Should you Stay or Go? A 5-factor framework for career-defining decisions

Nikhyl: Hi, everyone. Welcome to another episode of the skip podcast. I'm your host, Nikhil Singhal, and I'm with Carly Malatskey.

she and I are going to talk about the next mailbag episode. Uh, another question that came in and it falls into this sort of stay versus go category of, you know, should I take this new job? Or should I stay at my current job? And I figured because it's the beginning of the year and a bunch of you have spent the holidays thinking through what's the right thing to do.

Should you stay? Should you go? Environment's kind of crazy. Uh, I thought this would be a great one for us to pull out. So Carly, over to you. Uh, let's talk through, uh, this mailbag episode.

Carly: Okay, perfect. Okay, so I'm going to read it out like I did last time. I'm at one of those X growth companies, which was growing nicely a few years ago and raised at a high valuation. But these days, we're trying to restart growth and are worried that we'll see further headwinds from the disruption coming from AI.

I'm the head of product, but I've been looking for a new role for most of the year. One interesting company came up. I'm in the Bay Area, and this is an East Coast public company that's publicly traded. Solid team, number two role working for the head of product. The pros are I'd work on an AI product and work in a new market.

And the stock is liquid, compared to my current role, which is still private. The downside is the company stock price has taken a big hit from its peak a few years ago. The headquarters is on the East Coast, and I would be one of the very few leads on the West Coast, which isn't my preferred working style.

I'm not in a huge hurry to make a decision, but it feels like this role is better than my current one. What's your take on stay versus go? Okay, so, you even mentioned it, but this question almost boils down to when is good enough, good enough. So if the next role is better than the current role in, you know, some important ways, Should you pull the trigger, or should you keep searching?

the answer is always it depends. you know, there's no material out there that you can read and say, Oh, that exactly applies to my situation. So what I feel. We need to do in this episode is because it's a common question. We need to help people kind of think through a framework to be able to make decisions on like, when is your current job worth leaving?

Nikhyl: When is the new job worth joining and when does sort of the levels kind of even out to be able to make that decision? But it's that framework and job searching thinking that we need to kind of, really delay in this episode.

Carly: Okay, perfect. So, like you said, you said there's a framework, but before we even get into the specifics, I actually have more broad questions about job searching in general that I'd love for you to give your take. And one of those is, how active do you think people should be in job searching? Should we always be Passively searching for a job in case something comes up, or how do you, how do you reconcile that?

Nikhyl: I mean, I probably meet 5 percent of people. That are like, Oh, you know, I, I kind of really like meeting people through interviewing and I would say about one out of every 20 or into that, which means 19 out of every 20, find the whole freaking thing exhausting.

And I generally don't love the idea of constantly being on the hunt. you know, maybe it's sort of like dating. I mean, I think that, you know, you should sort of focus and settle down and try to make your relationships work as opposed to just constantly be like pushing, pushing, pushing for next. I also think it affects kind of your vibe at your current job when you're constantly like, Oh, you know, I'm here, but there's always another job before me.

Having said that, my broad framework here is that we should make sure that every person listening to this podcast episode has a sense of, is their job that they're in today career additive? And the concept of being career additive is kind of our core focus point. If it's career additive. Then I think you should absolutely continue to stay in your current company.

if it's not career additive, meaning like if you were to stay for another couple of years, the stories you'd tell would roughly look the same, or maybe the compensation would be under market. Or you're not really building a skill that is going to really apply anywhere else. Well, that's concerning.

And now the question is, if you're in a job that's not career additive, you probably should be talking to other people, and looking elsewhere. And depending on how acute the problem is, you might want to accelerate your timeline. But my sense is you should be only kind of chatting with folks in the side if you're, you know, in a non career additive role.

Now, the second thing I would just say to answer this question is, Sometimes it's useful to know like where you stand in the market. And so if, for example, you're 10 to 15 years in career. You've had some success. You're thinking maybe your next job is head of product, but you're feeling pretty good about your current gig.

Maybe what the one thing you might want to do is check with companies that are recruiting head of product and actually talk to them, perhaps even interview to see where you stack up. And let's say in that example, the company says, well, we feel, you know, that yes, you're interviewing for head of product, but we're worried that you don't have a strength and, you know, technical analytical skills.

And that's kind of a prerequisite. Maybe you hear that a couple of times in your. Kind of early exploration. Then, you know, boy, you know what? I should try to make sure I acquire those in the next one to two years in my current company. So if you're given a choice within moving to another role and staying, maybe you go and find that skill, which will help you, or maybe they'll say you've never worked for a company that's relatively large and successful, and that's a big problem.

And then you might realize. Maybe you had a product isn't my next job. Maybe I need to think differently. So that's where kind of interviewing, but very strategically can help, but generally it's for a reason and networking, using the kind of general term of meeting other folks can be just as helpful than doing the formal interview in the second case that I described.

Carly: bit of a follow up question to that, you mentioned how determining whether it's career additive. Do you find that some people are maybe too haste, hasty to make a decision, meaning that they join a company, they give it maybe a month to see like, oh, you know, this is not it, and I should start looking for a job, it's not what I expected.

