The Conversations That Move Things Forward

Something we keep coming back to while building Two Degrees is how easy it is to underestimate the impact of a single conversation.

And we're not necessarily talking about the conversations that land a big client, unlock an opportunity, or change your business overnight. We're talking about the unexpected ones, the conversation that gives you a different perspective, helps you think about a challenge in a new way, or leaves you feeling a little more energized, confident, or clear than when you walked in. The kind of conversation that reminds you you're not the only person trying to figure it out. 

I've been thinking about that a lot lately because, looking back, those conversations shaped more of my own journey than I realized at the time. After spending years building a career in corporate roles, I never really pictured myself building something of my own. But when I did, I found myself asking questions I'd never had to ask before.

How do I actually set this up? What should I charge? Am I thinking about this the right way? What am I missing? 

In a lot of ways, it felt like being an entry-level employee again. I wasn't new to the work, but I was trying to figure out things that felt surprisingly basic and, at times, a little embarrassing to ask. 

What I struggled with most wasn't information. 'How-to' information is everywhere. It was finding conversations I trusted. The kind where you could ask a question honestly and get an answer that wasn't generic, performative, or trying to sell you something.

LinkedIn felt too performative. Instagram felt too personal. Most networking spaces felt like something I had to show up for, not something I got much out of. 

So the conversations that ended up mattering most often happened one at a time. Over coffee. Through someone saying, "you should really meet ____." Someone taking fifteen minutes to answer a question that felt obvious to them but wasn't obvious to me. Sometimes through someone planting an idea that I found myself coming back to again and again.

One conversation that still sticks with me happened years ago with a business owner who eventually became a friend and later a client. Somewhere in the conversation he said something along the lines of, "If you're willing to work that hard building something for someone else, why wouldn't you put the same into building something of your own?" 

I doubt he even remembers saying it. But it stuck with me, long before I realized I wanted my work to feel and look different.

Those moments are a big part of why I'm here helping build Two Degrees. 

Not because we have all the answers (we're still building too). But because we know how much those conversations matter, how difficult they can be to find consistently, and because it's becoming increasingly clear that the way we work is changing faster than the systems, tools, and communities designed to support us. 

Getting to know amazing humans like Yon, Michael, and Angela has only reinforced that for me (check out their interviews in the links below). They're building different things, coming from different experiences, and trying to answer different questions. But underneath their stories, I keep finding the same thing: people figuring things out as they go and looking for authentic conversations, genuine perspectives, and the right people to help them move forward.

If any of this feels familiar, you're probably closer to the kind of people you need than you think. 

That's who we're building Two Degrees for. 

People in the middle of building something. Looking for trusted connections, better conversations, and a community that understands what it feels like to figure things out as you go. 

More soon,
Kayleen
Chief Growth Officer