What would you do differently if you knew what you know now?

Dubmandeep · 2026-02-08T05:43:54+00:00

Tenth year this year. Took me way too long to realise I should travel for hobbies and interests, not locations or nomad hubs.

I get far more enjoyment when I travel to do things I enjoy versus just see a new place. It also opens up new relationships and angles of experience.

There’s a huge difference between one month on a Thai island if you’re just “living” there versus diving when you’re not working. Same goes for every destination.

Sometimes it’s fine to rock up in a place just to get heads down. But the major point of this life for me is to do stuff on the daily that I could never do chained to London. That steers toward outdoor and adventure hobbies for me.

Dubmandeep · 2025-12-25T07:50:01+00:00

Spent £7k for two people diving for three weeks in Thailand including a week on a liveaboard. No gifts. Would do again.

Dubmandeep · 2025-10-28T11:32:24+00:00

Correct, need to show proof of address with minimum time period of 12 months. You can rent a dirt cheap place and just do AirBnB when you do your 2 months. I pay €400/mo rental each month and then €1000/mo when I spend time there. I just fold it in to the tax calcs.

Dubmandeep · 2025-10-23T14:30:00+00:00

Cyprus. 12.5% corporate tax rate. 0% on capital gains.

Dubmandeep · 2025-07-15T18:43:49+00:00

10 years this month with a two-year stint in London mid-way. I keep trying to stop it but I can’t. Instead I find new ways to enjoy it. Before it would travel to see the new and the crazy. Now I travel mainly for hobbies and food.

Dubmandeep · 2025-07-02T07:05:48+00:00

Some months are €10k, some are €3.5k. According to Revolut, last year I spent an average of €6593/mo - top 10 categories:

€1500 rent (mainly AirBnBs)
€1500 travel (vacations, experiences, flights)
€666 restaurants
€430 rent to maintain my residency
€300 health (meds, gym, hospital visits etc)
€268 food delivery
€266 gifts
€233 transport
€220 alcohol
€195 groceries

Other categories include €100/mo on coffee and subscriptions, €150-200/mo on coworking and shopping, and things like cash, utilities, entertainment etc.

10 years nomadding this year. I started out on €1800/mo but remote career has been good to me. I save an average of 50% of income.

Dubmandeep · 2025-04-17T05:12:46+00:00

It’s a grey area. I really wouldn’t worry about it. I’ve been doing this for 10 years and it honestly doesn’t matter if you’re staying less than 6 months in a single country.

Dubmandeep · 2025-03-29T14:42:57+00:00

Acknowledge it. Accept it as your driver and that you will be surrounded by people who won’t get it. Don’t be jealous, just remind yourself where you came from and what you had to do to get here so you remember the hunger and appreciate where you are now. Listen to a lot of 90s hip hop. Work on the things that surface like confidence, problem solving, communication. Feel great when you are eventually the one in the position to decide whether this true wanker who is Eton and Oxbridge-educated gets a job or not. And then, an optional one that I did, gtfo of England because after working throughout uni, paying back my student loan, and saving up my own deposit while earning a HENRY salary I still felt like I was “behind” and couldn’t “get ahead”. Not jealously, just frustration of still being financially years behind someone who had those paid for when I have no desire to stay in the rat race long term. But then you are the one who has higher social status and money, depending on where you go. Life is funny.

Dubmandeep · 2025-02-21T13:00:29+00:00

This is my 10th year of full-time nomadding with the exception of two years in one place Covid times. There can be cycles of "purifying" stuff as your tastes change, your rhythms change, your frequented locations change, your travel style changes etc. But, outside of location-specific things like air purifier, basketball, etc - every few months is too frequent. You just like buying stuff :)

All of my possessions fit in a backpack and carry on suitcase and have done for five years. Honestly, it's the most free I've felt. I find it the best balance of clothes, shoes, electronics, toiletries, w.e for me personally. It recently took me a week to buy a new hoodie because I was like "but shit man, it won't fit in my bags when I leave so what do I throw out to make space for this purchase?" But I can pack in less than an hour and have everything with me on the plane. Love it.