Versus, like, do you think there should be a set timeline to say, like, a month is too soon, you need to give it at least six months before you make a decision saying this is accurately how the work is and it's not for me.

Nikhyl: I took a call like this last year. And the call was. I think I made a mistake and I get a few of those and what I would say is that you would put your blinders on for 100 days with the exception of values.

So, like, let me go through the edge case and then I'll take the normal case of the edge cases. You join and you're like, hey, I think they cook the books. I think that they. Don't believe women should be leaders in this company. Like stuff like that. I'm like, time to go. It's just

like,

Carly: that won't change. That's like a set thing that probably won't change. Okay.

Nikhyl: it shows the character of the company.

The character of the company is that they help withheld information. And you know, that this is only going to be the starting point. It never gets better. It's not like, Oh, that was all like a one time event. It's just like, there's bad stuff there. So sometimes you can't tell until you go through the sort of threshold of the doorway to know what's behind.

And there's always going to be quote, unquote, hair on the deal. So there's always going to be some, you know, something under the rock when you lift it up, there'll be some issue. But if it's very value driven, I would say, you know, I just think that life is too short to work for companies that have weak values.

Having said that, when you pull it up, there's going to be things like, Hmm, the role that I signed up for isn't quite there. Maybe the health of the company isn't quite where it needs to be. Maybe the founders are more tightly held on what they want to do with the company or my boss has a very strong point of view and this idiosyncrasy and working style may not be right for me.

Give it a hundred days because they're also adjusting to you as much as you're adjusting to that. After a hundred days, you don't gain that much by giving an additional amount of time. Now, if it turns out that you're really, really shocked by what you see, and you had another company that was a finalist, maybe it is better for you to just sort of say, Hey, I now know what I know and make move, but these are pretty rare.

six months. Is maybe slightly longer than I would normally give, I would say a hundred days, not as much changes between a hundred days and six months in terms of understanding the environment. In six months, you might be able to deliver your first thing. It's hard to deliver in your first hundred days, depending on the scale of the company.

So that's where I'm like, Hmm, you're in that range. Generally, if you're going to start your search over again, you're not losing that much by taking a little extra time. And maybe you'll learn and you always learn the most when the company is doing great and not really well and not in between. So if the company is really dying, maybe you'll learn something and that'll help you as well.

Carly: So, follow up question to that is I'm actually curious on the employer side. how it's viewed when people jump around. And what I mean by this actually is, even on SheLeads, on my podcast, I have a lot of senior women who, you know, in their career, they've been at their, you know, previous jobs for, for eight plus years, 10 years.

Nikhyl: Nowadays, it's very rare to see that. You see people, you know, probably two years on average, they're jumping around. how is that viewed? 40 years ago. It's pretty normal for people to have like one or two companies on their background. And now I think, uh, to your question, the average 10 years, like two and a half years, you know, which means the average means that there's going to be some people that are less than that.

And some people that are more than that. I kind of look at sort of impact and storytelling. So the question is. If you came to me and said, Hey, I'm thinking about making a move. And yet one of the reasons I'm, uh, worried about it is I've been in my last three companies for two years each. And then your question, and to be more concrete is to say, is this going to be a negative on my background?

And I would say, look, you know, Carly, if you're, you know, rising quickly and you're outpacing the company and you tell me that, well, at company one, I deliver this and then at company two, I deliver this and a company three, I deliver this. And in each of those cases, they were bigger problems. And they were better solutions that, you know, than the previous one.

But I just kind of outgrew the company. You know, the company was moving like at this pace. And I was just like, there wasn't as much headroom or the problems weren't as interesting, or I took a lot of risk when I joined these companies and these companies, naturally some of them worked out. Some of them didn't, I would say, no, I mean, I think you're being thoughtful about career, getting what you need out of it and moving on.

If on the other hand, we start hearing like. You just didn't fit. And so you keep moving around because you're not fitting. I'm like, I definitely think you shouldn't be trying to force fit into a company if you feel like it's not career additive, going back to my earlier comment. But if it's like a pattern, it's been two or three companies, then maybe it's not them.

Maybe it's you, and maybe you need to grind it out. And maybe the, the, the value exists by grinding it out. Now, I also think that the larger the company, the longer it takes to really have impact. So one of the pieces of advice I give is that, look, If you're in a growth startup, you should be in a position where you would see impact in say six to 12 months.

But if you're in a late stage company like the Facebooks and the Google, it's not uncommon for those companies to really require you to be in year two or even year three before you really have some of the bigger impact because there's so many people to know. There's so much, the way that they build product is very unique.

It just takes a long time. So when you describe, you know, some of the people that you've had on your show who are very, very senior executives, it's not surprising that it took them four or five years to build a trust with their peer set and their layer leadership above them for them to give, you know, more of an opportunity for them to bet and risk on them.

And then once that happens, they see delivered, et cetera. There is value in staying, but I think that even in their case, their story every year or two was different. They were solving a bigger problem, something that was more important, and they were having greater impact. And in that case, every year is prerogative and made perfect sense.

