What I learned from interviewing 9 successful freelancers

Think of someone you really admire as a freelancer.

Have you ever wished you could just contact them out of the blue and ask permission to question them for 20 minutes on a specific topic they’re really knowledgeable in?

Last month, that’s just what I did. I interviewed 9 successful freelancers on topics like:

  • hiring employees
  • overcoming self-doubt
  • working with international clients
  • finding your niche
  • teaching design
  • and much more

(Stoked members can listen to them for free as they’re released, so if you’re not a member, go sign up!)

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The experience was amazing.


It was like going to a design mixer where you have an awesome, in-depth conversation with someone who knows more than you, nine times over.

Not only that, but I didn’t hold back. I barked up some pretty big trees, and it was a huge thrill to hear “yes” from famous designers like David Airey and Veerle Pieters.

I’d do it again in a heartbeat (albeit preferably at a less frenetic pace).

So, besides picking up a ton of fantastic insight from crazy successful freelancers from New Jersey to New Zealand (which you, too, can learn from at Stoked), what else did I learn?


A bunch of practical, no-nonsense tips that improved my professionalism and video conferencing abilities as well as my ability to talk with strangers without sounding like a ball of nerves.

PS – I also learned these invaluable credibility-boosting tips!

Here’s what I learned most:

Setting up interviews (or any collaboration) takes time

You’re busy. I’m busy. Everyone’s busy. From the moment you press send on the “hey, can I interview you?” email, it’s probably going to be at least 1-2 weeks before you both have a free 30 minutes of time.

Furthermore, for a smoother, engaging conversation with well-prepared answers, it’s in your best interest to send collaboration information (in my case, questions and instructions) well ahead of time.

Pro tip: Learn how to accept a “no” graciously. It’s not a personal affront…they’re probably just really busy. Thank them for their consideration and wish them well.

Pro tip #2: Busy people are more likely to accept commitments in shorter time chunks. I suspect I’d have had a much harder time getting interviews if I had asked for an hour interview.

Test your software and hardware before your first “real” use

Note: I used Skype with Athtek Skype Recorder ($30) to conduct and record my interviews…and of course a webcam and headphones. It worked famously.

Nothing’s worse than technological problems when you’re already a jumble of nerves and excitement.

So the weekend before my first interview, I Skyped my mom, who has the worst luck ever with all forms of technology. I figured if she could follow my instructions and I could successfully record our conversation, it’d be smooth sailing with everyone else.

And I’m glad I did, because I tested several recorders I couldn’t get to work before I settled on Athtek’s.

What a nightmare if the recorder hadn’t recorded my first interview!

Make your first interview (or collaboration) a friend if you can

If you already know the person, it’s much easier to overcome any technological issues, nerves, or goofs that pop up as you’re figuring this new thing out.

Besides, they’ll probably also be a little nervous, so the two of you can relax a bit with some chit-chat before the interview starts.

Flexibility is key

Remember my post about a freelancer’s greatest attribute? Well here it is again (and also look for it in Kat Topaz’s interview): flexibility is key.

Life happens. Kids get sick. Alarms don’t go off. Lunch meetings take an hour longer than you planned. Your ability to go with the flow, keep an even keel, and make yourself as available as possible (especially if you’re the one requesting another’s time) is key to a successful interview/collaboration…and your sanity.

That being said, in general, do what you’ve said you’ll do when you say you’re going to do it, even if it is a low-priority task.

It is AMAZINGLY frustrating to attempt to collaborate with someone who misses appointments without a heads-up or takes three weeks to send you the one document you need to move on.

(This is experience talking, and I’m still peeved. Can you tell?)

You will quickly make the “do not work with” list if collaborating with you is a hassle, regardless of how good your work is.

Always have a beverage and a soft surface to set it on

When you’re nervous or inevitably when there’s a big moment for you to shine, your mouth will dry up like a desert. Or you’ll get the hiccups. Or a tickle in your throat.

While it sounds silly, I never start a video/audio conference without a beverage nearby. (My beverage of choice is water, followed closely by tea.)

Equally as important, though, is where you’re going to set it. Use a coaster, your notebook, a stack of papers, or anything level that doesn’t make a lot of noise when you set your beverage on it.

Most desk surfaces make a LOT of noise when contacted by a glass or ceramic mug, and your microphone WILL pick that up…along with typing, clicking a pen, a motorcycle zooming past an open window, etc.

Listen to yourself and improve

After the interview, listen to your conversation and pick up on the things you can improve. Do you say “um” a lot? “Super!” or some other superlative? (Guilty.) Talk too fast? Talk too much?

Most of us don’t realize how we sound until we become the audience. And remember, natural conversations have pauses…it’s okay to have them! So often we think every microsecond must have noise, but sometimes we need to pause and let the audience digest what they’ve heard before moving on.

There’s something to learn from everyone

Every single interaction, let alone conversation, taught me something, whether on-topic or as an aside. Sometimes I learned what NOT to do!

I could go back and interview each successful freelancer again on a totally different topic. From each conversation, I had an entire different list of questions for them by the end.

Furthermore, I believe I could’ve interviewed 9 “rookie” freelancers and learned something. Or 9 janitors. Or 9 clerks.

Bottom line: if you didn’t learn a thing, 99% of the time it’s because you weren’t paying attention.

Freelancers are AWESOME people

Last, but certainly not least, I confirmed (again!) that freelancers are awesome people.

(And if you don’t believe me, listen to Mike Jones’ interview.)

Each freelancer I interviewed was polite, professional, friendly, very excited to tell their story, and 100% willing to share their tips for success. Most of the time, they could’ve (and would’ve) kept talking long past the 20 minutes of time I asked for!

And even the really successful ones think of themselves as just regular people like you and me.

Seriously, when I sent emails asking them to share their “expert” insight, I got more responses that started with something like, “Thanks for your kind words! I don’t know if I’m an expert, but I’d be happy to share…and here’s the expert you really should be talking to.”

The ultimate takeaway

Don’t be afraid to contact the successful freelancer you look up to.

BUT, know what you want to ask. You’re more likely to get a general answer from a general question.

“What helped you be successful?” might breed, “Preparation and a little bit of luck.” — kinda disappointing, don’t you think?

So get the best, most detailed information (and be more likely to get the response you’re looking for), make sure to ask specific, well-thought-out questions on a specific topic.

Examples: “How did you land your first big client?” “What tips could you share for finding great subcontractors?” “I really love this particular technique you use…how do you do it?”

What tips can you share?

Have you learned something valuable from interviewing or collaborating with other freelancers? Share your stories, tips, and words of wisdom in the comments!

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  1. Nice article, but the title is a little misleading. Was disappointed it wasn’t about what you learned from the successful freelancers…and only about the interviewing process.

    1. Lyndsey,

      Preston and I had a bit of a miscommunication – he wanted me to put a few teasers from the interviews in and I misunderstood and thought he wanted me to write about the process. It’s my fault for not clearing it up, and I’m going to be sharing some nuggets of wisdom in next week’s posts.

      Stay tuned!


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