Move This Way
Move This Way cover graphic

Move This Way

Navigating the Emotional Transition to a New City
by Brian Sun


I was sick, almost broke, and no one within a thousand miles cared about me. I walked around the Inner Sunset neighborhood late that night, spiraling.

Less than three months earlier, I moved to San Francisco with a dream of switching careers from non-profit work to marketing in the tech industry.

Was I going to have to move back home to my mom’s house as a 28-year old dude? Did I have what it took to switch careers? Why didn’t I make new friends yet? Was I just a loser no one wanted to be around?

This moment of loneliness and failure wasn’t what I expected. At all.

The thing no one tells you about moving to a new city is that it’s not just physical, it’s also a mental and emotional transition. Yeah you’re moving outwardly—packing, unpacking, finding a new apartment, setting up internet, etc. But you’re also moving inwardly—new thoughts, new feelings, the mixed bag of emotions—in tandem with so much to love about the new place you’ve moved and all that you were looking forward to.

Perhaps you’re in a similar spot of transition. Maybe you’re getting ready to move and want to know what to expect. Maybe you’ve already moved and are feeling the pain of the in-between but don’t have the language to describe what’s happening. Or maybe you’re settled in life after your move and reflecting on what you’ve just experienced. Wherever you’re at in your transition, Move This Way is for you.

Based on my own personal moves from Phoenix to Flagstaff, Flagstaff to San Francisco, and San Francisco to Los Angeles, I’m going to walk you through a three-part framework—made up of movements—to help you navigate the emotional transition to a new city.

Movement one: Exit.
Movement two: Endure.
Movement three: Enter.

My hope is that you won’t feel alone in your move to a new city. I’ve been there, so I’m not sharing from a place of theory but from lived experience. I also hope to give you clarity and language about what you’re experiencing, and practical things to keep moving forward into your new life.

Let’s hop in.

Movement one: Exit.

The first phase is Exit. You’re leaving a place. You're moving on. This season in this city is coming to a close. What characterizes this phase is a mixed bag of emotions. Equal parts excitement for what’s next and equal parts sadness for leaving the city you’re in now. So much joy, so much loss. It’s bittersweet. In this movement it’s important to finish well, lean on friends, celebrate the past, and tell your story because you’re about to leave home.

illustration for: Movement one - Exit.

Chapter 1: Finishing well.

Cool Runnings is a film about the first ever Jamaican bobsled team and their journey to the Olympics. The group trained in the beautiful sunny climate of Jamaica (as in no winters), used a bunch of worn out equipment, and were athletes who’d never seen snow or ice in-person, let alone ever bobsledded in them. After multiple bumps along the road, the team surprised the whole world with their performance. Where things fall apart, and where I cry every time, is when on their final Olympic run their rickety old bobsled breaks and they go crashing into the wall about fifty yards before the finish line.

The Jamaican Olympians could’ve stopped there. Crashed. Broken. Done. But they didn’t. Their driver says “we have to finish the race,” and the four of them pick up their bobsled, and walk it across the finish line to the sound of a slow clap full of respect and admiration. They had finished well.

As you begin the Exit phase of transition, where you see the finish line—your move out date is set, you’re starting to pack up, you’re telling everyone you’re moving—resolve to finish well like our fun-loving Jamaican friends.

Finishing well is making the commitment to give your very best to end of your time in a place.

This is a hard thing to do. When we know we’re leaving a city, and won’t have the responsibilities in that city anymore soon, it’s easy for our mind and heart to drift to the new place that’s on the horizon. It’s the equivalent of moving senioritis. I get it. 100%.

We may say things in our inner dialogue like “I’m ready to get outta here” or “I’m so over this place” or “I don’t want to do anything I’m peacing out soon anyway.” Honestly, these thoughts are as normal as breathing.

But, and this a big but and I cannot lie, there is something special and significant to finishing well.

First, it’s a character thing. Being the kind of person who finishes well is a good trait to have as a human being. Everyone wants to work with or be with a person that sees things through to the end. No one has ever said, “Oh I love how Tina can’t see projects all the way through” or “Whoa Bob leaves friendships at the first sign of trouble, I definitely want to hang out with him.”

Second, it’s also a way to honor your relationships in your current city. For example, if you’re about to leave a job as part of your move, leaving people with a bunch of half-baked stuff on their plate isn’t cool. Finishing well is a great way to not burn any bridges and leave a good taste in people’s mouths.

Third, finishing well is a part of living a good story. When you look back on this previous city after the romance of the new city fades away, you want to be able to say “I finished that chapter well.”

With the why in mind, I want to highlight four specific areas where you can finish well. Your relationships, workplace, school, and humble abode.

Relationships. Say bye to everyone you want to say bye to. Ideally, do it in person. If you can’t, give them a call. Worst case, send a text.

What’s cool about goodbyes to people when you’re moving away is you can be as cheesy and sentimental as you want. I literally did this with my coworkers on my last day in the office. You walk up to your friends and say “Hey, I think you’re an awesome person and here’s why” and “Hey, I’m grateful for our friendship and here’s why.” No one ever does this but it means the world to people so do it.

Workplace. Don’t leave any half-baked projects on the table. Hand stuff off to the person taking over your responsibilities. Write LinkedIn reviews for coworkers you enjoyed working with. Leave a good taste in people’s mouths since your network often leads to your next thing that leads to your next thing that leads to your next thing.

