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How to get the greatest freelance advice you’ve ever received: tips on learning from the best

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Pretend you’re Saul Bass.

You’re one of the most famous designers and filmmakers in history when a young designer approaches you and says, “Mr. Bass, I’m a huge fan of your work and one day I hope to be just like you.

Do you have any advice for me?”

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If you really were Saul Bass, perhaps you’d respond with your most memorable quote, “Symbolize and summarize,”  for this aspiring designer.

But think about all the many years of study, the endless sketches, the refining of your design process, and the many varied business lessons you’ve learned from experience. What advice would be most useful to this young designer, and how can you possibly share the volumes of advice you have in a few sentences?

Flash back to real life.

Have you ever received advice from someone you consider an expert and been disappointed?

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Maybe you got advice on an aspect you’re already learned in, or perhaps you wanted specifics and you only got the big picture. Consider this: you might need to ask better questions.

“How?” you ask. Keep reading…

There’s no such thing as a stupid question

…but there is such a thing as a poorly-worded one. Follow these three tips to get better answers:

1. Be specific

Broad, sweeping questions tend to provoke broad, sweeping answers.

It’s not because the adviser doesn’t want to give away their trade secrets. It’s because without direction they don’t know where to start, and they know too much to tell you everything at once.

Asking for “any advice” might elicit a response such as “get an education” or “follow your heart.”

Who do you listen to and where do you go for marketing advice?”


“What’s the best business advice you received and how did you implement it?”

gives the adviser direction. With direction, they can focus on a specific area of expertise and provide a detailed response.

Ask for a story

People love to tell stories, so appeal to the grandparent (or future grandparent) in them by asking for advice through a story.

Tell me about how you took the plunge into full-time freelancing.”

Then listen. There are nuggets of wisdom strewn throughout the story if you pay attention.

Well, you know, I didn’t just decide one day to be a freelancer. I wasn’t happy at my full-time job, so I spent time improving my portfolio. Pro bono I designed the shirts for my son’s baseball team and redesigned the bulletin for my church. Really I wanted to get into an agency, and I knew I’d need more skills, so I took on programming the mobile site for my existing job and also took a web dev course at the local college, where I met a yoga professor who needed design work for her studio…”

See there? There’s a ton of information on how to go from employee to entrepreneur. Everything from how you can improve your portfolio by finding good causes to how to get paid for learning and where to find people in need of design work.

But don’t stop there! Ask for more details!

How did you find out the yoga professor needed design work?”

Were you afraid that your pastor would turn you down? How do you approach someone out of the blue like that and ask to ‘fix’ their design problems?

And keep listening – take notes if you need to in a verbal conversation.

Know that it’s okay to ask about mistakes and failures, but don’t start the conversation that way. Few want to tell a stranger about their most expensive business mistake, but they’ll be more likely to open up after several exchanges.

Be prepared

When you’re asking for help rather than advice, do your homework. It shows you are serious about your project and value your adviser’s time.

Have put some thought and time into the project at hand before approaching your adviser. Otherwise, be prepared to be sent back to the drawing board until you are prepared.

Advisee: “What font should I use for my business?”

Adviser: “How do you want the world to perceive your business?”

Advisee: “I’m not sure Maybe classy but modern? What do you think?”

Adviser: “That’s not a question I can answer; it’s your business. Before you can create a visual business identity, you need to know what your business does, who your audience is, and what adjectives you want associated with it. Once you spend some time answering those questions, we can talk about font.”

PS – Helpful study guides for understanding your business: From Passion to Profit, Tips for Setting your Business Goals, and Finding your Target Audience.

What question(s) do you ask?

Do you have a great question that often elicits great advice? Share it in the comments on this post!

And don’t forget Millo is starting an all-new YouTube channel where we’ll ask some of the top freelancers around some pretty awesome questions! If you have questions you want to know about freelancing, business, entrepreneurship, leave a comment on this post and we’ll be sure to ask our experts in our new video interviews.

And be sure to be among the first to know about these awesome new video interviews by subscribing to the Millo YouTube Channel!

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About April Greer

April is the Director of Projects at Reliable PSD, a design-to-code company for designers, by designers. She’s the glue keeping everything together, organized, and right on time, and giving everyone a fantastic experience while she does it.


Leave a Comment



  1. That’s really good advice. I find myself wanting to ask broad questions because I want ALL the answers, but this method will definitely get better results!

  2. As ever April, great advice wrapped up in a really engaging post. Love the analogy of grandparents. So true.

  3. One of the best “broad” pieces of advice I got from my first designer “crush” was: “Cultivate the kinds of clients that can pay you what you are worth.”

    I’ve always loved that concept, but never knew quite how to implement it…

  4. I think the best advice i received was…
    great advice from one of my peers, there is way too much competition on them.


  1. […] know it’s okay to ask for help! Whether you need a business advisor, mentor, financial advisor, or therapist (or some combination thereof), reach […]

  2. […] How to get the greatest freelance advice you’ve ever received: tips on learning from the best […]


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