28, recently lost my job, and torn between traveling and figuring out my career. Would love some advice! 🌍

I’m 28, currently living in Barcelona, and I recently lost my job as an Account Executive in tech sales. I’ve spent most of my career in sales (SDR and AE roles), have international experience, speak several languages, and have lived in different countries.
Last year, I took three months off to travel, and it was honestly one of the best experiences of my life. I loved the freedom, meeting new people, exploring different cultures, and just being carefree without the usual pressures of work.

Now that I’m unemployed again, I’m at a crossroads.
Financially, I’m fortunate enough to have enough savings to travel comfortably for several months and still support myself while looking for a job afterward. So money isn’t necessarily the biggest obstacle.

On one hand, I feel like this might be one of the best times in my life to travel. I’m still young, healthy, don’t have major responsibilities, and my parents are still relatively young and independent. In the future, I might want children, a dog, a mortgage, or simply have more commitments that make extended travel harder. There are so many countries I’d love to visit and experiences I’d love to have, and part of me worries about missing this window of freedom.

On the other hand, I already have around 10 months of career gaps on my CV, and I’m seriously considering transitioning out of sales into a career I’d find more fulfilling. I know that changing careers could be challenging and time-consuming, and another extended break might complicate things further. I’m also naturally quite responsible, financially cautious, and a bit anxious about uncertainty.

What makes it harder is that I’m not even sure how much of my desire to travel comes from genuine excitement versus FOMO or the feeling that I should make the most of my youth. Realistically, I know traveling doesn’t have to stop once I have a job. I could still take holidays, shorter trips, or travel between jobs.

And part of me genuinely wants to find a career I enjoy, build some stability, and feel excited about my everyday life rather than constantly looking forward to the next escape.

So I’m torn between taking a few weeks off, traveling for several months, or focusing on my career transition now.

Has anyone been in a similar situation? How did you distinguish between genuinely wanting to travel and feeling pressured to make the most of your freedom? And for those who took extended career breaks, did they actually affect your career afterward?

I’d really appreciate different perspectives, including from people who chose not to travel and were happy with that decision!

I'm the developer of DAY'S, an iPhone travel log. I made a free plain-text worksheet for the part that comes before entering trips into an app: getting the dates straight. It also works as a standalone note or spreadsheet.

Copy one row per country stay:

Country | Arrived (YYYY-MM-DD) | Departed (YYYY-MM-DD) | Source / needs checking

A practical way to fill it:

1. Write down the start and end of the period you're checking. A blank calendar doesn't prove you were away.

2. Collect possible trips from tickets, bookings, calendars and old notes. Keep future bookings separate.

3. Check what actually happened. A cancelled booking or a changed flight shouldn't become a confirmed stay.

4. Mark uncertain dates as 'needs checking' instead of quietly guessing.

5. Sort the rows and look for duplicate stays, overlaps and missing departures. Keep the original records as well.

The printable checklist and copyable/downloadable template are here, with no signup or upload: https://olegotka.es/travel-history-checklist.html

For anyone who prefers an app, DAY'S has a free manual trip log, document records and a stay-day calendar that work offline without GPS or an app account. Future forecasts, reminders and iCloud sync are optional monthly Premium features. The worksheet doesn't import into the app.

This is a way to organise dates, not proof of where you were or a determination of immigration or tax status. Leave passport numbers and booking codes out of any copy you share.

I’m a guy in my late twenties who recently left his job because of how incredibly unhappy I was. I’m at a point where I want to restart my life, figure out what I actually want, and give myself another shot at being happy.

But before jumping straight into another job and falling back into the same routine, I want to do something special with this time. Something memorable that I’ll look back on years from now and be glad I did. I have some savings, some time, and a desire to experience something different before starting the next chapter of my life.

The problem is that I have no idea what that something should be.

I’ve considered Workaway, particularly farm stays where you help out in exchange for accommodation. The idea of living somewhere peaceful, working with animals, being outdoors, and having a simple daily routine genuinely appeals to me. It sounds like a good opportunity to disconnect from everything and reconnect with myself.

However, finding a trustworthy host, figuring out the logistics, and putting myself in an unfamiliar environment with strangers feels quite intimidating. I’ve never done anything like that before.

I’ve also considered travelling around Europe. I’m from Asia, and I’d love to experience more of the world. I’ve travelled solo before, but honestly, I never really enjoyed it as much as I hoped. I struggled to enjoy myself in unfamiliar places, and the constant movement never felt particularly fulfilling. The idea of changing accommodation every couple of days while backpacking doesn’t appeal to me either.

That said, I wonder whether spending a month or two somewhere beautiful, staying in one place, building a routine, meeting people, and experiencing ordinary life in another country might be completely different.

Maybe a small farm in the countryside, a coastal town, a mountain village, or somewhere I could volunteer and feel part of a community. Somewhere I could slow down without feeling like I need to be sightseeing or making the most of every second.

I’m open to other ideas, too. It doesn’t necessarily have to involve travelling abroad. I just want to do something outside my usual comfort zone that feels meaningful and gives me a story to tell myself when I’m older.

**Has anyone here been in a similar situation?** Have you ever left a job, taken a break from your usual life, and done something that genuinely changed your perspective? What did you do, where did you go, and was it worth it?