School. I haven’t been in school in a long time but all the common sense principles apply. Give your all on your finals and your last papers since you're almost done, baby!

Your humble abode. Clean up well so you can get the security deposit back. Thank your landlord for renting their space to you. You might need them as a reference for your next apartment so don’t skimp on cleaning or kindness with them. Also, say goodbye to your place and relive the memories in the process.

I know you’re stoked to move on. But this is a chance to pick up your bobsled, get the slow clap going, and finish well in your current city. You got this.

Chapter 2: Leaning on friends.

John Donne, an English poet known for exploring the intricacies of love, sexuality, religion, and death, got sick in the winter of 1623. Apparently, being ill is when creativity strikes because at the time Donne penned these famous words that still ring true centuries later: “No man is an island, entire of itself; every man is a piece of the continent, a part of the main.”

No man is an island. If Donne were writing today, the poet would’ve likely said no person is an island because, progress. But anyhow the point still stands. A woman or man may believe they can exist apart from, or without the support of others, but we are most human and alive when we are in deep relationship with other people. What’s interesting is that the pull of a person being an island is strong, especially in America.

Anyone who’s lived in American culture for even a short time, sees the country’s focus on the individual. The rags to riches, pull yourself up by your bootstraps story wins praise and admiration. Thinking of “what’s best for me” is the norm, not the exception. Then there’s the all-too-common desire to “find myself” apart from others.

I'm not gonna lie, prepping to move to a new city on your own is tempting, but makes for a terrible solo act. Packing your boxes by yourself. Deciding the next job on your own. Mourning the place you’re leaving in solitude. No, not worth it. No, not good.

The alternative is equal parts countercultural and just plain practical: lean on your friends as you exit.

Moving to a new city is a moment in life where you can be extra forward and direct with your friends about how you’re doing and what you need.

You can be straight up and say “Here are the issues I’m dealing with. Here are the things I’m celebrating. Here’s what I’m learning. I’m bummed about X Y and Z.” Openness and keeping it real in this way gives your friends the opportunity to be there for you, and brings y’all closer together in the end.

Personally, I am leaning on friends right now as I prep to move to LA. Topics of conversation include being scared I’m not going to find an affordable place for my wife and newborn son where I don’t have to commute effing far to go to work. Also my work transition. I’m switching offices but still working with all the same people remotely at my old office. Will I lose cred I’ve built up over the past year and a half? Will I miss out on fun stuff that comes from being in the office? I don’t know how these things will turn out but I’m talking my friends’ ears off about all of it. They’re bearing the weight of the transition with me. Friends can help you and I do that when we lean on them. Friends can be the second pair of eyes you need to see with clear vision or the outside voice you need to bring clarity to your thinking or the listening ear you need to process what you’re thinking.

So, ignore the “you can do it yourself” voice and swallow your pride that doesn’t ask for help. Take a minute and think about a friend you can pick up the phone and call right now to talk about it. Ask them for advice. Share what you’re excited about. Get real about what sucks. Hear a different perspective on your situation than your own. Do it now.

You’re not an island, after all.

Chapter 3: Celebrating the past.

The peak-end rule is a psychological heuristic in which people judge an experience based on how they felt at its peak and at its end, rather than based on the total sum or average of every moment of the experience. Translation for when we’re moving: we remember our highlight living in a city and how we leave the city.

The definition continues on. According to the heuristic, other information aside from that of the peak and the end is not lost, but it is not used.

This is fascinating. The other information is not lost, but it is not used. But, that doesn’t mean we can’t tap into it.

One of your opportunities in the Exit movement is to dig deeper than the peak and the end to Celebrate the Past. Celebrating the past means reflecting on the good, bad, ugly, and everything in between from your time in your current city. The highlights, the lowlights, the everyday lights.

It involves asking yourself a lot of questions and giving yourself the space to think about your answers.

How did you grow as a person in character, wisdom, and experience? What did you learn that you can take with you into the future? Who did you meet that you want to stay in touch with because they’re a friend now and you love them? What are the moments that stick out in your mind because they mattered and made you smile and you never want to forget them?

Again, there’s always bad to look back on too. “Ugh I hated that part of the job.” “I’d never had a boyfriend with such bad B.O. ugh so San Francisco.” “Thin walls were the death of my sleep.” The good thing about this bad stuff is that it’s over and you can take with you what you learned. Loving the good and leaving the bad. Those are two great reasons to celebrate.

For example, I’m in the middle of doing this right now as I prepare to move from San Francisco to Los Angeles. It’s impossible to remember every moment of my seven years living in San Francisco, but I can go down the rabbit trail of asking every question I challenged you to ask, so I’m doing that. And there’s a lot to celebrate. I met, fell in love with, and married my wife here. I started a new career that’s fun for me to do everyday. I learned who I am as a city person. Also, I’m never going to share walls with neighbors again, putting on emergency car lights doesn’t give people a free pass, and I need to live near Southern California Mexican food. There’s a lot to celebrate.

Practically speaking, take an hour in the next week to sit down with a cup of chai, and write down everything you want to celebrate from your current city. You’ll treasure the list you make a year from now, ten years from now, and beyond.

Chapter 4: Telling your story.

Celebrating the past, our last chapter, is about you in your room before bed with the lights off, your iPhone on silent, and your mind and heart thinking about the previous season and being like “that moment was awesome” or “I learned from that.”

