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Book Details

100+ answers to popular freelancing questions covering 12 key topics

Chapter 1LifestyleLearn how to achieve a healthy work-life balance and work from home effectively
Chapter 2Career TransitionsLearn how to navigate tricky career transitions and start your freelancing journey
Chapter 3Pricing & RatesLearn how to price your freelance services and set appropriate rates for each project
Chapter 4Getting ClientsLearn how to attract freelance clients to your business rather than chasing after paid work
Chapter 5Marketing & PositioningFind out how to market yourself to potential clients and position yourself for success
Chapter 6Portfolio WebsitesLearn how to create a captivating portfolio website that clients find irresistible
Chapter 7Proposals & ContractsLearn the difference between proposals and contracts and how to use each effectively
Chapter 8Client CommunicationLearn how to communicate effectively with your clients and set clear expectations
Chapter 9Project ManagementFind out how to schedule and complete your projects in a professional and timely manner
Chapter 10Payments & InvoicingLearn how to properly send invoices and collect payments from your freelance clients
Chapter 11Finances & TaxesLearn how to manage your finances and save for taxes so you can grow your business
Chapter 12ProductivityGet tips on how to stay productive and make the most of your time each day
freelance 101 book table of contents preview cover

"I really look forward to your emails. You've inspired me to show up online when I was terrified. I admired your work even though you were a gazillion steps ahead of me. There's something about you that says, "get started and keep going" and thats why I appreciate you. Thanks for continuing to show up!"

Get expert answers to 101 freelancing questions from a seasoned freelancer + designer in this FREE, hand-crafted book:

  1. What’s it like working from home?
  2. How do I stay connected to my peers?
  3. How do I handle sick days?
  4. What’s it like not having a boss?
  5. How important is it to have a routine?
  6. How does vacation time work?
  7. What are the advantages of freelancing?
  8. What are the disadvantages of freelancing?
  9. How do I get health insurance?
  10. Is freelancing lonely?
  11. How can I gain more confidence as a freelancer?
  12. How do I know what freelancing advice is good or bad?
  13. How much should I charge?
  14. How do I estimate the cost of a project?
  15. When should I raise my rates?
  16. How do retainers work?
  17. Should I bill my clients hourly?
  18. What is value-based pricing?
  19. How many billing methods are there?
  20. Where do I find my first freelance clients?
  21. What if I can’t find any clients?
  22. Who hires freelancers?
  23. Is it realistic to have a “predictable income” as a freelancer?
  24. How can I help more clients find me?
  25. Is it bad to use job board websites like UpWork?
  26. Do cold emails really work?
  27. How do I ask my client for a testimonial?
  28. Can I sell my own products as a freelancer?
  29. What does subcontracting mean, exactly?
  30. Should I quit my day job?
  31. When is the right time to “take the leap”?
  32. How do I transition away from my day job?
  33. How do I know if freelancing is right for me?
  34. How much should I save before I start freelancing?
  35. Should I freelance part-time or full-time?
  36. Do I need to use a contract?
  37. What should my contract include?
  38. Do I need to use a proposal?
  39. What should I include in my project proposal?
  40. What’s the difference between a contract and a proposal?
  41. Should I hire a lawyer?
  42. What online tool can I use to get signatures?
  43. How do taxes work?
  44. What expenses can I write off as a freelancer?
  45. Should I set up a DBA, LLC, or S-Corp?
  46. Do I need business insurance?
  47. How much should I save for taxes?
  48. What are estimated taxes?
  49. Should I hire an accountant?
  50. Should I open a second checking account?
  51. Should I apply for a line of credit?
  52. What happens if my client sues (or threatens to sue) me?
  53. How much money should I collect upfront?
  54. Is it realistic to get 100% upfront payment?
  55. How many payments should I divide my project into?
  56. How should I send invoices?
  57. How should I name my invoices?
  58. Can I start work before getting paid?
  59. What if my client doesn’t pay me?
  60. When is it ok to accept NET terms?
  61. Should I accept credit card payments even though they have fees?
  62. Should I position myself as a company or a freelancer?
  63. Should I call myself a freelancer or consultant?
  64. What are the most important skills I need to learn?
  65. How can I get more visitors to my website?
  66. What social media accounts should I have?
  67. How can I make myself more valuable to my clients?
  68. Can I offer more than one skill or service to my clients?
  69. Do I need to have my own website?
  70. Should I add a blog to my website?
  71. What should I blog about?
  72. What pages should I have on my website?
  73. Should I show pricing on my website?
  74. Do I need a contact form or can I just use my email address?
  75. Should I show personal projects in my portfolio?
  76. Do I need permission to show client work on my website?
  77. What if I offer more than one skill or service?
  78. Does SEO really matter?
  79. How can I think more like a client?
  80. How do I find out what my client needs?
  81. How do I set clear expectations with my clients?
  82. My client is texting or calling me too often. What should I do?
  83. How do I set communication boundaries with my clients?
  84. What red flags should I look for when talking to a new client?
  85. How often should I update my client on progress?
  86. How often should I check in on my client?
  87. What if the project is taking longer than expected?
  88. How many clients or projects should I take on at once?
  89. What if my client asks for too many revisions?
  90. What if I do the work faster than expected?
  91. How do I schedule multiple projects?
  92. How do I estimate the timeline for a project?
  93. What do I need to find out before quoting a project?
  94. Should I present my work or send an email?
  95. What’s the best way to manage my time?
  96. Do I need to track my hours?
  97. What are the best apps or tools freelancers use?
  98. Should I pay for certain apps or tools?
  99. Should I work on nights and weekends?
  100. What’s the best way to avoid burnout?
  101. Should I have a dedicated office space?

