Ask Me Anything: Challenges, Style & Getting Started
My âask me anythingâ segment is where I take questions asked in my Insta Broadcast Channel and answer them, first and foremost, in my newsletter. Which, if youâre not on my emailing list, youâll totally want to be.
These are a couple of questions that came through recently, really good ones. So letâs get into it.
"What has been your biggest challenge so far, and how did you overcome it?"
MAN, this was a good question. I don't think I have one singular big challenge, but more an accumulation of challenges that I've worked through over time, which have all led me to where I am now.
If I break my career into stages, it looks something like this:
The side hustle era. Illustrating happened in the early mornings and late evenings, squeezed around a corporate 9 to 5. Tired? Always. Worth it? Yes.
The slowly growing era. I quit my corporate role and started figuring out how to mAkE ThIs WoRk. There was a lot of trial and error in this one. A lot of Googling things I probably should have already known. A lot of backing myself when it felt easier not to.
The primary caregiver era. Everything took a back seat while my kids were little (they're 5 and 7 now). Also known as the very juggly era. This one was hard in a quiet, unglamorous kind of way. There was no big dramatic pivot, just a lot of showing up imperfectly and doing what I could with what I had.
The woohoo era. (Current.) My husband and I swapped roles at the end of 2023 so I could pursue live illustration full-time. He became the primary caregiver, and we are both genuinely thriving. This era has my whole heart.
The challenges really happened in the transitions between each stage. That's where the uncertainty lived, where leaps of faith were required (from both me and my husband), and where the hustle was very, very real.
There's no clean answer to "how did you overcome it?" because it wasn't one moment. It was a series of small decisions, a lot of trust, and choosing to keep going even when the path wasn't totally clear yet.
"How do you maintain consistency in your style and jobs when first getting started?"
Great question, and I'll split this into two parts because style and getting jobs are pretty different beasts.
On style:
Accept that there'll be inconsistency at first while you figure out the mediums that work best for both your signature look and your speed (especially important for live illustration, where you're working in real time).
You actually have a bit of freedom here before you become super established and known for a specific style, so use it. Experiment. Try things. Some of it won't work, and that's fine.
There are also illustrators who move between markers and pencils, but their overall work still feels cohesive, if you know what I mean. Style isn't just about tools, it's about the feeling that runs through everything you make. That part develops naturally the more you work.
On getting jobs:
This is where the hustle comes in. If I were starting now and wanted to get some bookings in quickly, I'd do some (or all) of the following:
Show up consistently on Instagram with clear, repetitive "I'm a live illustrator and this is my service" content. Reels are basically free ads. Use them.
Look for specific gaps in your calendar that you want to fill ("I have 2 spots left for March 2027!") to create urgency without being pushy.
Consider offering specials early on while you're building your portfolio. Try not to work for free, but if you do, make sure there are agreed deliverables, do it for the content, and use it as leverage to book paid gigs.
Team up with aligned brands who share your ideal client, florists, celebrants, MCs, venues. Mutually beneficial relationships go a long way.
The combination of showing up online and building real relationships offline is genuinely the most effective starting point.
While I've got you..
If youâre still in âanswer my question, plsâ mode⊠I low-key launched 60 Minute Mentoring sessions for those who are either too advanced or not quite ready for my course, but have specific questions they want answered. So if thatâs you, go book your session!