Given that nowadays LinkedIn is such a powerful tool that people, you know, kind of create their own narratives just by looking at a LinkedIn profile. Is that something that people should tailor towards of almost wedging in a storyline or, you know, because what about the people who can't afford to give that storytelling and that, um, that narrative to it if it's just, you know, on LinkedIn?

Yeah. I think that the resume slash LinkedIn optics are sort of very much around. Here's a classic. This is the company. This is how successful the company was. This was my role and then this was the product that I was on and this is how successful it was and you and I both know that they're going to be like some top performers and they're going to be some bottom performers and they're going to have exactly the same paragraph written about LinkedIn and there's going to be actually no difference.

So my preference when I interview less, maybe looking at it from a resume point of view, but when I interview, I'm always asking people like, tell me the. Problem you solved, what was hard, what opinions you held, how did you overcome, did you fail to overcome, et cetera. That's the best way to determine it because they're going to be exceptional people at bad companies and exceptionally bad people at good companies.

And these days that that's really the question is what is the story? And then the reverse side is if your story is not good. That means you're not getting a career out of a position. And if the story is quite good, then that means that you're gaining something, even if the company may not be doing great, you know, not everyone's going to have the time.

You know, if you're interviewed by an AI, maybe they won't get the, you know, nuance or whatever, but generally speaking, that's the thing you want to optimize is am I building a career story? That's really helpful.

So, I mean, if you think about some of these best senior executives, That are, you know, part of our community. And then we work with the folks that, when they, you sit down with them, they're just like, Here's the story I did at this company. Here's the story I did at this company.

And then the products are increasingly more impactful. They're much harder problems. And you can just hear like, well, we had these choices and we made these decisions. And I had these opinions and this one worked out and this one didn't. And then I moved to this next thing. This next thing was a completely different problem set and we were able to overcome.

And then at some point you're like, wow, this person, no matter how big of a problem we get, tend to give them, they figure it out. Like, Hmm, my problem seems small in comparison. They're definitely someone we want to bring on board. that's the way to break through the branding, the tenure, LinkedIn math.

And it doesn't mean you have can't get, you have to get in the door. I get it. But then once you're in the door, it's these stories that really make the distinction between candidates.

Carly: Perfect. That's great. Okay. Let's dive into this mailbag question. First, lay the framework. Like you mentioned, what is the framework that you use? And then we'll go into more details for each for each element of it.

Nikhyl: Yeah, I mean, to sort of remind people, I mean, this person's trying to decide between, you know, they're in a growth company today, maybe arguably an ex growth company. So this company was doing well, is what I'm reading, but now isn't doing quite as well. And they're in a role that maybe they're in a leadership role, but they're like, hmm, maybe this isn't a great company, so my story is sort of flatlining.

And they have this other role, which is. Not a, as senior of a position, but it's a pretty different market. It's a different, compensation structure. And obviously it's located differently. And so now they're trying to calculate, like, how do you compare the two? Right. So I tend to use, you know, when I think of this type of question, I'm like, well, I want to understand compensation.

I want to look at skills. I want to make sure I understand the lifestyle choice between the two companies. You know, I very much want to know, like, can the person succeed, you know, what kind of story they'll tell is another way of describing that. And then what is generally the environment that they're going to fall themselves in?

So if you look at sort of this comp skills lifestyle. Success environment. These are kind of the traits that I would want to have everyone think about when they're thinking about stay versus go. Does that make sense?

Carly: Yes, totally. So let's start with comp. And right now, the context that we have about comp, he doesn't really give, or they don't really give a base salary, anything like that. But they do mention how this stock is liquid So walk me through what should people consider regarding comp when they're considering stay versus go?

Nikhyl: Yeah. So I think that, you know, broadly speaking, you're sort of running an A B test. In this case, you've got an A, which is the stay. What's the comp you make today? And then a B, which is what would be the comp in the next one. And I happened to list it first. It may not be the most important one, but it frankly is probably one of the easier ones to compare.

And so in this example, you've got someone who's, you know, getting privately held stock, exactly as you point out. And the stock used to be higher value than it is today because the company raised when the market was really hot. Now it's not as much. So there's some questions. As to like how valuable is the equity going to be worth and that's a big chunk of this compensation package and then you've got this other company that you're going to come in and you know it is a public and so it's essentially liquid comp and the sort of the two factors that now we're thinking through is.

you know, today, in either case, is it above, at, or below your market rate? So let's say in this case, the person made a million dollars a year, going back to our previous episode, you know, if the person stayed in 2025, are they going to make their market? You know, so let's say that this person was to stay throughout the year and then eventually leave and their expectation is it's probably going to pay them, in good faith, 500, And then they're taking another roll, and that roll is exactly a million dollars, but and it's like liquid. Then I would say, well, okay, we believe that said individual should be making a million bucks a year. They're making half that in their current gig, and they're making the full amount in the next gig.

