How to Live an Epic Freelance Life (in the time of Covid-19)

My name is Phil. I am a photographer in New York City and I earn over $100k a year taking pictures. I also travel about 100–200 days a year (last year 200, this year, haha), love my life, and am constantly thinking about how to do things better. I imagine you do too, and that’s why you’re here.

I am currently writing a book called How to Live an Epic Freelance Life. I have 20 chapters in mind. I’ve revised my book proposal five times now. It’s been a process. That is not a complaint, it’s a real life description. I’m in this for the long haul. I want to get published traditionally — find an agent, pitch it and get rejected at least as many times as Tim Ferriss did for The Four-Hour Workweek (Tim was rejected 25 times before signing a book deal. The book went on to sell over 2 million copies worldwide and spent more than four years on the New York Times Bestseller List. Sucks to be those 25 agents).

I learned recently that one way to get a book agent’s attention is by publishing an essay or sample chapter on something like Medium (or Reddit, or LinkedIn, etc). If it goes a little viral or the right person sees the article, you have earned a foot in the door of the publishing industry. I was about to publish the first complete chapter of my book here on Medium, titled Owning the Freelance Life — I mean my hand was literally on the publish button, but it felt…off. The topic and content are sound. I stand behind the writing. It could be a hit! But some of the sentences just didn’t work for the world that I am looking at outside my front door. Sentences like “If you just worked hard for 1–2 hours straight, give yourself a break. Walk outside. Go get ice-cream. That is freedom.” If you can find an open ice-cream shop in New York City, please let me know. Some of my action tasks at the end of the chapter are simply impossible: “Go to the movies or do something that you normally save for special occasions, and do it in the middle of a work day. Allow yourself to enjoy the activity and tell yourself (out loud!) ‘You deserve this.’”

This is the era of Covid-19.

I still think there are ways to own your freelance life, despite the complete immobilization of nearly all creative industries. I’m going to share in this piece exactly what I’ve been up to for the past five weeks to help my (photo) business and how I managed to put over $15,000 into my bank account during this time.

Let’s break this up into three parts for organizational sake:

Networking

Booking

Living

NETWORKING

In the past five weeks, from the time most people went into drastic self-isolation (March 22nd onward), I’ve “attended” about 98 networking events. Networking can be loosely defined, so I will break down those numbers for you:

I attended 61 group zoom meetings where people interacted with each other, either the entire time or during breakout sessions.

I attended 29 webinars within my industry (weddings and events, commercial photography) where there was no interaction with anyone, except maybe in the chat. These were presentation-style events, with learning as the focus.

I attended 8 instagram lives, participating in the chat function with the host and with other viewers.

Oh, and I made 143 phone calls (actual conversations with people).

I was also interviewed for three different podcasts and I did two virtual shoots! Also, a few lovely walks in my neighborhood during quiet hours and when the weather was nice.

This is why my calendar looks like this during this crisis:

and not this:

Ok, I get it. You’re exhausted. I’m exhausted just researching all of that. It took me an hour just to count up all the things that I’ve done. I’m not here to tell you that you should be doing this or that you need to be doing this. I hate those words. I’m just telling you what’s possible.

A lot of days I am sleeping in until 10am or later. I still play a ton of games on my computer, on my phone. Watch hours of TikTok. It’s not all work. This is a glimpse into the mind of a slightly obsessive ADD extroverted personality.

I have also skipped out on countless other webinars I had in my calendar but just felt too tired or lazy or hungry to attend. I started quite a few webinars and left after a couple of minutes because I wasn’t in the mood. I didn’t count those in my total.

I’m also telling you all of this because whatever industry you work in, it’s a guarantee there are multiple online events happening every week. I joined a random real estate agent’s group, just because I liked the guy in charge (hi Brandon Green!). I don’t think this is a time to disappear. We all have the opportunity (maybe even more than ever before) to put ourselves in the same “rooms” as people who are killing the game in your industry.

If you looked closely at my calendar you may have noticed a few things repeating each week: Caveday, Corona Creative Camp, Engage Besties. These things give me life and some of them give me business!

