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I've worked as a senior leader at Microsoft, Meta, and OpenAI, and ran my own startup. Many people consult me over email and LinkedIn. Instead of answering them privately, one person at a time, I wanted those answers to benefit everyone… so I launched this: a public archive of anonymized answers, open to everyone.

Serene Starling asked

answered 3d ago

I’d be interested to hear how seriously you expect AI to reshape society and the economy over the next few years. Do you think we’re heading towards a period of rapid change and, if so, has this affected the decisions you’re making today?

For instance, has it changed how you think about your career, where you live, how you spend or invest your money, or what you want your life to look like in five or ten years?

I’m particularly interested in whether your expectations about AI have translated into any concrete changes in your personal life?

Philip's answer

We're definitely undergoing a rate of change that feels at least as fast as things were changing in the early dot-com days. This time, the change isn't just to society at large, but also to the software engineering profession — so there is both a societal angle to this as well as a personal angle.

I think the changes to our society will be profound, but it's so hard to know which way to bet on this. It seems clear to me that AI will quickly exceed the intellectual capability of most people — if not in depth in one particular domain, certainly in breadth and general repurposability. But whether this is good or bad depends a lot on the question of "bounty vs. spread" (using language from The Second Machine Age).

It's very clear to me that AI will bring a lot of bounty. It's equally clear to me that, unless we change some laws and regulations, the spread of that bounty will be very concentrated toward intellectual property owners. I have no idea how to change this, at least for America, because it seems very difficult in a democracy to do things proactively to avoid disaster. It's sometimes easier to enact things reactively once disaster happens. Then there's the question of whether our reactive response will be wise and proportionate or whether we will destroy ourselves out of spite or desperation.

As to the personal changes you asked about:

  • I have some trouble deciding what job to get next because part of me is afraid to lock into one employer who goes down a path in AI that may be obviated by a different approach. For instance, imagine if a year ago you had joined an employer who only allowed Codex. You would today be behind, since the industry largely uses Claude Code.

  • I'm a little worried about where I live. If we don't spread the bounty of AI and people don't perceive its benefits in their own lives, there could be a backlash against people who've worked in technology. I haven't yet heard of people being physically attacked or killed for their involvement somewhere in the AI stack, but it's not unimaginable.

  • I have not changed my investments at all based on AI. Instead, over the last five years, I've pivoted my investment philosophy based on my conviction that the American government and its polity will be unable to address what will soon likely become a true debt crisis, complete with rampant inflation and other shocks.

You ask what I think my life will look like in 5 to 10 years. My genuine hope for society as a whole is that:

  • The clear and obvious benefits of AI can be distributed more broadly and perceived by everyday people.

  • Its reins of control are not held by just a few people.

  • The world resists the temptation to get into international escalations of AI-assisted war tech.

It's a little bit like wishing for world peace. Doesn't make the wish less meaningful.

Breezy Glacier asked

answered 4d ago

Keeping up while being rejected

I loved how you ended your OpenAI post with this sentence:

After that, it’s about the fortitude to keep persisting through taking many shots at goal

Could you elaborate on how one can keep their mental state healthy while dealing with rejection after rejection?

For context, I’m currently in a job where I make close to $330K a year. I know that I could make closer to $450K at peer companies for essentially the same role. I started preparing for interviews back in May while maintaining my day job and also taking care of a toddler.

So far, I’ve been rejected by three of my top target companies. I’m feeling pretty dejected right now and, frankly, part of me wants to give up. But the thought of continuing to toil away at what increasingly feels like a dead-end job, while knowing how much more I could be making elsewhere, keeps me going. At the same time, that thought also makes the whole process and every living moment feel miserable.

There are also some practical challenges. I did most of my coding prep at the beginning of this process and got quite good at it, but now, four months in, I’ve forgotten some of the neat tricks, patterns, and tactics needed for certain categories of problems. System design is mostly fine. And unlike studying for an exam, interviews aren’t evaluated on a clean binary signal, so it’s difficult to know whether I’m actually improving or simply getting unlucky.

I don’t really know how to keep my mental state in balance while continuing to push forward. How do you persist through repeated rejection without allowing the process to consume you?

Would love to hear your perspective.

Philip's answer

I'm not going to be one of these people who will blindly respond to you by saying you can definitely get a job at a more elite company if you just keep trying. I couldn't possibly know that for sure without knowing your actual skills.

That said, here are a few thoughts:

  • When I worked at OpenAI, and also when I worked at early Facebook (when it was only 500 engineers), the number of false negatives in interviews, where great candidates were rejected, was very high. This makes sense when a company is very desirable to work at, since it favors them to bias toward false negatives (which are so much better for them than false positives). This means a rejection doesn't necessarily mean you can't do it. It also means you should be rejected from quite a few elite places, the more the market skews toward going elite.