And maybe that company, you know, the stock fluctuates and maybe it'll go up or go down. But my, my general and broad point is that's like a two X difference. So that to me is like one, we see quite a difference in the compensation. Now, on the other hand, if the second job was also paying 500, 000, then maybe you would argue that that's their market rate.

Maybe you would argue that they're roughly the same. And both of these jobs are below the million dollar number that we described earlier. So what we're really trying to do is like, are you being paid below market? And how do these compare to your market rate is a big core question. And in this example, I think what we're saying is we're probably making below market.

The other job is going to pay more because of its liquidity and the fact that you can guarantee the equity is going to be able to be traded. And now the secondary question when it comes to comp is. What's this person burn rate, you know, let's say that the person's like, well, I need to make 700, 000 to not dip into savings.

Just given our family situation and expectation, I'm like, well, boy, the current gig is below that, you know, you expect, even if you take out the fact that some of your equity is, is not liquid. You're probably making like a couple hundred K and then hoping the equity works itself out. And you're saying the best case scenario that makes like two, 300 K additional.

you're way under your expectations. You're burning a lot of savings. That's sort of in the rad. You know, but let's say the person on the other hand is like, actually I don't need more than two or 300. I'm making that much liquid for my current gig. I think I'll make more with the equity. This one also was going to pay much more, but that one's letting me like solid green.

And I'm like light green. Then I would like, let's move to something else. You know, I'm just trying to figure out like, are you burning a ton of cash in either of these roles and are you like clearly over underpaid compared to your market rate is really the two questions that I would push on.

Carly: Okay, because it seems like, at the end of the day, when you are comparing the two, You also are thinking, how much does comp play compared to the other things that I'm optimizing for, do you find that it's still quite rare to have comp be the main, you know, maybe number one lever that people look at because even in this mailbag, right?

They mentioned the title, you know, the location of it and all these other factors. So how do you advise people to think of comp in the greater framework?

Nikhyl: Yeah. I'm looking for outliers. You know, what we're doing is we're sort of fishing for outliers. So an outlier in this example would be, you know, individual in this case is like burning tons of savings and currently in the current role or would burn tons of savings in the new role. that kind of immediately becomes the core question.

Like, can you afford to stay? Can you afford to go on the other hand? If we're like, Hey, both of these roles are basically paying me under market. You know, then I'm like, okay, we should definitely look at some of the other factors,

or if it's like one of these roles is like hugely advantageous. Like I have this conversation come up all the time.

Hey, I've been in this current position. I've been burning a little bit of savings. If I take this other role, like I had this come up recently, where a person's like, I'd been under my current comp value for eight solid years. I'd worked for eight years. And I had taken a job at a privately held company and that company had, you know, essentially paid me its minimum 150, 200 K and then giving me a huge amount of equity.

But after eight years, we're wanting the company down. And in that example, the person's like, I'm going to value going to a liquid salary. And I don't know if I care about the other four factors in your framework because I'm like feeling so behind. It's causing so much stress. I'd rather just get something that is liquid that I can guarantee pays me market, do that for a couple of years and I can take greater risk.

So these are the outliers that I'm kind of pushing on. I'm like, okay, in that case. If you can find something and it's a tolerable job, I'm not sure it needs to be that career additive. I just think you need to kind of restore. And maybe you could argue at year four, maybe they should have made the move 2020 hindsight.

But my point is, these are the outliers we look at in this configuration. And then if there are no outliers, then we kind of look at it in an aggregate.

Carly: before we go on to skills, I have the next part of the framework. I want to ask, how do people avoid falling into that trap to, to determine, you know, I'm not being paid under my market rate? It seems like my natural instinct, and you mentioned it actually in the beginning of this episode, which is, you know, take that call with the recruiter, you know, maybe go through the interview process to see what you'd be paid.

But are there other ways? Like, how do people, you know, not fall into that trap and determine that they're being paid market rate?

Nikhyl: so in this example, what happened is this person had taken a bet on a startup it would be the equivalent of like, look, going to join as a leader in a company, which is going to pay me less. Then my market rate, but it's going to give me a whole boatload of equity.

There's situations where a person knowingly makes this decision. And then there's a situation where they're like, well, I thought it was going to be like my market is X.

And in that example, yeah, it's joining a community, understanding how people get paid, looking at the information that's out there. but also just being like pretty cognizant of like, Hey, is this equity instrument, which in this case, a lot of times it's like, well, I thought this equity was going to be worth something.

You need to be really clear on like, what does that number need to be? And trying to essentially work with a company to determine like, is this really worth it now? Again, this is only comp, like it might be the case that, Hey, I thought this thing was going to be worth 250 K a year. And my guess is it's only going to be worth 50.

That's kind of what the example is in this question. Then it's like, okay, then just let's make sure that the other things you're gaining are worth that trade off. What I don't want people to do is say, well, I'm hoping it all works itself out. And then year in and year out goes, they don't think it's going to work out and they don't gain any of the other experience.

That's when we're in the non curative zone.

Carly: So why don't we go now into, to another element of the framework, which is skills. What skills are you learning? How do you determine that?

