Battling job search anxiety

Nikhyl: Hi, everyone. Welcome to another episode of the skip podcast, a podcast dedicated to your tech career and getting you ahead. Today's episode is another live coaching conversation. A friend of mine who was a coworker from my past called me because she was just starting her job search and, arguably not just starting,

she had taken a few months to get her bearings and was just starting to test the waters. The climate today is really tough. She being a design leader, wasn't necessarily my area of expertise, but in the conversation, as I started talking with her, I realized that she was struggling a lot with her mindset.

she just had a bit of a crisis of confidence and how to get started when you're on the bench and, you know, seeing the game, pass you by was really on her mind.

In that conversation, we explored both some real tools that can help her start her search, but we also explored the mindset needed to really push hard. You know, this crisis of confidence came because she was starting to feel like maybe she'd been lucky in the past. Or maybe she had taken too much risk. Left a job that was going fairly well, but maybe wasn't as career additive market shifted and now the music stopped and didn't feel like she had a real seat to sit in.

And so this was really on her mind and my guess is some of you that are listening that are in transition or feeling the same way. Was I lucky in the past? Did I make some bad moves? Is the market really, not for me? So this episode is really devoted to really help you come up with some concrete ways for you to navigate job transition.

Well, what I'm thrilled to announce is that she actually did find a role partly due to our skip community. This network that I've been building surfaces all kinds of roles and in this case, was able to find an opportunity through our network and get placed.

So, as we enter into the episode, instead of sharing the full conversation, I'm just going to share the most compelling clip where the caller is really struggling with her mindset. This is not AI generated. This is actually a real live conversation. and then afterwards, I will come back and I'll share with you about a dozen or so tricks, tips, techniques, mindset, and strategies that can help you navigate a job transition. These techniques are based on the dozen or so years of me talking to folks that were entering into the job market or frankly, feeling a little stale. And they're particularly focused on how to think about leadership transitions, which I think are a whole different class of transition. So hopefully you'll find this episode valuable, especially if you're in transition. Share it with folks who you know, that are in transition and let's get to our conversation.

Guest: I've definitely been feeling rusty. It's easy for me to get in my head. you know, I'll have these days where my confidence is just totally obliterated, right? That basic loop of, okay, yes, my skill sets valuable, it has this impact, the data points are just in the past and it's harder to draw on them. And it's definitely made me feel yeah, a lot less tight, easier to doubt reality even, you know, um, it's just sort of get lower on my own stock.

Nikhyl: So part of me, when I felt like the merry go round, was spinning and I was off of it, because I think there's two parts of the equation, right? there's you, your story and your energy and your speed, and then there's the market and how it's whizzing by. And I think when I've taken time off, everyone's like, take time off. It's the best thing, but I think that I felt when I've taken too much time off, or when I was starting to get back in, all the buses were whizzing by and I was sitting on the sideline.

One part of this search, I think, is for you to get your speed up, you know, I think that's different from the approach of managing the process. And so that's part of the reason why I may be pushing a tiny bit on not just the skill development, but, maybe consulting, maybe volunteering, doing things that professionally start bringing speed back. I don't know if you've thought about that as a, way to get on the on ramp before you're on the highway.  So I think you've got this sort of, okay, the buses are whizzing by and I'm not at the speed as I was, but I'm mentally ready.

So now we have a technique to maybe increase your speed. Then you go back and say, okay, how do I, brass taxes?

How do I start managing the sort of pipeline of opportunity?

And you made this note that look, the market does seem like there's a lot of folks that are out there. Companies are just starting to open their doors, particularly this time of year but if it's just sort of the wait for a recruiter or ping people on their jobs website.

It doesn't feel like that's the most effective way I think what you ideally do is furnish a list of 20, whether they're hiring or not, you would say, okay, these are the 20 companies that I would be curious about talking with who might see my areas of strength to be disproportionately valuable and take risk on me. that's the way you think about it.

And is that number 20? Is that number 5? Is that number 100? I don't know. And let's say the number you come back with as well. 20 is a good number, but I found 12. It's like okay, fine. Now, the second part of this is you build your board of directors. Your board of directors is like a WhatsApp chat thread, Five people, four people, six people, three people. It's not 53 people, it's not one person. And it's people that you think know you and are incented, because they know you to have actually both increased that 12 list to 20 and can actually say I do know the head of product and I would love to talk to them and present you.

And then you essentially say, great. Well, here's the email that you should forward to them. And then I'm like, got it. And then you're now running process. You're literally like a salesperson. Here are the companies that I had, here are the ones that others suggested that frankly, I never heard of, here is the intros that I've made here is the process. And the concept is, after you get a handful of interviews, I think that there's something about karma in this whole thing, because what happens is just somehow there's an energy and momentum that starts to build and you start to melt away some of the doorways, the mental blocks, you come across a bit more in demand.

