Building Resilient Leadership in Tech

Technical organizations face massive scaling pressures, making Resilient Tech Leadership more critical than ever. Host Adam Markel sits down with executive coach Jossie Haines, a former software engineering leader who built Emmy-winning teams at Apple and served as VP of Engineering at Tile. Together, they tackle the high-stakes transitions, burnout, and imposter syndrome that often plague senior tech professionals. Jossie shares her journey from software engineer to leadership coach, detailing how to manage the intense zero-to-one phase without losing your sanity. You'll learn how to build a healthy relationship with negative feedback and build the emotional muscles needed to weather industry crashes. Discover why the secret to scaling high-performing teams lies in clear prioritization, active recovery, and intentional self-belief.

Show Notes:

  • 03:26 - Connecting Beyond the Code
  • 07:15 - The Real Value in Your Follow-Up
  • 12:06 - Dismantling the Illusion of Linear Success
  • 16:04 - The Cost of Staying Silent
  • 23:57 - Slaying the Perfectionism Dragon
  • 27:27 - Narrowing Your Ideal Customer Lens
  • 40:02 - Building a Muscle for Hard Truths

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Building Resilient Leadership In Tech With Jossie Haines

Welcome back to another episode of the show. I'm excited for the guests that I've got. I know we're going to have just an amazing conversation and one that is aligned. I feel like there's a lot of the things that we feel about business and in particular, how we show up in a business context that we have great alignment on, so let me share a little bit about her. I'm going to read her bio, and then I'm going to jump right in.

Her name is Jossie Haines, and she spent 25 years in software engineering leadership, including leading an Emmy-winning team at Apple and creating the VP of Engineering role at Tile. She is now an executive coach for senior tech leaders, coaching them through the moments that matter most, new roles, team turnarounds, building something from scratch, and high-stakes transitions so they succeed in the role and drive real impact. What sets her apart is that she can get into the technical weeds, drive 10,000-foot strategy conversations, and coach mindset shifts underneath. You're going to love my conversation with Jossie Haines, so sit back and enjoy.

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Jossie, so you heard me read your very impressive CV, your introduction. What is one thing that is not part of that bio, your history, your CV, that you would love for people to know about you at the outset of our conversation?

That is an interesting one. I have played with computers since I was five years old and had a Commodore 64, but my undergrad degree is in Chemistry and Materials Science.

First of all, we're literally dating ourselves now, so anybody can look it up. I remember the Vic-20 or whatever, the Commodore 360. I remember those things. We had a Tandy in school. We had a Tandy T2000 or something. I don't know what it was, but it was so rudimentary. It's an obvious question, but what was it about computers that didn't overwhelm you? On some level, the word geek gets used, so it's fine to say that, but there were people that geeked out on that thing and people that were intimidated, I want to say, by it.

That's a fair word to use, too. I was probably of the latter. It wasn't great. I'm going to blame this on my freaking teachers. I'm taking no responsibility whatsoever for being crappy at math. I had crappy teachers because I love math now. I was not math or science inclined. Therefore, computers intimidated me. Why was it different for you, Jossie?

A few things. One, my brother was an electrical engineer. I got to see him do this for a living. It’s slightly different, but I got to see him. He always encouraged me to play around with computers. I enjoyed it. Growing up, I didn't have that many friends. The computer was my little lifeline to the world. Also, we didn't have social media. I had AOL starting when I was in high school or something like that.

Connecting Beyond The Code

Something about getting to play with a computer and using it as a way to talk to my friends and be like, “I did this thing on my computer and it was cool. Do you want to do something similar?” It was something to talk to people about and it was fun for me. I feel like in the modern world, it can be a lot more overwhelming.

Resilient Tech Leadership: A 'no' in business rarely means never. Most of the time, it just means 'not now.' Master the art of the follow-up and build long-term trust.

Super. That's an origin story. Not everybody has that cohesive look at where you are and looking back then and go, “I can connect the dots. I see all of the breadcrumbs.” Let's go from that experience to what you ended up doing in post-graduate work because you were on an Emmy Award-winning team at Apple. That's a big deal. Maybe there's a lot of unemployed people or people coming out of college, let's say, that are not quite unemployable, but the marketplace is pretty rough. A lot of people are pivoting. That's a cheap plug for my book called Pivot. There are a lot of people that are interested in that. Is there a secret sauce? Is there a special story associated with you making it into Apple? That's no small feat either.

It was about my network. I had been at Zynga for five years. Basically, Zynga helped Facebook grow into the company it is now, because gaming was what blew up the platform. I was there during that time. We went from 1,000 to 2,000 employees at Zynga in my first year there. A year before I had left Zynga, my mom passed away after struggling with Alzheimer's for eight years. I left Zynga and moved to Florida to take care of my dad for nine months.

