Lots of people, at some point, have thought that they must be able to monetize something they enjoy doing in their spare time. Perhaps create a company.

Example? You enjoy quilting and figure that you could earn a little on the side by taking in other people’s projects to finish them. No big deal. After all, you love doing it. Where is the harm?

Another? You have a camera and people are always telling you how good your pictures are. What if you could have a little piece of the seniors market? Or pets? Or weddings?

Another? You have a dog. You walk it. The neighbors seem busy and don’t spend enough time with their mutt, perhaps you could start a dog-walking business?

Another? You love working on computers. People ask for your help. They would have to pay if they went to Best Buy, right? Why wouldn’t they pay you?

Another? You write a blog that is getting great reviews. Its insightful, witty, refreshing, fun. You are approached to syndicate it and get paid.

Stop right there!

I’m not saying that these couldn’t take off for you. I’m not saying that five years from now you won’t be sipping champagne on your private jet on the way to Tahiti. I am warning you to be very careful, because when you start down this path, the fun might get left behind!

Part of your fun is that there are no time limits. With the money comes time limits. Yes, they do. When people pay for something they expect to be able to let you know when you take too long; and when it doesn’t turn out exactly the way they expected. And don’t forget the paper work. Sales tax. Property taxes on business assets. Depreciation on the car you claim mileage on. Quarterly taxes. Home office deduction.

Worse, most of these people, your first customers, are probably friends or co-workers. Now do you see the slippery slope stretching below?

It could work for you, I’m just saying Think Twice.

In a perfect world, your job/career would be something you enjoy doing. Take me. I work with computers all day; programming, troubleshooting, etc. When I go home, I get right back onto a keyboard. I might be doing something for the day job, or I might be doing something for myself. But sometimes the line between work and fun is blurred or completely invisible. I am always happy to help a colleague or friend fix their home computer. I have a ton of parts at home, why not? And I have a skill that people pay good money for if they go commercial. I don’t charge people. I am clear up front: I’ll take it today and let you know what’s wrong with it: If I have the parts I will fix it: I don’t guarantee when it will come back to you.

A couple of years ago I let a neighbor persuade me to edit a video for them, for a fee. I didn’t have as much free time as I expected, the quality of the footage was crap, the timeline kept slipping, you know where this is headed. We don’t speak to each other any more.

Lets go back to the guy with the camera. (No, its not me!). Your friends/colleagues might see one of your photos that they really like and persuade you to do a family picture for them. That good picture might have been one out of a hundred, perhaps a thousand. When you start putting money in the mix, you have to be reliable, accountable. Lets say they choose a location that is just not suitable for your equipment: wrong time of day, bad background, you don’t have the right lens, they don’t dress suitably. Lets say it all goes completely pear-shaped: your camera has a malfunction, you end the shoot without checking that eyes were open, focus was good, nothing was growing out of anyone's head. Sure, they might be good sports and let you re-do it. But think of the stress you have put yourself through.

On the other hand, that kind of stress can be a high for some people.

If you are thinking about doing weddings, I highly recommend you get proficient with your camera and then find someone who will let you second-shoot with them. And learn. Weddings are high stress. Most things that happen, happen once, and you had better be awake. But they do happen (mostly) predictably.

I have not done many weddings, and only do them by word-of-mouth. I do not go looking for them. They are a lot of work. There is a saying among wedding photographers, that the less you are charging, the more demanding and possibly unreasonable the client will be. Ask $10,000 for a wedding and they will be no trouble at all. Ask $1,000, look out! Rule of thumb, your mileage may vary!

While we are talking about weddings, lets break one down. Just for fun! They are very misunderstood.

A photographer might spend 30-40 hours on a wedding, over several weeks. This includes selling yourself to the client. Then meeting to sign the contract and discuss what shots will be needed, where it will be, do they want getting-ready shots, who will be the liaison person. Are you making your money up-front, or relying on after-sales? If you are not familiar with the location, you make a visit to check out the lighting and angles. Then on the day you prepare your equipment: never less than two cameras, preferably three. Check the lenses. Get the memory cards ready. Batteries. You might be shooting four hours, six, or more. Drive to the location. Get all the equipment out, check it again. Make sure you get the shots parents will want, even if the couple did not ask for them. Keep everyone-with-a-camera from eating up all the time. Accommodate requests throughout the event. Then the reception. Get the lighting ready. Change batteries. Change memory. After the event back everything up. In three places if you can! Make sure nothing was stolen while you were busy. Then you have to edit everything: cropping, color correction, special effects. Probably a couple of hours for each hour of shooting.  Then the meetings to discuss which shots they like.  Perhaps you design a wedding album, and one for the parents.

When you factor in equipment purchase ($5-$10k), equipment replacement (same), your time, your overhead, your profit (this is why you are doing it), insurance, only shooting weddings one-to-two days a week, one per day – you get the idea. As a full-time job, you will make about $30k per year. Don’t forget the constant competition from Uncle Larry: “He just got this great camera and loves to use it. We think it has cured his blindness. His seeing-eye dog carries all his stuff. He said he would be happy to help us out. Tell me again why you are more expensive than the flowers?”

Sure, some make a lot more than that. They have years of experience, excellent portfolio, a great “eye”, skill, etc. A lot of people play football, only a few make it to the NFL.

Now, get out there and start that dog-walking business! But at some point you have to make the leap from hobby to business.

Don’t forget to have fun. It just might be different than the fun you had in the beginning.