Is It All About the Money?

7 min readOct 28, 2021

By Andrew Daub, Chief Operating Officer at oneTILT

Image Source: Planning Capital

Money is a tricky, slippery, powerful, dangerous, helpful, harmful, necessary, weird thing. In a capitalist, patriarchal, white supremacy world where we’re taught to value the penny over the person, money distorts work and worth as one and the same. It can seduce us into a race for more — more dollars, more things, more decisions, more goals — which, in turn, can send us into a flurried state of going too hard, too fast. It can signal a mindset of scarcity, leading to stress and anxiety. Money can be a key way organizations create inequity in how they communicate value to their people. It can suck you in so fast that we forget about why we’re doing what we’re doing at work in the first place. So, is it really all about the money?

Real talk: I feel like I haven’t calibrated a good, healthy, human way to talk about money. I find that either I’m talking about it too much or not talking about it at all. In the past, I’ve gotten feedback that I talk too much about money with my team, spending a lot of time on things like financial goals or invoice considerations. I’ve become the leader I’ve criticized at former jobs: I’ve taken too much airtime to focus on money and not enough on critical pieces of our work — feelings, culture, program, impact, just to name a few. That all has had a compoundingly negative impact on my team; I’m a white cis guy sending a message that money is more important to talk about than the people in the squares staring back at me on Google Hangouts. I’ve also swung the pendulum in the face of this feedback, shutting up about money, rewiring my brain to form habits in meetings to elevate considerations that go beyond the dollar signs. At times, I’ve then gotten questions from colleagues who desire more insight about our finances at oneTILT or who want more support in figuring out how we approach setting a quote for a client. Silence around money also hasn’t been helpful, leading to team members feeling confused, stressed, or isolated. Like I said, I’ve struggled to talk about money at work in a way that acknowledges its purpose and value and simultaneously doesn’t override everything else or dehumanize my team.

Earlier this year, Kimberly had our team do an exercise where things started to shift. Instead of talking about money in all the ways I’ve seen folks talk about money at work (e.g., what’s our budget, are we on track to our goals, what do we believe about compensation, what’s the plan for Giving Tuesday?), we put money front and center and talked about that: money. What is our relationship with money? How is that rooted in who we are and our identities? What makes talking about money easy and hard? Why do we want to talk about money at work? What would be most helpful to know about one another when we do talk about money? Taking time to actually press pause and interrogate my relationship with money gave me the opportunity to explore a lot of the background noise in my own life that was making things hard.

To be clear, as a white cis guy who grew up with college-educated parents with salaried jobs, I haven’t had major challenges with money. I didn’t grow up poor. Food was always on the table. Each school year brought a new backpack, new sneakers, some clothes from the GAP Outlet at Exit 149 in Georgia. I knew a lot of the kids in my IB classes had a lot more than me; heck, my best friend drove her own Audi in high school, and many friends dropped brand names that just went straight over my head. But I also knew that I had a lot more than most kids in my school, most of whom were Black and/or latinx and had to ride over an hour on a bus every morning and afternoon. I got to do things I loved: take dance classes, go to speech and debate summer camp, sell popcorn and go on that Boy Scouts ski trip come winter. I didn’t have to take undergraduate loans out thanks to a full-ride scholarship, and I didn’t start working until after college when I began my career as a teacher. My biggest experience with debt came by deliberate choice: choosing to start oneTILT alongside Kimberly with nothing but a dream, tacky turquoise splash page, and Twitter account led to personal credit card debt that caused early startup years of stress and anxiety. I’ve been able to make monthly student loan payments from graduate school, and I’ve always had a place to call home. So money itself isn’t something that on its own brings up a lot of pain.