  • Over the past few years, the market has skewed heavily toward the most elite workplaces, both because compensation has skewed that way and because there's not the same sense of plenty as there was in the dot-com days. In the dot-com days, you could work for elite firms, but there were also a boatload of startups, and many of the startups were compensating quite well. In fact, in the dot-com days, it was considered most attractive to work for startups because people felt like big companies just didn't get it. This increased competition squeezes far more people in through a tight little door.

  • There is, of course, also the question of whether you indeed are the right material for the ultimate job you want. I have no idea whether this is the case. As a frame of reference, I've worked on three different teams at OpenAI, and on each one of those teams I was the slowest engineer. This, in my 28 years of work experience, had never happened before, not even close. On most teams in other companies, I was considered a pretty strong developer. Are you a stronger engineer than I am? I have no idea whether that's the case. Can you get objective feedback about whether you are? If you're lucky, once in a while an interviewer will go off script and be willing to give you true feedback about your interview performance after the fact. Sometimes you'll even meet a recruiter willing to do that. Barring those opportunities, I'd encourage finding parallel routes to getting that all-important feedback, because my advice would bifurcate for you depending on the answer. If you truly are elite, my answer will be: take more shots at the goal and keep going. There are no shortcuts to that. If instead you're tilting at windmills, my advice would be to seek the best job you can obtain right now and make the most of it.

Wishing you all the best. It's a very tough market out there, and I completely empathize with the difficulty of getting some jobs. I was flat out rejected the first time I applied to OpenAI.

Mighty Koala asked

answered 4d ago

Hi Philip,

I work as a senior ML engineer at a MAG7 company. My career is going well in absolute terms. Past me would kill to be where I'm at now, I find genuine interest in the work I'm doing, and I also happen to enjoy working with my teammates.

However, I am not immune to the AI hype that's surrounded internet discourse for the past few years. Everywhere I turn, I see someone publishing cool research at a frontier lab, signing an offer at a frontier lab with comp packages that make my eyes pop out my skull, or telling me about how important it is to get on the "rocketship" ✨right now✨ regardless of the seat or how hard you'd have to work.

Because of this, I experience FOMO and sometimes the fear of falling into the "permanent underclass". I know it's silly -- I work on AI (albeit not at the frontier) and with AI, and I enjoy learning bits and pieces of this area and think that's enough to keep me going. I'm also not even sure if I could thrive in a frontier lab while maintaining the other things in my life I care about.

However, thoughts of frontier lab FOMO are loud enough in my inner monologue that they distract me from appreciating what I have now and focusing on my current career path. There is only so much grass I can touch and twitter I can turn off before wondering "what if". I find myself internally conflicted between curiosity for working there (and potentially destroying my WLB if I were to go) versus focusing on the path I'm on today (which really isn't such a bad career path). What would you suggest?

Many thanks!

Philip's answer

The fact that you're already working in ML is a huge plus to not being outmoded by the rapid development of AI worldwide. In fact, one would argue that if Jevons Paradox does turn out to be the case in our industry, people like you will become even more valuable as AI adoption throughout all sorts of industries requires more and more people who actually know what they're doing.

That said, I completely hear you on the FOMO. In 2004, when Google opened its first office in Seattle, one of my skip-level reports went over there. He was very nice to work with, but he was an average developer, not exceptional. He ended up doing much better financially than I did, even though I was several levels above him and had a lot more scope for growth in my future. It can be hard to watch this sort of thing go on if we focus on it too much.

Here are a few different thoughts along different axes:

  • There's a question of intrinsic reward. Annie Dillard was famous for saying, "How we spend our days is, in the end, how we spend our lives." There's a strong argument for optimizing for the substance of your days themselves being very enjoyable. It sounds to me like your current role and job are very enjoyable to you. This, of course, doesn't mean you couldn't have the same level of enjoyment at a frontier lab. All I mean to say is to encourage properly valuing the situation you're already in (which you obviously do, given what you've said).

  • There's a sense in which, if our eyes rove the land far enough, we will always find reasons for FOMO. There will always be someone who is less deserving than you, someone who has it better than you, who makes more money than you, who looks better than you, who is younger than you, or who is smarter than you. It's easy for me to say this, but if I'm honest, I've had a very hard time in my life grappling with this, given that I've been an overachiever most of my life. The wisdom is in understanding that if our happiness depends on those seeming inequities not existing, then we shall resign ourselves to be unhappy forever.

  • A big part of the decision about whether to go to a frontier lab also probably has to do with your personality type according to the Big Five. I, for instance, rate very high on "openness to new experience." A personality like mine should switch and try new things often. There are many people who rank low on openness to new experience, preferring stability and predictability. Those sorts of people should stay in the already-good role you're in. There is intrinsic value simply in switching what we do: for the experience of the switch itself, even if some switches end up disastrous. But the amount of that value depends a lot on one's personality.

