I am a Photographer.


Dann—What does freelancing mean to you? I mean, what do you think when you hear that word, “freelance”?

Helena—[0:25] To be a freelancer means, to me, being free. For me it means having your own runway to do what you want, and to work as hard as you want, and to be your own boss. And to be in control of the path that you want to take, and the kind of work that you want to make, and the kind of people you want to work with. You have a little bit less choice in the beginning. You kind of take what you can get. The biggest thing for me is the freedom to do the work that I want. And maybe I'm not getting paid to make that work in the beginning, but I'm making that work so that someone else will hire me to make more or that work later.

Dann—How’d you get started as a freelance photographer?

Helena—[1:09] So my start as a freelancer happened kind of overnight, but, also, was a really slow process. I worked in Silicon Valley for many years before I became a photographer, and I didn't know at the time, but all of the work that I was doing in those years in Silicon Valley were actually fueling my freelance career that I wasn't even sure I was gonna have, yet. That is everything from building a network of people that you know and you love and you've done nice things for, and shown interest in people without asking for anything in return. Learning immeasurable amounts of skills, like learning... Just soaking in everything you can around you, whether that's how to build a business, or how to work with people, or, you know, how to communicate what you're trying to say. Like, all of these skills that you can take with you and become a freelancer.

All of those things took years to develop, and, so, you know, whether you're working a full-time job now... Which, if you want to be a freelancer eventually, you're probably working a full-time job now. That all is prep work for being a freelancer. But when I made the jump to freelance it was very fast. I kind of quit my job to be a photographer, which is crazy because I didn't have a real plan, and I didn't have the savings account, and...I wasn't totally sure what I was gonna do, but it turns out that all of those skills that I had building over the years fed what I'm doing now.

Dann—So when you knew you were going freelance, how did you start to promote yourself?

Helena—[2:45] When I started shooting as a hobby in 2013, on the side, I was shooting on nights and weekends, um, while I had a full-time job. And I immediately made a website where I put my work. I actually already had a Tumblr, which I mostly used to look at other people's work, and not share work. But Tumblr really became the place where I started posting. Whether or not that's the place now, you know, that's another story. But really just finding a place online, maybe that's Instagram, or a website, you know, just posting work as soon as you make it. I just would shoot hundreds of photos every weekend, and then immediately post them to Tumblr. And it was fun, you know? I spent every night editing. I had something photographic to do every day after work, and that was really nice.

But I think the trick is just to not overthink it too much in the beginning. Like, just make a sh*t ton of work and post it on Instagram or your blog or whatever, and then, you know, maybe after a month, you have enough work that you can kind of sift through and be like, "You know, those five photos really represent what I want to show people." And then you put those on your website. And then, maybe a month later, you've made a few hundred more photos. And you can choose, like, ten that you thought were exceptional, and then put those on your website, and that's basically what I did. And after four months, I had a full portfolio of work that I just shot on the weekends.

Dann—Incredible. Ok what about charging? How did you figure out charging on your own as a photographer?

Helena—[4:11] Charging is such a toughie, you know? That is the big question. And one thing that I learned early on is that no one charges the same thing, and no one knows what to charge. You really just have to guess and ask around and research, and then charge what you're comfortable with and what you... Not even what you feel like you're worth. Like, just figure out market rate, and, and be somewhere in that range. So, for me in the beginning as a photographer, I decided, you know, I'm gonna work in Silicon Valley. And Silicon Valley isn't used to working with photographers. So I'm just gonna figure out what a high end freelance designer or developer would charge hourly, and I'm gonna charge per hour because that's what Silicon Valley, um, understood at the time. And so that's what I did the first couple years.

I was just getting started as a photographer, and, so, I could've easily been like, "Oh, well I don't have experience. Like, maybe I'll charge $20 an hour." But it's like, no, you can't put emotions into it. You can't, like, put your own self-loathing into it. You just have to figure out what a lot of people are charging, and charge that. And just see, like... And if people hire you for that, then keep charging that. And if you get booked solid, charge more. And if no one's hiring you, charge less. You just kind of have to throw a number out there and see what sticks in the beginning.


If people hire you for that, then keep charging that. If you get booked solid, charge more. If no one is hiring you, charge less.

Dann—What are some of the qualities you think a person needs to have to become a freelancer?

Helena—[5:36] Oh, to be a freelancer, you have to want to run your own business. Being a freelancer is running your own business. Some people don't realize that. Where I'll reference my business, and they're like, "But you're a photographer." And I'm like, "Yes. I own a photo business." Like, I don't just click buttons. I run the business. And so, that's something to keep in mind, like, when you make the jump into being your own person and being your own boss there's invoicing, there's estimates, there's actual finance, there's budget keeping, there's paying taxes, there's all this stuff that you didn't have to worry about when you had a full-time job.