It’s solo. It’s individual. It’s your inner world.

As part of the Exit phase, all your reflecting, all your learnings, everything you’re celebrating good and bad, shouldn’t stay in the confines of your mind. You gotta let it out. You gotta tell your story.

Telling your story is about going public with your exit and sharing what’s happening. Write a blog post or a long ass Instagram caption if you want to be a stereotypical Millennial. Even better, meet up with friends who’ve went through what you’re experiencing. The people you trust that can be a sounding board that doesn’t try to fix everything. Trust me it’s therapeutic.

Telling your story is also intimate. Intimacy speaks to the shared experiences that we have with others and revealing of one’s self that leads to a lasting bond. By letting others in through telling them about this chapter you're ending, it's an opportunity to re-live, even for a moment, the intimacy and closeness you've experienced with one another.

For the socially awkward amongst us, here’s a few tips on how to initiate the meetup. A text. Assuming you’re already close: “Yo, drinks tomorrow night? Stuff went down and I want to give you the scoop.” This one’s easy since you’re friends already. Someone you haven’t talked to in awhile: “Hey, I know it’s been a long time since we’ve hung out. That’s on me. Would love to meet up and catch up. If you’re free, can we hang sometime this week? I’m buying.” This text acknowledges the reality, gives them out if they don’t want to chill, and makes it hard to say no since you’re buying. You could also do it the old-fashioned way by calling to ask.

Resist the urge to not meet up with others. Whatever the context, whatever the exit, don’t go through it alone. Tell your story.

Chapter 5: Leaving home.

Think of the city you live in. Your commute to work and/or school. The location where you go get groceries every week. Your fave hangout spot with friends. What’s interesting is when you’ve lived in a place for even a short amount of time, you have routes and spots and locations that come to mind. You know your way around. You don’t need Google Maps (most of the time). Your city is home.

When you move, you have to figure out these routines all over again. These are external transitions that come with the territory of moving to a new place. However, the real battle, the real jarring, comes from the internal transition of leaving home. The peace you no longer feel because nothing is the same. The uncertainty of how daily life will work. The bummed out feeling that comes from saying bye to friends and family. It’s all a part of the transition package, so let's call it out: you’re leaving home. This is happening.

If you’re excited about your move, and that’s the main emotion you feel, I totally get it. But a month from now when things are different, when your relationships are different, when your place is different, you are going to know deep in your bones that you left home.

I experienced this for myself. Before I moved to San Francisco, my heart overflowed with romance. The list of traits about my soon-to-be-home filled the pages of my journal like a sonnet to all the girls I’ve ever loved. The car-free commuting, oh la la environmentally friendly. The diversity of the population, so cool and cultured. The tech hub of all tech hubs, yesss. I fell in love with the idea of my new city, and wanted to get there as soon as humanly possible. Then I got here and realized I missed the mountain air of Flagstaff, the late night burrito runs with friends, and the city I’d spent the past nine years of my 20s in that became my home. The feeling was bittersweet. I’d made the move so many twentysomethings wax poetic about doing yet never do, but it cost me the comfort and security of home. I miss it.

Or, maybe you’re a different kind of excited for your move. As in you don’t care where you go, you just want to get away from your current “home” as soon as possible because you’re over it. Suburb life is boring, staying under your parent’s roof is a nightmare, and your high school friends are doing the exact same thing y’all did in high school and you don’t want that to be your story. I’m with you. Dissatisfaction is a damn good reason to move. But it was still home. That won’t change.

So whether you’re excited for your new place or tired of your old one, your Exit is here and that’s exciting. Everything in this movement brings you to this moment: you’re leaving home. Name it. Feel the weight. Finish well. Lean on friends. Celebrate the past. Tell the story. Soak it up. Pack your bags. Say goodbye. Because it’s time to get your move on.

Movement two: Endure.

The second phase is Endure. it's about enduring because this phase sucks. It's the hardest part of moving because you're navigating a weird in-between zone where there's no solid ground to stand on. It’s the first time in a long time you’re experiencing what your day-to-day life is like apart from your previous city. You have to find a new normal, build new habits, and redefine who you are in your new place. In so many ways, this phase is just about gritting your teeth and getting through it.

illustration for: Movement two - Endure.

Chapter 6: Acknowledging your need.

I sit in the airport waiting to board my flight to San Francisco. It’s not round trip, it’s one-way baby. I have three months’ worth of money in the bank to try and find a job and start a new life. A well of emotions bursts inside of me as I sit there on an ordinary day in the terminal—excitement and fear, anxiousness and anticipation, along with a whole lot of wtf am I doing and omg I love this place I’ve only ever visited for less than a week. Yes this is really happening.

Whether your one-way trip is on a plane, train, or automobile, the experience feels like the beginning of a new romance with infinite and nothing-but-amazing possibilities ahead. In a new city that translates to new everything. New place. New neighborhood. New restaurants. New friends. New work. New routines. New etc etc.

The newness feels fun and great and never-ending until it doesn’t. Without fail, maybe a week in or three months in, there’s a crash after the high. The romance of the honeymoon phase fades away and you’re left with the reality that all the new stuff isn’t as cool as you thought it would be. That public transit is good and green but crowded and smells like a homeless person. Or you liked your boo more when you were long-distance. Or your dream job you moved for really is amazing but it’s not the cure to your desire for a meaningful life.

