I’m Hannah. I write words, chase joy, read books, build habits, make lists, and drink coffee. Care to join in these adventures?

How to Anchor a Sailboat

I’m a metaphor kind of gal. Give me a good metaphor & I’ll spend hours mulling it over, thinking about how I can make meaning from it or how it relates to my life. I’m big on how things apply to my life & how I can make meaning from that. So yesterday, on a casual Monday, I came into the office with a mug full of vanilla toffee cream and sugar, with a little coffee added in, and began to play Ben Rector albums. A song popped up that I hadn’t heard before, and all these lines started jumping out at me.

I feel just like a sailboat, don’t know where I’m headed. . . I’ve been lost and found, mostly I’ve been waiting. Oh I’m out in the waves and I’m hoping and praying: please let this wind blow me home. Night after night there’s an empty horizon and my God, do I feel so alone. Sometimes life, most times, I feel just like a sailboat. 

I really want to be the kind of person who stays: the kind of person who can tie concrete blocks to her feet and comfortably stand wherever God calls her to be, the kind of person that sticks with things and sees them through, the kind of person that listens & plants roots when God whispers, “I need you to stay.”

I am not that person yet.

I’ve always been a little bit of a runner. Not physically so (lolz Hannah running). But emotionally, there’s a certain point I try not to go beyond. So you can hear me make some jokes about my family situation, but I very rarely open up about how much it hurt to not hear from my dad on my 16th birthday & I run away if you push me on it.  A boy once looked at me and asked, “Why won’t you let me in?” & I just said because that wasn’t who I am and wasn’t what I wanted. I craft escapes. I rarely go into anything without knowing how I can leave it. I’m big on outs and exit signs. I liked leaving because I always thought I learned more about myself when I left. But I’m not a runner, so the running metaphor never really worked for me.

When I heard about sailboats today, I thought, “That’s it! I’m out on waters, I’ve been mostly just waiting.” I think of sailboats: always adjusting the sails depending on where the wind blows. And when I think of who I am as a person, I am so guilty of adjusting the sails - generally because I’m scared of a storm. Or because I just want to follow a different wind. Or because I want to go to a new place or try a new thing. I am constantly shifting my sails and I never, ever stay put.

And I think, maybe, possibly, God is trying to teach me how to stay. How to anchor my sailboat.


I have to do this weird thing called “graduation” in ten months, and then this other weird thing called “adulthood” comes into play and a strange experience called, “real life” is supposed to happen. Naturally, the well meaning and curious questions of, “What are you going to do after school?” come up on a pretty frequent basis these days. I have no easy, concise answer to this question, so generally I ramble on about how I like a lot of different things and am interested in a lot of different areas: in universities, in fundraising, in designing greeting cards, in non-profit admin work, in weddings, in anything and everything. Lately I’ve started to tell people I just want to love people like Jesus did and help them tell their stories in whatever muddled way we can. (The looks people give me after I say that are pretty priceless.)

I’m becoming more and more comfortable with this ambiguous answer because my life has a tendency to change dramatically from what I thought it would be a year ago. If 20 year old Hannah knew what 21 year old Hannah was going to get up to, she would have laughed in your face and said, “Probably not. Try again.”

But I do make grand, sweeping statements about where I want to be after school. I’ve talked a lot about moving to British Columbia and trying out some university jobs there. Not because I know anything about the schools or because I’ve ever even visited BC, but because I like the Instagrams of mountains and I like the idea of leaving Ontario. I like the idea of a grand adventure & starting fresh, where no one knows who I am. I like the idea of adjusting my sails away from whatever storms Ontario may have in store for me. I also talk about various other universities. Or I talk about starting a business. Honestly, everything is an option and what I talk about depends on what day it is right now. But staying doesn’t often feel like an option.

Part of not wanting to stay is the fear of being seen. Of sticking around and letting people see you as more than a student, or to just see you as the authentic person you are, instead of Highlight Reel Hannah. Part of not wanting to stay is that it’s just not in my practice: I am a short term person. I spend a maximum of a year and a half at jobs, I have yet to have a relationship that goes beyond six months, & I don’t have a best friend that’s been with me since diapers. I shift sails too much to stay anywhere for too long, and I always shift before they can get to know me. And part of not wanting to stay is because if I’m always moving and if I’m always busy, I won’t have to deal with my feelings, I won't have to feel lonely, and I’ll be too busy to ever get hurt.

Right now, I think that’s why I’m comfortable in ambiguity: because I know I have the option to just sail away in 10 months.


At some point, I got so scared of sticking things out that I started to stay it out loud: “I’m really scared and I want to run away.” I could feel it in my chest, a desire to bolt before I was seen and known. That’s my survival instinct: I need to escape & I need to be in control, so you can catch me and my sailboat far away from here. I told my people - the handful of them that know me well enough to know when to call me out on my crap - and the best answer came from an unrelated sister.

“Leaving is a grand adventure and I hope to do a lot of that next year. But sometimes, staying can be a grand adventure too, even if it doesn’t seem like much.”

Then she dropped the anchor and walked out.

Staying can be a grand adventure too, even if it doesn’t seem like much. 

For the girl who had never even considered staying to be an option, thinking about staying as a grand adventure was a pretty revolutionary concept. I spent the next week playing those words over and over in my head.

Donald Miller wrote an entire book about leaving, and I loved it. He says this: "I want to repeat one word for you: Leave. Roll the word around on your tongue for a bit. It is a beautiful word, isn't it? So strong and forceful, the way you have always wanted to be. And you will not be alone. You have never been alone. Don't worry. Everything will still be here when you get back. It is you who will have changed.”

Right now, I keep replacing his "leave" with "stay". I'm rolling it around, repeating it over and over. I’m leaning less towards lost and more towards found. I’m trying to envision what staying looks like in my life. I say it out loud a lot because I love words & I love trying to make them feel safe. And every time I say it out loud, there’s this sense of calm that washes over me. Like, “Hannah, my dear. I know you like bright and white sailboat shoes. I know you like adjusting course. I know you feel like a sailboat that’s just going with the wind. Make staying the adventure. I know you hate staying, because that generally means I’m calling you to stand in something you are afraid of, something hard. I just need you to drop the anchor. Let me show you I do good things.”


I don’t know what dropping the anchor looks like. I don’t know where to drop it. I’m pretty sure I’m not supposed to drop it alone. I just know that right now, God seems to be teaching me how to anchor a sailboat. Even if that's a lesson I don't want to learn. 

So here’s my hope for all of us runners, for the ones that are scared to stay, & for those of us who feel like sailboats. I pray that when you want to run, you pray for roots instead. I pray that when you are scared to stay, you try to dig in a little bit. And I pray that when you feel like a sailboat, when you feel tempted to adjust sail, that you let others come alongside you to help anchor you. I pray that when God calls you to stay, you drop the anchor and you stay.

A Collection of Lessons Learned Over My Last 8000 Days on This Planet

Twenty Nine: Eleven to Thirteen (Alternatively Titled: Why I Got My Tattoo)