And, you know, that's just the money side. Then you have business development, you have to go out and get clients, you have to schmooze, you have to negotiate on the phone, you have to be comfortable pricing yourself, and negotiating. All of those things, um, you've got to become comfortable with. And it won't necessarily be comfortable in the beginning, but you have to feel a little bit energized by the idea of it.

I think another important thing, uh, to be a freelancer is risk tolerance. It is a risky thing being a freelancer. Your money is not guaranteed, you can be just milking it one year, and then the next year the industry is in the pits and you're not getting work. And it doesn't have anything to do with how good or bad you are. Like, sometimes the markets just fluctuate, and it's a rollercoaster.

So my advice is, learn how to be good with money fast. Like, stop caring about keeping up with the Joneses and spending money on, like, travels and food and fancy things. Like, save your money, um, because that's money not only for you to survive on, but it's money for you to reinvest in your own business. And, as your business grows, you're gonna have crew to pay, you're gonna have equipment to buy, you're gonna have all these miscellaneous expenses that are quite expensive, and you want to be able to afford them when you need them. So being really conscious about money is important.

Dann—Anything else? What’s a quality compared to full-time work?

Helena—[7:41] Just being comfortable with lack of stability. Full-time jobs, for a lot of people, are really safe and stable and fulfilling. And that's great. I just hated it, the stability side, the full-time job thing. I just hated everything about it. And so, for me, it just feels really natural to be, like, wandering on my own figuring this stuff out as I go. So I don't think, you know, it's a... it's a bad thing if you're not into that. But to be successful as a freelancer you have to be so comfortable with the unknown.

Dann—Is it possible to make a lot of money as a freelance photorapher?

Helena—[8:15] I think it's very possible to make a lot of money freelancing. I definitely make more as a freelancer than when I worked in Silicon Valley, and, you know, I have many people be like, "Oh, photography sucks. There's no money in that." And I'm like, "How do you think I pay my rent?" Like, what? So, you know, I am really fortunate in that I've figured out how to make more money, much more money, as a photographer than as a full-time tech employee. And I think it's very possible. It just depends on how hard you're willing to work.

So, you know, maybe as a freelancer you just want a couple of clients, and maybe those clients are $5,000 a month retainer. But, even then, you've just made $10,000 a month doing two clients and probably doing the same amount of work that made in a full-time job. So, like, even on that most basic level, um, you can make more doing the same, or maybe even less, work on the client side, but you can't forget that you have all of the work in building and running your business. So you can make more. You can make a lot more. It's almost the sky's the limit. It's just a matter of how hard and how much are you willing to work. And if you like working, then that works out.

Dann—What’s the best thing that’s ever happened to you as a freelancer?

Helena—[9:32] I think the best thing, uh, for me ... To happen to me as a freelancer is just getting paid. You know? Like, I, I'm still blown away that I can make a living taking pictures. That's crazy. Um. And, at the end of the day, as a freelancer, you have to survive, like, doing this for a living. So, you know, I think that money is incredibly important. If I didn't have it, I wouldn't be able to do this. So just the fact that people are still willing to pay for creative services—it is always amazing to me.

Dann—OK, now what’s the worst thing that’s ever happened to you as a freelancer?

Helena—[10:15] I would say, you know, the worst thing as a freelancer is, uh, the moments where you have no money. That is ... It's horrible. And, uh, I wish that, you know, it would never happen, but it totally happens. I was really broke when I first started. You know, I ... I literally recall ... The month after I quit my job, uh, and I was in LA, I had just gone to a conference, and I, I needed to drive ... Rent a car and drive to my friend's birthday party in Palm Springs. And I over drafted my bank account. And I had literally negative $40, and I wasn't with friends, so I, like, couldn't afford to buy lunch, and I was hungry, and I was like, "Man. Like ... Here I am. Like, here's freelancing. What am I gonna do?"

Just make a sh*t ton of work and post it.

And, so, I called my best friend, and was crying, and, uh, she wired me 200 bucks so that I could rent a car and drive to Palm Springs. Um. And then she took me home to San Francisco, but ... It was just moments like that that could really, you know, make or break you. And-and they'll probably happen. And they've happened to me since, you know? And you just ... You just have to be really good at surviving. Um. You have to be okay with maybe calling your best friend crying and getting $200 wired to you, and making that $200 last a long time. Um. You just have to be ... You have to be ready for that, and you have to be able to get through it. And then you'll survive.

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