Q&A with Claire Willett

👋 How did you get started as an arts grant writer?

Like many people in the arts administration sector, I sort of fell into it sideways. I have a BA in theatre and then I did a year-long internship after college at Manhattan Theatre Club, where I’d wanted the gig in the literary department working with playwrights but had been assigned to the donor relations desk because I was so good on the phone during my interview. The internship helped me get my first Portland job in 2004 at a theatre company in town with an open admin position that was half-time assistant to the PR director, half-time to the development director. The DD was the one who did all the grants, and he was very good at it, but - with love - spelling and grammar were not his strong suits. I’ve been a writer all my life and I love proofreading, so we developed a system where every grant passed through me for editing before it went out the door. Then when he left, the executive director said, “Well, Claire’s been working on grants, she can just take it over. It’ll be fine.” I think I was 24 then. They said, “Okay, your first task is to get us out of this mess we’re in with the National Endowment to the Arts.” Something had gotten screwed up with a grant written before I got there and the NEA flew out a site inspector from Washington DC to sit in our conference room and roast us. It was trial by fire, for sure, but in a way I think it was a helpful beginning. You learn a lot from experiencing a system when it goes wrong.

I stayed at that job for a total of three years, and then left it to pivot to freelancing around a half-time position (also a staff grantwriting gig) to have more flexibility when my mother was sick. That was around 2007. I had gotten a fair number of grants for that theatre company, so I had some successes I could point to and a bit of experience, but I needed to price myself low enough to be able to get some clients essentially by cold-calling. I started by contacting arts and culture organizations whose work I liked and who didn’t list a grants person on their website, and basically just said “Hi, I like you guys, I’m pretty good at this and I’m very cheap, can I meet with you?” That was how I landed my first few clients, and in fact one of them I still work with from time to time now.

As with many things, once something is on your CV, that’s what it looks like you are, so after you’ve gotten your first gig it’s easier to get the second and third. And the arts world in Portland is small, which had made a huge difference to me. A huge number of the jobs I’ve gotten in my 20-year career have been because someone I worked with once (many of them even from internships or volunteer projects) got a new job at a place that needed a grantwriter and said “Hey, I have someone.” (I write fast and well and I’m good at what I do, but I’m also a person people enjoy working with, and that goes a very long way.) 

I had a succession of staff jobs for many years at larger nonprofits that could afford to hire in-house grants support, and occasionally in other areas of the arts (I was only a development director once and I’ll never do it again), but I went full-time as a contractor in 2017. The whole long roster is pretty wide and diverse, but at the moment it’s still primarily arts organizations. That’s the area where I have the deepest well of knowledge and it’s really where my heart is still.

🔍 How can freelancers without prior grant writing experience get started?

The two things you need in order to get your first gig are 1) to learn how to write a grant, and 2) to find someone willing to take a chance on you to write their grants. The first is somewhat easier. I say in my classes that anyone who can write can write grants. If you were good at persuasive essays in high school English class, that’s basically what this is. You dress it up with various bells and whistles, based on what kind of information each funder is best persuaded by (three years of financial statements and spreadsheets? Video work samples? Letters of support from all your partners talking about how great you are?), but in essence you’re just trying to convince someone whose job is to give away money why they should give that money to you. Like I said, I learned how to write grants because I’d spent a year or so reading grants that someone else was writing, and I still think this is the best way to learn. It helps you get your head around the most common questions funders will ask you, and what kinds of things you’ll need to know. I work with a lot of first-time grantwriters who find the whole process sort of opaque and mysterious and intimidating, and I find that just cracking open a real grant application or two and talking through the way the pieces fit together is the best way to learn. 

There are a lot of free or affordable grantwriting resources on the internet (including mine!) like classes, workshops, YouTube tutorials, and more, and I’d strongly urge you to start by digging into what’s available to you with no or minimal cost; you might decide you do want to take a full professional course in this at some point (there are way more of those now than there were when I started out), but don’t let anyone ever tell you that you NEED to do that. I never did. 

Now, the second part is trickier. You can’t write grants in a vacuum. In order to build a practice, you need some clients on your CV, and that means getting someone to entrust their fundraising into your beginner hands. There are a few ways to do this.

