I’m a professional photographer in New York City and have been now for a little over eleven years – having fallen into the occupation after a chance encounter with a talent agency that tried scamming me into buying headshots from them. After the encounter I decided to just start taking headshots myself as I’d just quit my job, had a lot of free time on my hands, and was beginning to get a little nervous about the fact that I was thirty and doing nothing with my life.

Over the following decade I’d slowly build a business in one of the most cutthroat and over-saturated photography markets in the world and, with some extreme highs and some extreme lows, learned quite a bit about about what’s involved in surviving on one’s own.

Whether you’re new to self-employment or are a veteran simply looking for a fresh perspective, welcome to five key points that I share with you in my decade+ of being my own boss.

Do not put all of your eggs into one basket.

When I first started my business as a headshot photographer in new york city, I had zero experience running a business and zero experience as a photographer (I know it sounds a bit ridiculous that I became a professional photographer with literally no experience in photography, but shrug). As well, I had nowhere near the amount of resilience and

self-confidence I do now. I was absolutely not a cold-email or pound-the-pavement sort of person and was plagued with a constant sense of self-doubt. And so it was fairly miraculous that when I decided to get into photography I did so during what I like to call ‘the golden age of gig sites.’

In the early 2010s to 2015s, gig sites like task-rabbit, thumbtack, and others began to dot the startup landscape and not only was it their sole purpose to act as a bridge between the vendor and the consumer, they had hundreds of millions of dollars in startup cash to do so. And so, with this said, I was at certain points early on in my career getting somewhere between 20-30 leads a day from certain gig sites.

And with 20-30 leads a day, some of which were jobs that paid in the thousands, I was making upwards of 100k a year within my first two years as a professional photographer. I went from making 40k/year in New York City to 100k a year in New York city and felt that I’d finally arrived.

I had made it. I was beaming with confidence, self-esteem, and the belief that life from there-on-in was going to be a piece of cake.

Then reality set in, as it tends to do, and the gig sites I had relied on for the first four to five years of my career began to change. Prices per lead began to gradually increase and the heaving geyser that kept them flowing all day long began to slow into a little bit more of a trickle;

– I chalk it up to the fact that they were all startups and could no longer afford to shovel great big heaps of cash into the furnace that is adwords and, as well, their VCs wanted to get paid.

In 2020, when the world abruptly and radically changed, that was the final deathknell on my lead sources as they completely and totally dried up entirely. Couple this with the fact that said gig sites I’d relied upon for so long began to quadruple and in certain cases 10x their prices in order to compensate for the loss of business that resulted from covid.

And there I was, at the beginning of 2020, having been self-employed for seven years and with absolutely no idea how to function as a self-employed person.

How exactly did I let this happen?

I put all of my eggs in one basket, is the answer.

The thing about self-employment that no one tells you is that learning how to be self-employed is a bit like learning how to hunt and gather; the wilds that you hunt and gather from the modern-day society that you live within. Being self-employed is a skill that you learn and build upon over time – it isn’t just like one day you’re self employed and rocking it or that there are certain people that are cut out for being self-employed while there are others that aren’t. Over time you learn things, assuming your self-employment comes from the conventional methods the people have relied upon for so long (SEO, PPC, cold-emails, cold telephone calls,

cold-everything) and not from one freaking site that you’ve come to rely upon almost completely and exclusively. Because if that site company goes down, or changes it’s mind about things, or pivots into a balloon factory, you’ll be left standing there alone and with about as much of a clue as you did when you first became our own boss.

Diversify your revenue stream

When I first started out in photography, I made money in very literally one way – I shot things, edited them, delivered the images, and got paid. And while I dreamed about making more money doing other things or selling other things, I was affixed with the self-limiting belief that the only way I could make money as a photographer was by, well, photographing things.

And so with this said, this is a bit of a takeoff on the previous point in not putting all of your eggs into one basket, but one thing I’ve learned over the course of my self-employment is that there are, very literally, a million different ways to make money and that this truism spans hundreds upon hundreds of other professional services outside of mine (in fact, there are probably more like ten million ways to make money in your given field).

And so, you’re asking, what can a photographer do to diversify his or her revenue streams when he or she is not just photographing and editing? I’m glad you asked.

As of now, outside of my photography itself, I sell lighting diagrams online in the form of PDFs that aspiring photographers can use for headshots and portraits (I advertise on instagram under hashtags like #photography and #learnphotography), I host monthly classes in my studio for beginning photographers and advertise them on eventbrite, and I sell prints online from people’s

event albums.

Additionally, I buy a lot of clothing for my studio to use it on models and once done, will then flip it on ebay for a profit (the nice thing about new york city is that you can get clothing here that other people can’t).

Lastly, I’ll sometime in the near future start creating video educational content that I’m certain people will buy because there are always going to be people that want what you have (self employment and a particular skill).

Just because you’re selling a service does not mean you do not have a set of products

As mentioned above, in 2020 my primary source of business and leads completely dried up and, over the next few years, I’d live off what was a combination of savings, meager business that I’d scrape up after floating way, and government relief.

Those were some incredibly lean years and in the middle of them I’m not going to lie when I say that I didn’t think I’d make it through at times. It was a very long winter and in the landscape of capitalism I didn’t at the time have any survival skills.