You’ve entered the Endure phase.

At this point in your move, you have two options. The first is to live in denial that you’re in a hard spot with all the transition. You could do that, but it won’t be pretty. The reality of your inner world has a way of bubbling up to the surface even when you don’t want it to. The second, and better, healthier way, is to acknowledge your need.

Acknowledging your need is a fancy way of admitting “I need help in this transition.” The word “acknowledge” could also be said as be straight up about it, be honest with yourself, and tell the truth about what’s really going on. The Endure phase’s practices start here, and set you up mentally and emotionally to tackle the rest of the bummer things you’re going to experience before you feel at home again.

If pride and self-sufficiency are your natural go-to when any feelings of weakness or neediness pop up, I totally get it, but now is not the time or the place for either. The pull of moving’s difficulty is too strong and you want to navigate this transition well. Besides, I’ve heard it said it before that weak is the new strong, because it takes strength to admit your weaknesses. So do the strong thing. Acknowledge your need. The Endure phase is just beginning.

Chapter 7: Being lonely.

Here’s what loneliness looks like.

It’s a Friday night. You’ve been living in your new city for a month. Your two temporary roommates who you barely know went out of town for the weekend away from your temporary apartment. No one wants to spend Friday night hanging out with you because no one you’ve met knows you well enough to want to spend their Friday night with you plus they’re already chillin’ with their own friends tonight and you’ve already reached the end of Netflix so you just turn off the lights and lie there in the dark in your temporary nothing-on-the-walls room. And it’s only 7pm.

That, my friends, is the loneliness of moving to a new city. The description also sums up my typical Friday night for months after I made the leap to San Francisco. I lived it, and felt the sting. What no one told me that I want to tell you is that no matter where you go—Portland, New York, San Francisco, Boise, wherever—you’re going to be lonely for a season. This is normal. You’re not crazy. You will make friends. But for awhile, you’re going to be lonely. It’s a part of the move-to-a-new-city package.

Personally, I moved from a place where I had lived for nine years through college and my first job post-college. When you’re in a place for that long, relationships happen in a natural and organic way. College friends. Work friends. Sports friends. Mentors. Mentees. Roommates. Lovers. Random store and restaurant employees. It’s easy to forget that all of those people are in your life before you move. Then, you step foot into a new zipcode and the void hits you like a ton of bricks.

Susan Pinker, a psychologist, social scientist, and author of The Village Effect: How Face-to-Face Can Make Us Healthier and Happier, found that by interacting face-to-face with a diverse set of relationships in our daily life, we live longer, release more feel-good chemicals in our brain, and even gets jobs faster. For example, if you’re surrounded by a tightly connected circle of friends who regularly gather to eat and share gossip, you’ll not only have fun but you’re also likely to live an average of fifteen years longer.

As humans, we intuitively know these research-backed truths. Loneliness bad. Relationships good. I highlight Pinker’s findings not because we don’t believe them, but because building the village she’s talking about takes time when you move to a new city. A village isn’t built in a day.

What’s interesting is the situations where we move to a new city for a relationship or relationships. Like the long-distance girlfriend or boyfriend you couldn’t be apart from any longer, or the family you grew up with, or the group of friends you’ve been texting with everyday for the past five years. These moves come with a unique flavor of loneliness. On one hand, it’s like you’re entering the familiar space where you pick up right where you left off, but on the other, things aren’t the same as the last time you lived in the same place. There’s two reasons why. The first is the context is different. Home has changed since you left, you’re not in school anymore, and your people have routines that look different from your previous situation together. The second reason is a harder pill to swallow: the people you move for may not be able to fulfill all of your relational needs. Romantic relationships especially come to mind here. Your boo can’t be your everything. You need a village.

I eventually moved out of the temporary apartment, found some cool roommates, got involved in different communities, met some dudes I liked chillin’ with, and started a relationship with my future wife, but I still remember my Friday nights alone like they were yesterday. You’ll make it through. Just expect it, and endure it.

Chapter 8: Coping to get by.

Bad habits. Vices. Crutches. Whatever name you call ‘em, we all have ‘em, and they have a way of going into overdrive when you move to a new city. The reason why is transition is vulnerable. It’s like the feeling you get when you have stage fright and everyone’s eyes are on you and you feel like they’re seeing every imperfection you have. It’s like that but the being exposed part doesn’t require a stage, it’s already happening inside of you. “Why hasn’t this move been as cool as I’d hoped?” “How come I haven’t made friends yet?” “Can I really make it here or was this a mistake?” “Do I even belong in this city?” “Should I move back?”

A healthy person would think of these questions in their head, come up with logical answers to each, and then utilize proven tactics and techniques to deal with their fears and doubts. Yeah I didn’t do that when I moved to San Francisco. If you’re already an expert in not turning to your vices for comfort in difficult times, then feel free to move onto the next chapter. The rest of us are going to stick around and talk about coping to get by.

Earlier, I told you about my typical Friday night alone in my temporary apartment with my temporary roommates being out of town and me sitting there alone in the dark at 7pm. This was before I had found an apartment, a consistent full-time job, and any close enough friends in the same city who’d even want to chill together on a Friday night. Major bummer time in my life.