Like I said, I got my first clients by picking a small handful of organizations whose work I knew personally - where I’d actually attended their show or literary festival, followed them in the news, and understood what they did. I also stayed in the arts arena, and if you have the capacity to narrow your own focus around a niche where you have lived expertise, I think that’s a good way to start. (This doesn’t have to be a professional connection, by the way; it can be something that’s personal. I worked for a digital equity nonprofit for awhile where the development director who hired me had grown up in a rural area without a computer. It made her a really credible voice in explaining to funders how communities get left behind through lack of access to technology and why their work was important.) If you have connections, leverage them shamelessly. If you don’t, start with what you do have, which is your life experience. No one is ever going to be a better advocate for things like reproductive healthcare, support services for unhoused folks, programs that serve marginalized populations, etc., than someone who has benefited from them and can speak to why they’re important. If you live in the Midwest and you grew up swimming in your local river, you may already be better qualified to write grants for the local grassroots river cleanup nonprofit than me, coming in with 20 years of experience that’s mostly for theatres in Portland.

Now, here’s the big conundrum you are going to be up against: nonprofits operate on a shoestring budget. They will always want to get something for free if they can. That’s not a dig; they just never have enough money to pay everyone to do all the things that need to to get done. Sometimes what that means is that you can work out a mutually beneficial arrangement with a nonprofit who doesn’t already have a grantwriter by volunteering, or even by joining their board. If you do this, though, be incredibly clear and specific in what you’re offering, and put some parameters around it (maybe limit it to a year and see how it goes). This can be useful both ways; you get to put them on your CV and get a good recommendation to help you pursue paid clients, and you get to build your skills and experience. (You also get to deduct the value of your in-kind donation of services on your taxes!) In exchange, they get a year of services that you’d otherwise have to pay for. Then, at the end of the year, if you guys both like each other and it’s working out, you can transition to a fee system that’s mutually agreeable.

There are obvious downsides to doing this too much. For one thing, your time and labor have value even when you’re a beginner, and one of the most toxic aspects of nonprofit culture is manipulating workers into believing that the importance of The Cause means they should want to do everything for free, and in fact that they are working against The Cause by maintaining strong boundaries around work/life balance, what they will or won’t take on, and the value of their work. I can set those boundaries now because I’m a contractor, and anyone who wants me to write grants for them now has to agree to my terms. I didn’t have that when I was in my twenties and thirties, and I worked in some places where the staff were treated horribly. 

You may find that there is some cause or nonprofit really close to your heart and you want to help them however you can, and volunteering your grantwriting services accomplishes that. However, it is also true that setting a precedent where you give those services away for free will mean both that client, and other clients, will be highly motivated to keep getting access for free unless you unwaveringly hold the line. If you already have some comparable background to trade on - you have knowledge of the sector, you’ve worked in nonprofits before (especially in fundraising or marketing), you’re established as a strong writer, etc. - you could also skip that step and just start exactly the way I did, by cold-calling people you like and saying “hey, I’m open for business if this is an area where you could use some inexpensive help,” and price yourself low to get started. It’s easier to inch somebody up over time from paying a small fee to paying a slightly higher fee than it is to go from zero dollars to anything.

💡 What advice do you have for freelancers who want to become grant writers?

A lot of the tools people tend to offer here are things that cost a lot of money - workshops, trainings, professional development courses, books, software, membership organizations, even degree-granting programs. I am of two minds about most of it. On the one hand, I don’t endorse “push your early-career employees off the side of the boat to find out if they can swim” as a learning strategy just because it happened to turn out okay for me. A lot of the workshops and tutorials I do in my classes are things I wish I’d learned earlier than I did, or things I only learned because I happened to have a boss or coworker who was really good at explaining things, not because the organization was invested in training me.

On the other hand, I have seen so many people waste time and money going through pricey professional development programs that just aren’t designed for the type of organization they are. I work mostly with smaller arts organizations, by design, and I’ve sat through a lot of fundraiser trainings where all the advice seemed applicable to multimillion-dollar companies and gave me almost nothing I could use. I’ve also never gotten a real, workable lead from a pricey grant search software program that wasn’t a funder we already knew about.

Two things, however, that I do think are almost always worth paying for:

1. Membership organizations in either your program field or your geographic area. 

   Portland has something called the WVDO (Willamette Valley Development Officers), and if I was trying to get started here from scratch I would consider that a really strong candidate for networking and finding mentors, resources and trainings. It’s all other development staff in the same general region, which means we’re all writing the same grants and applying to the same funders, and those funders themselves are often also members. Ditto the Nonprofit Association of Oregon. It might be worth digging around to see if your state or region offers an alternative. You also may find useful resources through industry-wide networking organizations; for example, Theatre Communications Group is one I would recommend to anyone just starting out with the goal of writing grants for performing arts organizations who wanted to learn more. They’re a national organization you can join either as an organization or an individual, and they offer a ton of resources from trainings and workshops to jobs and funding opportunities. There are also organizations like the Freelancer’s Union, which can be helpful with a lot of the nitty-gritty logistics (contracts, healthcare, etc.) 

