We all have “an Asheville.” It’s the place on the other side of the fence. You know, where the grass seems greener. Where life would most certainly be better.

If only you could drop everything and jump the fence. Life would be perfect. Right?

This kind of thinking can sometimes make us feel like we’re on the brink of an existential crisis. Should you stay, or should you go?

What a great place to be!

It might seem like that’s “easy for us to say” as we’ve already made the decision and are taking the leap. But, the truth is, we’re only able to say this because we’ve been there — multiple times each — and we now have a great model for assessing the “to move or not to move” decision.

It’s a simple process. You just need to get clear on these four questions:

  1. Where are you now?
  2. Where do you want to be (5, 10, 15 years from now)?
  3. How can you test/taste that future hypothesis today?
  4. What if the worst case scenario actually freakin’ happens?!

Then you, make the choice. It’s simple but not easy.

We’ll dive into each of those bullets below.

Step #1: Where are you now?

Ok, sure, yeah, this is asking about your geographic location, but that’s not all we’re hoping to uncover. Where are you today, as a person?

Our friend and mentor Devon likes to say, “You gotta get accurate before you get active.” What he means is the best thing you can do is take time to get really clear on what the truth of your situation is. Pull out the judgment, get rid of the should-statements, and just state the facts.


  • I’m working at a job I am not inspired by and do not see a clear path for personal growth in the company.
  • My lack of excitement for work has me putting less effort in than I have the capacity for and it’s affecting my performance.

Of course, it doesn’t all need to be negative.


  • I enjoy playing music more than I let on to friends.
  • When I make time on the weekend to sit at the keyboard, even if it’s only for 10 minutes, my day is better.

After you get clear on your truths – after you get accurate – then you can start to think about the future.

Step #2: Where do you want to be?

Again, yes, geography is part of this but it’s not all.

When you day dream about yourself in 5, 10, 15 years, what do you see? What energy does future you walk around with and how is that affected from the people around you?

When we were thinking about where to move to next, we asked ourselves this question. We really sat with it and after a while, we had a few big ah-ha moments.

We saw the suburbs, proximity to expansive amounts of nature, and running our own businesses that were, more than anything, fun to run and fun to build.

Nothing about our present lives was supporting that future state explicitly and that was ok. It’s fine if you make that realization as well.

An essential part of this phase, like the last phase, is keeping judgment out of the assessment. Don’t ask yourself “why” questions. Only ask “what” and “how” questions.

When you get clear on your future state for 5-years out, do it again for 10-years. What themes show up? Do it again for 20-years.

Noticing anything? Now, let’s talk about addressing those themes.

Step #3: How can you test/taste that future hypothesis today?

“Well, shit.” You might be thinking. “Future me is really different than present day me.”

Fear not, friend. We’ve both been there. All hope is not lost. In fact, you’re in a great space. You’ve clearly identified an opportunity to wildly change yourself into a version of you that you’ve literally dreamed of becoming.

Time for bold and radical change, right?! Wrong.

Don’t go selling all your possessions and moving to Bali to start your coaching business just yet. We’re starting small with as tiny of a test as you can think of. Well, not the tiniest. It needs to be able to offer a taste of what the future might hold.

  • Want to move to the woods and build a homestead? Take a multi-day wilderness course.
  • Want to open a restaurant with no restaurant experience? Find part-time, weekend work in a restaurant.

Test the waters. Taste the experience. Start doing the thing today, right from where you are. You might find out that, even after a quick taste, it’s not all it was cracked up to be.

Only one thing is for sure, the way you imagine it in your mind is not how its actually going to be. You might realize that it’s even better!

And what then? How do you reconcile the realization that your hope for the future — after testing it — seems even better than you had originally guessed? You’re more curious and interested in pursuing the dream than ever.

Don’t make the decision yet. There’s more work to do.

Step #4: What if the worst case scenario actually freakin’ happens?!

Now, this is written to seem hyperbolic and playful — and it is — but it’s also serious. Take some time with this. Write it out. Get clear on the fears.

Tim Ferriss has a great process he calls Fear Setting (worth reading and watching after this article) where you write out the fear, what you can do to prevent it from becoming a reality, and what you’d do to clean it up if it happened.

Fear #1

Fear #2

Fear #n

Prevent Fear #1

Prevent Fear #2

Prevent Fear #n

Repair Fear #1

Repair Fear #2

Repair Fear #n

Taking the fear out of your mind and putting it on the page, takes a lot of its power away. But it also helps us to make better decisions.

If you’re 25-years old with an incredibly loving and supportive family, getting clear on worst-case scenario should empower you. You can change your career, you can move to a new city, you can take a part-time job as a barista while you try to build an app for dog-lovers.

If you’re a single father with two teenagers, no extended family that is really capable of pitching in, getting clear on what the worst case scenario should also empower you — but the effect would be different.

Getting clear on the fear, ways to prevent that from becoming reality, and a how you’d clean it up if it were to happen is meant to put things in perspective. It’s meant to empower you to make the best choice for where you are today and help identify what is the best course of action for you to follow.

Make the Choice

We support this four-step process of (1) getting accurate on today (2) painting a picture of your future (3) testing that future today and (4) defining the fear. Once you do this, make a choice.

Now, we didn’t say “make a decision.” There’s a semantic difference between choice and decision.

Decisions are made with a response to a hypothetical question of “why?”

Choices just are. When you make a choice, you don’t answer to a “why” you just chose one route out of many. Choices are not permanent. You can always change your choice.

We didn’t choose to move… right away

After going through this process the first time, we did not choose to move to Asheville right away. We chose to test our assumptions. We visited Asheville three times before the choice was ever “final.”

We also realize we might not be in Asheville forever. Should we ever run through this process again and realize we’re too far from our future, we’ll be open to testing new towns.

How about you?

Who are you hoping to become? Where are you thinking about moving? Has this process helped you think about your next steps?

We’d love to hear your story.

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