is so specific.
Another example of very memorable positioning, Meg Cumby does "client testimonials without the awkwardness." After a successful client engagement, she'll interview your client and write you a detailed testimonial to put on your website for building social proof.
Ben Lopatin and co specializes in Django web development, but "for the app you already have." What do you do after you've built your MVP and need someone to maintain it?