Things just start working out, but when you're standing on the side and the buses are whizzing by, you have to do something slightly unnatural to jumpstart things. And that's the techniques that I personally use in the past as well as naturally meeting with people and talking to them and listening to them, et cetera, which I suspect you're doing.

Guest: It's such a mental game as much as anything else getting through this process.

Nikhyl: The mental game as you point out is sort of it feels like the hardest part of this whole thing you're obviously been very successful career wise.

Despite where you're at at this moment, there's no doubt that you're not only employable, but you'll find a good job, but the mental part of this is the thing, like, the inside voice in your head is what I'm interested in.

Guest: Oh, it's been terrible lately. Like, it's just, yeah, I mean, it's been by far the sort of most notable part of the whole story, I think, It's definitely, revisiting past decisions, some of my riskier moves and things like that.

just taking my last job at the one even before that. I would not take back either of those. I really academically know that, but it's very easy for me to go, I'd be in a lot better situation and more comfortable if I hadn't. but that's the whole nature of taking a risk, right?

As sometimes they don't pan out, but it's like hard for me not to let the hamster just run on that wheel sometimes. But the thing is, I also am somebody that kind of hates being comfortable. I need something to push me or else I just spiral in a different direction of Oh, I'm kind of useless.

I'm not really doing anything here. I don't really have a huge impact on this and I can do better.

But in addition to just regret, I've been finding myself increasingly delusional during that part of the career that was going like this. And I felt like everything was clicking and I'm a hot commodity and put together a really, really valuable set of skills and I'm doing a good job at these things and people are really excited to talk to me which I was riding for a few years, and now it's crickets. And so it's easy for me to go rather than the rational thing that most people in my life would say, which is this is a fluke, it's a weird time, you were in a place that was a bad fit, this is now a strange time to be navigating a job search.

It's also very easy for the voice to start being like, or counterpoint, maybe I was just around a lot of hype people, you know, or whatever. And like, I was oblivious the whole time, right? And, you know, the external things sway my sense of self.

Nikhyl: Underneath it all, probably the core of this whole thing, were you a product of growth and lucky? And if you were, then perhaps the way you perceived career opportunity is foundationally different. Perhaps had you not gotten off the hamster wheel, and I think that that's probably this sort of crisis of confidence.

And I think if you were a less rational, less self aware, more male human. I think you would have basically been like, Oh, are you kidding me? You know, these people are all crazy. And, you know, but I think that the best people tend to be deeply empathetic and aware and that strength of yours is now causing a crisis of confidence.

The things that are on the brochure are clear, I could spend more time in running a search, I could push more aggressively, I could start getting more engaged in skill development, all those things are the obvious things that frankly, you probably already knew. The question that you should ask yourself is, how do you get some wins, to be more confident of yourself without having the wins coming from interviews? If the answer is, it's unclear that there is an appropriate way to get wins because your own expectations are high that even a small win, isn't enough, then you have to almost fake it till you make it. You almost need to sort of say, you know what, totally understand that it's possible that I was a beneficiary of growth and circumstance, but, I'm going to believe that there's enough substance there and enough success that I'm just going to believe enough in myself and bet enough on myself that this will work itself out an almost irrational faith.

Nikhyl: And I've been in this scenario before. It wasn't so much a product of growth, but it was a product of decisioning. My first dozen years of career, I had only done startups and none of the startups had done particularly well. so the late stages of my most recent startup, had been doing it for a decade, let's say.

And I was like, I'm pretty sure I'm good. I'm pretty sure that I had skills and all that. But I looked around at my peers that had perhaps taken less risk, to use your words, and those had done quite well because they punched it in every year and climb the ladder. And I started seeing, lots of economic wins of my peer set. Lots of companies that are getting founded that are doing much better than the ones that I'm associated with. And my betting on myself has not actually proven out that much. And so I wondering, there's a really rational perspective that I think more highly of myself or my skills and I was more grabby for validation because I was so worried that maybe this was all a bit of a farce, a falsehood. And I think that what's fascinating is there was this moment where a few things broke my way, you know, we sold the company, I ended up in a good project and then one thing led to another and I was in a nice leadership role.

And all the things that I had done in the past all kind of were necessary, but they were never packaged and branded. And then that last piece came. And then the story that I can tell is that, hey, all of the things that I had done, maybe in the quiet all led to sort of some of the successes. I'm going to just point out this speech that Steve Jobs gave the Stanford commencement many years ago, which I absolutely recommend,

if you haven't read it, And one of the points that he made, I still remember to this day. I actually went to that commencement speech because I knew he was speaking you know, you think of Steve Jobs as one of the most articulate humans out there and, you know, this great storyteller and it was more a matter of the fact but he made this very specific comment.

