Kerry E. Hannon - Great Pajama Jobs

Video conferencing, texting, and other collaborative tools have blown open the door to the workplace. “In the future, remote work options will be as common as healthcare coverage,” Schawbel says. “It will be sought after and almost a benefit requirement. Employers that don't offer flexibility will not be able to compete for the top talent. Many younger workers and friends I know are willing to work for less money if they can work remotely. They're asking about it in their interviews.”

Back in 2007, when Schawbel created one of the first social media positions at a Fortune 200 company, he asked his manager if he could work from home at least occasionally. “I justified not being in the office because I could conduct all of my social media responsibilities remotely,” Schawbel recalls. “I had created and managed the company's Facebook, LinkedIn, and Twitter accounts while contributing to their internal social media platform and helping various departments run campaigns. My manager wouldn't give me permission to work from home because, as he said, ‘it would make your teammates jealous.’ If my manager had responded by granting me the privilege to work from home, my employment situation might have sufficed and I would have stayed with the company longer.”

For those of you at mid-life, after years of commuting to an office, a work-from-home position can, in fact, be a dream job, and you may have just discovered that joy. It is for me. The top four reported reasons people seek remote work, according to an analysis by FlexJobs.com, are work-life balance (75 percent), family (45 percent), time savings (42 percent), and commute stress (41 percent). Other high-ranking factors for seeking flexible work options include avoiding office politics and distractions (33 percent), travel (29 percent), cost savings (25 percent), being a pet owner (24 percent), having caregiving responsibilities (18 percent), and living in a bad local job market (15 percent).

“Older workers want to retire from the office, not the job,” says Sharon Emek, founder of Work at Home Vintage Experts ( WAHVE.com), a site for professionals over 50 who work from home for over 300 insurance and accounting firms. “Meantime, employers are looking for people they do not need to train.”

One of the easiest ways to stay in the workforce as you age, or as life events shift for you (a marriage, a spouse transfer, caring for children or aging relatives, a health issue) is to have a great pajama job, as I like to refer to working remotely. This has been my mode of work for many years now, albeit not always clad in pjs. And I admit, I'm far from retired at 59, but I find the autonomy of working outside of an office environment suits my lifestyle.

Landing a job that's a great fit for both parties is rarely an easy endeavor, and that's especially true for one where an employee is working out of a manager's sight on a regular basis. There's a bond of trust and commitment that is integral to make these work relationships thrive.

You aren't reinventing yourself in order to work from home, you are redeploying. You already have many of the skills in your wheelhouse right now that will help make it work for you. These include organizational skills, an ability to focus, self-discipline, communication skills (both verbal and written), time-management skills, and a self-reliant ability to work independently.

Tech skills are especially important when you work remotely, and that might mean learning new computer programs and communication tools, such as web conferencing, video chats, and other tools, and making sure typing skills are up to par. The ability to troubleshoot minor computer and technical issues can also come in handy.

And it goes without saying that you have to be comfortable working without a pal to pop around the corner to kibitz with to break up the day. Importantly, you have to really want to continue to work—not to just dabble in it.

The hundreds of remote workers I have interviewed have told me what I already know firsthand, that it takes discipline, but the time flexibility to do things such as nonwork hobbies, volunteering, or simply the joy of working with their dog nestled under their desk (as I often do with my Labrador retriever, Zena) is what makes it worthwhile.

Another, lesser-known aspect to chuck into the pro column: When you work remotely, your “age” is not necessarily the deal breaker it can be when you're front and center in the workplace, face to face. Truth. And that holds true for those in their 20s as well as those in their 60s and over.

In this book you will find my strategic advice on how to land a remote job, to love it and make it work for you. This includes:

Do the inner soul-searching. Not everyone is hard-wired to be a remote worker. “You need to be honest with yourself,” Sutton tells me. “Are you self-disciplined, focused, organized, skilled at time-management? You must be able to set boundaries around your work environment with friends, family, neighbors, or when working in a co-working space and not being distracted all the time.”Are you tech-savvy, open to learning new tools, and comfortable fixing minor technical problems? They will arise.Do you thrive off of the stimulation of office colleagues buzzing around you? One of the biggest hurdles for remote workers is loneliness. “If it's going to be a real con for you, and you can feel it in your gut that it will be hard for you not to have that interaction and action environment, then don't consider remote work,” Sutton advises. “Part-time or a flexible schedule might be better.”I agree with Sutton. Succeeding as a remote worker really is an individual effort. If you're in your 20s and 30s, an office environment can be fantastic. You build friendships and a lifelong network. I loved working with colleagues during my 20s and 30s in the Forbes magazine office in Greenwich Village and at the U.S. News & World Report headquarters on the edge of Georgetown in Washington, D.C.Many of those relationships remain strong today. I could not have achieved what I have in my career if I had not had that in-office experience and learning opportunity from the veterans who mentored me and those with whom I shared bylines and reporting duties along the way. Those long days and eyeball-to-eyeball interactions formed the spine of my work ethic and solidly built my career trajectory.But for someone who has young children, or is an introvert, remote duties might be the perfect ticket to achieving a balanced approach to productive work. And for those gliding, or phasing, into retirement, or working part-time in retirement, the freedom to work remotely is a benefit you can't put a price tag on.That said, you can put a cost savings on some of the basics. The researchers at FlexJobs estimate that the average person could save around $4,000 a year by working from home. Dry cleaning and laundering ($500–$1,500) ranked as one of the largest costs of working from an office, as well as lunches and coffee ($1,040). Commuting also factored in, with items like gas ($686) or car maintenance ($767) costing additional money over the year.

Connect, connect, connect. The very best remote workers will reach out to co-workers and managers regularly. “A key skill companies who hire remote workers are looking for is communication,” Sutton says. “You need to be able to say, hey, I'm a little confused about this, or hey, can you help clarify this for me? You have to take responsibility and speak up. If you're not visible, it's hard for your manager to know something's wrong.”Network with people you know at remote-friendly employers where you'd like to work. UnitedHealth Group, Kelly Services, Amazon, Robert Half International, GitLab, and Dell are among the leading companies regularly hiring for remote jobs. Xerox, American Express, and about two dozen other Fortune 500 companies have made entire divisions remote. (See Part IIfor a deeper dive.)You might go straight to a company you'd like to work for, maybe even your current employer, and see if it hires remote workers. A good place to start is the career section of the company's website.