How to “Go Pro” and Leave Your Day Job With No Regrets

Issue #36

This is one of the harder topics to write about because I know how important it is to an aspiring creative to turn their passion into a profession.

I know how easy it is to start a business.

I also know how easy it is to fail at growing a business.

I don’t know where you are in your journey, but I’ll assume you’re a good photographer who has already spent a good amount of money on cameras and is now considering how to make some with all this groovy gear.

I don’t want you to decide if you’re going to become a FULL-TIME wedding photographer at this point.

I do want you to ask yourself if you’re ready to turn your photography into a business and a serious form of income for yourself.

My guess is you’ve already crossed that bridge of possibility, and you’re curious how this might look for you.

Now there are several ways to start a small business, and depending on your state or country, you’ll likely do so in the most efficient way possible.

If you’re unsure, go to your local bank and chat with someone there. You can start with a DBA (Doing Business As) Account right away and take the first step. It’s important if you’re making money with your photography that you keep records, pay taxes and do things by the book.

You can run a DBA for a long time until you want to get really serious. Then you’ll have to visit your city and state government offices for the next steps.

The main point here is getting your head straight that THIS is your path, you’re prepared to go down it, AND you’re willing to commit to it, bumps, curves and all.

Starting is easy - Continuing is where it’s challenging. Let’s talk about the next steps.

I don’t know your situation, but let’s look at two common ones.

Scenario #1 - You’re working a job, though NOT as a photographer, and you want to get started in wedding photography. Congrats, this is a GOOD start.

My best advice to everyone interested in wedding photography is to work as a second shooter for a pro who shoots weddings every weekend.

This is THE BEST place to start, and will let you shoot weddings and see if you even LIKE weddings. Not everyone does, and that is just fine!

I talk about second shooting in more detail in Issue #15, and you can read it here.

As you build your skills and confidence shooting weddings and perhaps even other things, you can turn this into a nice side hustle.

The good news here is that everything you do to set up your business transfers easily to another area of photography, like Commercial, Portraits, Sports or Photojournalism.

Scenario #2 - You still have a day job but you’ve been a second shooter and loved it. Perhaps you even booked a small wedding or two of your own and loved that as well. You can see yourself as a professional wedding photographer.

This is a special place to be, and it’s also a dangerous place because you have some money now, a little street cred and a passion that’s pretty hot.

You have a legit side hustle going, and you’re probably thinking, “When is it time to make this a business?” Another way that’s probably close to the mark is, “When can I quit my day job and make THIS my full-time gig?”

This is a very good question and a big one.

Someone smart once told me that the best time to quit your “day job” and make your side hustle your new full-time job is when the day job gets in the way of your growing side hustle. This is good, but there is a bit more to this sage advice.

Of course, this will take some time. Your day job is where your money is (assuming you’re working, of course) and you can’t exactly just take that big step all Indiana Jones and the Last Crusade-style.

Your side hustle is where your heart is. I get that, but I also get that you need more than passion to pay the bills. And before you start spending that extra income you got coming in, I want you to do something hard - Save your money.

Let’s back up just a bit before you poo-poo my money advice.

I’m sure you’ve done a little research and found you need a few more things before you can shoot weddings full-time...namely, backup gear.

That means you’ll have to spend a little more money, but you’re determined to pay for this with your earnings, right? Right?

Start slow and, if you can, I recommend borrowing gear as needed until you can shoot enough weddings to justify buying the bare essentials: two cameras, two lenses, two flashes, and plenty of batteries and cards.

Once you have the essential gear, your backup gear and everything you need to shoot wherever and whenever, NOW you’re in a place to start considering making this your top job.

Are you ready to pull the trigger?

Hold on there, cowboy! Remember the saving part? NOW you’re ready to save.

Since we’ve already established you’re working, and money is coming in, when you shoot a wedding, put that money away.

Shoot another wedding and put that money away too. During this first year or two of growth, you’re building your skills (photography and marketing), you’re building your relationships, and you’re building your confidence to do this for a living.

What you also need to build is a little nest egg of savings to get you started.

Have you ever borrowed money for something?

It’s not fun. You have the money, but you still have to pay that money back, and you won’t be free unless you do.

What I’m suggesting is a plan of saving that creates a Personal Pad of Pecuniary Protection (a really fancy phrase for a safety net that I’m now calling your PPPP).

While you’re working your day job and building your side hustle, you’re putting yourself in a position where you can fund The Big Launch.

My recommended PPPP is one year of income and a steady stream of bookings for the next year.

You need a backup savings account equal to your full-time income, and you have enough weddings committed to start a new year to pay all bills.

Once you’ve run the numbers and have a comfortable number of weddings “on the books,” you’ll be able see how much you’re projecting to make this year.

“But wait, Chris, this means I’m working practically two jobs! I’ll be really busy!”

Yes, you are and will be, my friend, but you’re building something for yourself and hopefully doing something you love (Remember that part about seeing if you even LIKE weddings?)

You’ll work VERY hard, but once you fill your PPPP, you get to make the decision you’ve been waiting for... dreaming of, dare I say.

And if you’ve built your PPPP properly, you can sleep easily knowing you have plenty of backup savings to help you build your business the right way.

Look, I’m not a professional money manager. I’m also admittedly a bit overly cautious about making life-altering decisions like this.

When I told my wife I wanted to quit my day job, the security and the insurance, it wasn’t easy.

We had two kids, and I was good at my job. But I had a vision, and I made a plan that made sense and made her comfortable. That’s all that mattered.

You can do this.

You can do it slowly or quickly, but the important thing is to decide TO DO IT and commit to doing whatever you need to make it happen.

With the right mindset, preparation and execution, you can design the work and life you’ve always dreamed of.

We all have dreams. But to make dreams come true, it takes an awful lot of determination, dedication, self-discipline, and effort.

Jesse Owens

Preparing yourself to “take the leap” is just one of the little parts of the inner game of wedding photography. THIS is what I write about each week in this newsletter.

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If you’re starting and haven’t quite figured out how to handle the hundreds, or even thousands, of photos from an event, I’ve created something special to help you.

It’s a guide to help you process your wedding in one week, and it’s a system I’ve used for over 25 years and still use today. Don’t spend weeks processing and miss out on The Glow. This system will help you get your photos to your client, make them happy and make you look like the professional you want to be.