He walked through all of these setbacks being fired from Apple, seeing NeXT not get off the ground, a lot of challenges in Pixar. And then he talked about returning to, Apple and how his insights that he had had with NeXT fueled the rebirth of the iMac.And he said that, going through each of these things, they all seemed like he was failing and then in the rear view mirror, we look back over time and we see it all as necessary to success. And he's like, the rear view mirror is always the self justified. And it always works out, but going through it, it's just filled with anxiety.

And then when you story tell it, it all seems to work. Because if you pause and you look around and you're like, I don't know if this is working, maybe this is not for me. Maybe I'm not good enough. I think that it creeps in you and in any job transition is debilitating.

It makes that voice way too loud. you have to just believe in the future justifying today.

Guest: To your point, it's like when you're just going through the forest and pulling the trees apart and hacking at the weeds and whatever it can be kind of like, okay, I guess, sure, this is

gonna end at some point, I will get out of here. But like, yeah, it's it can be easy to waver, I think a little bit.

Nikhyl: Perhaps that's a better way to think about it is it's less about your skills were only a product of growth. I think the ease of transition to next jobs was dramatically fueled by the fact that there was less supply and tons of demand. So what you're experiencing now, though, feels like a moment of crisis mentally, is actually like, no, the skills are there, it's just, it's tons more noise because the supply demand has been flipped.

So you might take six months to get a much, much better company. But in the past, you were able to take six weeks to get a much weaker company. And in the net net, it actually is much better to be on the first side, but it feels a lot more emotionally taxing.

You know?

Guest: Yeah, it's so easy to second guess now. Oh, you know, hubris got me right? I had a really secure job, the most secure job I could have gotten I went and had to go test my ego, basically, and can I be the boss. That is one of my sort of catastrophizing stories is I landed here because of hubris.

But on the other hand, I'm like, of course, that makes me a stronger design leader. So I'm like, I know at some point that's going to be visible.

Nikhyl: Okay. It's me again. And there's a lot more to this conversation that I just simply edited out. As I thought about the discussion, I thought how important it is to give good advice to those of you that are in transition and perhaps struggling with the job transition. And, there is no silver bullet, it's going to take, the right mindset.

It's going to take the right process. And it's going to take some thoughtful, approaches to what that next company should look like.

Let me start with mindset. I'm going to rattle off a number of misses that I see as people come to me in transition and some of the quick advice that I give.

So I'll start with confidence. And as you heard, as I was talking to this caller, you have to have confidence, almost unnatural confidence to be able to effectively look for a job. The employer is going to look for someone who can come in and quickly have impact.

And if you come across this tentative, that's always going to be a struggle. And then actually, if you're not finding a job very quickly. And you're coming off of a tough role, you're going to not feel very confident it's human nature. And so in some ways, what we want to be able to do is build that confidence in an angle and an avenue that's not related to interviewing as interviewing oftentimes doesn't come back with a positive signal. Keep in mind that a lot of times you can be a very effective professional and just not be a good match for a company.

Partly because you're keeping your bar pretty high. And partly because the market is such that there are a lot of good candidates that are out there. And there's a bit of chemistry matching that takes place.

But my first point is how long are you expecting to take in a job transition? so many people come to me and say, look, I've been searching for a few weeks.

I've talked to a few folks and I haven't really made a lot of progress. I feel like I'm a little stuck. the fact is, the more senior you go, the longer it takes to find a job. When I was in a transition between a late stage company in Google and eventually finding the role at Credit Karma, you know, I sat down with one of my advisors they asked me this question and I said, Oh, you know, I'll probably take about three months to find a job because that's the frame of reference you may have had in the past.

His note was it could take as long as a year. And you'd be lucky if you have a year in your expectation and try to beat it in six months. And at first I was really triggered by that. And I said, wow, six months, it seems like such a long time. But then in reality, you realize you're going to be talking to a bunch of companies and there's this chemistry fit and there's not as many roles at the top and 50 percent of the, ability to land a role is chemistry fit.

And 50 percent is just pure luck and hustle. what I want you to do is make sure that you have an adequate and realistic expectation that if you thought it was gonna be weeks, it probably is gonna be months. And if you thought it's gonna be months, it probably is gonna look like quarters.

Our goal is to then figure out a way to stay active and build confidence along a longer search. But it's a lot easier if you knew that it's going to take a few months or a few quarters And if you're eight weeks into the search, you wouldn't feel as anxious about the search. You'd feel like, okay, well, we're starting to make progress. But my expectation is we're still about halfway through the journey or a third of the way through the journey.

