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Topics I discuss in my newsletter & eBook
Learn how to achieve a healthy work-life balance and work from home effectively
Career Transitions
Learn how to navigate tricky career transitions and start your freelancing journey
Pricing & Rates
Learn how to price your freelance services and set appropriate rates for each project
Getting Clients
Learn how to attract clients to you rather than chasing after paid work
Marketing Positioning
Find out how to market yourself to potention client and position yourself for success
Portfolio Websites
Learn how to create a captivating portfolio website that clients find irresistable
Proposals & Contracts
Learn the difference between proposals and contracts and how to use each effectively
Client Communication
Learn how to communicate effectively with your clients and set clear expectations
Project Management
Find out how to schedule and complete your projects in a professional and timely manner
Payments & Invoicing
Learn how to properly send invoices and collect payments from your freelance clients
Finances & Taxes
Learn how to manage your finances and save for taxes so you can grow your business
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Each one of my newsletter emails is packed with valuable insights. You’ll get original perspectives not found on my blog every Saturday morning.

Have you ever wondered why freelancers have so many problems managing client projects?

Endless revision cycles, misaligned expectations, and trouble getting paid are just a few of the issues that can easily plague a freelancer’s career.

👉 Almost every major conflict you’ll face as a freelancer will stem from asking the wrong questions before starting a new project.

Most freelancers mistakenly ask specific questions about the scope of work right away.

That’s problematic because it allows the client to be too prescriptive and clients rarely know what they want or need.

Everything will seem fine until you start delivering work.

Then they’ll realize it’s not what they wanted and start asking for revisions (big surprise).

This is where most freelancers lose control of the project and the client — because your expectations were fundamentally misaligned from the beginning.

The timeline is thrown off, your original price estimate is no longer accurate, and you’re scrambling to keep things running smoothly in an awkward situation.

Now you’re stuck building the airplane as you fly it (with the client as your pilot).

I know there are countless articles about what questions to ask your clients — and most of them completely miss the mark.

My questions are specifically designed to:

  1. Weed out bad clients quickly
  2. Align expectations with good clients
  3. Show clients you care about their business
  4. Allow you to justify higher rates
  5. Set you apart from other freelancers

It’s a fine-tuned technique that’s worked wonders for me over the years.

This article is packed with detail and gets into the weeds of why these are the right questions to ask and how to ask them in practice.

Hit reply if you have any questions or comments.

7 Questions to Ask Your Freelance Clients Before Starting Work

Enjoy your weekend!


How did I become a freelancer?

I started freelancing by accident in 2009 when I fell in love with creating websites during a college course. Then, I discovered people were willing to pay for websites from individuals like me, not just established businesses.

So I started doing any web-related work I could find to make a little money on the side. I didn’t know it at the time, but I was a freelancer.

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

Before long, I was regularly picking up freelance work on the side. But by the time I graduated, I had only earned about $10,000 in total.

It was never my intention to become a full-time freelancer, so I got a salary job like everyone else.

Freelance work was exciting, but I needed a reliable income. I continued freelancing on nights and weekends for the next 3 years.

I loved that job, but after a while I couldn’t shake the feeling that working 9-5 for the next 40+ years just wasn’t for me.

At the same time, my freelance income was increasing each year. Every aspect of running a business and being my own boss was addicting.

What really kickstarted my full-time freelancing career was a redesign of my portfolio website. For the first time, I decided to focus on my clients rather than my skills. In other words, I transformed my portfolio website into a powerful business tool that attracted clients — and it worked!

Before long, I was making more money freelancing on nights and weekends than I was at my day job.

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.

I’ve since worked for some of the biggest brands in the world (with no prior connections to them) and earned over $1M of freelance income in just 5 years.

Wake up to my best freelancing advice 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 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.

Sign up and get my FREE book!

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 2,600+ other designers, developers, marketers, writers, photographers, and other freelancers getting my best advice and growing their business each week.

Last updated on May 22nd, 2022

About Me

I’m a UI/UX designer & web developer who turned years of freelancing into a full-time career, and recently 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.

This website (launched April 2020), is now dedicated to teaching thousands of freelancers how to succeed through my articles, newsletter, products, services, and freelance community.

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"Matt's emails really stand out and are some of a very select few that I actually read to the end. They're interesting, engaging, and I actually learn something!"

"As an introverted designer, Matt's advice inspired me to become more confident in how I sell myself, price my services, and maintain integrity when pitching to clients."

"I can't afford to make mistakes when vetting new freelance clients so this Slack community combined with Matt's insights and experience has been golden for me!"

"After reading your blog I am convinced that you have been following my life 🙂 There were so many points that I didn't even know I learned until I read your article. I'm glad I subscribed now, because I was definitely in danger of making all these mistakes over again!"