Michael Oliver graduated from Saint Petersburg College with a major in Photographic Technology and works as a freelance portrait photographer. Oliver was born in Florida, but also grew up living in Trinidad and Tobago. In this interview, he offers some fascinating detail that other aspiring freelancers can learn from about paying dues in a less glamorous role.

Michael Oliver - Freelance Portrait Photographer - headshot

What freelance photography so you specialize in?

I’m honestly still trying to put a finger on that part. I shoot weddings when they come my way. For now it’s safe to say that I call myself a freelance portrait photographer. For now at least!

I love creating conceptual portraits. Ideas don’t come as often as portrait ideas, but I’m working on getting more inspired to create what I love the most! For now, my clients are just people who hire me — no big dream clients, but I’m working on that!

What are your clients usually looking for?

I’ve trying to get more into the clean/hip fashion portrait style, if that makes any sense. I guess what you would see in H&M ads or similar fashion style.

What are some methods you use to grow and to acquire more business?

I’m currently using sites such as Thumbtack, and Craigslist (surprise,I know). I’ve actually gotten quite a few hires off of both. Apart from those sites, word of mouth and recommendations from family and friends also happen.

Photo by Michael Oliver

When did working as a freelance portrait photographer become a viable business rather than just a side hustle?

I would say my first turning point was when I first started assisting. A photo assistant is basically the helping hand on a photoshoot. An assistant helps set up studio lights, helps setup a backdrop and makes a run to Starbucks if needed.

The kind of work involved really varies from shoot to shoot. On some bigger shoots I may have to try to pre-light everything by setting the key light to a certain F-stop and basically try to make sure things run as smoothly as possible, just so the photographer doesn’t have to really deal with that extra load.

 With two or three clicks, your photo now looks just like millions of other photos out there in terms of the preset. The photo world doesn’t need another lazy photographer.

What were doing before this turning point?

I was working at a local health food store at the time. I stocked shelves, received deliveries, helped customers find items. I would even be a cashier if needed.

What was your first gig as a photo assistant? How did this transition into more consistent assisting work?

A buddy of mine who was in the same photo program in college asked if I wanted to assist with him on a week long job he was also assisting on. The crew he was working with needed an extra pair of hands.

I agreed, but long story short, things started to tumbleweed from there. It came to a point where I was turning down assisting gigs that would make me the same amount of money in one day that I’d make in a week at the grocery store.

So with some thinking I finally quit the grocery. Although there was a point in time where I picked up a job because summers are usually slow for assisting, but that job only lasted about two months and it wasn’t long before I was back in the assisting game.

It’s great because when I’m not assisting I’m able to stay occupied shooting my own jobs, such as weddings, portraits, etc. There’s so much freedom, I can’t see myself going back to a normal day job.

Photo by Michael Oliver

What observations do you have about how the gig economy is trending? Is this a good way to build a career?

I definitely think freelancing is a wonderful thing. It takes much more work to be your own business with the promoting and branding and such, but it’s so much more rewarding in the end. The freedom you have is unreal. So if you have the confidence, and zeal to become your own boss, I think it’s a wonderful career!

You just have to learn to learn to pick yourself up when you fail and try even harder.

How have you overcome those difficult days?

There are days, even months, where I can’t seem to be inspired to create. I’m sure every artist has gotten the infamous “writers block.” You really have to sort of encourage yourself and pick yourself up from the black hole you’ve become used to living in and just start creating.

When I first started assisting in college, there was a point where I had to take basically two weeks off in a row, and to my surprise, my photo professors were all about it!

You soon see a little light in the distance, and it becomes brighter as your creative process comes back to you. It’s like a breath of fresh air!

What are you planning to try in the next year to grow your business?

I think a route I plan on taking is participating in wedding expos. I think I would also like to be more vocal about being a freelance photographer! Sometimes I forget to be forthcoming and miss out on great opportunities.

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What would you advise your younger self about growing a business as a freelance portrait photographer?

I would recommend finding local creatives in the field you want to pursue and to learn as much as you can. I found that in being an assistant on photo shoots, I would learn so much. Maybe not so much on the business side of things, but as far as lighting, learning about gear, etc. it’s a gold mine.

I remember when I first started assisting in college, there was a point where I had to take basically two weeks off in a row, and to my surprise, my photo professors were all about it! They would tell me, “You learn much more out there than in here.”

Photo by Michael Oliver

So I guess my advice would be not to learn everything on your own. There are great photographers in your area who would be more than willing to teach someone in a position that they themselves were once in.

Related reading: Why You Need to Find a Mastermind Group (And How to Do It)

Also, I’ve found it pretty rewarding to post your work on Facebook and share it with your friends. I’ve shot several weddings just from friends on Facebook — one of their family members was looking for a wedding photographer and they recommended me. You just never know these days!

What are some mistakes you made early on?

A mistake I made early on was slowly finding my way into trends in the photo world. Example: applying premade presets in lightroom or photoshop. If that’s your thing then that’s your thing, but to me that doesn’t set you apart.

With two or three clicks, your photo now looks just like millions of other photos out there in terms of the preset. The photo world doesn’t need another lazy photographer. The world needs more photographers who are willing to make their art into something unique and different.

Related reading: Advice for My Younger Self: Independent Contractors Share What They Wish They Knew Starting Out




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