Well, since you have no control over this process, the last thing you want to do is spend all your time interviewing. Which again, seems a little counterproductive. It's like, well, isn't your goal to be interviewing, as many companies as possible? My sense is that because it's going to be a chemistry match, and because if you've, say, for example, been interviewing for a couple of months, I ask this question sometimes, well, how many companies have you spoken with?

And they'll say, Hey, you know, I've spoken to 12, maybe 15 I've looked at 20, 30 companies realistically, and maybe had, 50 reach outs that I was considering. Right. So you, have a pretty broad range. And then you ask someone, how's those interviews gone? And they're like, well, you know, in various ways, I've been not a finalist in any of these settings.

Well, if you've talked to say half a dozen or a dozen companies and you haven't been able to make progress, one school of thought is, you just have to keep burning and churning. if 12 became 50, you'd eventually get through it.

And that's possible. It's a little like say fundraising for founders. Sometimes founders will say, Oh, you know, I talked to 50 investors and only in the 50th one were I able to get money. At some point, if you start seeing that you aren't making progress, you have a couple of things that you have to chew on. One is, are you targeting things correctly? And two, are you making effective use of the time you do have to improve yourself? Some of that improvement is just becoming a better interviewer. And so you can practice the technique of interviewing. You can improve how you articulate your story.

Things that we've talked about on this podcast in terms of being concise, being clear on where you would add in impact, certainly we'll talk a bit in this episode about ensuring that you're not targeting too high or too low so that you're not wasting time trying to find roles that aren't interested in you or finding roles that are making you offers that you're frankly not interested in taking, even if they were to move forward.

But so many professionals who are listening to this podcast, who are not in transition will come to me and say, I know this is good for my career, but I don't have time right now. And that makes sense between family, between friends, between work.

It's really hard to invest in professional development. The big news flash here is you are in transition. You actually have time to develop professionally. So imagine someone who has the mindset, which is, I know I can be employed. I know that there's a good job for me. I know the market's tricky. And I know that it'll take months to quarters, instead of days to weeks.

During this period of time, I'm going to be thoughtful on who I'm reaching out to, but I'm also going to use the time to improve myself professionally. Now how do I do that? Well, one is I want to improve my knowledge. So not only am I becoming better at the tactic of interviewing, but I'm also building some things on the side.

If you're a product person. Building things is great. AI is one of the newest and most impactful things that are happening right now. And it's really hard if you're inside a company with the constraints of meetings and structure, et cetera, for you to have time to actually learn all the latest tools and heck they change almost every week, but if you don't have time, You have literally no excuse to actually roll up your sleeves, go and hack, go build something, go download all the tools, go make yourself more effective at these new technologies.

And in fact, the best thing about AI is that it's actually making it easier for someone who's non technical to express themselves with design or someone who's a little bit of a developer to actually be able to build something that's substantive. So during that period of time, not only are you staying busy, but you're learning the latest.

Now, when you go into an interview and they start asking you not only about some of the things you did in your last job, but you can actually tell stories about, oh, you know, I had this idea and I decided to go build this on the side and it was really helpful because it taught me something. Some people like more structured learning, so they can go to university classes that are available for free and learn whether it's data science, design, the latest tools like Figma, learning all kinds of process and product management.

There are a million things that you can use your time for, but the thing you don't want to do is burn yourself out on interviewing, realize that you're not making any traction, become more depressed and not have this outlet and using it in creative ways.

Heck there's even consuming content like this podcast, but learning is one big area that I want all of you to be investing in at least half of your time while you're in transition. Quarter of your time should be spent meeting people. 

Meeting people doesn't mean meeting people for the sake of interviewing. Meeting people is all of you should be keeping a list of folks that you really want to not only stay in touch with, but get to know a little bit better from your professional and personal endeavors. Now, often when you're in a job, you don't have a lot of time to invest.

Now I've made a note that you should actually spend more time than you probably are, 30 minutes a week is super career additive. But now you have way more than 30 minutes a week, and I would love for you to use this extra time to really lean very hard in and actually meet as many people as you can. Now What kinds of conversations do you want to have? Certainly people come to me and say, Hey, I would love to meet with you because I'd love to see who, you know, that's hiring. There's nothing wrong with that. I think that's this classic networking, but frankly, that's a very hard conversation unless you happen to be specifically skilled and the person happens to be connected with opportunities.

But I think there are many more interesting conversations to also have. I think you can get to know them better, listen to their career story, understand how they made transitions, understand how they learn, understand how they develop. See if there are people that you might enjoy getting to know that they know, see if they are working on something that you might find interesting.

Not only can we talk through that, but maybe you can help them. This being a big part of why it's valuable to connect with people. You have time. You also have a lot of interest in becoming more and more relevant to today's industry if someone you know is doing something that might be interesting or might have something that you can help, that is a great use of time, because what it does is it creates luck, it creates the opportunity to see something from the inside, and then share that story for an interview, share that story with someone else.

