A 20-Something's Guide to Starting Over

We shall not cease from exploration, and at the end of all our exploring will be to arrive where we started and know the place for the first time.
— TS Eliot

Ivan here. Los Angeles is our sixth city in ten years. This means that on average, we move to a new city every twenty months. With any luck, we plan on being on the move indefinitely. It’s how we like to live.   

To us, moving is living. I joke with Jennie that the day we decide to settle down and buy a house may as well be the day we pick out our own coffins (I prefer maple, she likes bamboo.) Or as Woody Allen puts it in his film Annie Hall, “a relationship, I think, is like a shark. It has to constantly move forward or it dies.”  The last thing Jennie and I need is to have a dead shark on our hands.

While you can certainly ‘move forward’ without changing zip codes, it’s a special kind of thrill to be able to physically hit a reset button. It’s like flipping over a Monopoly board when the game has dragged on for too long. Therapy.

Over the years, we’ve gotten pretty good at starting over. Here’s a rough guide to this simple art:

Recognize when it’s time

There are no hard and fast rules, but it’s usually time to make changes when your days become virtually indistinguishable from each other. Sun comes up, sun goes down. Sunday starts looking like the inbred cousin of Saturday.  

This requires introspection: what is it that you want out of life? What are your goals? Are your routines getting stale? Are you starting to feel stagnant?

We try to keep in mind that time is the only currency you’re always spending that can’t be replenished. When you find that you’ve grown numb to time's passage, getting punched repeatedly in the face is preferable to feeling nothing at all. 

Plan Your Exit

If only in your dreams, you’ve already traveled to the city you’d love to wake up in.  Here’s your chance to make that a reality. That said, as hard-core planners, we don’t believe in making follow-your-heart, impulsive type moves. 

Spoiler alert: you know that movie The Beach starring Leonardo Dicaprio as the young dreamer who decides to go searching for the perfect beach, even though the guy who tells him about it ends up committing suicide five seconds later? Yeah, do the exact opposite of that. Get your ducks in a row. Have a game plan and plan on following through with it at least six to twelve months in advance. 

                                                                       Don't be this asshole. 

                                                                       Don't be this asshole. 

Make a Moving Budget

Moving is expensive. Between flights, a security deposit, first/last month’s rent and new furniture, you’ll need a minimum of $5000-7000 in start-up costs to move to a new city. A good rule of thumb is to track your expenses for a month and multiply that by six. That’s your emergency fund. Then plan to save another $2-3k on top of that. 

Keep Your Relationships

In the digital age, your relationships shouldn’t be crutches that keep you from doing the things you want. Outside of the person you’re going to be living with, you don’t really have to compromise on anything. Distance has given us a new perspective on the relationships that actually make a difference in our lives, and those are the ones we make the extra effort for. 

Ditch Your Things

We regard possessions as major inconveniences, which is why in preparing for each move, we sell or donate all our cheaply purchased furniture and purge everything that doesn’t fit into two large suitcases. 

If you’re moving to a city that doesn’t require a car, do yourself a favor and get rid of it. Cars are the worst (more on this in a later post). Having the luxury of ditching yours is often enough to justify your entire move. 

Take a Scouting Trip

Scouting your destination beforehand can really give you a leg up. More importantly, it’ll help you avoid the costly rookie mistakes in your first couple of months.  You’ll be surprised how much you can learn in just a weekend if you tackle it with a purpose. Ask questions, meet people, get advice from locals and simply walk around the different neighborhoods. 

Savor the Countdown

Life is strange. Nothing makes you fall in love with a city more than when you’re about to leave it. Starting over isn’t about running away, it’s about giving you a new appreciation for the here and now. 

Start a New Life

The first few months should be a balance between exploring new things and developing a routine. It’s kind of like jazz -- you improvise over a steady rhythm. Exploration gets you out of your comfort zone and a strong routine eventually gets you to where you want to go. For us, that's everywhere.