Month: March 2026

We were at a somewhat remote place for a few days recently and had rented a car. We ended up buying enough groceries to last us a few days and had enough food throughout – so right at the end of the trip, we took the rental car and drove straight back to the airport.

Our kids pointed out that we didn’t end up using the car at all. Maybe we shouldn’t have rented one. Maybe we could have taken a taxi for example.

The conversation we had then was about the fact that the car had brought us optionality. If we hadn’t gotten the right amount of food or groceries, we knew we could always drive out of the remote location, get to a grocery store, and make it back.

The meta lesson – optionality always costs something. This is obvious when we buy refundable tickets or accommodation anywhere we go. However, it is less obvious when the costs are hidden. For example, if we’re choosing a path that gives us optionality in our career, that’s totally fine. But there’s a cost to doing so vs. say specializing.

It isn’t that optionality is right or wrong. It’s just important to be thoughtful about when we choose to pay that cost – and when we choose not to.

It felt fitting to wrap up my career transition series and share the update I’d shared on my LinkedIn. After a month of catching up on my backlog – across National Parks and career transitions, we’ll be back to regular service tomorrow.

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Update – I’m joining PayZen to lead the product team.

I’ve always been drawn to acute problems – those that are massive in scale and deeply personal in impact. After a decade working on the job search problem, I was drawn to healthcare affordability.

We’ve all experienced this: when there’s a health problem, everything stops. And yet affording the care they need is top of mind for millions of Americans. It’s so large, so complex… and yet so important.

What drew me in was what the team – led by Itzik and Tobias – has already built. Starting with payment plans and financial tools for patients and health systems, they’ve had real impact on patients and care providers. We all know healthcare affordability is a much larger problem – I believe we’re just getting started on what’s possible.

I’m grateful to Itzik for the opportunity – and it is all the more meaningful that this next chapter starts with Sanjeev, the person who took a bet on an eager grad student who dreamed of making it to the Bay Area and hired me into LinkedIn. Some things come full circle in the most wonderful ways.

PS: Healthcare is complex and I have a lot to learn. Alongside my notes on building LLM-powered products, do expect to see a lot more notes about the US healthcare system and the lessons learned along the way. :-)

#careertransition – #8 of 8 | I recently went through a process of career exploration and made a significant career switch. This series of 8 posts is a synthesis of the lessons I’ve learnt.

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As you navigate your transition, you’re going to meet a lot of people with a lot of strong opinions on what you should do. What’s right for you. What you’d be crazy to pass up. What you’d be crazy to take.

For what it’s worth, these opinions won’t be limited to the choice you make – they’ll even go down to something as seemingly benign as how much time off you take between roles. :-)

And many of these opinions will not make sense for you in your situation.

One of my go-to examples of really horrible career advice came from someone incredibly successful more than a decade ago. We spoke when I was living outside the US and really wanted to work in the Bay Area.

This person’s advice was simple – get to the Bay Area, spend a few months meeting as many people as possible, and convince somebody to give me a job. He said he knew a couple of people who did it as well.

This was high conviction advice from a person who had seen a lot of success in their career. And yet for somebody like me who didn’t have a US passport and who had just got married, it made little sense. What are the odds that this even works out? What happens to my wife and her career?

Since making the decision to leave my last role, I’ve spoken to many people – some of whom were upfront about wanting to leave too. A few of them, also immigrants, were upfront that it might be the right time from a career standpoint but not from an immigration standpoint. And I completely understand.

A couple of good friends went back to India for a routine visa stamping. At the last minute due to changes in guidance from the state department, embassies canceled appointments and rescheduled them many months later. For some, jobs were at risk – because you can’t be away from the office that long. A couple of friends had to find schooling for their kids for three or four months while they waited.

In another case, just as a wife found her way back to the US after months of waiting, her father-in-law passed away. Her husband, who was in the US all this time, made the gut-wrenching decision not to attend his father’s funeral – because who knows, he could be stuck there for months as well.

Can you imagine making such a decision? To not say goodbye to a parent because you’re worried about what it might do to your life? And yet I know of many who’ve made these decisions. During COVID. And right now.

I tell these stories because people who haven’t gone through this have no idea what it’s like to face such situations. And it’s so easy for them to give advice with high conviction without this understanding.

During times of transition, you’ll find yourself in situations where you feel like you need to explain yourself. You don’t. Nobody fully understands your circumstances. Only you do.

If you’ve given it thought, you’re making a bet. Make the bet. It may or may not work out. But it’s your life to mess up and your call to make. You have to do the work to reason from first principles and make a choice that you will be at peace living with.

Because ultimately, you are the one who’s going to have to live with that reality.

#careertransition – #7 of 8 | I recently went through a process of career exploration and made a significant career switch. This series of 8 posts is a synthesis of the lessons I’ve learnt.