It also might give you an opportunity to turn it into a paid consulting, which often becomes a great way to enroute into a company, or just to become a lot more relevant when you're in interview and giving you more time to actually look for another job and not settle on the next opportunity.

So connecting with people is absolutely key. And so if you think about your day, you're like, well, I've got this mindset, but I will be employed. I have a realistic expectation of how long it'll take. A good half my time is spent building and learning about new technologies, new ways to do my craft so I'm a more effective person.

Maybe a quarter of my time is being spent meeting with folks, trying to add a person a day. With Zoom, with video calls, you can reach people globally and connect with all kinds of past workers, friends that you've met at parties. People that you might have wanting to stay in touch with during the interview process, who you really hit it off.

There's a million avenues of where you can find resources to connect. And now only about a quarter of your time is being spent interviewing. Clearly, if you have more opportunity to interview, you can do it, but my point is you won't feel so helpless if you've only carved out a day and a half a week for interviews.

And that's about what you can get in the market. The rest of your time, you're staying active, you're staying relevant.

the last thing I would say is that we're talking very much around professional development resources, but this also might be a way to personally develop as well. how are you using the extra time that God has afforded you is a very different way of saying, are you interviewing tirelessly to find the next job and are you seeing success?

When you have this extra time, not only can you improve yourself professionally, but you can seek out the therapist that you never had time to actually stay in touch with. You can get back into the gym and build your physique and build your energy levels and make yourself proud of things that you can control.

In tech, we often ignore the mental and physical needs to perform at the highest levels. We're educated, we're learning on the job, we're sitting, we're obviously not physically laboring. but given the hours, the duration of career, constant alertness and attention that's required to have a leadership career, fatigue is very real.

We've spoken about this on this podcast before. And I think that all of us know when we're not at tip top shape mentally and physically, how that impacts your day, your week, your month, or even your ability to maintain a job. If you observe professional athletes, they take fitness very seriously.

That's the key reason why they have jobs is their physique, their mental, physical fitness. So they eat and they train carefully during the season. They have rigorous treatments after games. They make sure that during the off season, they pick areas to improve in, whether that's speed, whether that's agility, whether that's a new skill, A new approach to the game, building enough mental strength so that during the long season, they're able to perform all the way through to the end and through the playoffs.

This is the thing that separates good to great athletes and you hear it all the time. So why am I mentioning this? Well, in some ways your off season is now if you are in transition. You need to think about the off season as a way to build out that physical mental stamina, that strength that you can use during the season, which is your next job.

You need to ensure that you're using that time over the off season to expand your skills. There's no reason why the skills you left the last job are the same ones you enter the next job.

you have to take your craft as seriously as athletes. And why shouldn't you

the advantage of having your mind healthy, your body healthy, and then your mindset focused in the right way will dramatically improve your ability to not only land the next job, but just stay out of that negative mindset where you're overly reactive, waiting for the phone to ring, hoping that you'll eventually pop another job because that has low control versus some of the techniques I mentioned, which is high control, high agency over the search.

Okay. Now I want to transition into the process it takes to actually run a search. A little bit less about the mechanics and around the mentality and more around how are we actually running a search? the first thing I would ask is, well, how long have we been off from work? And I think that as you're preparing for a search, and sometimes people talk to me and say, Hey, I've decided to leave, or I'm in a last day situation.

I ask them, well, how much time are they looking to take? And usually I get two answers. Most of the time it's I'm starting right away because I have anxiety. I know the market's going to take a while that isn't necessarily the wrong answer, but I always worry that people are jumping into the next job and then when they're in the next job, they're working out issues they faced in the previous setting.

I'm sure you've actually met people or maybe you've experienced this in the past, which is I was really struggling with a position at work. I didn't like my manager, my peer, my project, the technology, the health of the company. I knew we could do more. I ended up exiting the organization one way or the other.

And now I'm looking for a job, quickly found something lucky me. I'm not unemployed for a long period of time. And now I'm in this new job and I find myself very quickly trying to create change or I feel myself very quickly trying to build a great win. And those types of things are coming because I didn't feel like I was doing that in the past when the reality is, especially for leaders, you need to take the time to absorb the culture, understand how to add value.

But the past and the frustrations of the past might be pushing you forward. So this to me is, there is some gap that's personal, but I very much like the idea of creating some space. But also on the flip side, you can become a little bit too sedentary when it comes to searches.

So my guidance is when I talk to folks, joining something from the past job within 100 days is pretty quick.

That's a three month search. And for most of the leaders I talk to, I'm always a little bit reluctant to say that's enough time. Now, sometimes people take a job and they're fortunate enough to take a month where they can really take a breath and then they join and that works out some of those transition demons.

