What We Would Never Do Again
This page exists because mistakes are where the real learning lives.
Most advice online is written by people who are either still in the honeymoon phase or trying to sell something.
This is the stuff we would never do again.
Not because it ruined everything. But because it cost more than it gave back.
Trying To Do This Life Halfway
The biggest mistake we made early was trying to live two lives at once.
Keeping one foot in “normal” and one foot in something different.
It looks sensible. It feels safe. It is exhausting.
You end up carrying the full weight of a conventional life while still chasing freedom on the side.
That is not balance. That is burnout.
Short Trips That Pretend To Be Seasons
We used to think shorter trips were smarter.
Less commitment. Less risk. Less cost.
In reality, short trips are often the most expensive way to do anything.
- Higher nightly costs
- More transport
- Less rhythm
- No time to settle
Staying longer almost always brings clarity, community, and better value.
Rushing feels productive. It rarely is.
Chasing Other People’s Versions Of This Life
It is incredibly easy to copy what looks good online.
Where people go. How they travel. How fast they move. What they prioritise.
The problem is you end up living someone else’s tolerance for discomfort.
That never ends well.
If it does not fit your energy, your family, or your values, it will quietly drain you.
Ignoring The Boring Logistics
Logistics are not sexy. They are essential.
Visas. Insurance. Schooling. Healthcare. Work windows. Exit plans.
Every time we avoided this stuff because it felt overwhelming, it came back louder later.
Freedom without structure turns into stress.
The boring work buys you the fun parts.
Thinking Travel Would Fix Things
This one is uncomfortable, but important.
Travel does not fix unresolved shit.
It amplifies it.
If something is broken at home, it usually shows up faster when you remove routine, comfort, and predictability.
Movement gives perspective. It does not replace self work.
Overcommitting Early
We said yes to too much too soon.
Places. Plans. People. Expectations.
It felt exciting at the time. It also removed flexibility.
Leaving space is not laziness. It is intelligence.
Comparing Timelines
This lifestyle messes with timelines.
You will be ahead in some areas and wildly behind in others by traditional standards.
Comparing yourself to friends buying houses, climbing ladders, or locking things in will fuck with your head if you let it.
Different life. Different clock.
Underestimating Rest
Adventure culture glorifies movement.
Rest gets treated like weakness.
That is bullshit.
Without rest, everything becomes harder. Relationships. Decisions. Parenting. Creativity.
We learned the hard way that rest is part of sustainability, not a reward at the end.
What We Would Do Again In A Heartbeat
Despite all of that, there are things we would choose again without hesitation.
- Staying longer in fewer places
- Prioritising seasons over schedules
- Choosing experience over accumulation
- Letting life look different
None of this is perfect.
It is just honest.
The Bottom Line
This page is not here to scare anyone off.
It is here to save you time, money, and unnecessary stress.
If you take one thing from this, let it be this.
There is no perfect way to live differently.
There is only a way that fits you.
Read what Living East Of Ordinary actually means.