Building a Freelance Business with Diana Davis


Building a Freelance Business with Diana Davis

In a recent search of the top employers represented from Financial Gym clients, I discovered that the number one employer is “Self Employed.” We work with a lot of freelancing, entrepreneurial clients and it’s one of the many things I love about the Gym. Freelancer finances are difficult to understand and plan for and we love helping our clients build businesses in a financially healthy way. I also love all of the ways people can build a business, so today I’m talking to Diana Davis, a Health and Wellness photographer in New York City, about how and why she started her business and how she’s built a successful practice doing the two things she loves most, design and photography.

What Are We Drinking?

Diana — Boda Box Red Wine

Shannon — Box Chardonnay 

Podcast Notes

  • Diana has been a Financial Gym client for a long time. Shannon and the trainers have had a front row seat watching Diana grow her business. 
  • Diana does photography and graphic design and went to school for them. Side hustlers tend to turn their passion and hobbies into full-time jobs. Diana has always known what she wanted to do and she has always been happy doing that craft, no matter what setting it was in, whether corporate or on her own.
  • When Diana first moved to New York City, she would get asked “what is your dream situation”. It was difficult to answer. She thought she would work for herself eventually, but more like 10 or 15 years down the road. 
  • Diana was doing corporate graphic design as her day job, and on the side she was doing photography, when she lived in Montana.
  • Diana decided to move to NYC without a job. She grew up on a ranch. She had been coming to NYC for food shows, as part of her job working for a local food company that did infused oils and vinegar. She was their in-house designer and photographer, she taught cooking classes, she wrapped pallets, she did sales, etc. They had her going to trade shows because she was so ingrained in the company’s culture.
  • Diana fell in love with New York and she knew she needed to be there. She didn’t see herself failing, because she was wiling to do whatever it took to make it. It is very hard to get into the NYC job market when you are from a different city, especially since her resume said Bosman, Montana.
  • She had a few opportunities where companies wanted her to come in for interviews the next day, but she was still in Montana. She decided she needed to move their to find a job.
  • Diana found a roommate on a website who was renting a room in an apartment on the upper east side, on 75th and 1st, and she didn’t know what the apartment looked like until she got there.
  • Diana had a nest egg of about $4,000. She moved to New York in September and gave herself a deadline of November 1, to find a job. She did have some freelance work that carried over from her former job, but she started networking immediately.
  • Diana found a job at Time Inc. in their branded content and publishing department. A couple of years later she was poached by Hearst. After that, she went into her entrepreneurial life. She was hired by Hearst as a senior designer, and about four months later, they eliminated her position. It was the biggest relief of her life. 
  • Diana signed up at the Financial Gym shortly after she was let go from Hearst. She had a photo shoot with Caitlyn, and she invited Diana to a Wine and Learn at the Gym. Diana committed to the Gym, because she didn’t want to fail being an entrepreneur because of finances.
  • Time Inc. offered Diana a permalance position, which means freelance as a permanent employee, but you don’t get health insurance. It is like working as a regular employee without benefits, and they can let you go tomorrow. This is common in the publishing world in NYC.
  • Time Inc. offered Diana three days a week at $20 an hour and she was so disappointed. She asked them for $30 an hour and they accepted. The next week, it ended up being five days a week. She was paid that amount for a little over two years. She quickly rose to a senior position, but she was never given a raise. She had been asking for a raise for about nine months. 
  • At Hearst, she was paid $60 an hour, without negotiating. She wasn’t paid for any holidays or vacation time. 
  • Diana had a side job doing social media design, while she was at Hearst, and she is still working with them. She was also doing some fitness photography on the side and that ended up feeding her full time.
  • Now as an entrepreneur, graphic design and photography fluctuate from month to month. In the last six months, photography has really taken over. Photography is her passion and it comes the easiest to her. 
  • Diana credits her business success to surrounding herself with successful women and networking. Emily Merrell, from Six Degrees Society, sat Diana down and asked her how she pictured her day-to-day life. Diana pictured herself working with tons of different people and different companies. It helped her decide to be a contractor. She really wanted to cast a wide net.
  • She put herself in networking groups, in front of other people, and attended events to meet people. When you do a good job, people talk. Almost all of her inquiries for the first seven months were word of mouth. Now it is mostly through Instagram.
  • Diana recommends Six Degree Society. She was invited to one of their events and had no idea what it was. She was laid off the same day as their event, so she decided to go in order to network.