But I think that 200 days closer to six months is the sweet spot. To having enough distance, having enough opportunity to reflect on what was the lessons from the past. Apply them to a new setting and actually join with enough energy. If you get into the 300 days or sort of the nine month type cycle, I think you sometimes slow down to the point that tech moves too fast.

And so what I would like to do is orient your brain to be like, Hey, it could take as much as a year. I'm hoping that it happens in six months. If it happens before, make sure that you have enough gap and what you'll find sometimes is if you took two months before you even started to interview, the quality of those interviews that you'll have will be dramatically better.

And they would actually combat some of the anxiety you face because here's the concern just came off this job. I abruptly had to leave. I'm immediately worried. So I immediately started interviewing, the interviews themselves didn't go great, partly because I was not ready, partly because I wasn't rested, partly because I was looking backwards.

Now I've talked to four or five of the employers that are hiring. I'm not getting anywhere. I have increased anxiety. The next conversation I'm having feels even more amped. I have a lot higher stakes on these conversations because I feel like I've been looking for six weeks. These are the things that we avoid by saying, take a a pause.

Those employers will still exist in six weeks, but you will be dramatically better rested thoughtful, possibly a person who has some space from the past is going to give you a much, much higher quality conversation. Yet that conversation is rarely held because people have this Immediate anxiety, or they do the reverse and they say, look, I can't think about work for six months and then six months in, it's just very hard to claw themselves back.

The second thing I want to make sure when we're running process is that you are pushing with grit and hustle. I cannot emphasize this point enough. This might be the most important point in this podcast is that if you don't have grit and hustle, you're not going to find a job in this market.

In the past, the market had more jobs than there were candidates. As a result, you could take time off. You could enter, raise your hand, recruiters would pick you up. You would find a job, companies would be growing, whether you were competent or not, it would grow with you. And you'd have an opportunity to get even a bigger job on the timeline that you're looking for.

That is not the reality today. So if you're just waiting for a job to come to you, obviously those that are listening, I'm not going to suggest that's your mindset. But what I am going to say is you need to have enough grit and hustle. To be able to create the luck needed to find that job. Grit is related to the things we've talked about.

It's keeping yourself in motion, meeting people, looking at opportunities in companies that might not be posted. This is a big one. a lot of times if you're interested in an employer, you can talk to someone that you know there and see maybe there's an opportunity that isn't available formally.

Sometimes if there's someone who thinks highly of you from the past, but they're not necessarily hiring, they might know of opportunities that you can be talking to them about. again, if you have a trusted set of resources around you and you're starting to get to know people and you make it clear to them that you're looking to find a new opportunity and you're looking to talk to folks, luck will come your way, but that is a gritty hustle thing.

That is you also following up after every conversation, making sure that you are well prepared before you go into an interview. What stories are you going to share? What are those one or two minutes soundbites around each of your roles? What is the one or two minutes soundbite for your full career arc?

What are you looking for next? Do you have that one minute story? Do you have the classic questions like, what are your superpowers? What are your development areas? What are the right ways to do things like crafting, collaboration, prioritization? You need to prep. Obviously the AIs are a great resource to be able to get sample questions and even some sample answers, but you need to stand out.

You need to be prepared, personal examples of how you would answer these very common questions, you need to come with the right energy, and you need to ensure that you're in motion, that you're active, and that you're very much engaged in each of these conversations before, during, and after.

The more creative you are about your past, the more Interested you are in the interviewer and the company, the more you will stand out. Now, the last thing I want to caution people on is an unstructured approach to recruiting. There's nothing that drives me more crazy than when someone calls me and says, Hey, I've got this offer.

And I'm wanting to get your advice as to whether I should take it or not. And I said, okay, great. Well, before we go through the decisioning on this offer, what are the other roles that you are considering?

And often the conversation is, well, you know, this was the only one that reached out to me and I was working at some place and decided I wanted to leave. And, I was always in the background looking and this company came along and they said that they have a position for me and I interviewed and now I'm thinking about taking it.

And so what's your alternative? Well, my alternative is I could just stay at my current employer. I could stay unemployed. Obviously the stay unemployed, your alternative is pretty dark. So people are very inclined to take it. And I look at that and I'm like, well, have you really run a process? And oftentimes people don't want to run a process because they don't want to put the work in or because they're shy and anxious about talking to companies.

Both of those I respect, but if you're trying to optimize, what I'm looking for you to do is to say, okay. We're going to take two months to go from interviewing to making a decision on a job. That's roughly how long it takes. Maybe on a more junior role, it takes closer to six weeks. Maybe on a more senior role, it'll take closer to 10 weeks.

