How do you stay up to date?

One of my favourite interview questions is to ask people how they stay up to date. I have never heard what I consider a good answer. Smart, successful, well educated, people – but it seems they have a poor information diet.

I am setting out my approach this to try to help people improve here – and open myself up to to feedback.


  • My professional areas are: law, tech, crypto, data. I’m generally interviewing for the role of being a lawyer in the technology sector – so would expect answers to cover ‘law’ and ‘tech’. These are broad areas, which touch on society in lots of ways, which I think is what drives people to think that generalist news sources are sufficient to stay ‘up to date’ in these areas.
  • The specific examples below are from these sectors, formed in the context of practicing law in these areas, so won’t be professionally useful for lots of people. I do think the approach probably applies to any information worker however.
  • I am not so focussed on method: rss, audio, websites, print, email. Yes, there are bonus points for being organised, but that’s not really the point here.
  • I am not against reading junk – I agree to an extent with Taleb’s idea of ‘barbelling’ what you consume (e..g. consume both classics, and junk) – but I am focussed here on the ‘job to be done’ of how to stay up to date and informed.
  • I think that being unstructured in your information diet, or not having thoughts on how to approach this, is a sign of an uncurious, or ill-disciplined, mind. The world is too interesting, too changing, and too noisy, to not have an approach on how you stay up to date with reliable information, and thought provoking analysis of it. An answer that vaguely talks about ‘the news’ is a non-answer, and reflects poorly on the candidate, in my view.
  • I am time poor, so choose to prioritise succinct, high quality, information. Of course, no-one is time poor: we all have the same amount of it, some people have more commitments than others, people make different amounts of pre-commitment, and people ‘spend’ their uncommitted time differently. The general point is that there is so much to do, see and learn in the world, being efficient in your information diet is important to either get more information in the same amount of time, or to spend less time doing so. This is why good information is generally worth paying for. This note doesn’t consider budget very much, but there is also lots of free information listed below.
  • Switching off and protecting your mental health is important. I’m not saying spend all your time staying up to date – digital detoxes, and true leisure time, are good – but when you are reading for information, read the good stuff.
  • I get that an interview is a stressful setting. But I still think this is an easy question, if you have good habits. I don’t see how the stress of an interview could lead someone with good reading habits to give a bland answer. There’s a time and a place for everything – lots of people consume media (even ‘staying up to date’ media) which is personal, private or edgy, and you wouldn’t want to share in a professional setting, and you might panic ‘filtering in in real time’ – but still, if you have good reading habits, there should still be plenty left to talk about.
  • I haven’t listed other more general interesting, high quality, information sources here – focussing on the ‘how to stay up to date’ in legal technology.

Categories of information


In my view, the best, most concise, most consistently high quality information I read is from newsletters, not newspapers. Analysts make a name for themselves and trade on their brand. Yes, you have to pay for this for the full content. As I’ve got older, I’ve become happier paying directly for good content. I appreciate this is a luxury, but it is also an investment. Most of these also have free content too.

  • Tech
    • Stratechery
    • Lenny’s newsletter
    • Light Blue Touchpaper
  • Finance
    • Matt Levine Money Stuff
  • Crypto
    • Pomp
    • The Defiant
  • Law
    • Calleja Consulting


Same benefits as newsletters – just delivered in a different format (and generally free). More and more newsletters and blogs are the same thing delivered in both ways, of course. For example:


Just for information gathering, probably better than newsletters, but you need to put a lot more in, to get anything good out: curating your feed, deciding how much to weight each source, and the incessant nature of the feed meaning it’s not a good way to try to get an overview of things. It is outstanding at throwing lots of ideas into the mix, for you to assess and contemplate, and come to new views. Some of the greatest minds in every field, put their thoughts out for free on Twitter.


Great resource – super high quality information – surfaces lots of information to then go and read into in more detail.

  • Tech
    • Exponent
    • Dithering
  • Finance
    • a16z
    • Infinite Loops
    • Invest Like The Best
    • Panic with Friends
    • Waters Tech
    • vc:20
    • Real Vision
  • Law / Legal Tech
    • Legal Tech Arcade
    • LawNext
    • Technically Legal
    • Evolve The Law
  • Crypto
    • Unchained
    • What Bitcoin Did


Again, very underrated, and I think a part of a solid and respectable answer. For example HackerNews or Slashdot for tech, or a well curated list of subreddits (for any topic) might be some of the best ways to stay up to date and have a diverse set of new sources pushed to you, with (sometimes) high quality discussion surrounding it.

Industry specialist websites

Another great resource – the exact resources will depend on your industry. For example:

  • Market data – Waters Tech
  • Crypto – Coindesk
  • LegalTech – Artificial Lawyer
  • LegalTech – Legal Evolution
  • Law – The Lawyer

Professional subscriptions

These can be very good. The legal ones which I have access to can be a little dry (and very broad) – and so I don’t always believe people when they say they read it a lot. Still, the right sources here, read diligently would be a solid base for legal areas – but you would have to factor in the lag time between new events and these sources having proper write-ups of things. Examples in law:

  • PLC
  • Mondaq


I generally consider this to be a weak answer. Fine for entertainment or general social matters, but to really be up to date in your professional area, I generally find them them (on the whole) too vague, too broad and too superficial. FT is nearly the exception here, which I read a lot, and do pick up some good info, but it’s mostly for entertainment.

Internal training sessions

Yes, these can be very good. But everyone gets them. They is a lot of delay often between an event to the session. It doesn’t show much hunger or proactiveness, and is not enough. Someone needs to run those sessions, and they need to stay up to date – where does that person get their info from?

News Magazines

In my view, these sit somewhere between newspapers and industry specialist sources for usefulness. They are likely to have more detail than the newspapers, but the breadth of topics each magazine needs to cover means that minor but still important topics will slip through, and there will not be enough nuance or opinions on the critical topics. In an interview, I don’t see this as a very impressive answer – not bad, but not great.


Books are great. An important part of the information diet. For ‘staying up to date’ purposes, the delay in books coming out should be balanced by also reading fast information sources – but that helps to create a rounded range of sources and information types.