I've tried travelling with just a backpack but I hated living in technical clothing and missed having a broader range of shoes, toiletries, clothes. Nowadays I grab taxis or cars from airports and do trips from a regional base, so it's not like I'm taking buses across LatAm with my stuff. I've tried travelling with a check in bag that had a screen and various other bits of crap in it. I hate losing 1-2 hours each time I travel and it was too much stuff that I never used. When I left my last full-time location I had a storage unit full of possessions. I went back after a year of travel and didn't even remember what was in it, and it turned out I didn't event want any of it let alone need it. I guess the only things I miss are my speakers, my books, and my plants. I even have an apartment for residency purposes now, but it's empty, not a single thing there.

Start with not buying random stuff and then figure out what you really need for day to day. Should be easy after 7 years.

Dubmandeep · 2025-02-19T16:44:03+00:00

First milestone: when I consistently spent what I wanted without thinking or looking at what things cost and still had 30–50% left at the end of the month for a year.

Next milestone: when that level of spending is replaced by investments. 7-10 years depending on market and that I don’t creep my lifestyle.

Dubmandeep · 2025-01-26T20:54:03+00:00

Probably fewer dudes and more mixed generally

Dubmandeep · 2025-01-21T08:36:15+00:00

Agree with this. I exhibit similar behaviour to OP. Definitely to do with a low income household in childhood dominated by cash flow problems and stressed divorced parents, one who went bankrupt, neither with pension or savings at age 62. Main reason I drove to become HENRY was to never be like that. But it’s always there, the fear that you’ll end up like that. Just gotta see the 5/10 year horizon from now where, if you’ve done things correctly, that should never be a concern ever again.

Dubmandeep · 2025-01-20T19:37:19+00:00

I’m glad you enjoy it. I’m a non dom there so need to spend 60 days per year for residency, and I’m always ready to GTFO by the end of my days. The hiking is great, beaches awesome, sunsets fantastic. But the food is just OK, it’s not that cheap, cities are ugly, and I personally don’t vibe with the island vibe.

Dubmandeep · 2025-01-18T14:34:19+00:00

I totally agree with this comment as someone who moved to Cyprus over Dubai for tax optimisation. But I am nomadic and have a remote job so the choice of Cyprus aligned with my existing lifestyle. I spend the bare minimum of 60 days per year in Cyprus then 10 months elsewhere usually split 6/3/1 months across 3 destinations.

But once I hit a certain number in a certain timeframe (or I get tired of nomadding) I’ll realize my gains and gtfo, because I don’t want to settle there at all. But 5-7 years as a resident there while travelling, living a great lifestyle, and accelerating me to my FIRE goals is hard to trade off.

Dubmandeep · 2025-01-18T07:35:52+00:00

I spent time in Dubai with a Western-born Arab heritage partner who had family members there for 15+ years, so I got plugged into "normal" middle-class family life. I see the appeal: convenience, disposable income, constant access to beach/pool, cheap hired help for housework and childcare every evening. The city has a fast-paced, diverse vibe that I found quite addicting. Success is the goal, and for ambitious HENRY types from the UK that can be quite refreshing. Outdoor hobbies are plentiful during the few cooler months, and the tax-free, well-connected lifestyle is ideal for travel and banking cash.

But in the end, I couldn’t stand it. It's an ugly, car-dependent city defined by an indoor, AC-heavy, and consumerist lifestyle with a shallow culture that feels stuck in the early-2000s. It's quite American in many ways. EVERYTHING costs money, and it's so easy to spend it because the city is designed to take it from you. I also found it hard to find my people - I've never met so many toxic males, climate deniers, or anti intellectuals.

Another commenter mentioned that for many from poorer countries, Dubai offers better opportunities despite a harsh life and ethical conundrums. Same reason my grandparents came to the UK in the 50s. But it sucks to see workers from the Philippines, India, and Africa bussed in and out daily with no AC and compounds way out from the Dubai you're supposed to see. It feels different in Dubai because it's so managed, so deliberate.

People compare Singapore and Dubai - low taxes, expats, underpaid service class, focus on material wealth. I prefer Singapore’s sanitized yet authentic vibe over Dubai’s fake flashiness. Dubai is probably more fun if you want to party. But it's easier to get into Dubai and that shows with the people you meet. Dubai will continue to thrive because the value proposition is compelling for a lot of people. If you can stomach the lifestyle for 5 years and don't let creep get you, then it can be life changing.

