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Freelancer Spotlight: Halley Gray

Halley is a rock star when it comes to making real connections and collaboration online. She’s running an awesome freelance marketing business, a internet domination Facebook group, and is a true inspiration for how real marketing should be done. 

Today she shares her freelance to freedom journey, and trust me, this is someone you should definitely get to know!

Welcome Halley!

Halley Gray

What kind of freelancing do you do and how did you get started?

I’m a marketing strategist for small businesses.

For the past 8 years I’ve known I wanted to run my own business but I never knew what it would be for. In the spirit of scientific exploration, I started businesses –

  • designing & producing vintage kimono handbags (handmade products are hard, props to artisans who do it for years)
  • Adventure Life Coaching (no feelings for me, thanks)
  •  copywriting (writing other people’s copy makes me itchy)

– and closed them.

I finally worked with a career coach (Michelle Ward, if you’re curious) and finally figured out what I really love doing – product/service creation, selling & writing. I’d been working on my friends’ businesses for about 18 months at this point – expanding their services, creating new products, helping them promote and connect with the right people – and it still hadn’t hit me. Till one day I was working on a friend’s business and they burst out, ‘YOU SHOULD DO THIS AS A JOB!’ It took another few months for that to sink in but once it did – Evolve & Succeed was born.

I launched my first service in November 2012 – The Quantum Leap Pack (full business assessment and plan forward) and it sold out within a week.

Are you freelancing full-time or on the side?

I’m full time, baby! Since July 1st 2013. I worked many an un-satisfying day job to squirrel away money to provide for my business. Plus any free minute was spent on my business or clients. I made about $4,500 in my first month of business from all that hustling & beavering away – definitely worth the hard work.

If you are now working full-time freelancing, how long did you freelance on the side before you made the jump?

Evolve & Succeed has been live since November 2012 and my day job contract was up on June 30th 2013 so I decided that was my last job working for the man, no matter what.

What is your favorite part of working for yourself?

Selling! Not because of the money (although that’s really nice) it’s because the whole process makes me happy.

One morning I came up with a new service while drinking coffee and then had it launched by lunch time! 72 hours later I had sold 9 out of 10 sessions!

It can be nerve-wracking but it also makes me feel so alive. (I may be an adrenalin junkie.)

What is the biggest challenge you’ve had to overcome in working for yourself?

Loneliness! I talk to heaps of people online but real interactions are what I need to satisfy my extroverted self (that and exercise). I tried co-working but the social aspect wasn’t there and it was hard to not feel like a dick when you’re chatting someone up who is working.

Now I go out for coffee a lot or meeting up with friends after work. It takes effort but it pays off in mental fortitude and happiness.

Walk us through your typical workday.

9:15 – crawl out of bed in my Batman PJ’s and make coffee so dark Cthulhu winces.

10:11 – Go to my desk and either start the day with a client call or checking emails.

10:34 – MORE COFFEE. Check my free FB group – Evolve’s Internet Domination Club – to see what fun/interesting stuff is happening and answer any questions (I check this group a LOT during the day).

11:02 – Work on sales copy, emails, guest post requests, setting up free workshops or anything else.

12:29 – Eat left-overs.

1:04 – Either pop out to gym or work some more or a nap.

2:54 – Then jump on the weekly call with my contractors to fling around upcoming deadlines, tasks, questions and Star Trek jokes.

3:33 – 5:59 This is when my laptop dies (semi) unexpectedly. It’s narcoleptic.

6:00 – Make dinner (I love cooking) for my boyfriend & myself.*

*Sometimes I work thru weekends. Sometimes I take a random day off and read books or webcomics.

What advice would you give to someone a few steps behind you in their freelancing entrepreneurial journey?

Make services/products specifically FOR someone. Then use their words in the sales copy to make them feel like it was made for them.

Build up connections and visibility thru Twitter, Facebook, free workshops, guest posting, FB groups or emails. The more people see you the more likely they are to talk about you (which is fab) and makes selling easier.

Thanks Halley!

I’m Halley Gray, marketing strategist and I work with online superstars like Michelle Ward, Tiffany Han, Lola Falk, and others to get them sold out, booked out and booming in business. Wanna take over the (digital) world? Join my free FB group – Evolve’s Internet Domination Club!

And you, lovely FTFP reader?

Can you relate to Halley’s story about “starting” a bunch of wrong businesses before you found the right one? I sure can! I’d love to hear some of the things you tried in the comments!

And if you have any questions for Halley, be sure to ask away!



Leah Kalamakis Leah Kalamakis is the founder of The Freelance To Freedom Project and a web designer/developer for brilliant entrepreneurs. When she’s not hanging out in the FTF Community, you can find her people watching on the streets of NYC. Come say hi on Twitter, Instagram, or Facebook.

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{ 4 comments… add one }
  • I just set a quit date of 5/31 for my gut-punching day job. So scary and thrilling at the same time! I love reading interview like this… I feel like I can REALLY do this thing. Thanks for the inspiration!

    • Leah Kalamakis Leah

      Yay Maisie! So excited for you!! Be sure to remind us on 5/31 so we can have a drink with you virtually!! Great job setting a date- that makes a huge difference it getting things rolling before then.

      • Leah Kalamakis Leah

        Oh and I just realized that was my quit date too- best day ever 🙂

  • I’m so glad that I’m not the only one who doesn’t wake at the crack of dawn to start working! It’s also inspiring to know that it’s okay to change your business direction.

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