The Introverted Fundraiser
Lessons I Learned About Niceness, Transparency, and Creativity
In late Spring 2023, I was navigating a stressful process of stepping down from a law professor gig I’d held for seven years and switching academic institutions to start an exciting new role. Things felt hectic. One day, I received an email from a friend and colleague at another school. This person I love and admire was asking a favor. Distracted by a million things on my plate, instead of scrolling through the entire email like a responsible communicator, I scanned the words “would you mind” and “committee” and said yes to whatever she was asking because I would do anything for this woman. She’s awesome.
A month later, I received another email. This missive I read word-for-word: “Thank you for agreeing to serve as Sponsorship Chair for the institute’s biennial conference. The institute’s mission depends on volunteers like you to ensure we raise enough sponsorship funds to help finance the institute’s work for the upcoming biennium plus this important conference which attracts 450+ attendees. Please read the attached fifteen-page memorandum outlining your duties in this vital role.”
Wait, what?
Me, fundraise? As in, ask other people for money? I’m an introvert! Can I get out of this?
Unfortunately, I couldn’t bail. My friend — who’d just been tapped as president-elect of this organization — was counting on me. Pouting, I scrutinized the memo and tried to figure out how I was going to do this thing I definitely did not feel cut out to do.
At initial glance, the steps outlined in the prior Sponsorship Chair’s transition memo didn’t seem so daunting: Update two sponsorship brochures — one for commercial vendors and another for academic institutions. Send them out. Collect money.
Okay. I can do that.
But, as I attended the premiere of a year’s worth of monthly conference planning committee zoom meetings, I realized this process was not going to be that smooth.
For starters, my seemingly straightforward task of updating the two existing sponsorship brochures kept derailing. Each time I revised details — dates, the conference site host’s name, the registration process, perks tied to each sponsorship level — committee members (with a LOT more experience in conference planning than I had) tagged new snags to fix. I modified the documents in accordance with such feedback, re-submitted, yet was advised at the next meeting to switch the same specifics again. Perplexed, I checked my notes. Did I hallucinate the directed tweaks? Around and around we went. I felt like we were editing the Magna Carta — inefficiently.
I realized though, getting annoyed or regretting saying yes to this job wasn’t going to change anything. I needed different motivational fuel.
Motivational Maneuver #1: Know Thyself
Leaving the third committee zoom meeting, I paused to ponder why I felt so frustrated. I mean, who cares? Just type in the new edits and be done with it! But then a book literally fell off my shelf and whacked me on the head with an answer.
In Erica Ariel Fox’s book, Winning From Within, she outlines four “inner aspects” that govern the way we approach tasks: Dreamer, Thinker, Lover, Warrior. I’m in the Warrior category. According to Fox, warriors initiate action, make performance happen, get things done, and hack through administrative kudzu to achieve goals and objectives. Crossing items off to-do lists is our jam. Guess what is not our jam? One-step-forward-four-steps-back scenarios.
Dreamers (visionaries), Thinkers (data crunchers), and Lovers (consensus builders) all, of course, play pivotal roles in project management too. I realized I needed to honor my introverted, independent, impactful Warrior self but also figure out how to not go crazy.
Armed with refreshed self-awareness, it didn’t take long to tap into an appropriate vein of ambition.
Motivational Maneuver #2: Light Thy Fire
At the next committee meeting, I snapped to attention when I thought I heard it implied that if we didn’t fundraise enough to meet the budget line (a high five-figure dollar amount), fiscal disaster could ensue.
Part of me reacted, Disaster? Ok, no pressure or anything. Another part of me (a rebellious one I sometimes need to rein in) thought, Ok, now we’ve poked the bear. Imma gonna triple that number.
Having a concrete target number to aim for made all the difference in my attitude. I summoned four personal facets. My “Pips.” (In the 1990s TV show Ally McBeal, her therapist suggested she imagine backup singers like Gladys Knight’s rooting her on.) Here are mine:
- My inner Aries: A hilarious Instagram meme once described my astrological sign as “a magical pony with the rage of a thousand suns.” This fundraising thing had now become a physical, mental, and emotional challenge at which I would not allow myself to fail.
- My inner Warrior: I ordered a new to-do list notebook from Ink+Volt to give my inner problem-solve-y nerd a blank canvas to try to make money magic happen.
- My Top Five “signature strengths”: From the VIA Character Strengths Survey, my Top Five are perseverance, curiosity, creativity, love of learning, and zest. Time to get zesty.
- My introverted persona: I am fiercely independent, love working alone, and would rather fork over a million dollars than speak on the phone, like ever, to anyone. But I knew my love of writing, of words, would help me amplify my voice — now in the role of fledgling fundraiser.
