How I Learned To Work From Home & Why You Should Too


When I was running a small nonprofit and prided myself on being a workaholic for the right cause, I secretly judged people who wanted to work from home as little bit lazy and/or less committed. I also believed (and still do) in the magic that happens simply from being together with your colleagues and the people you serve, and did not feel that employees working from home could maximize their potential.

How the author used to think, before embracing remote work. / via
How the author used to think,
before embracing remote work. / via

I thought that wanting to work from home was an understandable but selfish desire of people who wanted a paycheck but did not want to go through the pain required for quality work. I thought it was especially unacceptable for nonprofiteers to view work this way. Nonprofit work is too important, I thought. In my mind, commuting through each transit strike, illness and occasional East Coast “storm of the decade” and power outage earned me another invisible badge of honor.

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I did have a special place in my heart for people who, even though they really wanted to work “harder” and longer, suddenly could not do so because they had babies and could not afford quality childcare all day (nonprofit job, anyone?), or people who fell ill or whose family members did. I truly sympathized with them, but believed that it was up to each individual to “figure out” the logistics and get to work on time every day, and get focused as quickly as possible. If they could not, I thought, they should voluntarily seek a less important, or different kind of job before it became a problem for the organization. When I had grave family and other life issues to deal with in my twenties, that’s simply what I did. I also remember thinking that I had no choice but to put off having kids as long as I could, exactly for these reasons.

My view has shifted quite a bit from what I just described. I still think that there are times when you have to just suck it up and work more, harder and longer than you would prefer, and that there is definitely something special that happens for the team and organizational culture when you work with folks face-to-face. For me, it was when external forces kept me from being able to keep my regular long hours in the office, and when it felt like me leaving the organization was detrimental to the health and state of the organization, that I felt compelled to jump into the world of remote work. My own remote work experience helped me to see the issue from the other side, and through reflecting on what happened, I have slowly morphed into someone who advocates for flexible and remote work as a skill one should learn and develop, and that employers should embrace. Here is how it happened the first time.

NYC job and Kentucky husband

In 2003, I was finishing up a tumultuous first year as my employer’s second executive director ever, succeeding a universally beloved founding executive director. Then I found out that my husband’s work was going to send him to Louisville, Kentucky, for a year, and he truly did not have a choice in the matter. My organization was a small nonprofit in NYC, so Kentucky had nothing to do with my work. I was also newly(ish) married, and worried about jeopardizing my marriage by not moving with him, even if it was for just one year.

Quitting my job to leave with him did not feel like an option to me, not because there was something special about me, but because I knew another executive transition would have been too much of a blow for the young, fledgling organization that had just gone through its first executive transition. I also thought, What would the funders say? What would my board members say? I was just getting started on this big job they had trusted me to do.

keep-calmAfter consulting with my mentors, including couple of board members, I finally mustered up the courage to ask the board of directors whether I could divide my time equally in Louisville and NYC. This being 2003, I did not know a single person who worked remotely, except for some fancy management consultants. It was much less common for people to work remotely. It certainly was not being done among peer organizations or anyone in my organization. I was terrified that the board would think I was not up for the job, or that they would say no to me continuing my dream job. I developed a monthly schedule for the next twelve months and came up with a budget for how much it would cost to make this work (and who would pay for what). I laid out how my work would be divided, how I would announce this temporary change to the organization and who on staff would take over some of my responsibilities when I was not in the office half of each month.

I don’t think the board was pleased with this newest challenge. However, they carefully considered my proposal, asked some very tough questions, then helped me strengthen my plans. And they backed me up all the way. To this day, I am so thankful for the board that decided to try this. And I’m grateful to my colleagues who did not grumble (at least to me), but instead provided so much support: Emailing me documents after documents I could somehow not access remotely, or calling me with something funny that happened in the office to help me feel connected. They were instrumental in me (and the organization) getting through that year.

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I learned a lot that year. In New York City, I learned to organize my schedule to maximize my time there, bunching all in-person events and meetings during those weeks. I also gladly worked into late evenings to get my face time in with NYC staff, donors and partners.