When I came back to the Bay Area, I ended up back at Zynga, but working on the ads team instead of on gaming. While ads tech was interesting from a scalability perspective, it didn't do it for me. I love working on things that make an impact to the world and help people or at least are aligned with what is fun. To me, ad tech was like, “How do I build the thing that people like the least crappy experience for people? Nobody likes ads. Nobody goes and is like, “I loved that ad experience.”

One of my friends was working on the Siri team in the infrastructure side, and they were looking for a new manager to come in to work on the Siri on Apple TV experience. A funny story. I had applied to that job two years prior, right before my mom's health deteriorated and it became clear that she was passing away. The manager remembered me from when I had previously applied.

The Real Value On Your Follow-Up

That's one of those things that, again, not that we're giving out career development advice here, but there's a level at which the fruit is in the follow-up. On our team, we've always talked about this. We like to refer to our no's, for example, as not now's because it is not now. It's not a never. Unless somebody says to you, “I will never work with you.” Which nobody's going to say that anyway. Even if they feel that way, they're never going to tell you that. Unless that's the vibe, then it's not now. How good are you?

How organized are you? How meticulous are you at the way you either keep in some ways nurturing a relationship or trying to create a budding relationship and circling back and thinking about the places where, maybe not now, but two years from now. I keep saying it, and I hate that I keep saying this, but you blink your eyes and a year goes by. You blink twice, it's two years, blah. Now, you're working at the company that you were not now for earlier.

I say this in my coaching world all the time. I literally had somebody I mentored years ago when she was just becoming a product manager reach out to me a few weeks ago and say, “I'm in my first director-level role, and I need help. Can you coach me?” Also, it's about just building relationships. Sometimes, as technology leaders, people get overwhelmed around, like, over-optimizing their networking too.

I went through this with one of my coaching clients. She's like, “I'm connected to a thousand people. What should I do?” I was like, “We can use a little bit of Claude to help you narrow down the list and then just start.” Plan. Pick ten people who you intuitively feel like from the list you want to correct with and connect with them. Sometimes, we try to over-optimize the networking piece, and it is around relationship building. It's our second-degree connections that are the ones most likely to find us roles and opportunities and all of those things.

Indeed. I didn't expect that we'd go there, but I'm super thrilled that we did. Again, this concept of pivoting had its origin in. I was using it when I wrote the book. I was using the pivot as an analogy, but it was a pivot on the basketball court because there's a way to pivot on a foot and get a 360-degree view of the court. All of that is within the rules to do and all that thing.

It's very defensive, but it's also assertive. It's a vision-creating, clarity-creating exercise. I wrote the book, which was a story of my own personal pivot out of practicing law into this business arena, consulting, speaking primarily at that time, keynote speaking. The pivot concept has been so tied to the startup world, to the VC world.

Tweet: Your tech stack is only as powerful as the human connections you build with it. Relationships always drive true innovation.

Silicon Valley and technology. It was pejorative at the time. You pivoted meant you basically failed. F'd up. The model didn't work, but there are some great pivot stories. YouTube started out as a dating site or something like that turns into what it's now. Those successful pivots are remarkable. You've pivoted a number of times in your career. I think it's fair, given where the breadcrumbs have led us so far, to ask about that. What do some of those pivots look like for you?

I love talking about this because, especially in the social media, LinkedIn world, you see people talking about careers. There's this belief, success means you're always going up and to the right. You're getting more promotions.

It's totally linear.

Dismantling The Illusion Of Linear Success

If I mess up once, the world is over. I have this conversation with folks all the time, even in more senior roles. I've taken it to be like, I'm going to follow what I find passionate and interesting. I love to play. Back in 2018 when I left Apple, I was burnt out. I was going through a lot of imposter syndrome. I almost left tech entirely. I made a decision at that point, which was that I had built enough career capital that I was never going to put myself in a position where I was not enjoying what I was doing.

Also decided I was never going to apply to a tech company through traditional tech means again. I've still had roles since then, which we can talk about too. Part of it is also this understanding that it's not this linear thing. When I came back to Zynga after I had left. I came back as an individual contributor for a little bit.

I was like, “This is what I want to do for a few months,” before then I ended up being director of engineering for ads. It was like a great little pivot back into like settling back into the company. After I left Apple, I took six months off. I thought I was going to start a business back then. I didn't end up doing that. A former boss who was the head of engineering at Tile at the time convinced me, grudgingly, to come join.