But if it's a rough two month time period for the first two, three weeks, like any sales process, you're going to build a pipeline. You're going to say, Hey, I've known these six, eight companies are hiring. I know I'm in a position to interview with them. I'm going to time them. So we start all of them in roughly the same time period, Two, three weeks in, we're all in motion together. I'm interviewing. I'm active. I'm practicing my story. and so I'm getting better.

because it's intense, it doesn't come across that I have nothing else going on. I come across as in demand. Now, two, three weeks, we start our first rounds, two, three weeks later, we get through process and now six weeks total, maybe we started with eight or 10 companies. And we're down to maybe a couple that have made a decision on us.

Now, along the way, other companies will come into process and you have to think, look, if I can't finish process in this period of time, they should go in my next wave, you run a two month wave. And if it turns out that you don't like what you come along with. Then you end up starting this next wave and you continue to go forward.

I'm not suggesting that if you're not talking to anyone, you should hold off arbitrarily on interviewing with someone.

What I am saying is if you do find yourself running process with multiple companies, try to organize it into these waves so that they make decisions at roughly the same time. It is the number one factor in negotiating compensation. Obviously, if you have three alternatives and three companies looking to make you offers, you're just going to get a much better offer than if it's one.

You're also going to make a much better decision because you'll be able to see this particular opportunity versus a couple of others versus just well, I could keep being unemployed or I could take this offer. I'm trying to optimize the tenure in the next role. And the more choices you have, the more you'll start to say, well, that intangible really bothers me.

or that travel really bothers me, or I really feel like the manager here is so much more substantive and it'll be a much better career decision to work with someone who could tell me the ropes, but I'm willing to take maybe a little bit less in comp.

So that wave approach, building the pipeline for getting the next job is really helpful for those of you that are looking at many opportunities that you're interviewing for, and you're just not sure how to organize it, and it avoids the serial decisioning that tends to come up, which is obviously suboptimal.

And the last thing I just say is when we look at the calendar, when I mean the calendar, I literally mean January through December, keep in mind that there is definitely ebbs and flows to the calendar. if you think about February is roughly the time period where planning is complete for the year and people know what budget they have for the year.

Then you go from February, let's say, early February to around late May. And that period of time has very few holiday breaks. So if you start your search, then you get four solid months of being able to search maybe five, if you include January, then when you hit June, June, July tends to be for obvious reasons, much slower.

It's much harder to get all the right people oftentimes people taking summer breaks, particularly those with kids. And so it's hard to get traction. And then when Labor Day hits early September, you've got a 10 week period of time again, between September and Thanksgiving, where you can make a lot of damage in terms of your search.

But then between that Thanksgiving and again, early January, you've got the holiday period, which oftentimes is quite slow. The reason why I mentioned this, everyone's like, well, yes, I understand the U S calendar. I'm like, no, no, no. But do you understand the U S calendar as it related to your job search?

People all the time will come to me and say, I'm about ready to start my job search. Then six weeks later, they're like, I'm depressed because I'm not making as much traction. I'm like, Oh, when did you start? Oh, I started the first week of June. I'm like, great. Between the first week of June and mid July you thought you would make more traction. One, it's probably going to take months instead of weeks, as we said. And two, these are like the worst months, except for maybe Thanksgiving and Christmas to expect that you're going to make traction. So your expectations are totally off. So if you find yourself like, ah, I'm going to take some time off and it's like early January, take advantage of that period of time in mid Feb to really push hard.

More importantly, what I don't want people to do is I don't want people to say, I'm going to take time off in September and October. I'm going to start my search in November. If you do that, you're almost certainly going to find yourself four months into a search, meaning you're in January now and not have made a lot of traction simply because of the calendar, not because of your qualification. So this is the reason why the structure of where you start the waves, looking at the calendar, making sure you're putting a fair amount of force, and then of course, practicing those stories is so critical.

Okay. The last thing is what is the right job? How do I ensure I'm not perhaps targeting too high and certainly too low. this is a hard thing to state generically because so much of this is personal. Your situation is going to be different from your next person, but there's a few truths and a few gotchas that I just want to cover quickly.

So the one thing is you obviously want to avoid trying to over optimize and find the perfect role. There's a class of person, maybe 10, 15, 20 percent who constantly come to me and say, Hey, I'm looking at this position and let me walk you through all the issues I see and why I'm anxious to take it.

And what you're really looking to do, and especially for leaders is to figure out what are the challenges that you feel you are comfortable in not only living with but actually managing and perhaps addressing. You get paid to solve hard problems. If a company comes to you and says, we don't have any really hard problems. We can't wait to hire you. You should probably avoid it they're not being realistic. the more likely scenario is we need you, you solve our problems. Here's the hair on this deal.