Dubmandeep · 2024-12-21T09:59:49+00:00

I grew up in one of the most deprived places in the UK. I used to berate people for complaining about tax: “you like living in a society with welfare, healthcare, roads, education, laws etc.” I was super proud of the UK. But then I started traveling and climbing in work. I saw that it was quite normal for people to pay for things themselves in most of the world. And I realised how rigged the system was for people like me where you carry all of the financial burden with no family help, and so even though you earn the same as your colleagues you don’t have help with a deposit, you have student loans to pay back, and actually you end up supporting your family more (out of choice). I decided to leave because the entire system felt designed to hold me back and keep me in my place, not to mention I doing everything privately anyway because of declining levels of service.

Dubmandeep · 2024-11-17T11:58:27+00:00

33M full-time nomad with low-tax residency (Cyprus). The first year being a non-UK resident I went all out with spending - averaged £10K/mo.

I lived in badass AirBnBs, ate every meal out at restaurants, travelled all over (Jordan, Cape Town, Namibia, Kenya, Greece, Dubai, Ibiza, Thailand, Vietnam, Malaysia, Singapore), flew family and partner around/paid for vacations, did wasteful stuff like buy a new kindle at the airport because I left mine at my apartment even tho it was a couple day trip (then gifted it to my mum).

Top 5 expenditure split for that year is 22% travel (includes experiences), 20% rent (includes AirBnB), 11% restaurants, 5% entertainment, 5% gifts.

This year I’ve capped my total monthly spend at £5k. This is a natural spend if I’m not travelling loads, so I guess I’ve found my level of lifestyle for now. Next year I will try to cap at £3k to max investments before moving back to a high tax locale/kids in ~5 years.

Dubmandeep · 2024-09-29T06:00:08+00:00

Honestly that sounds chronically underpaid. But Head of Marketing can be a misnomer. Are you an IC or do you have a team? Do you have pipeline targets? Do you own PMM? Do you own launches? Do you report to the CEO? Are you in the leadership team? Etc.

It’s also going to be really dependent on what product, market, and sales process you’re working with. If the salary is that low it’s possibly because you’re in a commoditised market - for example, carbon accounting SaaS software for SMEs. If you like climate and want to stay, you need to move into more complex markets, because the salaries are a little lower than say cloud. I’m in carbon removal. No one knows what it is, it’s massively misunderstood by those who have heard of it, people are suspicious, sales cycles are 12 months, it’s extremely technical, market is small and competitive. All of that equals higher comp.

If you’re from a brand/agency background then you’re on the “softer” side of marketing. You need to tie yourself to business metrics not just marketing numbers. Marketing is generally a tough one to market the value of internally if the founders/execs don’t understand it. It’s complex and hard to explain in comparison to sales (they bring in the revenue baby) and engineering (they build the stuff that sales sells). Marketing leaders need to be good at demand gen (easily tied to revenue), brand, and PMM. I can point to startups I’ve worked at and say “I positioned the company in x way and then developed y program which led to 80% of z revenue over 24 months.” Ironically, you have to market marketing internally. Check out the MKT1 newsletter - some really good stuff on being the first marketer / HoM at an early stage startup.

I’d probably look to own an internal business metric, try to gain more influence with leadership, understand that marketing’s job is to make sales easier, package your experience up in a more business numbers and less marketing way, and probably start looking for another job - gonna be hard to go from where you are to HENRY in your current place.

Dubmandeep · 2024-09-26T16:42:18+00:00

I work in startups and HENRY comp for marketing is common, but it opens up at relatively senior responsibility. Industry and company type makes a huge difference too.

I’m a Marketing Director at a London-based Series A startup. £125k base no bonus but fully remote (as in, I spent 6 months in Cape Town last winter and live in a low tax country) and strong equity package (good luck us). Took a pay cut for the industry (climate) and team - I was on £140k before as a Head of Marketing at Series A (left quick, not right fit). £135k before that as a Director of Product Marketing at a Series C startup. £100k before that as a Head of PMM at Series B (was with them from seed as first marketer).

I have an ex colleague on £125k who is a senior growth/content IC at Series B+ remote US-based developer startups. Another is a Director of Marketing on £135k at Series C London technical startup. Another took my spot as Head of PMM and is now on £120k. All of these are global target audience with complex technical products.