He was like, “It's fine. Come do it part time. The web team needs some help. Come do it 10 to 20 hours a week. It's cool.” I came back, and it was so nice just being like an individual. Again, I was an individual contributor on the team. It was nice to come bouncing back into that. It helped me build my self-confidence, then I finally decided, “I'll come join as director of engineering for partnerships.” I share these stories because sometimes you think your career needs to go up and up. I created my VP of engineering role at Tile, which we can talk about.

Tile was acquired by Life360, and I was on the executive team. I could have stuck around at Life360 and made most likely quite a bit of money from stock options and stuck around for 2 to 3 years, whatever but I decided to leave. I left after the acquisition, and I helped the team transition because I wanted to go into coaching. I had seen the power of coaching in my career, and I was like, “This is what I want to do.”

I've worked on multiple products that have been used by billions of people and that has its own reward. There is something truly rewarding to me about being able to help people make deep transformations in their lives and connect back with happiness and success and defining that on their terms, not what somebody else wants.

I want to create a bridge between that type of coaching and the way that you support leaders in the technology space, because I want to talk a little bit about what that's like. Before we get there, I do have a question. It's not an easy question, but I'm going to ask it anyway. You've been coached, as you just said, has had a big impact on you, which is why you wanted to do the same thing for other people. What's maybe one piece of advice or some counsel that you got that is part of your daily life?

I know most people have gotten some decent or great coaching at some point. Not every piece of great coaching has a season or great at the time, but maybe ten years later, you're not still thinking about that or utilizing it. Is there something that you're still utilizing that a coach shared with you some time ago that you could share with us?

It ties to this pivot piece. I talk about this when people are talking about crafting their roles, which is, if you don't ask, it's a definite no. We are so scared sometimes to ask the question. We are afraid that no is going to come. The other thing is sometimes we make up stories in our head that somebody's going to get upset. The worst that usually happens is somebody says no. As you said, that doesn't mean no forever. That means no right now.

Resilient Tech Leadership: Stop rejecting yourself before anyone else does. If you don't ask for that promotion or project, the answer is already a default no.

The Cost Of Staying Silent

It's funny because a mentor of mine some years ago used to phrase it similarly. He would say, “No ask is automatically no.” That's the thing about it. If you don't ask, you've already given yourself a no. The answer is always no when you don't ask. It's as basic or simple or simplistic as somebody might be thinking that sounds. Try that out in your life.

If you've never heard that advice or if you've not applied that advice, more importantly, if you're not applying that in your day-to-day, the things that you want you don't ask for. You make up whatever the stories are in your own head as to why it's not appropriate, it's not the time, it's pushy or whatever your little voices and your view on that is. Challenge that. Disrupt that.

Something related to that I see a lot of technology leaders doing, and I have to catch myself doing this too, if we try to over-optimize. I'm good at catching myself like, “Am I spending all this time learning about this thing?” Instead of taking action on it because I'm worried I'm not going to be “perfect” or great or amazing at it. That's the question to ask yourself every morning. It’s like, what's the aligned action I can be taking?

That is a great distillation of something that's big, and you put it into something finite like that anybody can do. It’s powerful. I want to talk about that part of your career history where you're involved. As you say, you were at Zynga and then it got acquired by Life360, but you were working on a particular product before that got acquired. I love to get into that hackathon piece of it because I want to unpack a little bit of what it looks like to be that. It's like a VC mentality around how you move through a product cycle and the speed of that.

I used to work at Tile. It's a little Bluetooth key tracker. You can put it on anything, but the default thing people put it on is their keys. There's also a wallet. I've had it help me find my purse on airplanes before I left. Apple has created their own AirTags, but Tile's existed long before. Apple took the idea and created their own.

I worked at Tile for five years. Right around when I crafted my VP of engineering role there, we had hackathons. It’s like every six months to a year. My hackathon project was we were noticing in the usage data that most people, on average, have two tiles. Five is a stretch. The average is two, but we were seeing a number of accounts having more than 100 tiles. We realized that it was businesses using this.

The tile app, let's be clear, is not focused on having more than like 10 or 20 of these things. This thing does not scale. It literally crashes at over a thousand. It is not meant for scale. We noticed that there were some interesting use cases. I had a hackathon project and basically built a web interface for companies to do B2B asset tracking through using Tiles. We were going to build that product within Tile.

Tile was acquired by Life360. Life360 is a very consumer-focused company, so the project was killed. However, one of the Life360 co-founders who runs Hubble Network, his own company, which is Bluetooth and Space, said, “That's an interesting project that we should be kicking off.” He ended up hiring Tile's chief business officer to basically run this project. It's called SmartPen. He ended up reaching out to me and was like, “Jossie, do you want to build the thing we were going to build back at Tile?”

That idea got killed when the company was acquired by Life360. They said, “That B2B idea, not so much.”