Is this the type of thing that you both have experience and excitement to go solve? So in some ways your job search is a search for finding the problems in each of the potential employers that you enjoy solving and that you're qualified to crush.

A few other truths that I want to make sure that you're chewing on as we're going through this search. Related to the idea that you want to over optimize the perfect role, you also have to recognize that, working is definitely a feature when it comes to career.

And so I want to avoid a situation where you're keeping the bar so high that you're waiting for six, 12, 18 months for the right thing to come along. If you think about it, a job these days might be two, two and a half years in tenure. And I wouldn't be surprised if we see the jobs of people that are chosen today to be shorter in tenure because the market's changing so rapidly.

So in that case, if you have an opportunity to start working for something that you think is career additive, but not optimal, and you can do that versus take an additional six months for a search these days, I'm inclined to maybe take the risk and start working because working brings you motion and it gives you opportunities to time the market in some way where 12 months from today, perhaps this job was good, but not great.

But you're so much more in motion and you've learned a few things and now your ability to find another role is much, much higher. And your confidence is much higher. So definitely getting in is a value. This of course is within reason, definitely not looking for perfection is a value as well.

Recognizing also that sometimes it takes multiple roles within a company to find the sweet spot. So if you think about how organizations often work, They today have perhaps more qualified people internally for roles than they have roles to offer. And then there's a few roles that they've decided to go out to market with.

And so that's the dynamic that's at play. So if you're within the company and a new role opens up a lot of the internal folks, because they're on projects that aren't growing, et cetera, they flock to those higher quality roles. So the ones that are say on the brochure that are externally available often are not the best roles.

So if the best roles are going to internal candidates, your mental model might be that I should take a position and then perhaps take a second role down the road where I'm now inside the tent and I'm able to navigate much more effectively. And in this case, you're thinking, well, if the company is good, but maybe the role is maybe less valuable, that might be normal for all of these external positions.

I'd almost rather have a little bit of a longer tenure, navigate my way through it. And I'll grit it out just because A, I want to be employed. And B, I want to be in a position to work at this company, but in, a role that's probably six or 12 months away.

This is a long way of saying that flexibility is key in your job search. Every job you're going to take is going to have issues, particularly the ones that are externally available. you want to instead think about, okay, given this issue, could you have a story coming out of it, that actually is going to be career additive, knowing that tenure matters. Can you bet on yourself? Can you live the idea that the cream rises to the top? I talk about this all the time where someone is coming to me and saying, look, I've got two opportunities, a bigger role at a less healthy company and a smaller role at a healthier company.

And my note is, well, if you bet on yourself and you believe the cream rises to the top, take the healthier company and maybe bank shot your way into a second role, which will perhaps be the role that you wish you were to get in the first place. But the first role, which is a much larger role, might have a shorter tenure.

It might have a lot of challenges that you are not simply able to overcome. And then the stories between the two will be dramatically in contrast.

Okay, so in summary, I think there are a few points I want to make sure you take away from this. One, ensure your mindset is really tight when it comes to the search, build confidence in yourself, have a realistic expectation around how long things are going to take.

Use the time to your advantage, to improve yourself, your stories, to ensure you're prepared for your interviews and to ensure you're learning and connecting with other people. This is going to drive the hustle, the grit, and frankly, the luck needed to be able to land something. For those of you that have a number of choices, be very thoughtful on how you structure the time of the search.

Think about the calendar. . Don't start immediately because you're anxious that you're out of work. Take enough time so that you hit the market with impact.

If you have a reasonable expectation as to how long things will take, if you start with enough of a gap and you create enough of a wave where decisions are being made roughly at the same time, you'll be able to compare opportunities. Recognize that the best opportunities are probably not available to anyone that's not internal, especially given the market has more qualified people within companies than there have opportunities to provide them. So bet on yourself. The cream will rise to the top in high quality growth environments. Prioritize for healthier companies. And ensure you're always thinking through the stories that will be available to you after you succeed in the role that you are looking to take.

Because those are the ones that are most career additive, and those are the ones that keep you going forward and drive you towards your skip position.

Okay, hopefully this has been helpful. Love to get your feedback on the types of challenges that you're facing in your job transition. And if you have advice that has been particularly impactful on your own search, I'd I'd love for you to share it on LinkedIn or share it back with me and I'll summarize and post back.

Thanks for listening to the skip. If today's episode resonated with you, please consider leaving a review or sharing it with the people, you know, who want more out of their career. You can subscribe to this podcast on Apple, Spotify, YouTube, or wherever you currently listen. You can also follow my newsletter on Substack.

And if you have questions or feedback, leave a comment or send a note on LinkedIn, Threads or Twitter, I try to answer each one directly. As always, I'm Nikhyl and this has been The Skip.