Do Your Dream | Anna Hollingsworth

December 17, 2012

When I was 20, my friend Danny introduced me to a tiny girl in our university cafeteria.  Danny had to run to class, but the girl and I ended up sitting for hours at one of the long tables, talking about boys and our parents and our dreams, until the cafeteria staff started vacuuming the floors around us and giving us strange looks.

A few days later, the girl and I were driving around town, looking for an apartment to share.

Our junior year, we lived in a beautiful apartment in a sketchy neighborhood, where we nursed each others’ heartbreaks and learned from each other about selflessness and sharing and friendship.  She introduced me to some music and art and people that are still my favourites today, 10 years later.

Her name was Anna Naphtali Newman.  There is more to our friendship story, but that is for another day.

Today is for this: for me to present to you my friend Anna – one of my favourite photographers and entrepreneurs.


Name: Anna Naphtali Hollingsworth

Age: a young 31

Location: Charlotte, North Carolina

Business name: Anna Naphtali Photography & Creative Living: Editorial, Wedding Photography & Styling


The Colorful Living Project: Creative Project blog.


How did your dream begin?  I’ve been living & dreaming of a creative life really since childhood. My first creative venture was crafting these little bows out of paper and selling them by the street for 10 cents. I sold one- but it was my first sale as a 7 year old.

For years I’ve been scheming, daydreaming and trying a little of everything. That’s how The Colorful Living Project began. When most people go out and have relationships, I’ve usually been the one at home, building something, painting, experimenting with different mediums. (Remember you’d come home to a mess quite often when we lived together ;)). I still do the same things, I am just a little more refined in my approach, and focused about my goals & projects.

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What was the thing that finally gave you the courage to start?  I used to cater events for some of the elite in my city. I’d be serving crabcakes in mansions with sculptures and waterfalls and I’d daydream – wherever I was – about what I was going to do with myself, and I’d let my jobs inspire me even though I was the one washing dishes in the back oftentimes. Frequently, these amazing clients would ask for my personal business card – to hire me for their own personal parties. So I went home and created The Colorful Living Project to show these clients I could do anything and everything creative. (Of course it was a completely different site then, so you won’t find any of those posts on my current site.)

For photography- I’ve been carrying my camera around with every creative venture. I used to shadow other professionals on shoots for fun – just because I loved shooting and creating and understanding camera process.  I never thought it would ever be a business like it is now – I just wanted to create beautiful images with my camera for fun. So it’s like I’d work during the week, and shoot in my spare time. The courage came when my first wedding client asked if I’d shoot her wedding for $500.00 because she loved my work so much. This was the beginning of several more requests…

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What has been the biggest surprise about owning your own business?  The biggest surprise to me is that I actually own my own business! 😉 Sometimes when I’m booking clients, going to meetings, doing my taxes and cashing those checks, I get filled with giddy joy and thankfulness and think, “I cannot believe I’m getting paid to do what I love and feel creatively fulfilled.”

Building a business is such a slow progression, at least it was for me. It’s years of work and building- so sometimes I just can’t believe I’m finally here and struggle with the mentality that this won’t last long.

Have you made any embarrassing mistakes?  Dear Lord, of course. Many of them are wardrobe malfunctions. My shoe broke once during a wedding, like the sole came almost completely off, but just enough stuck on there to where I had to walk like a limping duck… and go in the bathroom and saw off the bottom before the reception…

What advice would you give to someone trying to get the courage up to start their own business? This is a complex question. It totally depends on what the business is, where the person is in their skill, investment etc… I have a lot of friends who start up “businesses” without thinking them through and sacrificing a lot of money and time and in the end going in debt because they didn’t have a plan. If you are going to spend money, quit your job or put your family at risk financially: HAVE A PLAN.

