What People Regret About Moving (And How to Avoid It Before You Do)

Mar 30, 2026

Most people don’t regret moving for the reasons you might expect.

It’s usually not just about the house.
Or the city.
Or even the job.

One of the most common things people regret after moving to a new city is this:

“This isn’t what I thought it would feel like.”

The move looked right on paper.
It made sense logically. (If you’re still in that decision phase, trying to figure out whether moving is even the right choice, I wrote more about how to think through that here: Should You Move or Stay)

But once they got there…

It felt harder.
Lonelier.
More overwhelming than they expected.

And that gap between expectation and reality is where regret starts to creep in.

The good news?

Most moving regrets are avoidable...if you know what to look for ahead of time.

1. The Biggest Regret: “This Doesn’t Feel Like I Thought It Would”

This is the one that shows up again and again.

People expect:

excitement
a fresh start
a better lifestyle

What they don’t expect is:

feeling unsettled for months
not knowing where anything is
lacking support
struggling to find their rhythm

Everything is different.

And that’s the part no one fully prepares you for.

Because even when a move is right…

it can still feel really hard at first.

This one hit me like a ton of bricks after my move to Sioux Falls.

It was like my life as a musical came to a screeching halt and I didn't know how to turn the music back on. It was not at all what I had expected to feel like 3 months into the move and, it sucked.

2. Underestimating the Financial Reality

This is one of the most common relocation mistakes, and one of the most preventable.

I’ve seen this especially with employee relocations.

People assume:

costs will be covered
reimbursements will come quickly
everything will “work itself out”

But without asking the right questions upfront, they’re caught off guard by:

what isn’t covered
when money is reimbursed
how much they need to float financially

Cost of living is another big one.

On paper, it might look manageable.

But in reality?

Your dollar doesn’t stretch the same way.

And suddenly:

you’re spending more
cutting back more
or living differently than expected

Some people move knowing it’s temporary for career growth, but that only works if you can realistically sustain life there in the meantime.

You have to be able to live there...not just land there.

We have had employer-paid moves and self-funded moves. Allowing for "cushion" with our financial planning has always been incredibly helpful to ease the stress of unexpected (or greater-than-planned) expenses that inevitably come along in both kinds of moves.

This is where a lot of people unintentionally set themselves up for disappointment.

3. Expecting a Lifestyle That Doesn’t Match Reality

Before a move, we imagine what life could look like.

And that’s normal...you have to.

But this is where unrealistic expectations sneak in.

People often:

focus on the best-case scenario
overlook the hard parts
assume current struggles will disappear

But here’s the truth:

You bring your life with you.

If there are:

relationship challenges
career uncertainty
stress patterns

Those don’t magically disappear in a new location.

And one of the biggest traps I see?

Viewing a new place through a “vacation lens” instead of the “real life lens.”

When you visit, you:

eat out
explore
stay somewhere comfortable
avoid rush hour

There is excitement in the air...

But real life looks like:

commuting
routines
errands
responsibilities

A helpful exercise is to ask:

👉 What will my average Tuesday actually look like here?

Not the highlight reel.

The reality.

(If you’ve been feeling that pull toward something different but can’t quite explain it, this might resonate: Feeling Restless Where You Live)

And this is the part that catches even the most prepared people off guard.

4. Not Realizing How Long It Takes to Build a Life

This one hits people hard.

Because they expect:

to feel settled in a few months
to quickly find friends
to feel “at home” sooner than they do

But the reality is:

It takes 12–18 months to truly adjust to a new place.

You need time to:

experience all the seasons
build routines
find your people
feel familiar

And friendships?

They don’t happen overnight.

You have to:

put yourself out there
meet a lot of people
keep showing up

Even when it’s exhausting.

But the effort pays off.

The more you engage, the faster you start to find:

your places
your people
your rhythm

I can remember feeling truly accepted, loved and almost like family when we were invited over to our friend's house one Christmas Eve dinner.

We had been living in this community for almost at a year and had put time and effort into making friends.

This invitation was a major "friend milestone" for us. We had spent the better part of a year building the friendship...it took time.

That is normal.

5. Not Having the Right Conversations Before the Move

One of the most avoidable regrets happens before the move even starts.

Not talking enough.

Especially with the people who are moving with you.

It’s not just:
“Should we move?”

It’s:

How will this actually look day-to-day?
What will be harder than we think?
What do each of us need to feel supported?

Big decisions made by one person alone (rather than collaborating) often lead to friction later.

Everyone affected should have a voice...at an appropriate level.

Even kids.

Because while they may not choose the house…

They are still experiencing the change.

This one surprises people the most...they haven't usually thought about it like this.

6. Researching the Wrong Things

A lot of people research what looks good…

Instead of what actually matters to their life.

It’s easy to get caught up in:

big attractions
trendy areas
“nice-to-have” features

But what matters more is:

👉 What will you use regularly?

For example:

Where will you grocery shop?
What does your daily routine look like?
What activities actually fit your lifestyle?

It’s not about what’s impressive.

It’s about what’s functional for your real life.

At times I have been distracted by big shiny objects (like an incredible downtown, zoo or coffee shops), when the reality is that I go downtown about once a month, we might go to the zoo once a year, and I am not even really much of a coffee drinker. All things I do not need to spend a ton of time researching for my move.

Conducting a lifestyle assessment is an incredibly helpful way to keep your researching in check with what you need versus what you want.

7. Moving Without a Real Plan

I’ve seen people move on a whim and do great.

And I’ve seen people do the same thing and struggle deeply.

The difference usually comes down to:

expectations
financial stability
and awareness

A lack of plan often leads to regret when:

finances get tight
opportunities don’t show up as expected
reality doesn’t match assumptions

You don’t need a perfect plan.

But you do need:

awareness
flexibility
and a way to navigate challenges

I'm a big believer in having some sort of plan in place. Not to follow perfectly, but to know what matters most in how you move forward.

I've customized a lot of transition plans for people during my work with relocations and I can tell you more often than not, something is better than nothing.

8. Regret Isn’t Always a Bad Thing

Regret feels heavy, but it’s not always negative.

It often leads to:

clarity
growth
better decisions

I’ve had moves where I felt regret.

As a young adult one of my moves taught me that I didn’t actually want what I thought I did.

That was a lot of fun for me to realize...Not!

But in the end, there was invaluable insight gained about myself and what I needed and wanted moving forward.

Another move pushed me to grow in ways I didn’t expect.

The regret and feelings I had were really hard but I was able to do a complete 180 and turn it all around. The regret turned into new opportunities for me to make the most of and I ended up thriving.

Sometimes a move isn’t forever, and that is OK.

But it can still be valuable.

And it can still be an amazing chapter in your book.

9. What Most Moving Regrets Come Down To

When I look at all of this together, most moving regrets could have been avoided if people had:

taken the time to truly understand their life, their needs, and what the move would realistically look like. (If you're still trying to figure out whether it's actually time for a move, this is a helpful place to start: How Do You Know It’s Time to Move)

Not perfectly.

But intentionally.

Because a successful move isn’t about getting everything right…

It’s about knowing what matters most before you go.

A Question For You

If you were to move…

What would you want to make sure you get right the first time?

Or—

what would you want to avoid getting wrong?

Feel free to email me your response ([email protected]). I love hearing from you all!

- Rhiannon