Thanks, guys . This is helpful. I consider myself a confident person, but this makes me break out in a cold sweat. I have a year off of work to at least try... I can always close shop and "go back to work". I'm surprised at my self doubt. The prints vs files is a hard thing, ST. I'd love to hear more about your own experience and pearls of wisdom.
A few things to think about:
--How do you want to structure your business? You need to be formally set up to be able to collect and remit sales tax. And you really need to do this. I recently found out not paying "Nanny taxes" can put any licensed professional's (like a doctor) license on the line. It's rare, but possible. If you were audited, I'm not sure if not collecting sales tax would be considered in the same way, but I would CYA just in case. And it is still income, so you have to pay taxes on that too.
--As a corollary to that, a sole proprietorship is relatively easy to set up. However if you were ever sued, your personal assets are at risk. If you aren't doing weddings, you are probably much less likely to ever experience a lawsuit, but it could still happen. Someone doesn't like there pictures? (there are assholes that will give you hell). Grandma tripped and broke her hip during a session? There are other types of business structures that give you more protection, but they are harder to set up and a PITA at tax time.
--As far as investment goes, you could start with what you have, but you will very quickly need to invest in proofing software, extra camera body, lenses, any other needed software (business workflow software helps a ton), a website/branding, hosting fees. Some sort of hard drive backup or backup service. Then there is insurance. I don't know how many people actually follow through with it (I didn't), but liability insurance is good to have in case Grandma does break her hip and a must if you do weddings. (Sidenote--I wouldn't do weddings. You don't need that drama).
--You definitely need a contract of some sort detailing your terms for the session/delivering the images, what happens if X, etc. I've heard tons of stories of people being saved by their contract.
--Then you have to consider your time. People tend to want sessions on evenings and weekends--do you want to give those up? Do you need babysitting? Consider how much time it will take you to actual travel to/from, shoot, edit, and deliver the session. At least 4 hours, probably more like 6-8 in the beginning. Divide your session fee by that and figure out how much you would be making an hour, gross. Then consider your businesses expenses and look at how many sessions you would need to do to make anything. Now you understand why people charge so much once they are established. The newbies aren't making squat or aren't doing things legally.
Not that you need to do all of this to get started--I never got that far. But I did take it all into consideration and decided in the end it wasn't worth it for me right now. It might be for you, especially if you want to build it all up and continue to keep this as your career going forward as your children grow.
I'm not trying to be a wet blanket. Once you get things running and established, it is a whole lot easier. I might go back to it later, but I felt I had enough on my plate in the immediate future. You can always dabble and back off if it is too much, but I would make sure you do things legally from the get go because you have so much to lose.
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