My intuition is that you will do very well regardless of your choice here, because the way you describe your situation does not take your existing circumstances for granted, seeing only green grass on the other side. Your personality is likely to find things to be grateful for regardless of circumstance, and that serves you well.

Emerald Moose asked

answered 4d ago

I am 42 years old currently employed as staff software engineer in Twilio Bangalore. I am upskilling myself to become an Applied AI Architect + Distributed Systems Architect and apply for AI Architect roles in Bangalore from mid-2027. Currently, I am enrolled in an Agentic AI cohort and undergoing the programme. Side by side, I am learning from DeepLearning.AI.

With the pace of change in AI with Agentic AI taking over almost all knowledge work which might lead to significant reduction in team size in software companies, I forsee reduction in compensation/job loss around 2029. Given the circumstances below:

* Post 2029 onward, I would like to move into a fractional AI architect working with startups if I dont have a permanent job or work with remote companies if I have a permanent job. I am keen to contribute to AI initiatives for the society while still earning a reasonable amount to manage the monthly household expenses - my kid is 2.5 years old as of 2026.

* There is a lot of ground to cover about AI/Agentic AI and gain production experience; but the window of opportunity is closing for me - the demand for AI/Agentic AI software architects might normalize beyond 2028 mid and might not be a niche anymore. I also dont want to loose my edge over my distributed systems expertise.

* I also have to be present as a father as my kid grows up and for my mother who is already 74 years old who health is deteriorating year over year.

* I have kept aside ~ 2 years worth of expenses as emergency fund. Because if I loose my job now due to a layoff, I dont expect to land a similar paying role within 2 years.

Given my constraints, my long term plan and my conflicting situation which will only be made worse with the macro situation of the world around AI, how does a practical path look for me ?

What would be your advise for me ?

Philip's answer

Thank you for being so open about your situation. The reality is that you have some hard choices ahead of you. Both the young child and your aging parent will indeed be dependents who increase the gravity of the choices you make. Some thoughts:

  • It is very difficult to forecast what will happen in the industry three years from now. If you look back three years, it would have been impossible to predict where we are today. In fact, even one year ago, it was still quite the hype to talk about "prompt engineering" being the future of software development. That prediction turned out to be completely wrong within 12-18 months of it being made. I have similar suspicions about us projecting out three years from now.

  • That said, one principle is that the cream tends to rise to the top, even in industries that are shrinking. I'm not at all saying that your industry is shrinking, but what I am saying is that even in shrinking industries, the best people tend to be kept. If anything, this is just an encouragement for you to continue being the best that you can, which will give you better odds regardless of how things shift over the next three years.

  • Winter is coming. I've been telling people this for a few years, but winter is truly coming. As it comes, if we're smart, we will behave as animals do when we know winter is coming. We should store up, as you have wisely. We should build ourselves up for leaner times. We should spend cautiously.

  • I agree completely with being present wherever possible for your family. What I don't agree with is the popular Instagram breathless profiles about people who are supremely physically healthy, spend all sorts of time with their family, and are yet at the peak of their careers executing endless hours of work. I don't think you can have it all. The truth is there's got to be compromise, and sometimes you do a hard thing in order to make another thing easier. Let me give you a concrete example: perhaps it is true that you can spend far more time with your child, but might it also be true that at a certain point, spending too much time with your child will tip you into not having a stable career later on? A career that arguably supports the totality of your child's development? I'm not going full "Cat's in the Cradle" on you or anything... but I'm just trying to say there are real tradeoffs.

  • Lastly, remember that there is not a strict ordering of what is optimal for everyone to do. There is instead an ordering of what's optimal for you as a person to any particular job. What is optimal for a generic person might actually not be best for you, whether that has to do with your talents or interests, or your own opportunities. When it comes to forecasting the future, in addition to having humility around the error bars in any such prediction, be sure to also map possible futures to the ones where you have strengths so that you choose the path that is best for you personally. I don't know if an AI Architect role is indeed that best future for you — but you should have an introspective sense of whether it fits you well.

You strike me as very thoughtful and considerate when it comes to balancing various responsibilities in your role as an individual, a husband, a father, and a child. Your great sense of duty is a credit to you.

Kind Hawk asked

answered 4d ago

Is there a way to answer questions for free on ReachVIP? I don't care too much about revenue and want to make it accessible. Or is that pricing actually detrimental to the actual value of answers?

Philip's answer

Update! This is now supported: https://ask.reach.vip/host. Thank you for suggesting it!

= = = =

This is an awesome suggestion, and something I want to build. Let me put that in the hopper. I suspect the cleanest way might actually be to extend ask.reach.vip to not just be for me, but for anyone.

Thank you for the inspiration!

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