2. Support with writing or craft.

   As with most things, you learn grantwriting best by doing it, but it’s a specific form of writing and it takes specific skills. You have to be able to digest a lot of people’s messy scribbled notes pretty quickly and turn them around into one short paragraph. You have to be able to write fast on a deadline. You have to develop a kind of writer voice that’s punchy enough to keep the interest of someone who has to read 600 proposals, but professional enough to make them take your organization seriously. You have to write to an imaginary person on the review committee who has never heard of you or your work or even your field, which means things like never using an acronym without explaining it, and knowing when insider jargon is helpful and when it hinders you. (I worked for a ballet company for four years, and I often had to remind people that we couldn’t assume grant review panelists spoke French.) You might find, if you’re coming to this from a different freelancing discipline, that you feel more confident with some training under your belt that’s really just focused on making you a stronger writer. 

A lot of these tools and offerings are going to try to push you into a dependence on AI, and I implore you not to fall into that trap. For one thing, you do not want to be the reason a great organization gets their grant declined because the AI text you used contained errors or hallucinations; but also, you cannot shortcut your way to being a better writer. This is an absolute rule. Training yourself to write sharp, clear prose with a persuasive hook inside a restrictive word count is a muscle that builds over time, and if you teach yourself using AI then you will be totally at sea the first time you end up with a client who won’t let you use it because they don’t want their sensitive proprietary information fed into the environment-gobbling plagiarism machine.

💻 Arts and science funding is quickly being dismantled by the Trump administration. What advice do you have for grantwriters trying to raise funds for organizations right now? And what advice do you have for freelancers wanting to become grant writers even as some funding disappears?

God, it’s so dark. I mean it’s truly hard to even know what to say. I’ve been reporting on federal arts and culture funding cuts for an independent journalism outlet called Oregon ArtsWatch since early this spring and I really just thought it would be a one-off NEA story and then I could shift gears to writing about things at the city and state level, but it feels like every week he does a new thing that undermines the whole foundations of the industry, and it exploded well beyond what one writer could cover. We all have to be on that beat now. I’ve been immersed more deeply in the minutiae of it as a grantwriter than a lot of other journalists are, so that’s kind of my lens in approaching it; what do the people trying to keep nonprofits alive need to know? 

Quite honestly, the conundrum is this: a lot of nonprofits who have been dependent for years on stable, consistent federal funding are about to be massively screwed financially, and are going to need extra hands on deck to explore other new avenues for funding to fill those gaps. At the same time, they may be struggling to find the funds to pay for those services; I’ve had a number of smaller clients in the arts who never fully bounced back from COVID closures and are still struggling financially either cut back their hours with me or just not be able to afford to renew our contract, and I expect to see more of that as bigger federal arts funding cuts kick in next year. When the NEA canceled everyone’s grants in May - funds that had already been promised to organizations, who’d budgeted for them and were already doing the work - a lot of folks had to start looking at layoffs. So they may be more in need of help than ever, and also not able to hire the help they need. And then of course, the third prong of this here is that private funders already get more applications than they can fill. I’ve talked to people on the grantmaking side of things, the folks who actually give out the money, and found them incredibly emotional about all of this. They see so much need in their communities and they already can’t do enough to fix it all, and the Trump administration immediately made everything a thousand times worse. There simply is not enough money in the private foundation sector to provide a public safety net; that’s what we have a federal government for, and they can’t adequately replace it. So I think it’s also important to remember that grants are about to get a hell of a lot more competitive, because everyone needs money so badly and has fewer places to find it. 

This is where I think you may find yourself a real asset if you choose a specific niche and stay there. Arts funding always plummets down everyone’s priority list when other community needs around us start to spike (it was like this during the 2008 housing crisis too), so you have to be able to translate what you do into the language a funder speaks. Why are the arts still worthy of support, even in lean times? Maybe the angle to focus on with one funder is freedom of expression, or uplifting the voices and stories of marginalized populations through platforming their creative work. Maybe for another funder, it’s about the efficacy of the STEM-to-STEAM shift in schools (adding arts to science, technology, engineering and mathematics) by helping kids learn through creative activities. Maybe it’s about how many union workers your orchestra employs. Maybe it’s about how ensemble-based performance teaches “soft skills” that we’ve learned the hard way are load-bearing components of our society - listening, collaboration, empathy, team-building. There are a lot of potential inroads to help people understand why the arts are important and still worth funding. Your niche might be something different, but the value is the same; the better you know that world, the more angles you can find to explain why it’s in need of support.

