You won't make much money doing this (you're capped at 20 hrs per week at around $14/hr, and usually there's less than 20 hour of work available per person so it ends up being much less) but he should look into Lionbridge or Leapforce. It's a work at home job assessing Internet content and searches. I did it for about a year and a half to supplement our income when I was going back to school and working part time at Kohl's.
I also agree that graphic design is a very good field to be in for flexibility/WAH opportunities. Network, network, network. He has to put in some time making calls and emails to people he's worked with before, updating LinkedIn, etc. to let people know he's looking for jobs.
An Etsy shop is a great idea for a start if he's interested in that kind of avenue.
But as someone who WAH for a former employer, it's not going to work if he has to simultaneously do childcare. I pay for 20 hours of childcare per week so that I can work in a way that's professional -- i.e., no kids interrupting/screaming during phone calls, or being stuck in front of the TV all day. In the fall, both my kids will be in full-day programs and I expect it to make my WAH life much, much easier. But with a two-YO, it depends on your plans -- if he's supposed to be childcare until they hit kindy, or at least until you guys can do part-day or full-day preschool, he's better off starting with a night/evening/weekend unskilled job and working on building up the GD stuff slowly, so that he can aim for it to be a reasonable chunk of income within the next 2-3 years.
Good luck, I know it's not easy. I hated freelancing the few times I've done it. It was a ton of work and while some people thrive on that kind of entrepreneurial stuff and selling themselves, I prefer regular assignments and an employer other than myself.
ETA: Clarification, I work at home for a company that I used to work FT for.
Where do you do the most shopping? Target? local grocery store? Can he try for a job somewhere like that in the evenings/weekends so you 2 have an income and you get a discount at somewhere you shop regularly.
This is my thought as well.
I know someone who waits tables at an upscale restaurant on Friday, Sat and Sunday. His wife works an office job M-F. It gives them the boost they need for him to stay at home during the week.
No really, the most flexible schedule I have EVER had. Even in college.
I have considered doing this as a part-time job to bring in some extra money, but worry that the orders would be a challenge for me. Getting a lot of directions, orally, and quickly can be a challenge for me. I have worked in restaurants, delis, etc though.
The graphic design field is not easy, and not simple, as a freelancer. You need real talent and motivation and it can come as a hit when you realize that your talent isn't as great as you thought, because there are a million designers without any schooling who are putting you to shame in India.
That written, if he is motivated, he just needs Google, and a strong portfolio. It will be easier for him if the portfolio is diverse. I've learned the hard way, that if you have a certain style, you'll only get so many clients. People love clean, technical-looking work. They also like cheap--most people aren't willing to pay much for decent work, because you're an artist and you don't deserve it, apparently. It's very annoying and you need to stand your ground.
Best bet for a less-than-motivated and/or disillusioned freelancer is to work in a print shop or as a marketing coordinator. Something that doesn't require you to go out and obtain clients. Instead, you're able to take home the check for simpler/sometimes less-stressful (but not always) work. The feast/famine nature of freelancing is a luxury (assuming you don't have a laundry list of repeat clients for website maintenance, etc.), and not for everyone.
Yes, he used to work in a print shop. His salary basically went to putting the kids in daycare though.
He is opening an etsy shop, and he is a talented artist. He's going to have to network that shit though, and I can help him with that. The other issue is that he doesn't know web design stuff. He is great with photoshop, illustrator, corel. But not web, and it seems like everyone wants web design.
I think that waiting tables is a good option for him, especially if he can find a nice restaurant in the area. Maybe not one directly in our tiny snobby town, but one nearby.
Preschool is a huge chunk of money for us right now so I think we might cut that. He is capable of teaching a 2 and 4 year old, and he can set up playdates. Between that, refinancing, and cutting a few more things back I hope we can make it work.
You'd be surprised how much you can make delivering papers. DH has been doing it as a 2nd job for YEARS. It sucks to get up super early every morning, but it's easy money and you're done within 2 hours a day (give or take an hour).