Here’s how it all unfolded…
Step One: Reaching Out to Past Givers
Once the brochures for the commercial vendors and academic institutions were finally complete and approved by the planning committee and the institute’s board, I emailed the documents to veteran sponsors of prior conferences, thanking the representatives for their past support and inviting them to sponsor the event again. In my message, I focused on context (the institute’s mission), purpose (education and positive innovation), flexibility (a range of sponsorship levels to fit most budgets), and benefits (the opportunity to showcase each sponsor’s offerings to 450+ conference attendees).
Step Two: Brainstorming New Commercial Sponsors
I pondered other commercial sponsors who might be interested in promoting their services to 450+ academics. Generative AI is obviously a hot topic at the moment, so I researched every vendor I could think of in the law-related and academic GenAI spaces. I made lists of companies who sell educational products related to the subjects attendees teach. I identified businesses who might help teachers better serve their students. I sent my sponsorship brochure (and a tailored note) to all of them.
Step Three: Academic Institution Outreach
I posted the academic institution brochure on the institute’s Listserv, but I felt like a more personal approach would be more effective, especially for schools that had never sponsored before and might be looking for a way to enhance their visibility within the institute. I found a list of relevant contact persons at the nations’ two hundred law schools. I crossed off the schools I’d already corresponded with (as past givers), then circled the names of folks I knew well from past committee work or interactions within the academy. I customized emails to that cadre next and attached the brochure. With more than 150 names still remaining on the list, I needed to design a communications plan that wouldn’t exhaust me. I crafted a welcome message for new sponsors, included two sentences I could easily adapt to each school, incorporated an emphasis on new “conference special features” schools could sponsor without spending a ton of money (like food truck meals and shuttles to philanthropic projects), and then set a reasonable quota of ten email communiques per day. (One of my favorite travel photos from December 2023 is me sitting on a yoga mat outside the Sphere in Las Vegas at 5 a.m., fulfilling my daily ten-email quota typing invitations to potential academic sponsors on my laptop, waiting in line to receive Early Access General Admission wristbands for a U2 show.)
The sponsorships started trickling, then streaming, in.
Once the cash influx began, my motivation increased further. The warrior in me created a chart to track progress. The accumulation of names and numbers propelled me to think divergently. No idea is a bad idea. At 3 a.m., my brain whirred, ideating other fundraising angles.
Step Four: Creating Two New Sponsorship Categories
Collaborating with the president-elect and the planning committee, we brainstormed two inaugural sponsorship categories: one to help fund a full day of conference programming devoted to practitioners (non-academics) in our field, and a second one (my personal favorite) focused on funding well-being content that would permeate the conference. Using the commercial and academic institution brochures as templates, I created two new pamphlets describing these additional avenues of sponsorship possibilities, choosing fun names for the various tiers, like Papyrus, Scroll, Quill, Codex, Stylus, and Lexicon for the practitioner sponsors…and Eudaimonic, Transcendence, Thrive, Flourish, Vigor, and Bloom for the well-being sponsors.
As a writer and public speaker in the well-being space, I wanted to offer a sponsorship tier that wouldn’t break the bank — a dollar amount that colleagues in my well-being network (coaches, podcasters, and book authors) likely could afford as individuals. While the commercial sponsorship tiers ranged from $1000 to $15,000, and the academic institution sponsorship levels spanned from $500 to $5,000, I decided the well-being sponsorship opportunities should start at $100. I sent the brochure to every coach, podcaster, and book author I knew, and took screenshots of Instagram accounts of other relevant well-being providers who popped into my feed to remind myself to contact them as well.
Step Five: Being Nice, Creative, Transparent, and Problem-Solve-y
Problems inevitably arose. Despite periodic heightened concern from others (likely Thinkers, in Fox’s “inner aspect” framework), I refused to treat any of the dilemmas as calamities. Instead, quandaries became puzzles to creatively and collaboratively solve. Through this process, I learned a LOT about the power of creativity, niceness, and transparency. Situations like these:
- Creativity: One veteran sponsor pledged at a high tier, but the chosen level did not include the perk of giving a breakfast presentation to conference attendees — which the sponsor strongly desired. Strategizing solutions, I suggested we explore a co-sponsorship option with a corporate affiliate. Ultimately, the two entities joined forces and became our highest tier sponsor — and got their breakfast presentation!
- Niceness: A logistical predicament arose when the highest tier co-sponsors signed on after the deadline to submit logos for co-branded conference “swag,” which technically they were entitled to in the brochure. I was nervous they might be upset the branded conference swag had already been ordered without them. I picked up the phone (not my communication preference as an introvert!). A nice conversation with them revealed they didn’t care at all about co-branding. The swag they proposed as a workaround was awesome!
- Transparency: A different veteran sponsor expressed frustration toward the cost of sponsorship, especially to qualify for one of the higher visibility locations at the conference site. Working with the conference site team, we created schematics of the various locations where sponsor tables could be positioned, transparently explaining fire marshal rules and other spatial constraints. After talking through the options multiple times over a period of months (nicely), this sponsor ultimately selected a higher-dollar tier than in previous years.