Nikhyl: Yeah. And again, it's sort of an inside the building, outside the building question. Outside the building is the easy one. Like if I'm looking at an AB between stay versus go, One question is like, Hey, are the skills you're picking up either in the current job or in the future job going to be great for the environment?

You know, like an example would be, Hey, I'm learning AI skills like we all can agree that that's helpful, you know, and again, AI skills can be everything from really the deep technical how AI is being built all the way up to like, we're using AI all the time and we're becoming more efficient, which frankly, I think is super, super helpful.

And you could argue that one of these two jobs could be that, or something a little softer, like, I feel like my current job is a very, very hands on role, and I have a lot of stories to tell because I'm in the detail, and this next job is a little higher level. It's a little unclear as to what the expectations are.

I'm like, hmm. That could go wrong because these days people want detailed hands on in the weeds type leaders and the sort of org builder manager type is less important. So I'm going to ask like, Hey, skill wise, I'm trying to determine like, what are you picking up naturally? What do you think the next one's going to be picking up similarly to succeed?

Sometimes you have to build some skills that are unique to the environment. So when you're at a company like Google or Meta, a lot of times you're learning their way of building product and sometimes their way of building product is like, you know, super, super valuable. Like I was talking to someone recently and they were saying like right now, a lot of people that are working at DoorDash are under great demand.

Because DoorDash and Meta maybe 10 years prior were great growth environments and they knew how to do product growth. So anyone that was in those buildings have a lot of experience in doing that type of work. So that's a very valuable skill that unique to DoorDash or Meta back in the day is now very valuable to the general environment.

I'm sure working at OpenAI today is going to be very valuable for others. But there are companies that are also very idiosyncratic that are like, well, you know, spending a lot of my time convincing my boss, my boss's boss, my boss's boss's boss. How to get things done. I'm like, that's a good skill, but it really applies to later stage environments or companies at this mega scale.

And if you have literally no interest in your next job, being that knowing that skill is like marginally translatable, but it's somewhat unique to the environment. Or let's say I'm spending a lot of time working in a detail around security, and I'm like, not interested in working in this space again, but I'm building all of this detailed work, like a friend of mine used to run the tax business at Credit Karma and became one of the best tax experts.

And I'm like, if 90 percent of your energy is becoming a great tax expert, but like you're never going to work in tax again, you kind of have to ask yourself, like, is that career additive? Is that a skill that you really want to translate? Well, maybe learning how to work with like institutions is valuable, but tax is not.

So you sort of need to look at what skills you're picking up from the internal and external and how esoteric. And how translatable is it is the second part of this equation that I kind of scorecard. So I'm like, okay. And this example, comp felt like it was substantially better in the new environment as we don't think the equity is going to be very valuable as it played probably below market in the current situation.

The second one, we're like, okay, skill wise, his note is a sort of AI leaning and his current environment is maybe less so, but at the same time, he's a number one right now. So he's a leader and there's a lot of very valuable things of being a number one where your peers are engineers and marketers as opposed to other product people.

And this new job sounds like he's not a number one, sounds like he's going to be working with some other folks who are product folks. So it's maybe a little bit more like someone that worked in his own team. So that's step down. So maybe there's some like fungibility. So new product line, but perhaps not as senior, right?

So that's kind of a, maybe that cancels itself out, but it's sort of in the zone is what I'm seeing.

Carly: what do you find are the best ways to try determine what skills you will be learning in that new environment if you were to join? Is it talking to just a bunch of people at the, at the company? Or do you have any, any like tangible advice to really learn? Okay, if I join, this is a new skill I would learn and I have good confidence about that.

Nikhyl: Yeah, that's a great question. I think sometimes it's a combination of the skills it takes to get things done in the company. You can kind of tell by the peers as to like what skills. Have they had what background they've had? And sometimes it's a question of like the role specifically and what the expectations of the manager is.

So let's, let's take the 70 percent case, you know, everyone knows that at meta tends to be very data oriented, less engineering driven, less technology driven in say their product management. So you know, if you go and you succeed. There's a certain style of product that you need to be able to adhere to, to get things done.

And it doesn't take much than just talking to the successful product people and just understanding, like, how do you work? What are your skills? Where did you come from? And you'll figure that out. So I knew when I came in to Meta that they did product differently than I'd ever done before. The fact that I'd be good at data, I'd look at pre read documents, I would be much more in the detail, they do a lot of system design, product makes a lot of the decisions, like I knew that that's like how I would come out, or I would fail trying to come out that way, but that was a skill that I would need, and it's true, I mean, I built a ton of great skills that I wouldn't have gotten elsewhere.

When I was at Google, I was very much an eng driven person. Culture with a very technology savvy product management team. So they build product through that technology lens. And I knew that's how I would end up having to deliver. And that skill was similar to being a founder in my example. So it was a relatively translatable.

And the flip side of the question is. But if you're going to enjoy, in this case, kind of an AI leaning project, maybe it's a zero to one that they're looking for a new leader. Well, those are definitively a skill that maybe your peers don't even have that they're trying to bring in from the outside. And then the question is going to be very much focused on, hey, what are the expectations of the manager?

