A Conversation with Matt Olpinski

DG: Hey Matt, how are you doing? As the tradition goes, let’s start with a little intro.
Matt: I’m an independent design consultant who works with startups and small businesses to help them succeed. I also write articles to help freelancers become better on my blog and in my newsletter.

DG: For how long have you been working as a freelance consultant? And how has the journey unfolded so far?
Matt: I started freelancing during my freshman year of college in 2009. I didn’t even know what freelancing was when I took on my first few projects. They were small and didn’t pay much, but I gradually learned and started charging more for my experience. Eventually, I was able to leave my full-time job in favor of a full-time freelancing career.


DG: You write a lot about helping freelancers, what made you start a freelance-focused blog in the first place?
Matt: I’ve always enjoyed helping others. I started a blog about 5 years ago, but it didn’t have a specific focus. I felt like it failed so I took it down. Once people started asking me for advice on freelancing several years later, I decided to just restart the blog with a focus on freelancing.

DG: How do you go about finding new or recurring clients? Any tips and tricks for the budding freelancers?
Matt: I don’t find my clients, my clients find me. That’s the trick that most freelancers miss. You don’t want to be in a position where you’re constantly pursuing new work. My advice is to focus on making it easy for clients to find you. They are already looking for you, all you have to do is make it easier for them to find you. Ramp up your social profiles, refine your portfolio, rebuild your personal website with a more specific focus, and improve your sales pitches/funnels. Then reach out to your immediate network while the changes start to take effect and bring you new work.


DG: You seem to be a very professional and organized person, how did this trait of yours got developed?
Matt: That is correct. I’ve been extremely organized ever since I can remember. Part of this was inherited from the way my parents disciplined, but I also attribute it to my early fascination with Legos and K’NEX, when I was 6 years old. In order to build things quickly and efficiently, you have to keep the pieces organized and follow the instructions carefully. Years later this mentality carried over into how I organize my finances, hard drive files, home, and life in general.

DG: What does your work stack comprises of?
Matt: My stack changes as new apps and technologies emerge, but at the time of this writing, I’m primarily using Photoshop and Illustrator for design, Slack for communication, Trello for task management, Google Docs for file sharing and organization, Sublime Text for coding, ConverKit and WordPress for my website and newsletter, Harvest for time-tracking and invoicing, and Google Calendar for events and meetings.

Matt's Workspace
Matt’s Workspace

DG: How is the present scene for freelancers? Is the market doing justice with the freelancers?
Matt: Freelancers are more in demand than ever before, which makes it easier for them to find new work. In general, I think clients are starting to understand the freelance world more each day, but websites such as UpWork and Freelancer.com are promoting a lot of low-tier competition that drives pricing down and causes the quality of work to suffer. To overcome this, it’s the job of a freelancer to separate themselves from this mentality and these platforms. Freelancers and consultants that want to get paid significantly more money for the value of their work are first required to help the client identify the business problems, goals, and objectives and deliver a high-value solution. That’s something most freelancing websites have yet to figure out.

DG: As a freelancer, people often struggle with maintaining their schedule, how is your normal work-day like?
Matt: My work days vary all the time. I used to beat myself up over it, but then I started to realize that it’s exactly what I wanted. When I wake up in the morning, I figure out what I need to get done that day to keep my business running and my clients happy. Then I do what it takes to get it done. Sometimes I work really fast in the morning. Other times I procrastinate until the evening. Either way, I make sure the work gets done. I try to refine my habits each day and always look for ways to optimize my workflows to save time.


DG: There’s a lot of buzz about product design in the industry, but there’s a very thin line of difference between the product and UI/UX design. How would you define or rather say differentiate these both?
Matt: I don’t really think they’re different. Product design mostly refers to the type of thing being built, for example, an app or website that is being marketed as a product to the customer or user. UI and UX are just types of design that are required to make a product.

DG: It’s kinda tricky and difficult to manage the project status or revisions while freelancing. How do you get your clients on the same page and make them believe in your work?
Matt: Managing projects can be very difficult. It’s important to communicate clearly and effectively at all times as well as set the right expectations for your clients from the beginning. I think the process starts on your website, before the first communication ever happens. You’ve got to convince clients to contact you in the first place. Most people use a portfolio website and testimonials to get the job done. Once the prospective client contacts you, the rest of the sales (discovery and proposal) process should be fairly easy. Invest into a great website and let it do the hard work for you.


DG: What’s your say on the side projects or freebies that people do just out of fun and passion?
Matt: I think side projects are great, especially when you’re first starting out. It shows dedication, passion, and motivation to do well. If you’re doing your own side projects in addition to college, freelancing, or a full-time job, chances are you’re the type of person who can be a successful full-time freelancer.

DG: Any piece of advice for the budding freelancers/consultants? We had love to hear it from you.

Work really hard and stay humble. Read books and articles that can help you learn. Don’t be afraid to dive in either. Most people don’t know what their doing and mistakes are inevitable. All you have to do is learn from them.

Rapid Fire Round

A freelancer is _______.
One who
works for themselves.

If a Freelancer is focused on selling time, a Consultant is focused on selling solutions.

Your perfect idea of date night?
Chatting with my fiance at a coffee shop, going out to dinner, then home watching a movie together.

Fantasy is _______.
An amazing design company.

If you’re sent to a beach with a laptop (with internet connection, of course), what would you be doing?
Swimming in the ocean.

A babe who can design is _______.
Probably not single.

You must be ______ to be a successful freelancer.

Darshan is _______.
A pretty cool dude.


Matt has been working independently and helping freelancers and consultants for quite a long time now. Following his blog and newsletter on a regular basis has helped me a lot on both professional and personal levels; the reason why I had included Matt’s blog in my list of top blogs for product design. Thank you Matt, for this amazing Conversation. It was great to get a sneak peek of the life of a full-time freelance consultant. Such good work you’ve been doing for good time, kudos!

Don’t forget to check out Matt’s blog and subscribe to his awesome email newsletter. Also, Matt is pretty humble and amazing in solving all your queries related to freelancing or design in general. Go ahead and tweet him @mattolpinski and witness his neat and clean designs on Dribbble.

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