#2274 How to pursue a career in blogging/fashion/life

N.E. asks: To be honest, your blog makes me really anxious. I want to pursue what you are doing as a profession but I’m scared that I will mess everything up. Don’t take this in a bad way. Your work is very inspiring and this is why I am anxious because I want to do your kind of work but don’t have the full ambition or motivation to actually get what I want. I guess what I am asking you is, how did it all start (your career) and how can I shape my future to develop successfully like yours?

First off, thanks for your kind words. [Insert appropriate sentence about being humbled here.] The good news is you’re already halfway there. The most important thing is knowing what you want – once you’ve established that, you just have to spend every moment of your time figuring out how to achieve it.

Here’s how it happened for me:

I became obsessed with fashion before I even knew what fashion was. I’d never heard of Fashion Weeks, didn’t know that modelling was a job, and thought Prada and Louis Vuitton were boat companies (because their branding was all over the America’s Cup yachts).

That said, I always had a clear idea of whichever company, destination or spot was the best in its field – As a 14 year old I wanted to be a kitchen hand, so I begged Honeypot Cafe for a job washing dishes; at 16 I wanted to work in radio, so I started out reading community notices for Plains FM, a small state-funded station, to get experience so I could apply for a job in promotions at The Edge (the biggest pop music station in NZ); as a 17 year old I wanted to work in hairdressing, so I volunteered at my local mall salon to get experience so I could apply for a job at Carl Watkins and Associates (the most famous salon in the South Island); as a 19 year old I decided menswear was the field for me, so I harangued Murray Crane at Little Brother to give me a job until he gave in. I also failed high school but gained university entrance after a successful meeting with the Dean of Arts and Canterbury University.

All this taught me that getting what I wanted was simple: I just had to ask enough times until the person saying no saw that I wasn’t going to go away, and decided to give me a chance.

I kicked around for the next few years doing odd jobs here and there – styling, working for Wall Fabrics (the greatest fabric merchants in the world), writing, PR – and then I decided that I wanted to work as a model agent. So I got a job at the top agency in New Zealand, 62 Models and Talent. It wasn’t my cup of tea, so I decided to give magazines a try. I became the market editor of Urbis, New Zealand’s answer to Wallpaper, despite a distinct lack of experience, qualifications or know-how.

After I was fired, I decided to give blogging a go full time, but I knew that in order to succeed, I’d need some powerful backing. So I approached my homeland’s largest newspaper, the New Zealand Herald, and asked them to syndicate my posts as I travelled around the world going to Fashion Weeks. They agreed to pay me a weekly fee for my words so long as I paid for everything myself (flights, accommodation, expenses etc).

At the time, men.style.com and The New York Times were my meccas, so those were the companies I knew I had to eventually work for. I started emailing Tim Blanks, Josh Peskowitz and Tyler Thoreson all the time – probably six times a year for three years straight. When men.style.com shut down, Josh and Tyler worked for other publications until Gilt picked them up. I ran into Tyler around this time in New York and told him I was the guy who was always emailing and that he had to hire me. I started the emails again, and after about six months, he decided to give me a shot – I wrote my first piece for the MANual in April or May, then he hired me to interview editors, stylists and designers at the menswear shows in June of 2011. One of the guys I interviewed was Bruce Pask from The New York Times, and we got along so well that he told me to send him an email if I ever came to New York. I landed in New York in August of that year, and he very kindly gave me a job as a contributor.

Since then I’ve worked with companies including Hugo Boss, Lacoste, Gant Rugger, Barkers, Little Brother, Gucci and Ermenegildo Zegna; and done personal styling for Tyga’s record producer, TVNZ’s Jack Tame and a whole raft of lawyers, CEOs, architects and other gentleman around the world.

I guess the point I’m trying to make is that where I am now isn’t the result of being the most talented person in the room, it’s been the result of being the most enthusiastic person in the room, never being afraid to ask for what I want, and seizing an opportunity once it’s been presented to me.

I truly believe that success is 1% talent, 49% ambition, and 50% likeability. Show people you care about the work, you really want to succeed, you’re fun to be around and you’ve got a bit of a knack for the business and you’ll win. It’s as simple as that.


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  1. says

    I totally want to be more like you, Issac. Confident, motivated, and not afraid to go after what you want. Chur for the inspiration bro! And Merry Christmas and stuff :)

  2. says

    “Getting what I wanted was simple: I just had to ask enough times until
    the person saying no saw that I wasn’t going to go away, and decided to
    give me a chance.” – Cheers bro, now I’m going to email you six+ times a year till you let me shoot for you when you get back to NZ

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