Have goals, and keep yourself accountable to them. Otherwise, you can build as you go. You can begin offering your services on the side as you go, you can take your time building and without sacrificing everything on the line. I was doing my dream since I was a child, creating, shooting etc… I just wasn’t getting paid for it until the past several years. I look at it like moving from a freelancer to a business owner. I still freelance other things here and there, but now my business is more the focus. When I started out, freelancing was the way to make money and the business was a slow build.

What has been the single best investment you’ve made in your business? Honestly, at this point- my 50 1.2 lens and attending workshops. They’re expensive, but the value is better than going to school for 4 years and having a degree I don’t use. (PS – I’m hosting workshops starting Spring 2013 if you’re interested!)

Is there anything you miss about life before being a business owner? Not really. Sometimes I miss getting dressed up and working for a big company and feeling important and making a steady salary. But now I can work in my pajamas or travel to the beach and work…a way better trade.

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What inspires you? Often when I need inspiration, it’s because I need something to refresh me, creatively, spiritually etc…

There are places on the web I go for quick inspiration, to get ideas, renewed color palettes, or to study the composition of other artists I admire. But often inspiration comes from sitting in the quiet, when it’s available, writing my thoughts, listening to music, going for a walk, exploring somewhere new. Sometimes getting out of my office and being around other people does it for me.

What has been your proudest creative moment? I have had a great year, my photographs made it into The New York Times, although they weren’t that great because it was a picture taken from a debate between Harvard & Columbia – not that riveting. But I was pretty excited when I was interviewed on The Fashion Spot with Nigel Barker for photography & modeling advice. All those years watching top model – I never dreamed I’d ever be included in an article giving advice alongside of him.

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Any artists/women/entrepreneurs/anyone you really look up to? My grandmother runs a bed & breakfast/retreat center and has for as long as I can remember. She runs the books, the scheduling, the ordering, cooks the food and takes care of really everything. She was the person who introduced me to Martha Stewart, and in a time when women didn’t go to school as often – she went to culinary school. When people eat the food she prepares, they often end up crying, never wanting to leave or becoming life-long friends of my grandparents. They are everything I want to be.

How many hours a week do you work (be honest!)? Totally depends on the season. I used to work 40 hours, deep into the night. But truthfully, I’ve really worked on developing my aesthetic and can move much more quickly and shoot what I’m looking for in camera without having to do much edit work… But then there’s the whole blogging, submitting, advertising world that takes forever… I’m thinking of hiring an assistant to handle that at some point. So maybe 20 hours? Work & random facebook stalking sometimes mesh and I don’t know how long I’ve been doing either ;).

You’ve got $100 extra to spend on something for your business – what’s it going to be? I need a lot more than $100 for my upcoming updates. But if it’s just laying around, I’d probably purchase some office & packaging supplies- that’s my weakness and favorite part of being a business owner ;).

What one thing makes your life so much easier? Having good equipment – and knowing how to use it.

What calms you? Breathing, worship music, forgiving

Accountant or DIY Finances? DIY EVERYTHING!!!!

When you’re working, do you like noise or silence? Music almost always.

9 responses to “Do Your Dream | Anna Hollingsworth”

  1. larkandbloom says:

    I love this. And really needed a bit of inspiration today. Thanks!

    • Faith says:

      I did too. Looking at Anna’s photos always gives me a lot to think and dream about! I’m so happy to have watched her develop into the talented woman she is today.

  2. nate says:

    one day, i will have one. my own.. 😀

  3. Love it! Thanks for sharing! I love hearing the story of entrepreneurs and one day I’ll join the ranks! 🙂

  4. Callie says:

    Love love love 🙂

  5. Becca says:

    So inspired. Struggling to get started up as a self-employed wedding photographer, good to be reminded that’s it’s possible!

  6. Marlise says:

    I am truly upset that as an artist and mother of this talented girl, that I didn’t get the mention for inspiration…just kidding, I’m honored by her success and thank you Faith for this creative encouragement to us all!

  7. […] Do Your Dream | Anna Hollingsworth ( […]

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