Interview by Madeleine Dore

Photography by Bri Hammond

Jeremy Wortsman:
Director, Jacky Winter

Meet Jeremy Wortsman. He is the director of creative services agency The Jacky Winter Group and Lamington Drive gallery, the Melbourne host of Creative Mornings, a keen yet admittedly terrible ice hockey player, and the proud father of a newborn baby girl.

Born in New York, in the early naughties Jeremy fell in love with Melbourne and soon decided to make the move to Australia – in which he fondly refers to as ‘The Lucky Country’ – a permanent one.  

Luck has long been on his side, and something he tries to maintain a constant awareness of as he humbly acknowledges the relationship between being open and passionate, successful and lucky.

But just a glance at Jeremy’s impressive career trajectory, it’s easy to see that hard work, creativity, collaboration and determination have all played an important part in setting his trail ablaze. He has worked as a Finished Artist and teacher, and co-founded and designed award-winning Is Not Magazine with four others, as well a design studio called Chase & Gallery with Stuart Geddes.

Combining a strong foothold in Melbourne’s creative community with an entrepreneurial eye, Jeremy founded Jacky Winter from his bedroom. Today, the fully-fledged creative services agency represents over one hundred talented artists, photographers, and illustrators and brings hundreds more ideas to life.

Generously, he shares with us the details of his daily commute, the disruptive joy of parenthood and what it’s like being a little on the shy side in the jostling, extraverted world of the arts.

A day in the life

Around 7:00 or 8:00

My whole morning routine is something I have been struggling with my entire life. It’s the one area I have no control over because I just love sleeping so much.

When I get up I try to meditate for twenty minutes, then do back exercises for another ten, then I have a green smoothie. I blend up six bunches of kale every Sunday, and make these frozen blocks so that everything is ready to go in the morning. Then it's cuddles with my newborn daughter Winifred.

Around 9:15

I live about an hour away from work in the Dandenong Ranges, so listening to podcasts is an essential part of my commute. WTF is probably my favourite podcast. I listen to This American Life once a week and How Was Your Week, then I’ll switch to an audiobook.

I really love mysteries. J.K. Rowling did  two books under the pseudonym Robert Galbraith. The most recent, The Silkworm, is incredible… So suspenseful. That actually helped me wake up earlier because it's a thirteen hour listen, but I would also drive around aimlessly at night because I wanted to hear more of it! [Laughs]

Around 10:00

Arrive at Jacky Winter HQ

Around 10:30

They say the key to being on time is being early, so I’m really careful in terms of knowing when to schedule meetings. I usually schedule meetings around ten-thirty or eleven, because I know if I have to be here at ten, then if I hit traffic I’m not late. 

I think being late is one of the worst things – it can be such a sign of disrespect sometimes – and it kind of sets the tone for the rest of the day. That’s why I hate being late myself.

Before lunch

Our line of work at Jacky Winter is incredibly reactive, and things are coming in that we have to respond to quickly.  So I try to keep the hours between ten and six as open as possible.

As the owner of the business, there are some things that I do that are regularly scheduled like payroll and bookkeeping. I don’t have to do it, but I feel like in order to know what is happening with the business I need to be on top of the finances. But it probably takes around a full day each week that I would love to have back in some other way.


I don't really take a lunch break and I’m really weird about food. I will get in a trip and do the same thing for years. Right now I am in this porridge trip… I’m just loving porridge. It’s amazing – it’s a slow burning food, it's delicious, and I just love porridge!

Around 14:45

The five hours that I would take for lunch I allocate to playing ice hockey once or twice a week.

It is the hardest thing for me to do, because I hate leaving the office. Even when I’m at hockey, I’m always on the phone at the rink, everyone makes fun of me for working while we are playing – it’s so hard for me to focus! But it’s really important for my mental health to play.

Especially getting older as well, maintaining your physical health is so important to your mental health, energy levels and doing your best work.


I always have a lot of big picture goals I will chip away at. My approach to work has always been a very cumulative one. It’s about finding as many pockets of time as you can to do a little, so eventually over time it adds up.

But it can be really hard when you are working on a big project – how do you break that down and get in the right headspace and generate from your own thoughts while not having other things come at you? So usually the best time is on the weekend or at night when it’s kind of quiet and I really get a lot of stuff done.

