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Quitting Your Day Job Part 4: Booking My First Wedding and Beyond

By Chris Nachtwey on July 16th 2014

What Really Happens When You Quit Your Day Job – This is a unsugar coated look into what life is really like when you walk away from the steady paycheck and enter the world of being self-employed. I will be sharing my experiences, thoughts, and anything else that comes my way as I navigate the waters of being a full-time photographer. I also hope to interview other fulltime photographers to share their experiences with you as well.

Disclaimer: This entry in my ongoing series Quitting Your Day Job, is a very personal look into how I booked my first wedding and what happened after that. I am by no means telling you to just quit your job. This industry is hard, and you need a plan. Hopefully, this article inspires some of you to go after it!


Part 4: How I Booked My First Wedding

Fighting  ‘Normal’

By normal standards, I should not be here writing this. No, I’m suppose to have a job with benefits, and a steady paycheck, not be a wedding photographer or SLR Lounge writer. I was supposed to follow the same path as many before me. Work a job that you might not enjoy to support yourself and your family. Suck it up everyday, and suffer through another miserable eight hours of work. It’s all good, you can pay your bills, you have a good 401 (k) plan (like that really means anything when retirement is years away) and countdown to one vacation a year. It’s normal, everyone does it, and it’s what’s expected.

I broke the rules…

I felt lost, plugging away at my steady day job, not happy, but had no idea how I was going to make enough money to support myself with my photography (portrait sessions were not going to provide the income I needed). I actually never thought I would be a wedding photographer, it happened kind of by accident. I didn’t really know if I would like shooting weddings, and I didn’t even have one under my belt to show anyone, but I wanted to give it a try. I had plenty of portrait work, but no weddings. There I was, not one wedding in my portfolio. I didn’t even know if I would like shooting weddings, and there was no way to leave my job by just shooting family portraits. For three months I felt lost, it was late fall, winter was coming, the holidays came and went, I shot nothing!

A Blizzard Changed My Life

My girlfriend and I were staring out the sliding glass door at our old apartment watching the snow begin to fall during an East Coast blizzard, when out of nowhere she said, “Can we go make some portraits of me in the snow?” I grabbed my gear, and off into the blizzard we went! We had about an hour of shooting time before the snow really picked up. When we started to hear sirens in the air, it was time to get back to our apartment before the roads were no longer drivable. I left feeling like I got nothing (if you have been shooting long enough, you know that feeling very well). When I imported the images into Lightroom, I quickly realized, this was some of the best work I had done in a while. I picked the photo you see below to post on my Facebook business page. It got tons of likes, and ended up helping me book my first wedding job!


How I Booked My First Wedding

I know your saying to yourself, how did a portrait of your girlfriend in the snow help you book your first wedding? Well, my cousin had some friends who were getting married later that year. She mentioned to them that I was a photographer, so the couple checked me out on Facebook and the bride to be loved the image above (and other images of mine). They sent me an email, and wanted to book me to shoot their wedding. I didn’t even think about it, I jumped on the opportunity.

I shot my first wedding for five hundred dollars; yes, you read that right, five hundred dollars. I charged so little because, one, the couple didn’t have a large budget for wedding photography, and two, this was my first crack at a wedding. I didn’t feel I should charge very much.

We all start somewhere never forget that…

I had never second shot a wedding or knew much about photographing a wedding. I knew the basic stuff and had the gear to do it. I went into shooting my first wedding with a basic plan of attack, and said to myself, “just capture the day your own way.”

How I Felt After My First Wedding

Shooting that first wedding was exhilarating! I felt alive. I loved the hustle and bustle of a wedding day, and was doing what I loved – being a photographer. I turned that wedding around quickly – the client was happy, I was happy, and I had a wedding under my belt. I started to market that I shot weddings. I ended up shooting one more wedding that summer, and had plenty of last minute inquires for fall weddings that year and a handful for the following year.


Overcoming Challenges

I had a problem though. Due to my job in television industry, I worked every weekend. (I managed to get the time off to shoot those two weddings my first season). I had to turn down all those last minute and future inquiries. I was completely stuck! It was then that I made a drastic decision – I was going to try and book weddings for the 2014 wedding photography season, and not worry about my job holding me back anymore.

Truthfully, not knowing how I would get the time off from my job to shoot any more weddings I booked was not the best decision I have ever made. At that point, the thought of leaving my job was very strong, and I knew my time in television was limited. I was done being told how to live my life and driven as hell to change things.


In January of 2014 I launched a full on marketing attack – Wedding Wire, Facebook, Google Ad words, and some great help from friends and family using word of mouth. The gamble paid off! I booked wedding clients from Tennessee, New York City, and Connecticut! With weddings booked for this year for a much larger commission then my first few weddings, a good business plan, and some serious guts, I quit my day job.

