Ask. You Won’t Sound Stupid.


When I was twenty-two, I left New York for San Francisco, determined to move past a failed relationship and a failed presidential campaign. I had done all I could for both–all I was able to do at that time–and was ready for my adult life to truly start.

That adult life began with a healthy amount of mooching off family members. I stayed at my brother’s Berkeley dorm, a co-op, while he was out of town for spring break, sleeping in his bed and reading his roommate’s Harry Potter books. I felt like an interloper even though I had permission to be there, so I tried to stay under the radar, eating meals at the taqueria up the street and sneaking to the communal kitchen only for cereal. The cereal and milk were dispensed from large canisters that seemed impossible to empty. Nevertheless, I found a nasty note on the windshield of my car, which I’d parked in one of the many vacant spots in the co-op lot. The author of the note assumed I was a homeless person, and told me that I’d been seen stealing food from the kitchen and that I was trespassing. It was the result of a miscommunication that was quickly cleared up upon my brother’s return, but I felt attacked and too timid to plead my case, so I decided to move on.

After a short stint at my aunt’s house nearby, I moved into San Francisco proper. I took a receptionist job while applying for something more interesting. Eventually, I found a posting for a coordinator position at a voter mobilization nonprofit. The interview, in a cramped room on a college campus in Oakland, was conducted by four people who didn’t quite seem to fit together. It went well. My discomfort at my brother’s co-op, where I felt–and was treated–like an interloper didn’t translate to my interview skills. Once asked to demonstrate my abilities, I took up the challenge. I have never felt unqualified to do something I wanted to do; I’ve always assumed I would learn what I needed to know, and I could make things up as I went along.

I was offered the position and a salary of $35,000 per year. That felt like a respectable sum, even if it was partly contingent on my fundraising skills. When I asked about our offices, I was told that everybody worked in a different location. Well, why not? This was 2005! We were wired! Much of what they told me didn’t make perfect sense, but expressing ignorance felt like demonstrating weakness, so I went with it. I’d figure it out.

It became clear as I dove into the work that this was a fledgling organization, or, more accurately, a fertilized egg that I was expected to birth and raise. I was the sole employee. The people who had interviewed me were not employees; they were members of a board that had yet to be defined. The organization was strictly nonpartisan, a 501(c)3, but the board members all worked for politicians; one was herself an elected official.

Was that fishy? Maybe. Did it seem less than strategic to have such bold political affiliations for a nonpartisan group? Probably! But though I had inklings of concern, I didn’t have the experience to back it up. After all, I had strong political beliefs myself. I had worked the previous summer to register voters in North Carolina, and had discovered that even though that should be considered a nonpartisan activity, conservatives counted on voter suppression to keep themselves in office. Everything nonpartisan is truly partisan. Maybe this was how it had it be. And maybe in the ultra-progressive Bay Area, this was how it was.

I pushed ahead. I learned about bylaws and charters, and board roles and responsibilities. I read about fiscal sponsorships and applied for one. I learned 501(c)3 guidelines, wrote grants, and met with local organizations who would be involved in the work. I edited voter guides, designed trainings, met with potential donors, and threw a launch party. I tried to get the board members to donate money and found it difficult.

I held a stakeholder meeting in which someone asked me, “Are you the coordinator or the director?” When I stumbled to reply, he said, “If you don’t know, that’s a problem. You need a director.” The board members shifted uncomfortably in their seats. This allowed me to persuade them that the organization needed to show real leadership to succeed. I printed business cards from a Microsoft Word template that said “Executive Director.” I raised enough money to cover my salary and a little bit more.

And then, quite suddenly and unexpectedly, it was over. Right after a controversial runoff election, the board told me on a conference call they had decided to discontinue the organization. So many questions occurred to me, but I didn’t ask any of them because I thought I should already understand. I hadn’t asked the questions that nagged me when I’d started, I hadn’t negotiated my salary or pushed for clarity on the structure of the organization, and now I wasn’t negotiating the terms of departure or digging deep into what was happening. I had fled the co-op after one nasty note even though I had permission to stay there. I didn’t like bad news and wanted to move past it as quickly as possible. I wasn’t willing to admit ignorance.

I was completely devastated at losing this job, the first real career move of my new adult life. I thought I was building an organization from the ground up. I’d had a fancy title to trot out at cocktail parties. I was going to cocktail parties. I was living in a nice apartment with a friend from college.

Once I got over the acute feelings of hurt and betrayal, I realized I now knew quite a few things. I knew a lot about voting rights in California. I knew something about grant writing and foundations. I could create a budget and write a strategic plan. I could write press releases and web copy and set up stakeholder meetings. I knew about boards and fiscal sponsors. During that time I found a community of people doing impressive, progressive work in the Bay Area, and I met the person who would–almost ten years later–invite me to apply for my current job, where I now use many of the skills I acquired during that time. And I started to learn the importance of asking questions.

This was a lesson that only came with experience. At the age of twenty-two, I was desperately ready to be a full-fledged adult who could run her own organization that I wasn’t interested in building-block jobs or internships. Children ask, “why? Why? Why?” I wanted to know better. Even though everyone else must have seen me for what I was, a recent college graduate with some smarts, passion, and not much substantive work experience, I wanted to play in the big leagues. I felt ready for the show, and planned to fake it till I made it.

It’s possible not much would have been different if I’d asked more questions up front. I would probably still have taken the job. I would still have hustled to learn what I needed to know. But I could have asked tougher questions about how to message the complicated political reality of the organization. I could have focused more on process and expectations. Maybe I wouldn’t have felt so blindsided at the end. Even at the co-op: what if I’d just asked someone who was in charge, introduced myself and explained my situation, and inquired as to where I should park my car? I could have saved myself the feelings of imposition and the bitter slink away.

I still feel vulnerable admitting ignorance, but I figured out that, most of the time, my questions weren’t too stupid. I finally connected my confidence in my own abilities with a helpful conclusion: don’t assume everyone else knows more than you do. You may be inexperienced, but if you’re smart, and you’ve done a decent amount of research, your questions won’t make you look weak. They’ll make you look interested, and conscientious, and careful. Much of my work throughout the years has been to make wonky information accessible to a wide audience and create memorable messages. If I don’t understand something, chances are the audiences we’re trying to reach won’t either.

This may not be entirely clear; I’m happy to answer your questions.


Shantha works in communications for progressive nonprofits and campaigns in New York.

Image: “Tiger in a Tropical Storm (Surprised!)” by Henri Rousseau (1891)