The drive home

I listen to more podcasts and audiobooks

Arrive home

Having a child is about learning to live differently – you are at the mercy of your baby. They grow so fast and their needs change so much. Winifred has to be in bed by 7 o’clock, so that changes what my partner and I do.

Around 19:30

My meals are made in advance, but the same thing as with lunch, I kind of get stuck on having the same thing for dinner. I have this huge salad that I make every night, or I’ll have a steak. I'm really into eating good food, but everything is pre-made on Sundays so its all ready to go. 

I hate cooking and doing the dishes because it takes so much time. There is this very limited window after work because it takes me an hour and a half to get home, and let’s say I’ve had to stop at the pharmacy or at the supermarket or run an errand, I might not get home until eight, and then if I want to be in bed by ten, I only have two hours to do things.

Around 21:00

TV used to be a really important part of my evening, and I still watch the The Daily Show from America four nights a week. If we are watching a series we will try to nail an episode each night as well. I just think it’s a nice way to shut off my brain, which I think is important.

Around 22:00

That whole concept of sleep debt is true – it’s like a bank. To wake up at seven I need eight hours sleep. Everyone is different, but for me that means being in bed by ten because it takes me an hour to fall asleep.  I’m addicted to Scramble With Friends so I have to play at least two games before I go to sleep.

Around 23:00


“Waking up begins at the end of the day – it’s not the first thing you do, it’s the last thing. It’s the culmination of your day – if you can end your day properly, then you can wake up properly.”

Weekend routine

My partner and I are both creatives – she is a freelance writer – and we are both very active apart and on our own paths during the week,  so the weekend is a bit regimented. 

We might go out for breakfast – The General Food Store is our favourite place. Or we go to Cameo Cinemas in Belgrave… we go there a lot.

We really love having people over. Living far away is tricky, so when people come over we like to make a big deal of it and usually have something special planned to make it worth the trip.

I usually have a hockey game every Saturday and I referee and officiate on Sundays. Then the rest is spent kind of preparing for the week.

Jeremy Wortsman interview Extraordinary Routines
“There’s the laundry thing, the cleaning the dogs thing, the take the dogs out for long walks thing, and go out food shopping and cooking and cleaning.It gets kind of crazy, but it’s life!”

Jeremy Wortsman interview Extraordinary Routines

Behind the scenes

On a clear desktop, a clear mind…

I’m very particular about having a clean digital desktop, downloads folder and having my browser tabs organised.

Because we do so much work in a digital space, the computer really represents your brain in a lot of ways.

On integrating your life into your business… 

As a business owner if your whole life isn’t about your business, it’s going to be hard to make it. Well, that might not always be true, but that’s how I found it to be – it has to be something that envelops you. 

I try to be very involved in community or industry
related projects. I don’t necessarily set aside time,
but that’s just kind of part of my job – it all kind of folds in.

“They say creative people occupy a messy environment because it kind of inspires them, but I feel like I need a neat office, desk and desktop to get into the zone.”
Jeremy Wortsman interview Extraordinary Routines
Jeremy Wortsman interview Extraordinary Routines

On overcoming shyness…

Through therapy…

I don’t know if I really have [overcome shyness], but therapy has been a big part of it. I’ve been in therapy half my life – which I love – and I think it’s hugely important for someone who works entirely with their brain.

If you’re an athlete and work with your body, you get regular massages and physio. I always say that when you work in a creative field, you need the same thing for your brain.

Through meditation…

I think meditation is a part of that as well. Even though I’m horrible at meditation and I can’t do it properly, it still doesn’t stop me from trying. It helps to be mindful and know when I’m being crazy – like when I’m having a gallery opening downstairs at Lamington Drive and I’m just staying up in the office. I do that a lot.

Through stepping outside your
comfort zone...

Try to continuously make yourself uncomfortable whenever you can. It’s really hard, but try.

A lot of it comes from having confidence in what you do and knowing who might, or might not, be interested. And knowing yourself is a really important part of it. But that kind of self-awareness is tricky.

“Try to continuously make yourself uncomfortable whenever you can. It can be really, really hard – and I struggle with that all the time – but try.”
Jeremy Wortsman interview Extraordinary Routines

On making things with inherent value…

There is this idea in advertising and marketing where you are constantly expected to be like, “Hey, hey, look at me, let me tell you about this thing,” and I think it’s really hard to get people’s attention now.