I’d especially love to hear from people who aren’t naturally adventurous, who struggle with uncertainty, or who found solo travel difficult but eventually discovered an experience that worked for them.

I’m feeling a little lost at the moment, and I’d really appreciate hearing about your experiences. Maybe someone else’s story will give me an idea I haven’t considered yet.

Thank you in advance

I will travel in Asia for a year, starting with Thailand. I take HRT, and I need to take a year's supply, as I might not be able to find the same ones everywhere. But seems I should only take one month's supply. I don't know what to do. Is it bad to take the risk?

How should someone with only a U.S passport go about long term traveling in Europe? I’m aware of the Schengen visa rules, so I’m just trying to find an efficient way of working around that. I’m fluent in Spanish as well but find Latin America too chaotic for my liking, so it’s not really in the cards.

I receive enough in passive income to comfortably keep me afloat in most places. I’m gonna turn 30 soon if that helps in anyway.

I’ve narrowed down my options being: cycling through Serbia, Albania, Georgia when not in the Schengen area. Does anyone have experience in this?

Hey yall, I just graduated college with a BSW, did the most amazing 8 week trip of my life this summer, and I’m searching for jobs that will allow me to travel with my degree or just in general, but preferably with my degree. Remote jobs, where are we finding them? What are you guys doing for money when traveling full time? I looked into being a flight attendant but unfortunately I’m not willing to permanently relocate to a specific base long-term.

Hi again everyone! 👋 Thanks so much for all the warm replies on my last post, I loved reading your travel stories 🥹

A few of you asked about life in Korea, so I thought I’d share something from my side. I work at an agency in Korea that helps international visitors with medical care (things like health checkups, eye surgery, dental, dermatology). I see a lot of people combine treatment with a long trip, so here are some honest tips:

1. Check if the clinic is registered for foreign patients. Korea has an official registration system for clinics that treat international patients. It’s a good basic filter.
2. Get the full cost in writing before you go. Ask what’s included (consultation, aftercare, medication) so there are no surprises.
3. Plan your recovery time around your travels. For example, after eye surgery or some dental work, you may need to avoid swimming, flying or certain activities for a while.
4. Ask about interpreters. Many bigger clinics have English-speaking staff or coordinators, but it’s worth confirming.
5. Health checkups are surprisingly affordable and fast here. A lot of long-term travelers use a stopover in Korea to get a full checkup done.

I’m not here to sell anything, just happy to share what I know. If you’re curious about healthcare in Korea or have questions, ask away in the comments 😊

Any advice would be appreciated!

Hi all. Basically, the title, I just got this job two months ago. The opportunity kind of came up and it was hard not to take it as it would result in a 62% salary increase and was fully remote.

However, I’ve been saving up for the past two years, to temporarily or indefinitely move to another country. I am currently 28 and have about 50k saved between in brokerage accounts, HYSA, and my checking account. I have about 50k in my Roth IRA.
I received an opportunity to work in the other country doing job that is similar to what I’m currently doing, but would pay a lot less (enough to cover regular expenses), more hours, more stress/responsibility.
Since I just got my current job, and it is the first time I’m earning this much, I am debating on riding it out for a little more as i’d be able to enjoy this salary and save about 3k every month leading up to the move (6 more months) or just pulling the trigger and taking the other opportunity.

On one end, I don’t know if fall be able to find another opportunity like what I have right now so easily. I also don’t know if I will be able to find a job that pays well enough for me to cover all of my expenses in the other country so easily so I’m a bit torn. Looking for some advice from you all.

Thank you

Edit: wanted to mention that my current job is based only in the United States

I am turning 28 in a few months and I share an apartment with my long term boyfriend. I have ~50k in short term investments, ~25k in retirement, and ~$20k in savings. I have no debt.

After my current lease is up, i want to quit my job and take a flight to Asia. Be in Asia for 3-6 months, and then fly to central America and be in central and South America for 3-6 months.

Is $20k enough to travel for a year or close to a year? Is it crazy to think I can leave my apartment and my boyfriend behind but stay together?

I have always wanted to do things like see orangutans in Indonesia and hike in Nepal. I think I would be unsatisfied if I never tried long term travel. I just don’t know when the right time to go is.

Twenty eight years on foot.

Been thinking about this a lot lately. Some people’s goal is to buy a place and settle, others just want to try a few cities and see what happens. Or not decide at all, at least for now.

I get wanting a home, I do. I just don’t love that going somewhere has to be a forever thing.

But then people ask “doesn’t that scare you??” or “ok but how long are you gonna do this?” and I honestly never know what to say. Like yeah, some of it is scary, obviously. Doesn’t mean I don’t want to try.

Do those questions get to you sometimes, or are you fully at peace with “this works for me right now”? I feel like I go back and forth.

I am thinking of backpacking and moving around maybe out of India for a few months maybe, country hopping, has anyone done this? And would anyone be interested to tag along? Like hostels and stuff, I have a remote job so moving around is not an issue kinda workaction, has anyone done that before? Is this a bad idea? I earn a decent amount (like what a big tech employee ig) I am 24 and like exploring things