In Louisville, I focused on writing and planning. Being a late English learner, I had always dreaded conference calls, especially with people I had never met in person. Well, I got much better after that year with all the practice I got! I also learned to let go more and trust my staff members to do their jobs, and to do my best to hold people accountable for the deliverables they were responsible for, rather than how late they stayed in the office or how hard they seemed to be working when they were in front of their computers. I also ended up logging in so much fun, quality time with my husband because in Louisville, all we had was each other.

Since my “triumphant” return from Louisville, I have been much more receptive to more flexible work arrangements both for myself and others. I know from my own experience that with the right structure, training and people, remote work can be effective and beneficial for all involved.

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Converted: Why I Endorse Some Remote Work for All

By meeting my needs to telecommute that year, and again accommodating my remote work needs at different points in my career there, my employer got my loyalty for life, in addition to getting to keep a key employee. I was so loyal that I would never even take a call from a headhunter until I made an announcement to leave the organization (which is not a smart thing by the way, because there is nothing wrong with building a relationship with headhunters and broadening your network when you are not looking for a job, but let’s save that for another article).

For me, I got to keep, and grow in, my dream job for an organization I deeply cared about. Through telecommuting, I also unexpectedly got to learn and practice what I now believe are crucial skills everyone should learn in the rapidly changing world of work:

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Leveraging technology and communication tools to get work done: You really can get a lot done without sitting through long meetings every single time.

Keeping my network activated, even with limited face time: I build and cultivate my network by being active on Linkedin, checking in with my former colleagues and clients by email, forwarding job and consulting opportunities to people who might want to know about them, and building in time in my schedule for coffees and Skype calls with people I want to get to know better.

Trusting my people and learning how to delegate for success: I tried to achieve this by 1) defining desired outcomes both for my performance and my employees’, then 2) appointing and tracking appropriate milestones, 3) knowing when to step in to provide extra guidance and 4) measuring what was done, not necessarily where it was done or how many hours it took.

Managing my own time and energy: I know I’m a grown up and I should be able to focus and bring my best to work every day, whether anyone is looking or not. But we can all get in a rut, and spin around at work. Knowing what I need to do in order to snap out of that kind of haze is a skill I don’t think I seriously worked on building until I started working remotely. Sometimes it’s working in 15- or 30-minute increments to get something specific done and moving to the next. It could be physically moving myself and my laptop to a different room or table to get a fresh start. Sometimes it’s starting a new project. Some days it might be knowing when to take a break. I might go for a five minute walk, start a load of laundry or marinate something for dinner, and come back to work with a new mindset! It is not, however, wasting an hour surfing the Internet to look busy.

Setting yourself up for success with back up plans for everything: It is not just about getting your home set up with fast Internet connection. It’s also having several go-to places if your Internet or phone goes down, and it’s about having neighbors or back up sitters to take care of your kids on the days you need to be on the phone and your babysitter calls in sick. It’s also about knowing what kind of equipment, space or other resources you need to get your work done, and investing in those things.

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What’s Next?: Part II!

People are beginning to think of work differently. More people are feeling that it is simply unnatural and unhealthy to feel as if their job singularly defines them or “owns” their time. They want to make sure they are doing great work and, unless someone can make a compelling case for how and where that work is done, they will not feel happy about having to be somewhere during certain business hours. This is especially true with the rise of millennials in the work force. With more women in the work place and wanting or needing to stay there beyond kids, and more men taking on active role in caring for their children and homes, some flexibility to enable people to work when and where they want to will become increasingly important.

The workforce of the future will definitely include more remote work whether we like it or not, and it is in the best interest of nonprofiteers and their employers to adapt to this change.

Writing this piece reminded me of all the fears that came up for me every time an employee or I wanted to work remotely. This summer, I will be researching for a sequel post on how important it is for nonprofits to embrace remote work, and why it has been difficult for many organizations to do so.

If you work for a nonprofit that enables its employees to work from home, please share your successes and best practices, as well as challenges. Send your story by commenting here, or by email.

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