I’ve been collecting these q’s for a while now, and this round of Ask Me Anything is finally coming together. If you're new here – every so often I open up the floor for questions, no topic off limits, and answer them here in the newsletter.
If you missed the earlier editions:
AMA #1
AMA #2
A lot of you asked variations of the same few things this time – getting consistent work, pricing, finding the right clients. Which tells me something about where a lot of freelancers are stuck right now. Let's get into it!
"Suggestions and advice on getting consistent work?"
motion.cj on IG
Consistent work comes from keeping the clients you already have and asking them for more, way more than it comes from constantly finding new people. What that actually looks like:
Ask for a testimonial the moment a project wraps, while it's fresh
Follow up a couple months later with a direct referral ask
Reach out to old clients during quiet periods, even with nothing new to pitch
Stay visible in between projects – comments, posts, just showing up
This is a system you build once and keep repeating.
Also, don't underestimate how much your online portfolio and general visibility do the work for you – most of my clients found me online, and that's still one of the best sources of new work for me!
I've never managed to take the plunge and try illustration for fear of failure... I have no idea how to get started, how to get those first clients when you don't have a portfolio of 'real' work.
adamwozniak.art on IG
Everyone with client work today started without any of it. Personal projects count for more than people give them credit for, as long as they're intentional:
Pick one direction you actually want to work in
Make 3-5 strong pieces in that direction, not 15 scattered ones
Treat each one like a real project – process, decisions, a short write-up
Leave out anything that doesn't point toward the work you want next
Clients care whether you can solve their problem. They rarely check if the last ten projects were actually paid. Mock projects are literally what you need to just get started.
This exact question comes up on almost every coaching call I do. If you want to actually work through it together, I only take a limited number of coaching calls each month – message me and I'll let you know what's open.
Here's what one mentee said after we worked on this:
Irene is the exact kind of person I was looking for with illustration help. She gave me very clear directions on what I need to do in order to build a stronger portfolio. Also, knowing that what I have currently can be reworked into more commercial looking pieces gives me so much confidence in what to do next. Irene taught me so much, and I couldn't be more thankful! – Laura Kaufman
My biggest struggle is accepting that clients don't want someone who can do the best work... they want someone who offers the least amount of risk. The idea that you can be a really good designer and still be viewed as more of a risk than someone who knows nothing about design but is an expert on the latest AI trend is really hard to grasp.
Chin Chukwu
This one is for sure frustrating, and worth taking seriously. Skill gets someone to notice you but reliability is what gets them to hand over the budget – two different things clients evaluate separately, and both need to show up somewhere visible: skill in the portfolio, reliability in testimonials, in how a discovery call goes, in how clear your process sounds. A brilliant portfolio next to a vague process or zero client feedback still reads as risky. Fair or not, that's the equation right now, and we have to find a way to deal with it.
I'm just starting up and terrified of doing my first contract 🤣 worried I'm going to miss something important. Also, if a client doesn't pay... what's the process? 🙈
Alison Poots
Ah we’ve all been there! :) Something always gets missed on every first contract. That's totally okay tho, and it fades fast once you've done a few. On payment – a deposit before starting handles most of what people worry about here, no exceptions, not even for the very first project. Here are some clauses worth having in writing in your contract from day one:
A deposit percentage and when it's due
A kill fee if the client cancels partway through
Clear payment terms and what happens if an invoice goes unpaid past a set date
Creal usage rights and terms on how the client can use the design/artowk
Once it's written down instead of just assumed, the fear around it drops a lot!
How do you figure out pricing when every client and project is different? And what does your end-to-end process look like – from pitching to final delivery?
Relish Sabalpara
Pricing depends on scope, complexity, and what the client actually gets from the work, not the category of project. Same illustration style can cost very differently depending on usage rights, client name, timeline, and how much thinking happens before the drawing starts.