That said, the actual talking about money thing is different for me. My parents divorced when I was two, and I was always aware of the sharp contrasts between life with my mom and life with my dad. Many things dictated that contrast: geography, religious belief, holiday tradition, home cooking, weekend fun, and — in an unspoken, acutely felt yet still muted way — money. Mom had less, dad (and then dad and my stepmom Teresa) had more. Mom made less; they made more. None of it was really talked about, but it was there. There were disagreements I’d overhear on the phone or in McDonald’s parking lots during exchanges between homes where I sensed they were arguing over money: needing more of it, giving too little, giving too much, frustrated over money issues that likely stemmed from court custody battles or even married days before I even entered the picture.

And then came FAFSA. Senior year and into college, our family of divorce was forced to talk about money. The stakes were higher, because my full-ride scholarship was also bound up in FAFSA paperwork. I’ve blocked out a lot of the details; I just remember bits. The bizarre feeling in my gut seeing my dad at my mom’s dining room table, peering over the paperwork we needed to file. The soft whisper of a conversation turning into a crescendo of arguments that had everything and nothing to do with money. The eventual broker role I took on. The tightlipped-edness of it all. And finally: a silent promise to myself that I would chart a path after college that wouldn’t depend on any of my parents so I could avoid this whole mess altogether.

Fast forward back to the workplace, and I realized in talking with my team that a piece of that Little Andrew is still with me. I sense that we all have different relationships with money, which provokes a whole host of feelings and stressors — and talking about money at work feels like a field of hidden triggers, where one comment here or one glance there might erupt in an argument, just like how I saw it develop with my parents. As an adult, I’ve also seen how money can be something that fosters autonomy and possibility. It’s enabled me to live alone, live where I want, pursue jobs that bring joy, travel, make time for things and people I love. And as an entrepreneur, acknowledging the power of money has also led me to see what money can literally buy at an organization, particularly as we build something from the ground up: increased compensation, more expansive and revolutionary benefits, wellness supports, a larger (though not too large) team so individual roles are more focused and sustainable. And in all of that, I can trace the chapters of my history to see that while talking about money is hard for me, it’s also something that I see is critical to do as we imperfectly, though so whole-heartedly cultivate a truly inclusive, human-centered workplace.

As I listened to my colleagues share their own reflections around money, I heard very different experiences. Their stories took different shapes given our differences in identity, relationship with power, ancestral and generational history, past workplace trauma, and personal set of values. These differences matter and shape how we each respond to workplace conversations about money. Our relationships with money are in the room when we’re making decisions that carry budgetary implications; they’re present when we’re engaging in strategic planning or going through our annual benefits exercise inspired by our friends over at EdFuel. They’re a part of why things come easy or hard when pitching our work to new clients or supporting current partners through conversations about what future work can look like. They show up when we engage new tiltForward fellows and find ways to support them in our program. Our relationships with money are there, period.

What I realized is this: there isn’t a right way to talk about money. Maybe there is a right way to calibrate how often and when to talk about money; maybe, there isn’t. But talking about money is hard — and for a lot of reasons. I don’t have all the answers on how to make that challenge easier to navigate, nor do I think I ever will. But talking about our relationship with money — and how that feeds into our own workplace cultures, our own values and attitudes around work, our own personal and professional dreams, our own opportunities and challenges — that is something that so often goes unacknowledged, left to silence, assumption, judgment, complete erasure. If we take the time to hold space to reflect on and share with one another our relationship with money, that might just open things up for a richer (no pun intended, truly) conversation where we can talk about money at work in a way that moves us forward but doesn’t suck up all the oxygen in the room. As we head into November, many of us are preparing for new strategic planning and budget seasons, Giving Tuesday and End of Year giving campaigns, perhaps decisions around compensation or promotions, new roles or even team structures. Money shouldn’t be the only thing we talk about in these conversations, but when we do make time to talk about money, we can approach things differently.

We can make space to better understand what talking about money means for one another, what it brings up for us, why it matters to each of us and our work. There’s an opportunity here to reimagine things, to take a different approach where we see people before and beyond the penny and still talk about money, where we see each other, where we see you.