when is it time

I’ve been thinking a lot about timing, trying to answer the question How do you know when it’s time for a change? Lately I’ve been spinning my wheels in what feels like a decades-old groove carved out of past decisions that no longer fit. When I look back at each big step that led me here, I realize most of my choices have been predictably safe. I would even argue that I’ve been a fairly passive participant in my own decision-making, merely taking other people’s suggestions and building a life out of them.

Where I went to college (my mom had a friend whose daughter went to Wittenberg); what I majored in (“Political science is so versatile, Annie, you’d make a great lawyer…”); even the start of The Envelope (someone literally called and asked if I wanted to go into business together)…all of these monumental life events were other people’s ideas, not mine. I’m not proud of it, but I didn’t spend a lot of time asking myself what might be best for me, or figuring out what inspired me so I could go after it. Someone plopped a suggestion in my lap, and I took it. Over, and over, and over again. And I have been extremely fortunate to have so many things pan out. That doesn’t change the fact that it largely feels like my life has happened to me, and I’ve just been going along with it.

At 17, before I had ever heard of Wittenberg, I applied to schools primarily in the Carolinas (I had fallen completely, irreversibly in love with the ocean), Florida, even as far away as Arizona. I craved change and was excited to see what was waiting for me, outside of the tiny town I grew up in. Instead, because it was geographically close and we knew someone there, I did an overnight visit to Witt, never questioning whether it was what I really wanted. It seemed fine, so I packed up my Ford Probe and moved to Springfield, Ohio, telling myself I had the rest of my life to land somewhere else.

Four years later, when I looked at law schools, I was determined once again to get out of Ohio. I applied to Wake Forest, Boston College, University of Maine, Notre Dame–not a single Ohio school. And then I got a letter from the University of Dayton saying they’d waive the application fee and more than likely offer me a scholarship. I spent 20 minutes completing their online app, received a scholarship offer, and realized a 30-minute move down the road would be easier than going out of state. I started law school at UD in 2001. Did I stop to ask myself if I wanted to live in Dayton or have a career in law? Not until a year later when I couldn’t stomach even one day in class as a 2L. But even then, it didn’t hit me that I was free to do whatever I wanted, and go wherever I wanted. I had just gotten to Dayton so it never occurred to me not to stay. Maybe I lacked conviction. Maybe I didn’t know how to dream bigger. Or maybe it was, simply, easier to stay where I ended up.

This happens again and again in life. We find ourselves in jobs, relationships, towns…repeating, repeating, repeating what we’ve always done. Even if there’s a whispering sensation in our gut saying this might not be what’s best for you, or pssst, you aren’t particularly happy here. The truth is, some of us tend to choose what’s comfortable, even if it’s not the life we imagined for ourselves back when we still made time to dream. But I am learning that what is comfortable isn’t always as meaningful as it should be. And I want to live an intentional life. To keep growing, sometimes we have to take risks.

So this year, with an empty nest and the ability to work remotely, after a LOT of discussion with (and encouragement from) Paul, I decided it’s time to head to North Carolina. Finally. We aren’t selling our Dayton house right away, for several reasons, but at some point this will not be sustainable and we’ll make the move permanent. Am I 100% sure I’m making the right decision? No. But I’m also really afraid not to at least try. For once, I’m making a decision for myself, without anyone else’s influence (OK, Paul did get a say, but that’s kind of par for the course when you’re married). It is still an uncomfortable decision. It is not the safe, easy choice. But we are still doing it. And that’s something a lot of people don’t understand.

Many people, especially our close friends, have asked me why we’re leaving. Some seem wary, as though by wanting something different for ourselves, we are somehow insulting their choice to live here. Others have actually made snide remarks, like the man at the post office who rudely remarked “how nice it must be having this problem,” despite the fact that I was just looking for some guidance about what to do with our mail while we’re going back and forth. And through all the scrutiny and lack of understanding, I have started doubting myself, questioning whether I did in fact make the right decision. Because the fact of the matter is this:

I have spent my entire adult life in one place. And that makes it hard to leave.

This was not an easy decision. We did not do this lightly, or without thought, and I have to remind myself of that. This is what we want. But it is not without loss. I am leaving nearly everyone I love, everything that I know, and all the comfort and familiarity that goes along with it. We have been fortunate to thrive here and there are countless things I’ll miss so much…Dorothy Lane Market, my Sunday tennis crew at Quail, and a whole slew of amazing restaurants and friendly faces. Dayton is a community that supports its own like no place I’ve ever seen. It’s a small city that feels like a small town, in all the best ways. I am not leaving Dayton because it isn’t good enough. I am leaving Dayton because I need to do this for myself, and I’m afraid if I don’t do it now, I never will. I am trying to finally make something happen that I chose, instead of just ending up with a life built on everyone else’s ideas.

I don’t know if this is going to be a good move for me. Hell, I don’t even know if now is definitively the right time to do this. How do we ever know when it’s the right time to do anything? What I do know is that if I don’t take a risk this time– if I don’t ever get out there and see what else might be waiting for me to come find it– I’ll always regret it.


Thinker, free spirit, mom. Lover of living life outside, breakfast tacos, and wood smoke.

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