Here’s my process, roughly:
Brief and questions, more of them than feels necessary
A proposal with clear scope and price (the proposal includes my T&C ALWAYS)
Deposit for the project, if accepted
Research, exploration, concepts, and sketches first followed by revision from the client with a set limit attached
Finalization and same revision process
Final files delivery and final invoice sent
Ask for testimonial
In 1-2 months – ask for referral
Having a repeatable process actually makes pricing easier, because the quote always maps to the same steps.
If building that out feels like a lot to figure out from scratch, I put together the Client Process Kit – briefs, communication tracking, delivery checklists, the whole system in one place. Grab it here →
No one answers me, basically ever. I jump on recruitment posts that are two minutes old and fill out an email about being interested, being a good fit, being ok with the day rate (even if I'm not)... I used to freelance 5+ years ago and had more work than I knew what to do with. I don't know what happened.
Oliver Kelly
What changed is the volume. Everyone's doing exactly what you're describing – racing to reply first, agreeing to a rate that doesn't actually work just to get a response. That approach gets ignored now because it's what everyone's running.
Referrals and past clients convert at a different rate than cold applications ever will, and agreeing to a rate that doesn't sit right tends to attract the kind of client who keeps pushing past that line anyway. Might be worth pausing the recruitment posts for a bit and going back through old client relationships instead – that's usually where the faster wins are.
My experience is the same, so I try not to take it personally when recruitment posts go nowhere, and focus more on the things I actually have some influence over (cold/warm outreach, current/past clients, marketing/social strategy, portfolio/positioning work, and so on).
For me it's not really a question – I'm getting better in fields like client acquisition, delivering, and negotiating. But I want to talk to someone who already overcame my current obstacles, so they can evaluate my blind spots and mistakes. It's hard to find that person.
Kamil Ismagilov
That person exists, they're just rarely free, because evaluating someone else's blind spots properly takes real time and attention. This is close to what coaching calls end up being in practice – less teaching from zero, more pointing at the one thing someone can't see from inside their own work. Happy to be that person if that's useful. Details here →
Where and how do you find your networking events? I see so many people recommend networking as the #1 way to grow, but rarely do I see real world examples on how they find the 2–3 events per week... And if it's virtual, how do you go about networking in a digital space?
CJ Mendez
I rarely go to networking events myself (I knooow I need to change this!), but local business associations, chamber of commerce events, and industry-specific meetups on Eventbrite or Luma might work better than searching "creative events," since that's where actual clients are, not just other creatives. For virtual networking I've only attended creative-focused ones, but the same logic probably applies – looking for industry-specific online events is worth trying.
For me it's finding the right clients. I started recently after working 9–5 and find it hard to do outreach or attract the right people. Most of the people I reach doesn't convert into a project :(
Ana Escardine
That is very common! Low conversion on outreach usually points to targeting rather than outreach skill itself. Reaching a lot of people who might need design converts worse than reaching a smaller list of people who clearly do. Getting specific helps more than reaching wider:
Pick the industries or project types that actually fit what you want
Set a budget range you're aiming for and stay close to it
Update the portfolio and positioning to reflect that focus clearly, so the fit is obvious before anyone messages you
A handful of the right people finding you beats a long list of people who were never quite right.
And realistically, response rates on cold outreach sit around 2-5%, no matter how good the email is. I tried a ton of different approaches and templates over the years, and that's roughly where it lands every time. If going more targeted – studios that consistently work with illustrators or designers, for example – can push that up to 10-15% response rate, but even then it's not always a yes. Style, taste, budget, how many projects they actually have room for right now – a lot of that is completely out of your control. Saying this as someone who runs a small design studio and sees outreach land in my own inbox too.
A big part of getting that response rate up also comes down to what people find once they click through – if your portfolio isn't doing its job, even the best-targeted email won't convert. That's exactly what Portfolio That Books Clients guide walks through. Grab it here →
Hope that was helpful! Thank you for sending these q’s in, and for how honest some of you got in the process.
Got a question for the next one? Just reply to this email.
As always, thank you for reading,
