Help please! Making a good choice between two jobs

The obvious choice is London.

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If you're seriously considering Glasgow, tell them you have a better offer and they need to beat it.

Will you able to be able to live near where you work in London? In Glasgow, you will almost certainly be able to afford to live in a nice place in the city centre where you can walk to work. People usually underestimate how much effect a long commute will have on their happiness (see e.g. here).

Also, you might consider trying this. If you're still unsure, chances are the expected value of the two options is pretty close, and you shouldn't worry too much about how you make the decision.

Disclaimer: I am in Glasgow, and would like to increase the population of LW-type people looking to make new friends who are here, so I'm probably biased.

Every job is the job before the next job. The age of careers is long gone. My grandfather and my father got jobs (singular) and toughed them out for decades. I am not able to list all the jobs I've had. Technology jobs are all the more mercurial. Some of the best opportunities in life come from being in the right place to have semi-random encounters (see The Luck Factor PDF). If these claims are not false, the choice might be more clear to you now.

Personally, I strongly weight city/friends in job decisions. The job is 8hrs of my life. The environs and people I enjoy it with influence all the other time (less sleeping). Having friends in the area is a multiplier for all the things I could enjoy myself (theatre, costume parties, etc) and is a good filter for hearing about other things I'll enjoy.

You can, of course, make new friends wherever you go, but I really like keeping the norm of maintaining particularly close friendships instead of having a bunch of one-to-two year connections. You can try to keep up close connections long distance but, outside view, you won't.

I'm in a similar demographic to you with similar goals. Move to London. It is a qualitatively different experience to living and working in other locations (based on a personal sample size of 4). You will be able to build a much more useful network, both professionally and socially, than if you attempted the same in Glasgow. Regardless of whether you move onto a startup or another job, you will be in a much better position to accomplish either of these in London.

I am massively, massively biased and have never lived or worked in Glasgow, but based on what you've said, unless you're acutely agoraphobic, I can't imagine Glasgow being the better option.

London is Ankh-Morpork - it's a smelly expensive dump, but the world is here.

Stay in London, and study in the evenings if you want. Benjamin Franklin said "three removes is as bad as a fire", meaning there's a high cost to rebuilding your social network. I'd guess it would take you about 18 months to fully build new friendships. I moved to a non-ideal city for work (twice!) and it set my career back by a couple of years. The cost of living in Glasgow is lower because people are happier living in London.

If you want to fully maximize utility, you're making a false choice by just looking at the two jobs. Get back in grad school and work as hard as possible until you're in the top half of the class at a top school (or otherwise meet the "great hacker" criteria that Paul Graham describes on his website). Then, start a fast-growing startup with one or two other outstanding hackers. When it stops growing after two to ten years, sell out. Then, you should be in a really high-utility space where you can do massive good and/or enjoy novel luxuries.

Besides Viliam_Bur's comment, I would say do the math. Assign a numerical value to each aspect to the location, weigh them accordingly, and compare the final values. After this is done, toss it all out and go with your (informed) gut instinct.

You have three conflicting goals that only you can weight accordingly:

• Work at a successful startup (fame, fortune, culture or vision)
• Find a mate / companionship
• Employment market desirability hedge (what-if...)

What I would really like to do is build my own startup, or join a startup that I think has good prospects.

Winner: London.

The pool of women I am interested in dating is much bigger there. Dating prospects are probably less good [...]

Winner: London.

[...] and also the long-term effect of accepting a pay cut - if I worked in London again later, would I be able to negotiate my salary back up?

Winner: London.

Everything else sounds like noise, or sounds like they should be assigned lower weightings than the three concerns above. Another factor that you only can answer is how much extra time you'll carve out to keep up desirable startup skills (designer? developer? business?) while in London, as you mentioned that the London job will only allow you to specialize in an unattractive skill. This statement alone makes me wonder exactly what your previous two startup roles were -- if your skillset was good enough to join two prior startups, why would 18months of another skill diminish your existing desirability, both to startups and larger organizations in general?

Until you can provide weightings on the above, London sounds like the better choice due to the flexibility it offers you in the future, provided you have enough motivation and discipline to (a) stay actively engaged in the (presumably) larger London startup/tech scene; (b) spend (some) spare time on side projects to remain desirable to both future large employers and startups; (c) find a mate.

One counterpoint that you already mentioned was that Glasgow would give you more money after-tax. If the Glasgow vs. London after-tax income delta is large, and if your true primary 18mo goal is to "[...] get a financial cushion under myself before trying again", then clearly Glasgow is the way to go. Also, quick Google searches show that there seems to be more interest in boosting the Scottish tech scene in Glasgow and Edinburough. Depends on how serious you are about jumping back into the startup scene after 18 months.

You can start a Less Wrong Meetup in Glasgow, or plan to travel to the London one once in a while.

Which one of these opportunities will give you more good choices in 5 years?

If one assumes that economic conditions are the result of reaching an equilibrium in which the "average" person is indifferent to the options (and there are valid issues as whether this is an accurate assumption), then the question reduces to whether you are more or less likely than the average person to prefer the Glasgow job to the London job. Not that this question is not necessarily easier to answer.

The other job is in Glasgow. It will pay less, probably by about £15k. The cost of living difference, after tax, will probably be bigger than this - I expect I will have more money in my pocket with this job than with the London job

Did you mean to say that the job in Glasgow pays £15k more?

Relevant

(Also, don't count this as a personal recommendation for (or against) the London LW group. I'm just posting the link because it is a relevant community event in one of the cities that you are considering -- just a clarification.)

Edited for Markdown fail.

Besides Viliam_Bur's comment, I would say do the math. Assign a numerical value to each aspect to the location, wiegh them accordingly, compare the final values. After this is done, toss it all out and go with your (informed) gut intinct.