Should we move?

Plan Your Next - Letter No. 2

Hello from Silver Lake! It’s called that because of this huge reservoir named after Herman Silver, which happens to be a cheap (or expensive?) imitation of a real lake. By cheap, it’s like comparing Totino’s party pizzas to Pizza Luce—or Tony’s Pizza if you’re in SF; so good. You can get about 30 feet from it before you’re forced to climb a chain-linked fence. Lovely.

I get asked a lot about where we live, and since no one knows much about our area; here’s a drawing to confuse you even more:

Now that week one is under our belts, I’m feeling a lot less nervous than before. Thanks to everyone who wrote in! We have a group of 37 right now, so I’ll try my best not to lose anyone.

But, if this really isn’t your thing, unsubscribing is only a click away; maybe two. I haven’t checked yet. No hard feelings.

Finding better questions

Back in 2013, when Alie and I were thinking of moving away from Minneapolis, we went back and forth on why we should move, what if we moved, and how moving might change our lives.

I grew up in Minneapolis, so I had a lot of built up equity in the place and our friends. It was all I had ever known, but I had recognized that the place was becoming less and less a part of my identity.

In the big picture, people are more important than the place, even though I was identifying the two as one for most of my life. It’s hard not to.

But, I started to feel that my identity was at odds with the place I was in, and so that made it easier to disconnect the two. The people will always be there.

I didn’t have anything figured out, but as I was listening to my gut, I took time to ask questions of myself.

It’s easy for kids to ask questions because they haven’t applied neatly organized labels to everything. As an adult, it takes a bit more effort to step back and remove that insecurity around saying, “I don’t know,” or, “what if?”

Professionally, my immediate internal reaction when asking questions is usually, ”Shit, this is going to make me look like an idiot.”

“If you don’t have that disposition to question, you’re going to fear change. But if you’re comfortable questioning, experimenting, connecting things—then change is something that becomes an adventure. And if you can see it as an adventure, then you’re off and running.” —John Seely Brown

That voice appears a lot. I’m the sole designer at a startup, and my role is to move fast and find solutions quickly. Not spend too much time sitting back thinking of a myriad of ways to tackle a problem. Although I do my best to do that too, Aaron. (In case the boss is reading this.)

But that’s where there the problem lies for people like me, who have set routines and patterns that our good ol’ prefrontal cortex uses in making decisions as if it’s a day at the beach. No work involved.

Back in 2013 when we started thinking about moving, my progression of thinking went something like this: (which happens to be a common approach in design thinking)

  1. “Why” do we want to move?

  2. “What if” we move and don’t like it?

  3. “How” do we start to plan this out?

It would be easy to make the jump and do something irrational, and maybe to some people it seemed that way, but a ton of thought went into that plan.

Starting with “Why” gave me a chance to dig into why I even wanted to live elsewhere. Seems obvious, for sure.

Asking “What if” gave me the chance to have fun with the idea of moving, and to start to question all the fears associated with it.

  • “What if it didn’t work out?”

  • “What if I can’t keep my job? Are we still doing this?”

  • “What if we experience an earthquake?”

I didn’t always expect to find an answer there, but rather to just think through the scenarios and find some comfort in knowing that I spent time addressing those issues.

I’ll admit that I also found myself saying, “I’ll just deal with the earthquake if it happens.” It’s either confidence or stupidity, for sure.

“Often the worst thing you can do with a difficult question is to try and answer it too quickly.” —Warren Berger

Asking, “How” is a way to go from idea to action.

For us, “How” crystallized the idea and gave us a number of steps we had to take. One of which was to sell a house. But, it made everything seem simple and clear for us.

“How can we make this happen in the next 6 months?”

Going through that process doesn’t always provide an answer, but the act of going through those steps can encourage you to do the work to take action.

Why, What if, How. Easy.

An even easier method to make decisions quickly is something I learned from reading Mr. Money Mustache. Yep, that’s the name he goes by. Not a joke.

“Would this ‘X’ make me happier than I was before?”

It’s great for when you’re thinking about buying something, but it can be used in a much broader context.

For me, that’s as simple as it gets and is easily applicable to most decisions in life. For now, living in Los Angeles puts a pretty big smile on my face.

Making time for yourself to think

I recently had a 30 minute conversation with David Sherry, founder of Death to Stock . It was a form of creative therapy, and he was offering up time on his calendar to talk through frustrations—or roadblocks—keeping us from pursuing our own ideas. It wasn’t about having the answers, but rather letting me vent out loud, allowing myself to talk through problems, and hearing objective feedback or support.

I don’t always make the time to think about these things. And maybe you don’t either. But, this was exactly the importance of the call for me.

It’s not a coincidence that this newsletter concept was born right around the same time.

First of all, it’s a brilliant idea, to begin with. But, what stood out to me was how good of a listener he was. Effectively, the reason why he is a good listener is his ability to ask good questions.

Questions I am always thinking about

  • What do I want out of life?

  • Does continuing to rent make us more flexible long-term than owning?

  • Why can’t I seem to make time to learn Spanish?

  • Would purchasing a Peloton make me happier? I still haven’t decided this yet. 🙂

What are you asking?

What questions are you asking yourselves? I’d love to hear (and share if you let me).

Insightful inspiration

Paying it forward

Sometimes all we need to move forward is to hear our own voice out loud or to have someone new hear your crazy idea and offer up a different perspective.

Feeling stuck sucks. And in an effort to pay David’s kindness forward, if you’re stuck on moving forward with an idea, I’d be happy to listen and ask questions to push you forward.

I’ll open up 4 spots on my calendar over the next two weeks to test this crazy idea out. I’m just as nervous as you are. Bring the fear.

We’re all in a different spot in life, so I won’t pretend that this is about giving advice; it’s not. I don’t know the nuances or complexity of what’s going on. But, maybe you just need a nudge.

Book a time now

Have a great week,


This is Plan Your Next. It’s a conversation about being ready for what’s next. Well, because there is always a next. I’m Nate, designer and conductor of this group.

If you have something to share or add, please hit reply and expect a response!