👀 Some organizations want to pay grant writers a percentage of awarded funds instead of an hourly or flat rate. How do you approach pricing your grant writing services? And what compensation models do you consider ethical and sustainable in this industry?

I always give clients who ask this the benefit of the doubt, because most simply don’t know, but I do not work on commission or percentage and I encourage other grantwriters not to either. It is wildly unethical, and it goes against both generally accepted accounting principles and nonprofit industry best practices from places like the Association of Fundraising Professionals and Grant Professionals Association. There’s a high level of risk on both sides. 

For the organization, it’s important to remember that a grant can be revoked if you apply any portion of it to expenses outside whatever you promised them in the project budget. It’s sometimes okay to add in a modest percentage of overhead to cover administrative costs, but most funders do not want to underwrite the cost of your fundraising.

For me, my time is my time whether the organization gets the grant or not, and there are any number of reasons for a grant to get declined which have absolutely nothing to do with how well it was written and put together, the only piece of the process that’s in my control. Sometimes they get more applications than they expected. Sometimes the review panel changes every year and you happen to get a group that isn’t as passionate about your specific field as last year’s panel was. Sometimes the problem is above my pay grade - maybe you have three deficits in a row, or your executive director transition last year was messy and public and the foundation trustees read about it in the news.

I am always really honest with clients when I think they’re taking a big swing and applying for something they may not get, or whether something about how they look on paper might be hurting their chances. That’s part of the job! But over the years, I’ve come to use this specific question - “can’t we just pay you at the end if we get the grant?” - as a helpful barometer for organizational stability. Successfully managing a grant requires that you have consistent, industry standard practices in place for accounting and financial tracking; if you cannot afford to pay your grantwriter until the grant comes in, you’re not ready to be applying for grants that require a grantwriter yet. I’m good at what I do, I’m smart, I work fast, and I’m a responsible steward of their investment, but I am not a wizard. If I feel like someone has approached me believing that all they have to do is hire a grantwriter and money will begin magically raining down from the sky, then they don’t have a clear picture of the nonprofit landscape or the challenges of getting first-time funding. (Especially in this economy, right now.) What if I write you ten grants and you don’t get any of them? The implication, then, is that my labor had no value.

When I first started freelancing in 2007, I charged $45 an hour, which was low enough that it helped compensate for my limited experience. I did that for about a year, after which I went back to working full-time and wasn’t freelancing anymore. In 2014, when I left my last staff job and went back to freelancing full time, I had seven more years of experience than I had when I started, so I kicked it up to $75 an hour, and it stayed there until last year. In 2024, I raised my rates - first for new clients, and then for returning clients - to $100 an hour. I could charge a lot more with 20 years of experience if I wanted to work for a much bigger place, like a hospital or university, where grant writers are bringing in six and seven-figure gifts. But I have spent my entire professional career trying to avoid having to wear a suit to work, and my heart is really with small scrappy arts organizations. I try to balance keeping my rate high enough to support a good work/life balance with space and flexibility to also devote meaningful time to my creative work, but low enough that the kinds of organizations I really want to partner with aren’t priced out altogether. My offerings through 8th House, and the South Sister Cohort specifically, came about as an alternative to be able to provide some degree of support and resource-sharing for organizations who couldn’t afford me otherwise.

One other thing I learned early on in my freelance career, which I recommend to everybody, has to do with the way I do my invoicing. When I went full-time freelance in 2014, I met with a former colleague of my dad’s who did business and technical writing, and she gave me a tip I use to this day. She told me she was often offered gigs early on by some startup or other who wanted to put her on a regular billing system and just pay her at the end of each month for however many hours she used. But many of them were really flaky about payment; checks would be late, or they’d pile up, or they’d get around to it whenever the harried finance person got around to it. Sometimes she actually had a company close their doors altogether, leaving her with what might be several thousand dollars in work she never got compensated for. So she changed her model and began offering people specific packages of set hours and deliverables, for which the contract always specified 50% of the fee at signing and 50% at the end. She figured that by the time she was halfway through her hours with any company, she had a pretty good idea of whether they were the kind of people who were going to flake out and fail to deliver on that second check at the end, so it gave her an out to protect herself. That’s still how I work with clients, though sometimes I might do a deposit and then two or three installments to break it up, depending on the size and duration of the contract (and how much I trust the people!) But I don’t start working until a deposit check has cleared. That’s a line you have to hold fast, because people will always try to push it. I always explain that if I make that exception for one person, then I’d have to make it for everyone.