Step Six: Capitalizing on Momentum
Each time my email pinged with another sponsor saying Count us in! my energy buoyed. To stay organized (#warriorproblems), I set up a separate email account to transmit invoices, contracts, W-9 forms, and logistical instructions. I responded to every communication right away, emphasizing niceness, gratitude, and enthusiasm.
Two months ahead of the conference date, I gathered the logos of all the sponsors (helping a few individuals — non-corporate and standalone folks — create fun logos for themselves!) and designed colorful sponsor summary sheets for all four categories: commercial, academic institution, practitioner, and well-being. I posted thank-you messages on the institute’s Listserv and on LinkedIn, giving shout-outs to the sponsors, attaching the summary sheets. This public recognition had the unexpected effect of nudging even more companies and individuals to reach out asking if it was too late to join the sponsorship wave!
Step Seven: Rolling With It
Of course, not everything worked or went according to plan. I invested a bunch of time reaching out to potential sponsors in the AI space, practitioner associations, and vendors I thought might appeal to such practitioners— but none of those efforts bore any fruit. Nonetheless, I felt a sense of satisfaction knowing we’d pursued all viable angles.
Other glitches:
- The fire marshal nixed an area at the conference site where we’d planned to situate three sponsors, requiring a re-shuffling of table allocations.
- When I sent all (58!) sponsor logos to the conference app liaison for uploading, we learned the tech platform couldn’t handle that many logos (though our brochures entitled each sponsor to acknowledgment on the app).
- When I transmitted the sponsor summary sheets to the printer to generate the conference program and signage, we discovered it would be prohibitively expensive to include every logo in color unless we resized every image.
- A week before the conference, some sponsors still hadn’t processed their pledged payments; various accounting offices had added extra paperwork hoops to jump through, delaying collection.
Each time, instead of letting the logistical wrinkle fan the flames of my Aries fire, I took a deep breath and thought, Okay this isn’t heart surgery. No one’s life is on the line. We’ll figure this out. (I did, however, discover Taylor Swift’s song, “You Need to Calm Down,” during this time period and played it loudly and repeatedly when I felt my anxiety percolating at 7 a.m.)
Step Eight: Savoring Fruition
When the conference date finally arrived, I flew to the venue, my persona Pips in tow. I vigorously hugged the members of the site team and the president-elect who had been so helpful even under massive pressure in the face of countless system hiccups. We adorned each sponsor table with thank you notes and local treats, awaiting the reps’ arrival. One-by-one, as the sponsors checked in and began decorating their allotted tables with wares — books, demo equipment, vibrant swag — the puzzle pieces we’d started configuring a year ago interlocked and fell into place.
A few final hurdles to clear…tracking down boxes of sponsor gear lost in transit…realizing we’d provided snacks for the sponsor reps but not bottles of water…gently reminding lingering late payers to please transmit their pledged funds…softening reprised grumbles from one sponsor about the conference costs…our collective mission was finito.
Conclusion
In the end, I did not succeed in my overly ambitious goal of tripling the high-five-figure fundraising goal set for me. But I did increase it by 74% to a low-to-medium six-figure amount. More importantly, I learned — once again — what motivates me. I thrive in feeling creative. Solving conundrums. Brainstorming solutions. Trying new things even if they don’t all work. I don’t respond well to rudeness or abrupt criticism (a “motivational” tactic I endured through two decades of law practice which left me with not-fully-processed PTSD). Rather, my style is let’s all be smart-nice. Nothing (in this context, at least) is a crisis. Everything is fixable — with a little patience, flexibility, kindness, and humor.
I also learned that, as an introvert, I can always count on writing practice to amplify my voice authentically. This time, my pen and laptop helped me carefully craft messages — of context, positive themes, options, possibilities, and gratitude — and forge connections that ultimately made lots of people feel comfortable enough to loosen purse strings and open checkbooks. Also, as a gal with a very robust blushing response, my writing allowed me to practice transparency — about sponsorship tiers, perks, spatial constraints, costs, upsides, realities, snafus, and perceived disappointments — without self-doubt showing all over my red splotchy face during the harder conversations.
As a logic-minded warrior, I recognized that setting up systems, routines, and processes— like my 10-email-a-day outreach quota — consistently helps me complete big tasks while minimizing stress, anxiety, overwhelm, or risk of burnout.
And finally, as an Aries, I learned…once again…to never second-guess my inner magical pony with the rage of a thousand suns. She shall leave no stone unturned to prove herself — to herself.
*Professor Heidi K. Brown is the author of The Introverted Lawyer, Untangling Fear in Lawyering, and The Flourishing Lawyer. She has a law degree from the University of Virginia School of Law and a master’s degree in applied positive psychology (MAPP) from the University of Pennsylvania. Her website is www.theflourishinglawyer.org. She can be reached at heidi@theintrovertedlawyer.com and at her awesome fun job as Associate Dean of Upper Level Writing at New York Law School (heidi.brown@nyls.edu). Heidi also writes about solo travel at heidiography.substack.com.