The way I dealt with it was even more sad: I watched more porn during that time than I ever had before. No matter where you stand on porn, binging on it was a bad thing because of the why underlying it. Honestly it wasn’t about getting off or whatever, it was about control. Porn was an escape from the shitty feeling of being alone and from being terrified that the new life I dreamed about and hyped up to my family and friends wasn’t going to work out and I’d have to go back to my previous city or even worse my hometown telling a story about how I moved to run after a dream and failed.

Porn was my vice. My unhealthy coping mechanism. I’m going to list a bunch to help you identify yours in case you don’t know it off the top of your head. Drinking, especially by yourself, to the point where you don’t remember anything because you don’t want to remember anything. Eating your emotions, which is bad because you gain weight and that makes you even more sad. Getting freaky with a stranger to feel any sense of human connection and catching gonorrhea. Doing the workaholic thing, which feels good for awhile but never satisfies like relationships do. Maybe drugs. I don’t know, you tell me.

If you’re in the middle of a new move and the honeymoon phase is over, your vice is probably upfront and center. The best thing you can do right now is to name it, call a friend to talk about it, and then do the stuff healthy people do like journaling to deal with it and joining a club to make lasting connections. Because the vices aren’t your way out. As humans we know that intuitively, the tough part is resolving to live it.

If you’re going to move and reading this book to prepare, that's awesome. Your big takeaway is to be mindful that your vices will likely come to the surface during your move so be ready. Be aware. Be prepared.

Even if you are stuck in or fall into your bad habits to cope, it happens. It’s the equivalent of stumbling through the Endure phase. Two steps forward, one step back. But don’t despair, there’s light at the end of the tunnel. Just keep moving forward.

Chapter 9: Living in the in-between.

When I want to zone out at work for a few minutes, one my my favorite things to do is open up LinkedIn and mindlessly scroll through my network’s updates. Most read like really bad poems or humble brags or thinly veiled sales pitches, but every once in awhile I come across a gem that actually teaches me something new.

A recent favorite came from a former marketing client of mine. He said that we only have time for seven things in life but realistically we can only prioritize three of them at a time. In no particular order of importance, the list includes family, friends, work, exercise, sleep, passion projects, and travel/vacation. I don’t agree that we can only prioritize three at a time, but that’s for a different conversation.

What’s interesting about the list that I want to highlight is how out of whack those seven things get when you move to new a city, because your individual relationship with all of them changes in the transition. If you move closer to family, does that mean you have to attend all the family parties you had an excuse not to go to before? How are you going to stay in touch with friends in your old city that you used to see in-person every week? What’s your commute to your new job look like? Where are you going to hit up the gym? What does your bedtime routine look like in your new spot? When do you work on passion projects? What are the coolest places for day trips around your new city?

These are probably questions you forgot that you asked in your previous city when you first moved there too. The reason why is because we ask these questions when we’re going through a change, when we’re living in the in-between.

The in-between is another name for the whole “Endure” phase of moving to a new city. There’s no rhythm. No routine. You’re still trying to figure out your relationship with all the pieces that make up the pie of your life. That’s on the outside.

On the inside, the in-between is where you don’t feel settled. I’m not talking about the bad kind of settled where you chose the lesser thing, but the good kind of settled where you feel a sense of place and rootedness and like you’re standing on solid ground.

I felt that unsettled feeling, especially on the work front in my move to SF. The only way this whole moving-to-my-dream-city thing was gonna work was if I got stable full-time job. Passion and excitement weren’t going to pay the bills, and a few short-term freelance contracts weren’t a good long-term strategy. Landing a legit job was also the key to unlocking the other pieces by freeing myself from the worry of going broke to think about things like where I wanted to exercise, who I wanted to be friends with, and how I wanted to stay in touch with family. I share this story because the work piece is usually the domino for the rest. Figure that out first.

My other advice to you as you’re living in the in-between: take the time to think about and build new habits and rhythms that you want. Unless you’re going back to your hometown, you’re working with a blank slate in regards to family, friends, work, exercise, sleep, passion projects, and travel/vacation.

Bring the best of how you did things back in your previous city, and combine it with the newness of the now. You’re headed toward settledness as you Exit, Endure, and ultimately Enter, but at this stage, the in-between is real. Both on the outside and inside.

Chapter 10: Receiving grace.

Grace is getting something you don’t deserve. It’s generosity backed up with action. A gift.

The beginning of the Endure phase starts with acknowledging your need, and ends with receiving grace. There’s so many vulnerable and tough moments along the way. Coping to get by. Making friends awkwardly. Living in the in-between. Experiences like these tend to nudge us back toward the people we’re comfortable with who can come alongside us in our bumpy ride. Their friendship is gift. Their friendship is grace.

So take a minute to reflect on the family and friends who’ve been a rock for you during this time. Thank them. You aren’t meant to go through tough times like these alone, and the people who walked with you through it are keepers.

My sister was one of those people for me, especially on my worst night in San Francisco. This is the moment I talked about in the introduction, which was about three months after my move. I was almost out of money. If I ran out, I’d have to go home, a failure. I was sick so my voice sounded weird. And the few friendships I’d started were out of town. Meaning, there wasn’t a person within a 1,000 miles that cared about me. So I did what any twentysomething dude would do—I got drunk. Just kidding. I called my little sister.

