If you WAH and FT, do you mind sharing your job?
I agree it's definitely easier to transition from working in an office to working remotely for the same company - you've already established your credibility and relationships with co-workers, and people know you and trust your work. I WAH FT (when I'm not traveling, which is about once a week - probably not what you wanted to hear) for a large consulting firm. I started out as a remote employee because I was hired to run a project in a city where the firm did not already have an office. They eventually opened an office in that city and I hired staff and ran that office for awhile, but then eventually the family moved out to the sticks and I became a telecommuter (mostly). There are lots of telecommuters/remote employees at our firm, but honestly, 99% of them started out as in-office people who then transitioned to WAH. It's really expensive and time-consuming to replace employees so there's growing acceptance of the WAH option as a way to keep good employees on board even when life takes them elsewhere (geographically). (On the flip side, as a supervisor, I have not approved 100% of these requests from my staff; some people work better solo than others.)
I would say if you are interested in breaking into a FT WAH gig, you might get farther by offering to commute into an office location (even if that commute is incredibly onerous for you - mine was 3 hours in each direction!) for a period of time to allow the firm to get to know you and vice-versa. If the commute is really awful it shouldn't have to be a daily run, but doing it a couple of times a week helps to make connections and shows the firm you are really serious.
I do variations on traditional WAH jobs, that pay better and fit my family's needs better than the usual. Not exactly career types, but the money I save in commuting, career wardrobe, training, etc and the flexibility make it work for me.
I do respite care for special needs kids. One or 2 kids at a time, I do overnights or whole week care - so although it pays just over minimum wage, I get paid for 24 hour days. Paid by the state Developmental Disabilities Department, it required little to no training, just a criminal background check.
I also tutor adults in English as a Second Language. I set my own hours, meet at my home, their home, or in the community. I do have certification in this field, but there is no real requirement. Very little expense or investment. I am looking into doing online (Skype) sessions to increase the geographic area my students can be in.
I also have a real job/career that allows me to work from home or in the community about 80%. I am a social worker with a small, flexible nonprofit. I meet my clients at their homes or in the community, do my paperwork at home, and only go into the office once a week for staff meetings and to turn in my paperwork.
I had various home businesses when my kids were little (the 2 youngest are now teens), and did things like sewing and online book sales. More suited to being available to kids even during "working hours". I would suggest thinking about turning a hobby or passion into a job, especially since you aren't pressed for the income.
I'm a self-employed dressmaker, specializing in costumes and special occasion/bridal. I work anywhere from 25 hours a week to 40 +, depending on the time of year. My main source of income is a contract job, sewing for a company that specializes in 9th to 15th century reenactment clothing. I also contract to do bridal alterations at a local bridal shop. I work one 8 hour day a week at the reenactment clothing company doing the cutting. The bridal fittings are done at the bridal shop and I either sew there or bring the gowns home to sew, depending on what needs to be done.
I also home school our 14th yo son. His desk and books are in my sewing room. We do school in the morning together. In the afternoons, he works alone but I'm available for questions and discussions. I started working at home full time when he was 3. Before that I worked full time at the bridal shop while I built up my at home business. He still went to daycare when I transitioned to being at home full time.. He loved the daycare; he was bored at home with no one to play with and I didn't get enough work done with him there. He went to public school for K-6th grade. We didn't start home schooling him until 6th grade.
That's what I did, both out of the home and at home. My sister has done family daycare for over 30 years now. She started out doing daycare because she hated (still does) to drive and facing a daily commute was way to stressful for her. She got her child development certificate, opened up her home for daycare. And never looked back. She loves it.
My father-in-law became a lawyer in his 50s and had his law office in their home. I've had 2 friends who taught music lessons in their homes. My other sister also does dressmaking in her home, part time. Her full time job is in the costume dept. of a theater. Another friend does probate work at home. One friend does taxes so she only works full time during the tax season. The rest of the year, she works part time doing quarterly taxes for small businesses. My brother does restorations and reproductions for historic homes. He runs his business out of his home.
I just read your post and it caught my attention as I am a bilingual certifiied translator from English to French - written (I am writing from Canada) and have been thinking of starting tutoring either English conversation or French conversation here in Québec for the new immigrants. As a single mom of two, I could use the extra income and the flexible hours.
However, I do not know how I would contact those people to offer my services...From your experience, may I ask how you proceed to find your "sudents"? And how you build your sessions?