We asked if you had questions, and you most certainly did! We can’t answer all of them, so we picked the ones that were asked many times or the ones that raised the most universal issues. Barbara Chandler Allen, a 2010 Purpose Prize winner, who founded and runs a nonprofit called Fresh Artists, answers the first three questions. And I answered the last three.

If your question isn’t answered here, look for answers on Encore.org. Specifically, check out our Get Started Guide.

Salleh: Barbara, where do you get funding to do all that you do, and what is your business model?

Barbara: Fresh Artists is basically a corporate art program. We approach businesses and corporations and say, “You have vast expanses of white walls. We have brilliant, affordable artwork that carries the value-added gift of civic engagement. Your staff and your clients will admire you for supporting this innovative, entrepreneurial nonprofit that delivers art supplies and exciting educational programs right back to the kids who made and donated the artwork in the first place.” We have also been fortunate to have several generous foundations support us in our first three years, but the core model is a social business, not a charity. We have a product and have found a market for this product. Also, we are fortunate to have many volunteers and in-kind gifts of services.

Caitlin: I’ve worked in a purpose-driven career all of my adult life (social services). It’s been great work, but I don’t have a lot of savings as a result. I would like to move into work that still feels like the right livelihood, but steps up my income significantly. Entrepreneurship seems like the best route, but I’m not quite sure where to begin.

Barbara: I wonder what kind of social services you are in currently and what constitutes a step up in income. If helping people has been your career, I might look at all aspects of keeping people in their homes and start a small business providing service to support this. You could develop a business providing shopping, errands, respite care or pet care to home-bound folks. You could market yourself to an in-home nursing company to take some of the more mundane chores off their plate. I have a friend who started a pet care service—vet trips, grooming, walking – for home-bound people and it was very successful. Flexible hours, too. Personal chef services are getting to be lucrative.

The trick is to do your research. Dig around and find out who is doing interesting things. Look at upscale glossy community-based magazines and read the back ads. Can you provide an adjunct service or find something that people need doing and are willing to pay for?

The bottom line is to try to line up your skills and experience with a service that people need. Once you’ve got the idea, learn by talking to others in similar fields, potential customers, other entrepreneurs, local bankers, business students who might help develop a business plan, and so on.

Ann: I was downsized nearly two years ago and am not ready financially for retirement. I have begun to think about starting a business employing personal care assistants who would work with aging adults to help them live independently. Do you have suggestions for how to get started?

Barbara: Internships are not just for teens and college kids! I believe that internships for mature folks are a terrific way of scoping out a prospective new business. I recommend finding the most highly respected service of this kind in another city, a city where you know someone you could stay with for a couple of months.

A good way of finding them is to call the head social worker at the best hospital in that town and ask who they recommend. Then make an appointment with the head of the company, and, if you like them, offer to be an intern for that agency for two months. Be forthright about your offer – they help you learn about the business, you provide free labor for the duration of the internship and agree not to start a competing business within X miles (like 100!). Be prepared to offer to sign a non-compete agreement to show your integrity. And be prepared to be a line staffer doing real work that is needed in the organization.

If you are lucky enough to find the right match, this can be an invaluable way of seeing that business from the inside and finding a mentor who might stay in touch and help you well after you have left their employ. Rotary Clubs and local Chambers of Commerce can be a good way to find a connection like this in another community.

Barry: How does one realistically overcome the constant objection that “you are overqualified” or is it simply code for tool old at 57? I would be happy to pass on my skills and expertise without the need to be the boss any longer.

Marci: There’s no simple answer for this one. Age discrimination is certainly a fact of life. And many employers just haven’t considered older people for some jobs. You may find some useful information in a Civic Ventures survey of nonprofit employers. One tidbit: Many employers are concerned that older employees won’t want to learn new skills or will have outdated technology skills. Be honest with yourself about whether you have an age issue or a technology deficit. And if it’s the latter, fix it by taking the right courses or figuring out some other way to get up to snuff. You can also learn to emphasize things that will shake employers out of their stereotypes.

But if an employer doesn’t value your experience, the organization may not be an ideal fit for you, even if you are able to change some minds. Better to focus on places where you see evidence that older, experienced people are already part of the team. It would be a good idea to tailor your resume so that it shows your strengths as a mentor and adviser. And certainly talk about mentoring in your interview and explain how gratifying it is to you to pass on your expertise.

Grant: I’m a 57-year-old who just lost my job to restructuring. I’m considering finding a full-time job outside of my profession that would pay less, be less stressful and have me home at a reasonable hour. Is this something other boomers are doing? What are the challenges? And what are your thoughts?

Marci: You are in good company, Grant. Lots of people want to decrease their hours and dial down the pressure of work, while still doing work that’s meaningful and substantial. These are realistic goals. But most jobs don’t come with “less stressful” labels.

Your job search will have to begin with a self-assessment. Examine your talents and skills, then move on to a phase of research and exploration where you learn and test things out. Ultimately, you’ll apply for jobs. Maggie Mistal, a career coach I admire, calls this process “soul search, research, job search.”

As you get into your research and network with people in fields that interest you, then you’ll be able to start figuring out what kinds of positions match your lifestyle goals.

Bill: My expertise is as an electromechanical technician. I want to work with either disabled, elderly persons or disabled American Veterans. How would I transfer my skills to attain this sort of work? 

Marci: I’ve got one word for you, Bill: Volunteer. Contact a veterans organization that engages community volunteers and start volunteering immediately. In no time, you’ll figure out a way to match your skills to some unmet need. Volunteermatch.com is a great resource to help you identify volunteer opportunities near where you live.

If you’ve got more questions, check out our Get Started Guide.