Jade, my four years younger than me sibling, is the best listener and counselor. Plus she’s my sister so she knows what I need to hear. We hopped on the phone and I gave my sob story of “I’m almost out of money blah blah blah why can’t I get a job blah blah blah the people here suck blah blah blah.” She listened. Let me process. And at the end of the conversation, my sister told me something that stuck with me: “Brian, you’re going to be okay.”

She was right. I was going to be okay.

I’ll tell you this just in case no one’s told you yet. You’ve been through a lot in this transition. You’re going to be okay. Yes, you’re going to be okay.

There’s a second dynamic of receiving grace I want to go into. It’s the grace we give ourselves when we don’t have it all figured out but we feel like we should already. Let’s stop there and talk about a word in that last sentence. That word is “should”. It’s a subtle word that’s usually followed by the thing we think we’re “supposed to be doing.” Try noticing every time you say “should” in regards to yourself, especially in a move to a new city.

“I should have made my friends by now.” “I should be at this level already in my new job.” “I should feel settled.” “I should I should I should.” Stop it. In a move to a new city, there is a natural flow of Exit, Endure, Enter, but the word “should” isn’t included in there. Rome wasn’t built in a day, and feeling at home in your new city doesn’t happen overnight. Give yourself grace to stumble along in the process of it all in your journey from old home to new home.

If you’ve made it this far, the hard part of the Endure phase is over. You’re on your way up. One time I was reflecting and this visual came to mind to illustrate the journey of moving to a new place. I’m standing. I kneel. I’m face down, desperate, needy, vulnerable. I’m humbled. I receive grace. I’m kneeling again. Now I stand again. New.

The journey to a new city is standing proud and tall and rooted, then being humbled by the difficulty, getting to your lowest and letting that shape you, then slowly learning how to stand up again proud and tall and rooted, because you endured to get there. We all want to stand again. That’s the next section. Where we Enter.

Movement three: Enter.

The third movement is Enter. It's what comes after enduring, where you're close to or figured out your new normal. It's the feeling of settledness. You say goodbye (again) to your previous life stage but it feels different because your new life is here. It’s like when you start a new job. It's the moment where you transition from ramping up to saying to yourself "Okay, I know what I'm doing now. I belong here." You've entered a new season, a new stage, a new you.

illustration for: Movement three - Enter.

Chapter 11: Saying goodbye (again).

There are two major goodbyes in your transition to a new city.

The first happens in the Exit phase when you’re looking back on all the people, places, and things you’re going to miss. Your inner dialogue may have sounded something like “I know I’m leaving. I know I need to do this. I know I need to say goodbye to this season of my life. But this sucks.” It’s a fresh wound with unknown after unknown in front of you, and the rough Endure phase throws an ungodly amount of salt on the wound. That goodbye is hard.

The second goodbye starts the Enter phase. It’s an active decision that helps you commit to the here and now.

Let’s take a quick step back and look at what you’ve experienced so far. At this point in the journey, you’ve been through loneliness, coping, and the desert wandering of the in-between. But you’re stronger because of it. You’ve hopefully made a few friends even if it’s been awkward. You’re starting to feel settled, maybe hopeful, and you know deep in your bones you’re not going back. This is a more rooted-in-your-new-place goodbye where you say bye to your old place again. As a different you.

I’d love to put an exact time frame on when the second goodbye goes down and say something like “oh this happens about seven months in” or “you can expect that during week sixty two at 7:29pm” but I’d be shooting in the dark. Instead, let’s talk through what the second goodbye feels like to help you recognize when you’re ready to do it.

The second goodbye is when your day-to-day life in your new city starts to feel more natural to you than your day-to-day in your old city. New friends. New job. New commute. New apartment. When you stop placing the word “new” in front of all that stuff in your own inner dialogue. They just become your friends. Your job. Your commute. Your normal. This is a telltale sign you’re ready to say goodbye again.

Another sign is when you find yourself daydreaming more about your future in your new city than about your past in your old city. This sounds like “Omg my list of restaurants to try keeps getting longer” and “I could see myself here for awhile” and “Living in that neighborhood across the city would be way cool.” It’s a shift where when your mind wanders it goes from there to here.

Then there’s when your new routines start to feel like second nature. Habits like where you eat, shop, hang out, go on walks or whatever becomes “this is how I do things” instead of “ugh but I’m used to doing it this way.”

But most of all, it’s when you wake up in the morning and realize you’re not going back. Your life, for this season, is here. And you have peace with that. Shortly followed up by a renewed resolve to figure this shit out and make the best of it. To enter well.

Chapter 12: Resurrecting your values.

The Myers-Briggs personality test comes up all the time in my conversations with friends. We use the different types as a springboard to explain how we recharge, take in information about the world, make decisions, and manage our life. It’s interesting that four little letters turn into endless conversations about how we’re wired as individuals. It’s also like crack for people obsessed with self-reflection.

My personality type, the INFJ, spends endless brain power figuring out what we value and why we value it. As the INFJ goes about their day-to-day on planet earth, every conversation, image, place, and message helps define and redefine an INFJs constantly updating value system. If this sounds crazy and stressful, you’re right, it is. But an INFJ’s inner world looks exactly like another person’s inner world: someone who moved to a new city.

Here’s what I mean. When you move, your life becomes a blank canvas. Your mind and heart starts trying to answer certain questions consciously or subconsciously. “What do I want my life to look like in this new place?” “Who are the people I want to hang out with?” “How am I going to spend my time?” “What do I care about now?”