My Journey to Full-Time Freelancing

I started freelancing by accident in 2009 when I fell in love with creating websites during college. I was amazed to discover people were willing to pay for websites from individuals like me, not just established businesses. So I started designing websites to make a little money on the side.

Things were pretty sloppy at first. I fumbled through projects and had no idea what to charge or how to talk to clients. I made a lot of mistakes and every project was a learning experience.

I did freelance work all through college, but only earned about $10,000 in 4 years.

Knowing that I needed a stable income, I got a salary job, but continued freelancing on nights and weekends for the next 3 years.

It was never my intention to become a full-time freelancer, but one day I realized that working 9-5 for the next 40+ years might not be for me.

Around that same time, my freelance income eclipsed my annual salary thanks to my website, which was generating dozens of high-quality leads each year. That’s when I decided to make the transition into full-time freelancing. I quit my 9-5 job with confidence and minimal risk and doubled my income in the first year.

For the next 7 years, I worked with startups, small-medium businesses, and some of the biggest brands in the world earning over 1.5 million dollars of freelance income.

Wake up to simple, actionable freelancing tips every Saturday morning.

I built my freelancing business from nothing and I want to show you how to do the same thing. If you want to get more clients, raise your rates, quit your job, or just earn a decent side-income, my newsletter is for you.

You won’t have to rely on job boards like UpWork, Fiverr, and 99 Designs where freelancers are often seen as cheap commodities instead of valuable partners.

I’ll show you how to attract ideal clients to your own website so you’ll never be in a position of weakness that requires you to chase after your next paying project.

Weekends are when freelancers dedicate the most time to side projects and self-improvement. That’s why when you join my newsletter you’ll get simple, actionable advice in your inbox every Saturday morning.

My goal for this newsletter is to share the key decisions that led to my success so that you can find that same success in a fraction of the time.

If you’re ready to learn more about how to freelance the RIGHT way, join over 3,000+ other designers, developers, marketers, writers, photographers, and other freelancers getting my best advice and growing their business each week.

Last updated on December 7th, 2023

About Matt

I'm a web designer & developer who turned years of freelancing into a full-time career, and later into my own company, Matthews’ Design Co.

I’ve worked on major design projects with some of the biggest brands in the world, including Marriott International, Bloomberg, Facebook, DHL, Porsche, PayPal, Coca-Cola, and American Express.

I now teach 50,000+ freelancers each year get more clients, raise their rates, and build a successful freelance business through my articles, newsletter, products, and free book.

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