And what's probably new to the company, where do you need to hire from? And so it's a kind of a discussion there, but most of the time you kind of get for free this sort of what's the stock, who succeeds here, what have they done? Well, what have they done in the past is like the core thing that you almost can guarantee you're going to have to figure out.

Carly: Oh, I really like that. I like that question too. Almost just who succeeds here. And that's a good way to know of what skills you, you will get. Okay, let's go on to lifestyle. That was another, another element.

Nikhyl: I think this is the one that I think hurts the new company the most in this specific example, because we had, we had teed this up. And we'd said, well, you know, I've been at this current company for a couple of years. I know the people, maybe the company's slowed a little bit. but I kind of have a pretty clear expectation of what this 12 month looks like.

I'm not sure I'm moving fast enough at this phase of my career. So I want to maybe take some more risk, but from a lifestyle point of view, you know, there's a lot of known in this example from this new company. There's an immediate West Coast, East Coast. I'll be the one of the few people that are on my coast.

I'm like, okay, that's not let alone. Is it a new company? And you're going to have to kind of surge to get to know the environment, the culture, the people, but you're also like a remote executive, which is in contrast to the current role. And then on top of that. It does seem like there's a fair amount of pace in this new company because it's a relatively urgent.

It too has not been a pure every year growing. It also has had its challenges and it's a public company. So there's going to be a lot of pressure to make kind of expectations. you know, in the same way we talked about comp is like clearly being substantially better here because it's liquid and it's probably at market lifestyle, I think is substantially worse.

you know, I think a lot of people will be like, Hey, I'm willing to take that. You know, I, I can work hard, you know, that I'm like, Yeah, but I think it's important to put on the scorecard because you might be better off choosing option C, the next company that we have yet to determine exists.

And so part of me is like, is it worth taking a role that has such a substantive hit in lifestyle than, uh, taking a role? That, you know, maybe like not yet identified, but available in June. And so that's the reason why I call out lifestyle in a pretty big way that I think, you know, every one of us has got constraints and I want the role that you're considering, whether it's your current or the next one.

To fit into those constraints, work should fit into the constraints you give it. And I shouldn't just envelope everything. And by the way, this could be the flip. It could be a, Hey, I'm burning out. And I, you know, I just hate the environment I'm in. I'm just like a very negative person because I just feel like work has kind of overwhelmed me.

And so then you're like, okay, well, that's a very urgent situation, a remedy, even a role that may be less career additive, but as dramatically simpler to measure and as a lot better lifestyle is worth considering. and I think that there's something to say that that then bubbles up to the top. So I'm again, outlier lifestyle seems like an outlier in this example.

Carly: I also love how you also just, like, be honest with yourself, you know, like, even if it's, if it's not good, like, that goes on the scorecard. It's not great. And don't, you know, push it aside just because it is a new opportunity that came up and there are other things that maybe are more exciting. So we'll get into that because I'm, I'm, I'm curious of what you ultimately advise this person.

Nikhyl: want to double click on this point that you're making, Carly, because I think. We're talking about things like lifestyle. We're talking about compensation. Sometimes we're told, Hey, you know, suck it up. Sometimes work as a grind. Hey, comp is something that should be a lagging, not leading indicator.

You always want to build skill. And I guess the point I'm trying to make is like, look. You should get paid, and you should be paid fairly, and it creates a lot of stress when you're not, and it causes you to have short tenures and, like, worry, and if you can't do good work because you're burning out, because it's asking too much, and you're a horrible person at home, and you're having to make some trade offs, we should probably talk about that.

We shouldn't just say that the biggest job at the best company is the one that we always need. I'm like, no, no, no, no, this is a marathon, not a race. Like pick the right company for who you are now, not who you used to be, not who you want to be. Be realistic because there is still a job. That's great. That fits into your constraints and your expectations.

It's just that you need to make thoughtful decisioning. And the better job than the one you have today is not necessarily the best decisioning because there could be even a better one. that's the reason why we're, we're kind of trying to break things down a little bit more scientifically here.

Carly: Okay, so there are two more that you mentioned in this framework. The next one is, will you succeed? How do you determine that?

Nikhyl: Yeah. And this is one of my favorite ones, because it's like one of those questions that people don't ask is, you know, how long do you think you'll be at the company that you're potentially in now, or you'll be in the next, like sometimes people are in a job. Where they're like, Hey, I'm going to take this role and it pays me more.

And I think it fits into these other criteria. And I'm like, well, what are the chances that you succeed? And you're like, well, I'm absolutely going to succeed. I'm going to, I totally get, you know, put me in the game coach and all that. Like, I think we should look at this pretty, carefully. In this example, there isn't another person who's held this role before.

It's a relatively new initiative for the company, and they're looking for outsiders, and they're also struggling a little bit, so they need this initiative to succeed, and they're trusting someone who's never been at the company, who doesn't know anyone, and in your case, this particular individual that's asking us the question.

Just generically, no matter how good the person is, it's like a 50 50 shot that this thing even works itself out. So, you know, where that matters is if you have a relatively high chance of succeeding in your current role, and it's in this case a number one position, but there's a relatively low chance That this new role work itself out.