You have two paths you can walk in response to these questions. Passivity is your first option. But that sounds terrible, doesn’t it? Who wants to be passive? Nobody. It’s the let-other-people-decide-for-you road. Doing nothing will lead you down this default path.

Proactivity is your second option. This is where you make the time to nail down what you value and why you value it. Intentionally. Mindfully. What do you care about in this new season of life? Why? What does this look like on a yearly, monthly, weekly, and daily basis? Go somewhere quiet. Figure it out. Make a list. Just do it.

Here’s an example of what your values list could look like. Bonus: I added actions in response to the values.

I value not being a selfish bastard, so I’ll donate 10% of my income every month to a charity I believe in.

I value my relationships with family and friends back home, so OK I’ll finally participate in that group text thread I put on “Do Not Disturb” a few weeks ago.

I value being awesome at my job, so I’m going to read one book a week to keep growing in my knowledge and craft.

I value being a well-rounded person, so I’ll take up a few hobbies and not just work or watch Netflix at night. Maybe cooking. But no vegetarian recipes.

I value mental, physical, emotional, and spiritual health, so I’m going to make a values list like the author of Move This Way said I should.

Get the picture? A simple list with what you care about, why you care about it, and what you’re gonna do about it.

Last thing: You are starting with a blank canvas in your new city. That’s true. But you also lived what you valued in your previous city. As you bring definition to how you’re going to live in the here and now, resurrect the values from your last town that still ring true, that stuck with you, that are a part of you.

Bringing definition to your values feels like taking the driver’s seat instead of being a passenger along for the ride. You choose the direction. You make the map. You decide what the ride looks like. And after you’re done, be glad you’re not an INFJ defining and re-defining your values all...the...time.

Chapter 13: Finding community.

Every month, San Francisco magazine features a “pictorial study of uniquely Bay Area tribes.” After flipping back through the old issues on my bookshelf, I discovered a number of weirdo people groups. My personal favorite: The Senior Sartorialists of Chinatown. The magazine chronicled their vibrant, unexpected style—think jade-colored Keds with a speckled 80s print. Urban Outfitters shoppers, eat your heart out.

Another group includes The Children of the Swoosh who, of course, exude coolness. Their name is code for people who chock up the dough for Kanye’s Yeezys and attend Sneaker Con every year (yes the conference exists and I want to go). Then there’s the Rice Rockettes (best name) and the crazies into clubbing at 7am before work.

The list of niche communities goes on and on and on. As it’s been said, there’s something for everyone. Which also means there’s something for you. Now, let’s find you a community.

Before we dig into why and how to do that, here’s a chart of concentric circles showing how to think about your different relationships.

concentric circles showing how to think about your different relationships

The center speaks to your relationship with yourself. I believe the timeless phrase goes something along the lines of “love your neighbor as you love yourself.” Meaning, you gotta love yourself well to love your neighbor well.

Your next concentric circle includes your family and friends. As in your family in both your new city and everywhere else, and your friends of old as well as the new friends you’ve made in your new home.

The party doesn’t stop there. Your communities come next, and then the world. As a good human being, you want healthy relationships with all parties involved. But let’s focus on your communities.

Once you’re in a good spot in your inner world and made a few friends, branching out to communities in your city is both a fun and natural next step. For our purposes, we’ll define a community as “a group of people pursuing the same goal or interest” It’s like the Senior Sartorialists of Chinatown pursuing style and fashion together. Your co-workers fit into this category too, but let's focus on outside-of-work communities.

Shane Hipps, author of Flickering Pixels, says that the three ingredients of a healthy community include intimacy, permanence, and proximity.

Intimacy. Going through things together. Good, bad, ugly, thick and thin. Permanence. Your relationship lasts a long time, like more than a three-month internship. Proximity. Being physically close to each other like living across the hall or sitting in the same pod at work.

Intimacy, permanence, and proximity all sound nice on paper but anyone who’s been out of college and moved to a new city knows how hard it is to find community as a grown up. Unlike college, the three ingredient recipe feels all the more harder to come by. So you have to take the initiative.

Step one is pick from this list of communities to join and/or add your own.

Weekly sports games. Find where the soccer, basketball, or ultimate frisbee regulars do their thing.

Faith groups. Seek out people running in the same direction as you are in your spirituality.

Improv classes and theater troupes. If you’re into acting and humor and performance and yes-and.

Writers, filmmakers, musicians. People on the same creative wavelength as you working towards making dope stuff in the world. Y’all can spur each other on.

Coworking space. Okay, I know I said outside-of-work communities but a coworking space is a great spot to get to know other people in your industry. Great if you’re career-minded.

What’s not on this list that you’re into? Civil war reenactments? United Vegans of America? Take a minute and brainstorm.

Step two is to pick a group and go.

This is where you go to the meeting / gathering / class and see if it’s for you. And by “it’s for you” I mean “can you picture yourself chillin’ with this group three months, six months, a year from now?” You might need a few visits to decide. Feel free to check out multiple groups at once. All good.

The final step is to pick a group and commit.

Remember what our friend Shane said about intimacy, permanence, and proximity. Let’s simplify the ingredients even more into one call to action: just show up again and again. Relationships in a community don’t happen overnight and the ones that last are built organically, small interaction and experience after another over time.

Don’t be a flaky city person who sends the “oh I can’t make it tonight” text then you just stay home and watch Netflix. Show up, put your best foot forward, and let relationships unfold organically. That’s how you put yourself in a position to find community in a new city.