Then, somewhere towards the end of 2023, my mindset shifted after I’d read the biopic of steve jobs and him turning apple around. At the time, Apple had dozens upon dozens of products – none of which even seemed like they were part of the same company. Apple’s portfolio of products was boated, unlinked, and sinking the company.

When Steve jobs took over, there’s a famous story of him being in a meeting with all of his executives as they argued over a whiteboard. The whiteboard contained their entire catalogue of products and the argument was over what would stay and what would go.

Steve Jobs walked over to the whiteboard, erased everything, drew a square, subdivided that square into four separate squares, and wrote ‘Pro’ above one column and ‘Consumer’ above the other. In the remaining four squares he placed just one product per square and declared that moving forward the company would produce four products and four products only. And that return to simplicity marked the beginning of Apple’s historic turnaround.

After I read this I didn’t think much of it until walking down sixth avenue one day, fretting over how I’d turn my business around. It suddenly occurred to me one day that I, too, made my money off of a very small set of services. I made money off of headshots and event work and that was literally it. Granted, those two products have sub-categories (corporate headshots and actor headshots for example) but, outside of this, I really only made money doing those two core things.

After that bolt of lighting I ran back to my studio, nuked my website completely, and built a new one from scratch – focusing only on events and headshots. After a few short months I was on the front page of google for event work in New York City and as well began to do PPC advertising on headshots. And finally, after a very long and very uncertain three years, I had some financial breathing room.

Remember that just because you’re selling a service does not mean you do not have a traditional set of products. You have a product, and people want that product, so focus on selling it.

• Your main asset is time, and you need to allocate it wisely

I once shot a CEO summit at NBC’s The Rainbow Room and one of the CEOs in attendance said something that really resonated with me. He stated that a CEO’s primary (and oftentimes sole responsibility) is resource allocation; or deciding what resources go where. If a company has, say, ten million dollars to work with for a fiscal year, it’s the CEOs job to divy up that ten million dollars while deciding what should get a lot and what should get a little. A CEO says ‘this is important and a priority and we should invest lots of money here’ and says ‘this actually isn’t huge priority for us and so we should rein in manpower, capital, and direct it elsewhere.’

That’s it. That’s a CEO’s job. Resource allocation.

And so, with this said, as a self employed person selling a service, you too are in charge of resource allocation – with your most valuable resource being your time.

Should you put a lot of time and effort into, say, building out a nice website to attract clients? Or should you put a lot of time and effort into, say, building out an effective cold-email campaign.

You need to weigh the pros and the cons of both of those things and determine which choice is going to yield the best results – oftentimes by looking along down the road, playing the tape forward, and seeing which outcomes for you are the most profitable and which outcomes for you are not.

Your product is still king

A friend of mine, a business owner of a traditional brick and mortar store, has been working on his social media presence of late. I’ve known him in the past to regularly latch onto things, decide that they were going to make him millions of dollars, and then drop them after they didn’t work in just a week’s time, and rinse and repeat unti the next token idea came his way.

This being said, he’s been uploading content to his social media pretty regularly and for an admirable amount of time, and so I texted him and told him to keep it up. I asked him why it was he was doing what he was doing (since he’s a local brick and mortar store and on instagram it

can be difficult uploading content strictly for locals) and he replied that a friend of his, also a business owner and on tik-tok, was crushing it on the tik-tok platform.

I asked him to elaborate and he led me to a woman’s business tiktok and at the top of it were three pinned posts, all of which had over fifty million views – which is impressive.

I looked at the fourth post down from the top, however, and noticed that the views on that were a meager 148 or so – meaning that the woman had clearly bought views on her tiktok and in order to make it look like she’s more popular than she is.

Here’s the thing, however. Nobody really cares about how many views or followers you have anymore because all of that can be bought and a hundred million views of something does not necessarily translate into any revenue because fake viewers don’t buy things.

Nobody is going to say ‘wow this guy has 50,000 followers. I better buy a widget from him, even though the content itself kinda sucks and the product itself sorta looks like a dead fish.’

A really good example of this is when I started shooting for one of the biggest modeling agencies in New York City in 2022 (and if you’re one of the biggest modeling agencies in NYC, you’re by extension one of the biggest agencies in the world). I assumed that because people saw that I was shooting for this particular agency, that the work itself was irrelevant and that my career would head in an upward direction simply based on who I was working with.

And I was so dead wrong. At the time I had just stepped into fashion and my work at times was pretty rough. Nobody at all cared that I was working with said agency and I gained absolutely nothing from it. It wasn’t until after I’d kept at it and kept at it and improved my product incrementally over a period of a few years that I really started to gain traction and really started to make industry relations.

People care more about your product than they do anything else. If you have a good product, lots of followers, views, and likes will absolutely help you out, but they also will not save you if your product is terrible.

In closing

In closing, I hope that the above points have been helpful to you. They were hard-learned and hard-won and the lessons I was taught were the product of a decade of work in one of the world’s most brutally competitive marketplaces.

If you’re motivated to be your own boss or simply curious about the life of the self-employed, take the above into account and you’ll be well on your way.