Derek Hagen

I'm drawn to questions people tend to avoid

The uncomfortable ones.The ones that don't fit into a spreadsheet.

Hi, I'm Derek

I'm someone who has always been curious about how people make sense of their lives, especially when money, meaning, and identity get tangled together.For a long time, I thought the answers would come from doing things "the right way": getting credentials, learning frameworks, mastering spreadsheets. And while some of that helped, it wasn't enough.What I've learned through experience... and a lot of uncomfortable questions... is that the most important decisions we make rarely show up neatly organized for us. They show up in moments of uncertainty, transition, or change - when people are trying to figure out what actually matters.That's the work I'm drawn to.

My name is Derek Hagen, but my friends call me "D" or "D-Rock," so you can call me D-Rock.I didn't take the traditional path through life. I grew up the oldest of four, raised by a single mom, moving often, and learning early how to adapt. College wasn't part of the plan, mostly because there was no plan. I didn't step into higher education until my twenties, starting with technical school and eventually transferring to a university a few years later.My late start changed how I relate to learning. I don't take it for granted. I'm curious in a way that's less about achievement and more about understanding; understanding how things work and why people do what they do.

I spent years working. I was deep in the spreadsheets-and-calculators side of money. I learned a lot about investing, personal finance, and how to explain complex ideas simply. But something was missing.Eventually, I started paying closer attention to the psychology underneath financial decisions. I paid attention to how fear, values, identity, and uncertainty shape the choices we make. That's when it clicked - information alone isn't enough. Knowing what to do doesn't mean we're ready or able to do it.That realization changed the direction of my work.

Today, I'm drawn to uncomfortable questions - the ones that don't fit neatly into a spreadsheet. The moments where people feel stuck, uncertain, or caught between competing versions of themselves. That's where the most important decisions tend to show up.

Outside of work, I live in the Minneapolis area with my wife, Katie, and our two pets, Bingo the dog and Whiskers the cat. I regularly play squash in its many forms: singles, doubles, and squash57.I value simplicity, adventure, curiosity, humor, and mindfulness. We spend as much time as possible outdoors hiking, skiing, biking, and exploring - and often in our Airstream. Along the way, you'll usually find us sampling local wineries and breweries.I'm grateful for a life that's included everything from rafting the Grand Canyon to skydiving to reading more books than I ever thought I would.