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Take the time to say goodbye. Meet anyone who wants to meet you. And make sure to take the time to meet people you want to thank. A simple thank-you note takes effort but goes a long way.

It helps to remember that the most important question in the mind of the person you’re meeting is “what does this mean for me?” That tends to be the central theme of such conversations. Keeping this in mind helps you be there for them.

Sometimes people react in ways that might seem unsettling or unkind. There’s no need to read too much into it. When you make a change, it gets people to reflect on where they are. Their response is frequently more about their headspace than about you.

When you have these conversations, focus on the good times. It’s easy to leave feeling bitter or sounding bitter. You might get the opportunity to share feedback. Do it as authentically as possible. But the goal is not to prove a point to anybody.

Multiple things can be true. You might have had a good run. You might have made meaningful connections. And it might be time for a new adventure. For you. That’s the key.

This is where internal clarity helps. When you’ve made a decision, be clear in the truth of why you made it and why it’s the right one for you. That clarity will help you shake away any unpleasantness and stay focused on doing the right thing. The goal is keep these relationships. It’s a small world and you never know when your paths will cross again.

Perhaps more importantly, in the final analysis, the memories and the people are all we have.

#careertransition – #6 of 8 | I recently went through a process of career exploration and made a significant career switch. This series of 8 posts is a synthesis of the lessons I’ve learnt.

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This applies on both sides – your current employer and your new one.

Let’s say you’ve run a process. You have a couple of offers. Or you’ve decided where you want to go and have gotten an offer. But your existing employer has also opened up an option or two that could be compelling.

The key here is to go back to that first principle of knowing what you want. Don’t negotiate if you know you’re not going to take it eventually. This is one of those things you really want to play well. If there is indeed something that would keep you, be upfront about it – but know that if it’s given to you, then you have to stay.

And on the flip side, if there’s nothing that’ll make you stay, don’t make asks. They’ll just end up wasting a bunch of people’s time and goodwill.

Your most helpful ally is being clear about what you want and what you’re solving for. And assuming that’s not something you’re going to get in your current place, you can just be upfront and treat any negotation or persuasion as a sign of love.

Some of these conversations can be hard – especially when you make an unexpected move. But it’s important to remember that you don’t need to justify it to anybody. It’s a call that makes sense to you, and that’s what matters. The key is having the conversation as respectfully as possible.

Similarly, at your new place – the best negotiations are simple and focused on one or two things that matter. Not attempting to throw the kitchen sink at the problem. Doing it respectfully matters because you want to start on a great foot.

And, in addition to speaking to friends who’ve been through similar situations, I can’t recommend using Claude or ChatGPT enough to prepare extensively for these conversations. It really goes a long way in preparing for sensitive conversations.

#careertransition – #5 of 8 | I recently went through a process of career exploration and made a significant career switch. This series of 8 posts is a synthesis of the lessons I’ve learnt.

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We spend a lot of time trying to get beginnings right. It makes a ton of sense to figure out how to get the ending right too.

Imagine you’ve made the decision to leave. That’s a big decision. An important decision. It’s important to time it well if you can.

This matters more the longer you’ve been somewhere. You want to leave on a high because it should feel like you’re running towards something, which is hopefully what you’re doing, rather than running away from something.

You don’t always have the chance to do this. Sometimes circumstances play the roles that they do. But if you have the chance, do your best to set things up such that you leave well. People remember peaks and ends. You want to make sure the end they remember is a good one.

When you have a manager you trust, you have an opportunity to give three kinds of notice. The first is when you’ve decided to look outside. The second is when things get serious. And the third is before you sign an offer.

Which of these is most relevant depends on the relationship, the company, and where you are in your career. I know somebody whose manager really appreciated the heads up before he signed. In my case, I was lucky to be close enough that I could give the heads up the moment I first decided to explore. So I was able to give months of notice.

If you have a team you’re responsible for, it helps to time it right – after a win, when there’s planned work ahead, where there’s a successor ready or a clear plan for one, and with well planned communications so it is all done professionally. All of this helps set the transition up in an orderly fashion.

Make the effort to get the timing right. Then sweat the details of the transition to ensure every detail is taken care of.

It matters.

#careertransition – #4 of 8 | I recently went through a process of career exploration and made a significant career switch. This series of 8 posts is a synthesis of the lessons I’ve learnt.

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As you explore, you’re going to come across jobs/projects/opportunities that look exciting. The question is how to evaluate them.

I think it comes down to four questions:

1. Do you believe in the space? Is this a space where the work matters to you, and where the trajectory makes sense for where the world is headed?
   
2. Do you believe in the company/organization? Is this a company that has a real shot at winning in that space? Is there something about how they operate, their strategy, their position, that gives you conviction?
   
3. Do you believe in the people? Are these people with that combination of intelligence, integrity and energy that you believe in?
   