What I'm nervous now is a personal is going to come in a year, a year and a half and be back in market. And that isn't as valuable as something that's higher chance of success that has some of these other characteristics. So this one, I would say is high risk, partly because it's new for the company and they're trusting an outsider.

Big kind of flag, partly because it's like a tough lifestyle, like, you know, to succeed, you need to have relationships. Person's going to be on the other side of the coast. They may not be able to be there for six, 12 months. You're the only one that's like that. So immediately our human nature is, is the outsider.

It's a new thing. So they didn't choose to trust someone who's in the building. So all those people are like, well, I can't believe it. I've been on this like project for so long and I don't get to do the new thing because we're trusting this guy. I hope this person succeeds. Expectations are a little out of whack.

So I'm like, okay, success matters. And again, the same thing applies to current role. If you're a head of product of a company that's not going to make it out, then that's also worrisome and then you won't have as much to show and maybe you should be more likely to look elsewhere. So success and the potential to success.

I know it's sometimes hard to know. But I'm going to probe as to like, how likely is this going to win? Are you going to win? Because winning is this part of the storytelling. You want to be able to say, I was working on something, it was hard and I have succeeded or I learned. And if you can't really say that in one of these two cases, it's sort of not career additive and going back to our original point, that's a problem,

Carly: And I think what you touched on as well, in terms of will you succeed, is It's not even just the tangible concrete skills. Are you shipping products? Are you doing that for the company? But it actually can be this all encompassing question of, you know, you are remote and you may not like being remote, you may have, you know, burnout, like all these motivations that can come into it of like, do you, will you be putting your best foot forward in a way?

So there's like other factors that can come into it that you already talked about in the framework,

Nikhyl: I'm almost fast forwarding to the conversation we may have with said individual in 15 months. And in 15 months, here's my bet. Conversation is going to be like, you know, I took the role and it was really tough I pushed really hard, but in the end, the problem was very tough for the company to go and create something new.

It was, they hadn't done it before. There was an urgency that was needed. in about six to eight months, I was asked by my manager to sort of be layered under someone else who had been at the company for a long time. after that, the company had decided that they just needed someone they could trust who knew how to operate.

And the role wasn't quite what I had in mind. And then I was realizing I was flying back and forth and I wasn't able to deliver on the thing that I wanted. And I just decided it wasn't for me. so I'm like, Hmm, is that a 10%, 50 percent and 90 percent chance that that's the conversation. And my sense is, I don't think this company really knows that they can't ask someone new on a different coast to go do this thing.

And they're going to figure it out in those 12 months. And you know, this candidate might be roadkill. So I think it's like in that 50 percent case.

They probably should have given it to someone who had the company. Cause the hard part wasn't cracking the code on the industry. It was. Teaching the company to do something new for the first time. And that was really hard. And there's no way an outsider in my situation would have worked it out. And then the thing that's going to be in my head is like, could we have guessed that was going to happen when you took the job and my job is to figure out what are all the things we could guess related to success.

Right now. And my calculation is 50 percent chance. The company probably shouldn't make this higher and you're going to be the one that they're going to experiment on. And that's too high of a risk. So that's why lifestyle was a factor, but success is like. Boom, that's the one that we're focusing and I'm discussing with

this individual.

Carly: So we're getting a good sense of ultimately what you advised this individual and we're going to wrap it up with that. But to wrap up even the framework question, the last thing is environment. So like current job, the job search, how much time they've been looking, how do you weigh that for the person?

Nikhyl: Yeah, I mean, this is an intangible on the current, like, you know, how bad is a person want to get out of there? And then how much am I telling them that, Hey, you know, suck it up versus like, Hmm, it sounds bad. Again, I get really pokey when someone comes in with values. You know, Hey, I think that the company is like mistreating me, you know, and that can be like paying me 10 cents on the dollar to my managers, you know, second guessing.

I'm like, look, we're in tech life is too short. You should be able to find a better gig. Let's translate that into some exit package. But for the most part, a lot of times people are like, yeah, I'm not sure that I'm going, this company's going anywhere. And I'm like, yeah, but if you're making money and you optimize the next job search by an extra three months.

That's totally worth it. So usually I'm like trying to figure out how bad is the current environment. And then I'm also next trying to figure out like, okay, if you've been in market, have you been in market for six months and interviewed with like 10 companies and have mostly not heard positive results.

then if the person comes in and they're like one out of 10 did come back with this, I'm like, Hmm, six months, person's not in an awesome environment. Definitely going to make money on comp, maybe 50 percent chance they fail, but I'm not sure in six months, we're going to get dramatically better result.

Like another company that's like massively better. I might be more inclined to say, move forward. But if on the other hand, the person's like, I, this is my first offer and I got it in three weeks. And I'm like, look, you know, the data probably shows you're probably get more. I mean, this is probably not a unique situation and you've got time.

I do think that this is, I mean, this is kind of the most obvious of all the factors, but this is a factor that like, what's the market, what are you people seeing in you? How bad is it today? Do I need to get this person to grind it out to really do a real search? And then in the new environment, is the environment filled with good people?