  • They do matched networking. Everyone has a bio and that information is sent out before the event. There is always two matched networking situations, where you talk to someone you were matched with for 15 minutes. The matches didn’t necessarily turn into her clients, but she was on the top of their minds if someone else needed something.
  • You need to make sure you are in a room of like-minded people who are there for the same reason, to connect and help each other out. Six Degrees Society and the Financial Gym do well with these events.
  • It was important for Diana to collaborate with others. Those people have referred her to a lot of other people. 
  • Shannon’s pro tip is networking. The way to successfully network is to build a garden. You need to plant the seeds and then tend to the seeds by checking in. At some point that seed is going to bear fruit when you need to be fed. Always play nice in the sandbox with others professionally. Leave your job on good terms, stay in contact with people, etc.
  • Shannon had a boss about 13 years ago at Bank of America, and she kept in contact with him after she left. Ten years later, he was the first investor in the Financial Gym.
  • When you start a business, you can’t be afraid of the freebies. Don’t be afraid to be free once in a while. That person will likely lead you to the next thing. It is part of the building process.
  • Last month, forty percent of the Financial Gym’s business came from referrals. That is a pretty consistent theme. If you treat your clients well, they are your ultimate salesforce. It is the best way to do business and to grow your business.
  • Don’t just hand your business card to 20 people and then leave. Try to make connections.
  • Diana has been on her own for about a year and a half now. Her total revenue was around $91,000 last year. Her goal is to get above $120,000 this year. As a freelancer, you are not bound to restrictions of hourly pay or getting a raise. You can make as much money as you want to make and choose who you want to work with.
  • If someone wants to take their passion or side job and turn it into a full-time job, they need to be able to hustle. If you are afraid of hard work, forget it. It is not a cushy situation and you need to pay for your own health insurance. It isn’t for everybody. You need to be all things in your business. It is exciting, but also daunting, especially when it is your only income. You need to wear a lot of hats.
  • It is always going to take time to ramp up. It took Diana at least six months for the momentum to really build.
  • The Financial Gym has helped Diana feel more prepared to handle her finances. When you take as many anxieties out of your life as possible, things are easier. On her lower payment months, she gets anxious and goes through what if scenarios. She just has to prepare the best she can and trust that everything is going to fall into place.
  • “Sometimes the best thing you can do is to not think, not wonder, not imagine, and not obsess. Just breathe and believe that everything will work out for the best.” – Hoda Kotb
  • The further you get into building your business, you realize this is suppose to be. Even with the ups and downs, you are certain this is what you should be doing. It took Shannon two years before she knew she was really on the right path.
  • Diana likes to look back at pictures from a year or two ago and see how far she has come. She is grateful for what is to come.
  • Shannon listens to Oprah’s SuperSoul Conversations and uses gratitude journaling to gets her through rough times with her company.
  • Diana’s word for 2019 is expansion. She does a lot of fitness photography and she really wants to travel to different places. She went to Montana last summer and photographed a yogi. She wants to travel outside of New York, because it is becoming her comfort zone. She wants to be able to announce that she is going to be in a certain city and be able to book photo shoots while she is there. 
  • No matter what you are thinking, picture your life. What does it look like when you get out of bed? Are you going to a desk job or working at your kitchen table? What feeds you in your mind’s eye? Let that lead you and go towards that. What do you want your day to look like? How do you shift your path? That looks different for everyone.

Takeaway: My biggest takeaway, and I think the number one factor in the success of any freelancer or entrepreneur, is hustling. If you’re afraid of hard work or the hustle, then this type of dream/career is not for you. 

Random Three Questions

  1. What is a show that you like to binge watch?
  2. What is a place you would like to travel to?
  3. What is a food you hated as a child and do you hate it as an adult?

Connect with Diana


Instagram: @dianadaviscreative

If you’d like someone to help you figure out if you can work for yourself or manage the business you’ve already started, I hope you’ll reach out to my team at the Financial Gym. We work with hundreds of people building businesses of all shapes and sizes and we’d love to help you.

As many of you know, we increased our rates in 2019 for new clients, but I have instituted a 15% discount for Martinis and Your Money listeners going forward so the new rates will not impact you.

If you’re ready to manifest your dreams and grow your business in 2019 like Diana, head over to to get signed up today.

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