Chapter 14: Putting down roots.

I’ve never been scared by a tree...until I went to Muir Woods. The tallest redwood in the area rises to 258 feet, or 86 yards, almost the length of a football field. Their height will make your jaw drop but the size of their trunks is what terrifies me, leaving me in awe and reverence.

Underneath the surface of the visible trunk and branches and leaves, what we don’t see are the roots. The roots go down deep into the earth providing nourishment, grounding, a foundation. Roots that took hundreds of years to get where they are today.

Moving messes with your roots. Leaving a city where you have family, friends, a job, habits, routines, go-to restaurants, and a home feels like uprooting a tree. The deeper the roots go, the harder leaving gets. Pulling out roots hurts.

Moving to a new city throws you into the opposite deep end and challenges you to put down roots...where you have none. The reason I say challenge instead of force is because we play a part in putting down roots in a new city. The process calls us to be active, not passive. To make things happen, not just hope they happen. Putting down roots is both an internal and external conscious decision.

When I was contemplating my move from Flagstaff, numerous times where I did my reflective person journaling thing, the phrase “put down roots” came to my mind and heart. I didn’t know what that meant. I just knew it sounded nice and it’d be good to do that wherever I moved. One night I told a bunch of my friends I was thinking about moving, and a friend, my homie Danny, encouraged me that wherever I put down roots. Danny saw a picture in his mind’s eye of tree roots going down deep into the soil, roots that represented relationships with people.

First of all, how cool is it that my friend saw the same picture/phrase I’d been seeing in my journaling without us ever talking about it before? The moment felt borderline divine, like I was receiving clarity from a power bigger than myself. Second, I now knew what putting down roots meant. Relationships. For anyone who’s gone through the Endure phase of moving to a new city, we know that no matter how cool a city is, living there without relationships sucks. People are greater than things.

I’ve lived in San Francisco for over six years now. I met my wife here. There’s a group of dudes I meet with monthly to talk about deep things. I eat dinner with my coworkers from my last job. I have a long list of places I want to show friends who come in from out of town. I put down roots.

As you Enter in your new city, choose to put down roots of relationships and place that go down deep into the soil. You live here now. Live each day like you’re going to live in this city forever. Live in such a way that if you leave one day, the uprooting process will hurt like hell.

The redwoods of Muir Woods come from a seed no bigger than that of a tomato. Start throwing some seeds and plant your redwood.

Chapter 15: Calling mom.

This is gonna sound weird. And totally not something a 34-year-old dude usually does. I regularly ask my mom: “Mama, why do you love me?” and her answer is always the same: “Because you’re my kid!!”

It’s a phrase of unconditional love that makes me feel all warm and fuzzy inside even as a grown ass man.

I called my mom a lot during the Exit and Endure phases of moving to San Francisco. I leaned on her when I wasn’t strong, and I needed a friend to help me carrrryyy on. She was there, as well as the other family and friends I leaned on.

But as you Enter, the dynamics with your family and friends back home changes. The reason why is because as you’re entering, you’re finding steady ground in your new city and as a result, becoming less and less dependent and needy. People gravitate towards their closest relationships in hard times, but you’re through the Endure crap already, which is awesome.

“Calling mom” represents more than calling your birth mom. The heart of it is to do two things.

The first includes calling the people who walked with you through the transition process and say “thank you for walking with me through this process.” Gratitude is good. In this situation, saying thanks closes the loop on the bummer part of moving, celebrates that you’re in a new season, and does both things with people who saw you walk through the fire.

The second thing is to build rhythms into your schedule where you call your friends and family in your old city. Weekly, monthly, every three months, whatever.

Personally, I have a call weekly-ish and monthly-ish list, a call every three months-ish list, and a call yearly list. Be brutally honest with who to put in each category when you make your lists. Don’t worry you don’t have to show the lists to anyone.

Yes, I recommend calling. Be old-fashioned. I call this “the hierarchy of communication.” Face to face beats all. Voice to voice (including video chat) ranks second. Screen to screen like texting or Facebook messaging comes in third. Texting isn’t as rich or fulfilling as hearing a person’s voice or seeing them in person. But if text is all you’ll do, then do that.

I’ll give you a bonus recommendation too. Put people’s birthday in your calendar, and call them every year on their birthday. No one does this. And the friends you do it for will think you’re weird, then think you’re cool, and then remember that you did this and be happy about it.

I’ll be honest, I call about 70% of the time and text the other 30%. I texted one of my high school best friends the other day to say happy birthday, and he texted back and said: “You say happy birthday to me every year and I appreciate it. Let’s catch up soon.” This small touch does wonders for keeping your bonds alive with people who live far away.

Relationships fill our cities, and our lives, with meaning. At the risk of sounding like an infomercial, pick up the


The same spot where I was at my lowest in my move to San Francisco is a spot I walked by hundreds of times over seven years of living there.

I made it past that night where I almost called it quits. I completed my move, the emotional move—I exited the old city where I lived, endured the terrible in-between, and entered into a new chapter of life in a new city.

No matter where you’re at in your move, I believe you are on your way to your new chapter in your new city.

You’re not alone. You now have language for the emotional transition. You’re making forward progress. You’re exiting, enduring, and entering. You’re moving forward. Remember to move this way.