Meet Leena Tailor

Alright – so today we’ve got the honor of introducing you to Leena Tailor. We think you’ll enjoy our conversation, we’ve shared it below.

Leena, looking forward to learning from your journey. You’ve got an amazing story and before we dive into that, let’s start with an important building block. Where do you get your work ethic from?
I cut my teeth working for a weekly magazine for seven years in New Zealand before moving to Los Angeles. The speedy turnaround and nature of getting a new issue out every week meant I was constantly working late nights, weekends and holidays, and frequently assigned multiple lead features for one issue. Being one of the younger members of the editorial team also meant I was often assigned more after-hours work since I didn’t have children or family commitments. Looking back, I probably should have made greater efforts to protect my downtime, but at the same time, that job instilled the strong work ethic I would need – and still need – in order to survive as a freelancer. I don’t think I would have succeeded being my own boss for so long without that work ethic!

Great, so let’s take a few minutes and cover your story. What should folks know about you and what you do?
I’m a freelance journalist from Auckland, New Zealand. I grew up obsessed with music, television and showbiz, but a career in the entertainment industry seemed like a far-fetched dream, especially in a tiny country at the bottom of the world. After studying journalism, I landed an entry-level job at a weekly magazine and was lucky to have amazing editors who recognized my writing talents and pushed reluctant me into feature writing. After moving to Los Angeles, I naively thought I wouldn’t have too much trouble finding a fulltime job at one of the many entertainment publications and websites based here, but failed to do so. In fact, while trying to make ends meet, I applied for all kinds of other gigs, and even got turned down by CVS! After working for a couple of photo agencies, helping with writing and photo sales, I began freelancing while jobhunting – and have been doing it since.
I primarily cover entertainment, celebrities, travel, lifestyle and health and some of the outlets that my work has appeared in include Rolling Stone, Vogue, Billboard, Variety, Huffington Post, Entertainment Tonight and Glamour.
Freelancing comes with so many challenges, including constant financial instability, and there have been many days where I question why I’m still slogging away at it. The answer? It’s still my dream job. I get to interview people I admire, travel to incredible places and do so many things I love, while calling it work. The highs make up for the lows!

If you had to pick three qualities that are most important to develop, which three would you say matter most?
Resilience, optimism and a strong work ethic. My advice for anyone thinking about going freelance is to accept going into it that there will always be ebbs and flows with work. Unless you’re extremely lucky, there will always be periods, sometimes lengthy ones, where you have no work and likely consider quitting freelance, but if you’re serious about making a long-term career out of it, you have to believe those periods won’t last and continue doing everything you can to chase new work, pitch new ideas, make new contacts etc.

How can folks who want to work with you connect?
I’d love to connect with editors open to working with new freelancers, publicists with clients in the entertainment, travel and lifestyle fields and any other companies who require writing services. Aside from feature writing, I have also enjoyed dabbling in branded marketing assignments and public relations/marketing work such as writing artist bios and one-pagers.

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