Caveday is a company founded by a few of my friends and it is basically a co-working container created to facilitate Deep Work. Deep Work is working on one task, something big/important, without distractions, for extended periods of time. It is in Caveday that I have completely revamped my website, written entire chapters or drafts of my book project, and where I am writing this to you right now. It cost me $35 per month to have unlimited sessions (every weekday twice a day and some Sundays), and right now I am on one from 1:30–5pm EST with exactly 73 other people from places like San Francisco, Colombia (the country), San Diego, Chicago, Florida, Los Angeles, and all over NY. My phone is off and in the other room. I’ve turned off notifications on my computer. No emails. No texts. Definitely no social media. Time to get into flow state.

Corona Creative Camp is a tiny community created by an art producer here in New York City. We meet every Monday, Wednesday, and Friday morning and the group includes mainly photographers, but also stylists, podcast producers, and people in the commercial photo world. It’s the first time I’ve been able to network in the commercial photo world and it feels really great to have a support group and these connections. Under normal circumstances you would have to pay to gain face time and advice with some of these individuals.

Engage Besties is a small group of industry best friends here in New York that I made while attending the Engage Summits conference (for luxury weddings and events). We started a group text about a year ago and never stopped. We recently started a weekly one hour check in on Wednesdays and it is so nice to connect without an agenda.

One more thing that I attended multiple times in the past few weeks is Six Degrees Society. This is a community geared towards women in all sorts of entrepreneurial fields, but men are also welcome. It looks like speed dating, but for networking. You are hand-matched by the founder herself with one or two others in the group who signed up, based on the bios you’ve both submitted. You get 15 minutes of one-on-one time with the other person (which is possible in Zoom breakout rooms), and then you return to hear a presentation from a professional. I attended two mastermind sessions, one podcast making session, and one Feng Shui session. Over the years I’ve generated literally tens of thousands of dollars in business from people I’ve met at Six Degrees Society. Some of them run PR firms that hire photographers. Some need portraits for their own businesses.

At the beginning of this period of social isolation I was seeing a lot of zoom webinars and meetings happening without me (via screenshots on instagram stories, etc), and I had major FOMO around not being a part of these events. My solution was to get on Facebook a little bit more than usual, go to the Facebook Groups where announcements for these groups were happening, and turn on my notifications for those specific groups I wanted to be in touch with. Then I would reach out to the people hosting some of the Zoom hangouts that I missed and asked them if they had room for more people, and let them know I would love to join. That got me into repeating Zoom groups and my FOMO started to disappear.

I also forced myself to check my email more from the various newsletters that I was subscribed to and put on the calendar nearly everything that was coming through my inbox. This was at the beginning. I quickly learned what was helpful, what was not, and which communities I wanted to remain a part of.

Side note: It’s helpful to have annual goals that you are aiming towards. This helps me determine what feels like fruitful uses of my time online. For example, I have a goal to book weddings and get paid $15,000, so I’m looking for that community of luxury wedding vendors to spend time with. I also have a goal to book more commercial work in the hospitality space, so I’ve started joining things like Corona Creative Camp to surround myself with more commercial photography minds. I also found two major photo communities in New York (APA and ASMNYC) and subscribed to their newsletters just to be notified of what they were doing online. I’ve already had a portfolio review done through one of the agencies! As I’m writing this I realize I should be seeking out online networking specifically in the world of hospitality. This is my opportunity to do something that would be much harder in real life.

The webinars I attend are pretty passive. They are usually running in the background while I play games or edit. But it’s nice to chat a little in the sidelines and if I know the people in the webinar I always make a point to text them during or immediately afterwards to thank them and tell them they did a great job. Compliments and support are always welcome at any level of professionalism.

As for the 143 phone calls, I started a small list of all the people I wanted to connect with more one-on-one. These included old friends, current clients/friends, or friends in my industry that I know through conferences, industry parties, etc. Also including my family (mom, dad, sister), and weekly call with my business partner.

This list is on my calendar. I keep adding to the list when someone crosses my mind or I see them in a group meeting online and miss them. Every day I copy the list and post it to the next day, removing any names I got to connect with from the day before. For the day that I talked to people, I leave behind only the names of people I talked with. It’s like my digital diary.