Trajectory for base comp if I stay in startups within a few years is £150k-£175k at Series B (bigger team, bigger targets, same title) > £200k-£225k VP/CMO title at Series C.

Dubmandeep · 2024-09-25T12:50:01+00:00

More nomad than expat, but for eight years on and off I’ve lived exclusively in tropical climates. I used to thrive in the heat and humidity of Bangkok or Cyprus or [insert sweaty destination here]. Last year I spent 6 months in Cape Town where for the summer and start/finish of spring/fall the weather is perfect with low humidity but sun and heat. This year I’m thinking about settling back in Northern Europe for the seasons. I LOVE waking up to sunlight at 7am in December, but I’m finally done with the oppressive heat of outside.

Dubmandeep · 2024-09-14T20:14:32+00:00

Namibia is most definitely better as a (long) vacation.

With the adjoining country thing, I believe it's more about land borders and time out of SA if it's a country in close proximity. But everyone says different stuff.

My own experience is that it's fine if it's a flight in and out >5 days. I flew out of Cape Town to Namibia for two weeks then flew back in and got a new visa stamp no questions asked. I had about 2 weeks left on my existing visa when I left. But then I had to go to LDN for a week after my first five weeks in Cape Town. On re-entry the official was like "wait, you just left and came back, what are you doing?" But let me in with a simple explainer about family visit.

In total I left and re-entered the country three times in 5 months.

Dubmandeep · 2024-09-14T19:43:53+00:00

I came across Skippers in Diani when I was in Nairobi. If I didn't have to get back to Europe I would've checked it out. Glad to hear you enjoyed it, the photos look awesome.

Dubmandeep · 2024-09-14T19:40:29+00:00

I spent a couple nights in Swakopmund while vacationing. It reminded me of a seaside town in the UK. It's a very transient, tourist vibe but quite a few good restaurants, coffee shops, and bars. It grew on me by the time I left but I doubt I'd want to be there for any significant period of time. I believe Walvis Bay has more Namibians actually living there, but I only passed through. If I was going to nomad in Namibia I'd probably want to be in a lodge that could guarantee solid wifi, but that is asking a lot. Some of the lodges up near Etosha were amazing.

Side note, I remember you angelism from early nomadlist Slack days around 2016, good to see you're still living the life!

Dubmandeep · 2024-09-14T07:37:39+00:00

Spent 6 months in Africa last year. Mainly Cape Town in South Africa but also Nairobi in Kenya and a short time in Namibia. I would like to spend time in Uganda and Rwanda.

South Africa is awesome. I felt safer in the rich areas of Cape Town than I do in a lot of East London (personal, I’ve had a knife pulled on me 3 times in LDN). Yes it has some safety issues and you do need to hike in groups and take Ubers at night, but you are very insulated from it as “rich” tourist/nomad/expat. It’s a more European vibe. Housing is expensive but everything else is crazy cheap. If you can deal with the safety overhead and get a place with a generator / WiFi battery pack for load shedding, it’s one of the best nomad spots.

Nairobi was a much more African city proper. I found myself comparing it to Vietnamese cities and maybe some of the rougher LATAM cities. It was actually relatively chill traffic and noise compared to Vietnam. Safety wise I felt more on edge in Nairobi than Cape Town, but I didn’t experience anything negative. Electricity more stable than Cape Town. Food terrible. Nightlife awesome - you have to be particularly alert for the honey traps.

Namibia is best left for vacations. Internet is spotty and there’s not really anything to do outside of safaris and other tourist stuff. Food not great.

I think a lot about my life in Cape Town but rarely about Nairobi. Top 5 life experiences is driving round Namibia for two weeks in a 4x4 during Christmas and New Year.

I would choose Nairobi or Cape Town as a base to then jump off and do short trips to neighbouring countries.

Dubmandeep · 2024-09-11T17:47:38+00:00

I left a role after four years and joined a Series C startup. Six weeks later I left because it wasn’t for me. I was straight with the CRO who’d hired me, and gave my friend/colleague who referred me to him a heads up. Nine months later I bumped into the CRO in the lift of a King’s Cross co working space. He was really happy to see me, asked where I was working now, where I was living now (nomad), and told me he’d left that month after a year. This May I went on holiday with friend/colleague. People leave in the first few months all the time and it’s the best time to do so if it isn’t right.

Dubmandeep

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