The Present

Every day, I’m either shooting an engagement session, editing, responding to inquiries, meeting with clients, blogging (I love blogging), helping a bride with wedding day details, or actually shooting a wedding. So much of being a full time photographer has nothing to do with actually shooting; you really don’t learn that until you are into the job full time.

I love the hustle, I love the unknown, and truth is I could not be any happier.


Here Are a Few Tips That I Learned From Making the Transition From Day Job to Full Time Photographer:

  1. Break the rules: Don’t feel like you have to follow the path of everyone else. Do your own thing if that’s what is going to make you happy.
  2. Embrace the unknown: When I shot my first wedding, I didn’t really know what to expect, but I rolled with the punches and fell in in love with it. Be brave and try new things. New things should not be someone’s wedding if you’re not prepared. Maybe you want to get into food photography, give it a try at home and see where it takes you.
  3. Believe in yourself: You will run into many people who will doubt your abilities to succeed as a full time photographer. Ignore them, believe in yourself and your business plan. Keep pushing, no matter what anyone says.
  4. Be prepared to work harder then ever before: Being a full time photographer is a lot more work then people think. In fact, I work harder now then I did at my day job. Be prepared for long days and more work then you could ever imagine.
  5. Only YOU can define success: Success is measured in different ways to people. For some, it’s measured by how much money you make, for others, it’s measured by your achievements. For me, it’s always been about connecting with new clients, running a business that can pay my bills, and waking up in the morning excited about getting to work. Find what success is to you and keep it that way.



There you have it. I promised this series would not be sugar-coated. I’m not going to lie to you, becoming a wedding photographer is about ten times harder than graduating college (at least for me). I know some of you will read this, and say I did everything wrong and some of you will feel inspired.

All I can say is: there is no easy way to get started, but if deep down in your heart you really want this, you need to find it in yourself to not let anything hold you back. I had plenty of reasons to give up: a tough work schedule, bills to pay, and many personal reasons.

There will be many people who doubt you and things that will deter you from living your dream. My job without weekends off would have stopped many people. Call me determined or crazy, but not a damn thing held me back. If you really want to be a full time photographer, you need to hustle your butt off, embrace failure, relish in what you have accomplished, and look forward to the unknown.

Till next time, keep shooting, building your business, and embrace the hustle!

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Chris Nachtwey is a full-time wedding and portrait photographer based in Connecticut. He is the founder and creator of 35to220 a website dedicated to showcasing the best film photography in the world. Chris loves to hear from readers, feel free to drop him a line via the contact page on his website! You can see his work here: Chris Nachtwey Photography

Q&A Discussions

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  1. Aaron Cheney

    Great article and beautiful imagery!

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  2. Joe Marshall

    This is a great series, I’m really enjoying it!

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  3. Cody Edger

    These articles have been very helpful. Planning on making the transition from weekend photog to full time photog once my wife finishes school and lands herself a teaching job. Roughly one more year!!

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  4. Nick Viton

    I’ve assisted many wedding shoots over the past several years so I know what’s involved – which is precisely why I have never shot a wedding before. It’s not for everyone. I’m about to shoot my first wedding in August, however. Wish me luck!

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  5. James Matthews

    Thanks Chris. I’ve really enjoyed reading this series, you’ve made some really great points.

    I’m trying to find some local wedding photographers that I can assist without much luck but I’ll keep looking. You could just move to San Diego so I can be your second shooter ;)

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    • Chris Nachtwey

      Happy your digging the series James. Yes, finding photographers to assist is not easy, with so many people out there a lot of photographers are a little guarded towards bringing in a new assistant. I suggest getting in some local Facebook groups with photographers that you admire and asking to met with them in person for coffee and show them your portfolio and what you can offer as an assistant and what your looking to achieve from assisting them. Just sending emails tends to not work, but if you can sit down in person you can convey your passion to help them and show that your serious about wanting to set up lights, carry bags, etc. I would love to go to San Diego, I could shoot weddings year round!! Best of luck, reach out anytime.

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    • James Matthews

      Thanks Chris! One step ahead of you :)
      I joined a few local fb groups a couple of days ago and have a couple of coffee meetings setup for next week :)

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  6. Jared Stewart

    Awesome series. Looking forward to the next one. Congrats on making the jump.

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  7. Christopher

    Very solid article Chris. I really enjoy hearing your experiences and comparing them to our own. Congrats on everything.

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  8. Jean-Francois Michaud

    Amazing! I love the honesty in the text where it is not all sugar coated but it is also not all dark.

    Makes me want to keep going in that direction.
    Thanks Chris for sharing that! Really inspiring.

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  9. Jeff Lopez

    Thanks so much, always great information. Looking forward to part 5 :)

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