The Real-life Carrie Bradshaw: Lessons in Love, Dating, Travel and Going Freelance

by / ⠀Personal Branding Startup Advice / October 18, 2012

Four years ago, never would I have believed that I would be freelance writing, offering love and dating advice for anyone trying online dating. And never did I dream that I would be travelling the world, visiting beautiful countries and cultures, and be getting paid for it.

But here I am –  a real life Carrie Bradshaw, writing about love, romance and travel, and exploring the globe in search of inspiration.

The path to freelance writing success

As briefly as possible, my path to freelance writing success (and by success I mean living well off the back of my work) went something like this…

  • A volunteer internship in Journalism and Communication with a non-profit organization based in Buenos Aires.
  • Six months of voluntary writing for a wide range of websites and printed publications.
  • Six months of writing for an attorney to pay the bills (while writing, around the clock, for publications and sites I believe in)… crucifying for the soul!
  • Gradually securing a few paid jobs for sites and publications that I wanted to write for.
  • Took a financial risk –  quit writing for the attorney and worked around the clock to get paid writing jobs on topics that interested me.
  • Only three days in I’d secured paid freelance commissions and was making comparable money.
  • One and a half years later, things just keep getting better. My commissions change frequently and my pay check improves, month on month.

Speaking purely from personal experience, freelance writing success (and entrepreneurial success in general) cannot be achieved without taking a financial risk at some point. Putting in long hours is also essential for the first couple of years.

Complicated relationships and a ticking biological clock

Having written regularly for the past two years about travel, culture, city life and volunteering projects abroad, I’ve recently been focusing on online dating sites, blogs about love and romance, and female interest magazines. Must be something to do with being 32 and single!

I’m thoroughly enjoying this chance to write about love, romance and the trials of dating, outside of my native culture. And I have, over the past few months, begun to carve out a real niche for myself.  I’ve become a real-life, nomadic, Carrie Bradshaw. And you may even read my work if you successfully met your match on eHarmony or you are considering taking the plunge into online dating.

Travelling the world as a freelance writer might seem glamorous (and it certainly can be) but would-be female entrepreneurs looking to make it in the world of freelance travel writing must understand that this job is not particularly compatible with long-term relationships or children. My career comes first. Unfortunately, writing about love and romance on a daily basis constantly reminds me of what I’m missing.

Learning from the mistakes of others

I may not have created an innovative product or service, but I believe what I do makes me an entrepreneur in many respects. I have imaginatively and diligently constructed an entirely new career for myself from scratch. I am the brand that I sell to others (normally editors and website or blog owners). And I have crafted a working life for myself that makes me smile every day.

I love the challenges of my work. They give me the opportunity to be creative and learn about things that interest me. My freelance writing career, for me, is a business that I have built by myself – and that fills me with pride. My journey has been one of an entrepreneur and I consider myself successful.

However, looking back, there are a number of things I would do differently, given the chance:

  • Ditch the paid writing work I didn’t enjoy sooner. Energy is better spent pursuing those jobs you really want to do.
  • Spend more time investing in my blog and promoting myself. It’s essential to generate a buzz about your writing skills.
  • Intern for three or four different organisations, rather than just one, in order to gain broader experience and generate a longer contact list.

Author bio: Tracey writes her way around the globe focusing on travel, culture and matters of the heart. She recently downloaded another Calle 13 album, plans to go on her own Eat, Pray, Love adventure to India at some point and notably misses living without daily coverage from the BBC.

About The Author


Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.

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