Who, even if the company didn't work itself out, they clearly are hiring some of the best and the brightest. Or are you like the smartest person at that company? And if I'm like, okay, well, let me get this straight. You're literally the smartest person at this company. The chances that you're going to really learn are going to be a little less from your peers.

And your current company, you know, you have good people, but not great people, but you can afford the time that's kind of like maybe more leans to stay versus go. So, in this example, I think the new environment's fine, but this person was seeing success in searches and generally was doing well in the company and get a number one, well liked they could afford to take extra time.

in the end, I know you recommended to hold for six months, so, and you kind of touched a little bit of where that came from, but how did you determine that in terms of even like the timing? Like, why six months?

Yeah. I mean, despite the comp being substantially better and the fact that it's AI and that was another positive, most of the other factors were negative. number one versus number two, sort of, I think is worth sort of looking at. Chances of success in lifestyle were super, super negative. And in my opinion, if the person in this example is a Bay Area person.

They're going to be able to find a local company that is a higher quality, than the one that they're being suggested. And I think they should be able to find that company, uh, with liquid compensation. And I'm betting because there's still pretty early in search and seeing some success that'll appear.

And I just think that it's probably worth the extra few months that it is to sort of jump on this one, because I don't think that. A person's going to be able to stay for more than two years, and it's going to be a rough two years. And then I think that they'll be like, okay, I have a sort of an okay number one role and a not an awesome position.

And then I'm going to have to deal with like, you know, they're not feeling very successful. So I'm like, I just didn't want to have to deal with that. So I was sort of like, Hmm, feels like you should probably see what else is out there.

Carly: it's so interesting because when I first read this mailbag and what you advised them, in my mind, I was like, that must be a pretty hard pill to swallow, right? You see this almost gift in front of you, and yet you're telling them like, nope, don't open the gift, don't, don't accept the gift, and instead, you know, hope.

that you have a better gift that comes around. So, I'm curious, like, would you have given the same advice, maybe if the market wasn't at a state where hiring is super rampant, and maybe it's a bit more of a risk if another job would come?

Nikhyl: Yeah. Or maybe even another way to describe me is what would I have to believe to suggest to leave? there's probably two things that would have tipped me. I think one is if the person was just out of patience. They're like, I have to leave.

Now, it's a question around unemployed job search because they're done versus this burden hand. And so I was not presented with that problem. I was presented with, I'm willing to kind of stick it out and I'm still open to searching. So when anyone comes to the end of their rope, they tend to make suboptimal decisions.

And this was not the case, but it could have been. And then the second case is like, if I was more convinced this person could succeed, even if the lifestyle would have worked itself, I would have been like, Hey, you know, this can be a grind. You're going to have to do it in the East coast thing for a couple of years.

But I'm pretty sure you're going to win because your current background makes you perfect or the company has a track record or you're going to be working with some killer, killer peers. I just don't think that person is going to succeed, but they could have succeeded, if the company was slightly better set up.

So that's why I would say that's the number one factor in this case,

Carly: I like that. I like that a lot. Okay, this has been, this has been great. You've given such tangible framework for how people can think about it. Is there anything else that we may have missed that you want to add on this whole overall topic of stay versus go?

Nikhyl: I think maybe if I was to summarize things, the most important thing is always bet on yourself in the end of the day, bet on yourself that, you know, if you've gotten one offer, you may get another one, bet on yourself that you can take on a big challenge, but you also have to recognize that sometimes a company has just set up against you or role set up against you.

So you want to always start with like, I'm betting on myself, but I'm being very wise as to that risk and whether it's like overly constrained or not. And that, that's kind of the broadest sort of general takeaway that I, pulled from this.

Carly: last thing I also really liked, it's almost thinking of, like, what is the conversation in 15 months from now that you can have? And I think for me, you know, like, when people consider, should I join a startup? Even when I had my own thought process of like joining a potential startup, for me, it wasn't of, you know, will the company succeed because those chances are so low, right?

So I almost think like, great, even if it completely fails, I at least know I'll be learning so many skills that come with, you know, running a startup, whether it's messy, whether it's not, you know, all of these other things that happen. So again, It's almost how can you frame that in your mind to be like, can you walk away from it in 12 months being like, that was great because I learned so much that I anticipated I would learn.

Nikhyl: Yeah, I think this is a great nuance how your point was a company may not have succeeded, but it was a high personal success and that we would weigh very much in favor, right? So this is a great example of everything's quite doesn't really lend itself to a book or a blog posting. And my hope is in today's conversation, you can kind of hear what it's like when I'm presented, like going through these nuances.

To eventually come to a conclusion, but more it's like showing your work makes all the difference. And you want to be very open with yourself because all of these constraints matter and all of these different factors kind of weigh into the decision.

Carly: Perfect. This was a, this was a good one. It was a jam packed one. I

Nikhyl: Yeah. Thanks for your time on this one. Thanks for going through it. And so clearly

Carly: course. Thank you.