As a contractor, I don’t have a union or a human resources manager to help protect me from being taken advantage of in a workplace. All I have is my contract, which means it has to be bulletproof, and I have to hold people to it even when they push back. I have the luxury, now, of being able to be really choosy about who I’ll work for and who I won’t, and I’ve had a few problem clients in the past, but for the most part, nonprofits aren’t trying to take advantage of you; it’s just that their priority is always going to be cash flow. I recently had to say no to a contract because the nonprofit simply wouldn’t budge on their refusal to pay a deposit; their reasoning was basically, “We don’t know you; why should we pay you for anything in advance without any guarantee?” And that’s a useful piece of information to have. It could mean that they’ve had negative past experiences with consultants taking advantage of them; and that sucks, but it’s also not a dynamic I want in a working relationship. If you don’t trust that I’m a specialist in this field whose expertise is worth what you’re paying me, then the first time I have to tell you something you don’t want to hear (like why you’re not going to get that grant), I can’t trust that you’ll listen. It could also be a financial red flag, if they’re balking at a dollar amount that’s not a problem for organizations much smaller than theirs. The organization with the multimillion-dollar budget demanding that the contractor waive one of their few protections is like an SUV driving through a crosswalk and expecting the pedestrians to move.

I think in many ways that’s the most important thing I would tell any new grantwriter about the money piece of the conversation. The client is looking at the cost of your services as an expense, and like all expenses, they’re sometimes a headache. We all know the feeling of wishing you could bump a handful of those bills out a few more weeks until the next influx of cash comes in. They’re not necessarily playing hardball with you; some of these folks operate very, very, very close to the line, and if they’re about to make their first-ever investment in hiring a real grantwriter, it may be because income is super tight. You will probably be charging more per hour than they make per hour, and sometimes that can feel fraught or gross. But what you have to remember is that we’re not just talking about money, we’re talking about value. I had a few people grumble when I raised my rates from $75 to $100 an hour, until I explained that I now have ten years’ more experience - from which they benefit directly - than I did when I set that $75 rate. The value of my skilled labor has increased as I developed new skills, and therefore I’m entitled to charge more for them. Artists hate talking about money, so this is a conversation I’ve had to train myself to get comfortable with, but it’s a really important one.

 📚️ Where can we learn more from you?

8th House is a project I started last year after a grantwriting class I offered in an auction to raise money for voting rights blew up rather unexpectedly and over a hundred people signed up to take it. I realized that a lot of progressive folks who had causes they were passionate about were looking for ways to support them that went beyond just donating and calling legislators. There’s a newsletter with both free and paid versions, which cover everything from reflections on the philanthropic landscape to practical tips on funder research and video modules of my “Grants 1010” class from last summer. The highest member tier is the Mount Hood / South Sister cohort (all the levels are named after Oregon’s natural landmarks), which also includes monthly Zoom gatherings, resource-sharing, and five hours a year of my one-on-one time to help people write a grant, develop a funding strategy, and more.

I also offer classes and workshops. I’ll be bringing back my prospect research workshop in the fall, which helps people identify new funding prospects to apply for. The philosophy of 8th House is really shaped by a lot of the things I wish I’d been told twenty years ago that it was okay to question or do differently, and I’m very frank about the challenges of doing this work under capitalism, which often means ethically murky questions about who you will or won’t take a check from. It’s been really energizing work for me and I come away from every class or Zoom meeting feeling better about the world, seeing what these tiny nonprofits with their tiny budgets are doing in their communities and getting to help them do their work better. 

The other facet of the South Sister cohort, which will be expanding into some exciting new opportunities later this year, is that several of the members are folks who are there to learn how to develop a grantwriting practice as a beginner, in the hopes of being able to transition into it as a sustainable career. One of the things I’m working on, with some exciting irons in the fire I can’t talk about yet, is how to bridge that “how to be a grantwriter 101” level of training into opportunities for South Sister members to actually find paid work for clients. I think the world needs more progressive, anticapitalist grantwriters who are able to see the challenges in the system and can push for change while helping the smallest and most vulnerable organizations get the funds they need to survive and thrive.