It’s because of these phone calls and zoom conferences that I have been invited onto a couple of podcasts recently. I also pitch myself to podcasts fairly regularly, especially if I know the person. I talked about networking on a recent podcast for wedding professionals. It’s great to have a speaking topic relevant or special to just you. For me it might be hyper-networking, or about my book How to Live an Epic Freelance Life, or how to travel for free, or whatever might be a little trick up your sleeve or project that you are working on.

BOOKING

In the past five weeks I sent out eleven proposals for jobs, ranging from $2000–$12,000. I booked four of these so far, and was able to put over $15,000 into my bank.

I raised my deposit amount from around 10% to 50%. Why? Because I run my business and I can do exactly whatever I want, but also — In one of my masterminds at Six Degrees Society all the women on the call told me to raise my deposit amount to 50%, and told me very good reasons why. By raising my deposit amount on an $11,000 wedding, I can put $5000 in my bank account now and not worry about how I will pay my rent or feed myself for the next month or so.

I attribute these bookings directly to the amount of activity I am putting out in the world. Nearly all of the booked weddings have come via referrals from wedding planner friends whom I’ve stayed in contact with (see phone calls above). Some inquiries have come directly through my website, and those tend to be the ones I’m not booking.

I also have not stopped being active. If I’ve taken a walk around my neighborhood, I’ll take my camera along. Just because I’m not earning money doesn’t mean I’m not shooting. It’s fun to tap into the freedom of photographing with no objective in mind. Especially in Manhattan, which is extremely bizarre to see completely empty. I had someone reach out after seeing one of my photos on instagram. They wanted to purchase a print of one of the cityscapes I produced. I quoted close to $1000 and they said yes! Once that money hits my bank I will update this.

I also had a couple reach out asking to do some engagement/bridal photos with some time urgency, since the woman is pregnant and not showing just yet. We decided 9am in empty central park, a safe distance from everyone else could work. This should happen tomorrow, if all goes according to plan. I’ll keep my distance, and we will get phenomenal pictures. I’ll earn enough to feed myself for two months.

I also had a friend that I’ve shot with before ask for photos around the city. Again, same as the couple, I think we can do this on an off day at an off time with minimal exposure to other people and to each other (I will ride a bike to these shoots, so no public transportation). We can discuss the ethics of this in a side conversation, but this is what I’m doing, after much thought and conversation.

I know coaches and therapists and writers who are all pulling in money monthly. Some of them I’ve witnessed generate around 20k right before my eyes. I know photographers who are editing weddings and jobs for other photographers.

We are nimble because we are freelancers. We can pivot easily because we are freelancers. Our overhead should be very very low. We have access to multiple streams of income because we are freelancers (teaching skills, providing services, offering innovative solutions to current problems).

LIVING

I am satisfied. I am content.

In the midst of all of this, I’ve managed to still enjoy living my damn life. There are tons of pockets of time in my calendar. Usually there is nothing happening from 6 or 7pm onwards, which is about 5–8 hours of free time for me. Also lots of free hours throughout the day. And as I mentioned before, I have fully fallen into the deep hole of game addiction with Dominion online and more recently Settlers of Catan. I’ll spend hours on TikTok because if you know, you know.

I go on mini walks around the neighborhood when it feels appropriate (to get groceries, or for exercise).

I enjoy connection with my friends on the phone and I love watching shows and YouTube videos. I’ve made some great improvements on my apartment during this time that brings me a lot of joy, including installing some epic wallpaper and adding some much needed tools to the kitchen.

I saw a model friend of mine post a FaceTime shoot that she did with another photographer and it looked so good I immediately asked someone I had shot with before if she would shoot with me. I did two FaceTime shoots and they were so much fun!

I’ve started and finished three books during this time. I have a podcast club that I adore; we’ve met three times online to discuss three different podcasts we’ve listened to (it’s just like a book club, but for one podcast at a time).

I am satisfied. I am content. Are you satisfiable?

I just joined a virtual book club/mastermind group to help create new habits and break old ones.

This is all to say, I’m not sure what others do with their time (maybe watch tv more than 4 hours a day?), but it’s possible to be busy, productive, earning money, enjoying your life, and still live in the time of Covid-19.

What did this bring up for you?

Phillip Van Nostrand is a professional photographer based in NYC. Currently working on a project titled “How to Live an Epic Freelance Life.”

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