But marketing and explaining our artists to clients is a big part of our job, so I always try to craft things in such a way that people will be inherently interested.

In a sense I try to engage in non-marketing marketing. If someone is coming to Lamington Drive on a Thursday night when it’s pouring rain, they are doing it because they actually want to come. And so that hurdle is already being jumped, and people don’t think it’s a pain or anything, it’s a much more pleasant way to communicate and advertise the work of our artists.

On life’s four burners…

In David Sedaris new book, Let's Explore Diabetes with Owls, there is a story called Laugh, Kookaburra where the characters have this conversation in the car where they talk about how life is like a stovetop and you have four burners.

One burner represents your health, one is your family, the third is your friends and the fourth is your work. In order to be successful in one area of your life, you have to turn one burner off. In order to be really successful, you have to turn off two.

And I think – from the people that I know – I find this to be true. I’m always kind of tweaking my burners around different areas. 

Jeremy Wortsman interview Extraordinary Routines

On the social life of an introvert…

I’m not a very social person – I’m incredibly introverted actually, and very, very shy. So I really enjoy bringing people to me where the focus is on a project. Like with hosting Creativ Mornings, that’s once a month where I meet a lot of people who are interested in what we as a group are putting out there.

Part of the reason I started Lamington Drive gallery was to create a physical space for friends and new people to visit the Jacky Winter agency and that’s where I do a lot of my socialising.

So the months are kind of bookmarked by the Lamington Drive openings and Creative Mornings. But as for just going out and socialising, I don’t really do that anymore in a kind of loose way, it has to be more regimented.

Jeremy Wortsman interview Extraordinary Routines
Jeremy Wortsman interview Extraordinary Routines

On sticking at things you’re not good at…

Ice hockey is my main passion outside of work – and I’m horrible at it! [Laughs]

Even though I’ve been playing my entire life, I’m still really bad. But I think it’s amazing to keep doing something you are terrible at. 

Being humble and wanting to get better at something is really important.

Something like playing hockey is so tied to the physical limits of what you can do, so it’s a challenge trying to get better. 

“Being humble and wanting to get better at something is really important.”
Jeremy Wortsman interview Extraordinary Routines

On starting a family…

You talk to new parents and they are just brain dead and that’s what it’s like at the moment. [Laughs]

One thing you realise is that you have a lot less time to pursue things. There are many things I’ve always wanted to do – I love taking classes, trying new things, and exploring, but it’s kind of a new reality now and I’ve learned to take satisfaction in different aspects of life.

So I spend a lot of time with my daughter, doing nothing and just sitting there and staring at her. But I feel that as time goes on, I’m going to really want to explore various things with her when she is able.

On sheer dumb luck…

There have been times, especially early on in the business, where I just didn’t think I would be able to make payroll, and then a job just comes through and it gets paid on time. The whole business could have collapsed if it didn’t work that way!

I attribute a lot to just being lucky. But I don’t think luck is an isolated thing – I think you have to work hard to have the right set of circumstances there. Luck is a reflection of how much you have invested in it yourself.

If you’re doing the right thing and putting it out there, luck makes sure the right people see it and opportunities present themselves. 

On the value of time…

Time is the most valuable thing you have, and I think what you do with it is a really interesting question.

I think everyone is working to have more time, and the idea is that you eventually get to a place in your career where other people are doing certain tasks for you, so you have more time.

Right now I am time poor, because of all the things you have to do just to keep the plates spinning. But I’m very happy.

“Time is the most valuable thing you have, and I think what you do with it is a really interesting question.”
Jeremy Wortsman interview Extraordinary Routines

Extraordinary Findings


Let's Explore Diabete with Owls by David Sedaris 
The New York Times iPad edition
E by Matt Beaumont
My bonsai-like pruned list of RSS feeds via NewsBlur


This American Life 
How Was Your Week
Slate's The Gist
NPR's Pop Culture Happy Hour & All Songs Considered


Slacker by Richard Linklater
How It's Made TV series
The Daily Show with Jon Stewart


Green Smoothies

Jeremy Wortsman interview Extraordinary Routines


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