4. Do you believe you’ll be set up for success? This one is easy to overlook. You might believe in the space, the company, and the people – but if the role, the scope, or the circumstances don’t set you up to do your best work, it’s going to be hard.

Of course, if you’re starting up yourself, some of these questions get modified. But they largely hold.

It’s worth being honest with yourself about where you have conviction and where you don’t. In my case, after many weeks of exploring starting up myself, I realized I didn’t believe in my ability to win. Founding a company requires some earned insight or unfair advantage that typically comes from deep understanding of a problem space – and I was drawn to problem spaces where I didn’t have any advantage.

That led me to realize that I wanted to join a small company in a problem space I was drawn to – a different path than what I thought I’d pursue but the right one at this point of time.

#careertransition – #3 of 8 | I recently went through a process of career exploration and made a significant career switch. This series of 8 posts is a synthesis of the lessons I’ve learnt.

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One of the things you realize through a career transition is that you meet a lot of wonderful strangers. There are just a lot of kind people who take time out to help someone trying to figure out their next step. In my case, this included people whose companies I was interested in and many others who I spoke to as a prospective start-up founder trying to validate an idea.

To be clear, you do meet the occasional unkind person. But for the most part, it’s incredible how much the kind people outnumber the unkind ones. I’m so grateful to such people. Many of them inspired me to become a kinder version of myself.

There are 3 things to keep in mind as you reach out to people –

1. It’s a lot easier to get help when you know where you’re going. When you’re clear about what you want, people can help you. When you’re not clear, it becomes harder and harder for anyone to fully understand how they can help.
   
2. Show up well and follow up. Make it easy for people to connect you with others. Be polite. Be thoughtful. Prepare. Say thank you.
   
3. Start by speaking to one person per week. You can start with people you know. Ask people who they would recommend you speak to. It’s amazing how quickly this snowballs and how much perspective it gives you.

#careertransition – #2 of 8 | I recently went through a process of career exploration and made a significant career switch. This series of 8 posts is a synthesis of the lessons I’ve learnt.

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Once you have a starting hypothesis of what you’re solving for, break down the kinds of paths available to you. Big company. Small company. Starting your own. A certain kind of industry. Lay them all out – and even if you have strong hypotheses on what you want, validate them against what you’re solving for.

The reason it’s important to go broad is simple. We regret the shots we didn’t take the most.

The process of exploring will sharpen your thesis and give you better clarity on what’s right for you and what’s not. That matters – because it’s easy to lose sight of your internal compass with so much external noise.

Every place has an inherent value system that adds noise. In Silicon Valley for example, it’s cool to be a founder. Does that mean it’s the right decision for you? Maybe. Maybe not. It’s extremely cool right now to work for a hot AI company. Before that, it was something else. No matter what captures the zeitgeist, that doesn’t mean it’s the right answer for you.

The way out is simple – speak to as many people as possible. Go down as many rabbit holes as possible. And then make a decision based on what works for you.

But while you explore broad, be mindful of the downside drivers. The most important part of this game is the ability to keep playing – you don’t want to get kicked out of the game.

For immigrants, the most pertinent downside is any decision that impacts your visa or permanent residency. Nobody who isn’t an immigrant can fully understand the angst of a tricky visa situation – the fear of getting kicked out of a place you call home, or not being able to get back in.

For everyone, anything that impacts your health or your wealth is a downside driver. If you decide to go to a small company, you don’t want to go in with the pressure of needing a financial exit – that’s completely out of your control. You’re much better off going to a bigger company if that kind of pressure exists. This is why common advice is to take risks when you’re younger – you don’t have those kinds of pressures yet.

Once you get past the major sources of downside, it’s a lot easier to make decisions based on upside. But it’s important not to confuse the two.

#careertransition – #1 of 8 | I recently went through a process of career exploration and made a significant career switch. This series of 8 posts is a synthesis of the lessons I’ve learnt.

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As far as careers go, there are three questions that I believe are worth asking from There are three questions worth asking every six months.

• What am I solving for?
• What am I choosing to do, and what are the trade-offs?
• And how often am I reevaluating?

There’s no right answer for whether you should stay or go. Whether you’ve stayed “too long” or “too short” is immaterial. These are random labels. You may have many reasons to do something for 20 years or 20 months. It’s hard for somebody else to judge. What matters is that you are internally clear about what you’re solving for.

Every decision has trade-offs. The goal is to be at peace with them. And the best way to be at peace and minimize regrets is to consistently reevaluate. If you’re making a conscious decision every six months, there’s nothing to regret. You made the best decision based on what you knew at the time. When you know better, you’ll do better.

Once you get a clear answer that the current state doesn’t make sense anymore, it’s time to leave.

Then use the same questions to get to clarity on your hypothesis. If you’re solving for a certain kind of learning, your starting hypothesis would be to seek that. Keep your list of what you’re solving for to no more than two or three things. That tends to be a good starting point.