We all knew it had value. We all knew there were legs there because people still reached out asking for this. He reached out and was like, “Jossie, do you want to do this? We can finally do this.” I was two years into my coaching practice, and I was like, “Alright, Jeff. I'll come do it.” He convinced me. I scaled back on coaching and brought in a few of my old team members. We basically, in around ten months, ended up launching SmartPen in May of 2025. It was remarkable even with very little marketing.

There was very little outbound. People were reaching out. People were finding us. I left in February of 2026. We got into some nice incoming revenue. I got a nice founding engineering team. I set up another engineering leader for success. Funny enough, this is the second time he's come in under it. I'd be like, “I'm leaving. Would you like to come run this team?” Again, this is where your network is very valuable. It makes it easy to build things when you already know talented folks that you can bring in to build something. The whole team now is a little over ten people in SmartPen. It was exciting getting to watch that whole zero-to-one journey.

I want to just focus in, like zoom in on the zero to launch or zero to orbit org when you escape velocity. Let's zero in on that. For me, it's an interesting follow-up question about something you just said a moment ago. What is it in ten months to move through that process? That's quite quickly, it seems.

Tweet: Career success is rarely a straight line. Sometimes stepping back is the exact micro pivot you need to rebuild your confidence.

We all had the benefit of having thought about this a lot. My role at Tile prior to being VP of software engineering was I led all of our partner integrations on the engineering side. I did a lot of zero-to-one work. We integrated Tile into Intel-based laptops. We worked with pretty much every major smart assistant that you can imagine to get integration. You can say, “Find my keys.” We were talking about Roomba for a while.

Slaying The Perfectionism Dragon

I'm very used to this like zero-to-one space. A lot of it comes down to being clear of what is the MVP. What is the must-have that we need to build? I coached some founders who used to be engineers. The biggest thing I always have to harp on about is we love to build. It is not about continuous building. It is about what is that minimum viable product that you can start iterating on and learning from your customers about.

We got the basics of things like, “Here's the web dashboard we need. Here's how people can do the minimum level of notifications. Here's where they can set up the equivalent of a little geo-fenced site.” That was it. I was like, “This is what we need to launch. We need to get customers to start looking at it.” Part of the other thing is, the business model that we have is different from the business model we launched from.

We were always going to do a subscription-based service, but it was like, is the hardware included or separate? How was pricing included and thought about? That evolved multiple times since launch. That's the thing. Sometimes, you get into this almost as fixed and on the flip side, you also need to realize there is ongoing engineering cost if you are pivoting.

It is about being clear that you don't want to pivot every month because then your engineers are never making forward progress. Sometimes the pivot isn't a backwards thing, even if it means throwing some things away. It means I've now learned new things. This is a very intentional pivot based on all of this new data, which will hopefully take us to the next level.

It's the Edison quote that's always used, and it's been probably exaggerated tons of times. It's the 999 ways to not make a light bulb. The 1,000th time is the one. It's reverse engineering on some level. When you mentioned the zero-to-one space, can you give us a sense from your perspective?

If you are creating a recipe for being successful in that zero-to-one space and since you're a coach, a lot of this has to do with behaviors. It's the mindset and behaviors. What's the recipe for the mindset and behavioral change that's required for somebody to be able to effectively move from zero to one the way you've seen?

First, be willing to start selling before you even build, potentially. Again, especially as engineers. I see this a lot with the engineers. We get into this like, “I need to build this thing and present it to them.” No, you need to talk to them and understand what the pain points are and then slowly iterate. It also doesn't have to be perfect at the beginning.

Narrowing Your Ideal Customer Lens

Don't let perfection be the enemy of good enough. In the future, you might need a much more complex notification system, but is that what you need at launch? I would say the last piece, which I have seen by people multiple times, is, you need to be really clear about who your ideal customer is. Only because your product could satisfy multiple customers that may have very different sizes, but the foundation. Let's talk about SmartPen.

A tiny little car dealership could use it to track license plates, or a huge enterprise could use it to track thousands to tens of thousands of invaluable devices that they don't want to walk out of a factory, for example. However, the needs for both of those are very different if you're thinking about what you're fundamentally focused on building. If you try to prioritize both at the same level, when you've got a small team, you're likely to build something that doesn't satisfy anybody.

I'm not saying don't think about the fact that maybe in the future you want to scale big or maybe you want to start with those bigger customers. If the little guys are happy with it enough, that's great, too. Having that prioritization crystal clear is what differentiates what I've seen like this zero-to-one launch and work.

Resilient Tech Leadership: When you try to build a product for everyone, you build a product for nobody. Get crystal clear on your ideal avatar to win.

The question now that I want to circle back to is based on something you said earlier. This moving through that process of an idea, ideating, discovering something, sensing an opportunity in the marketplace to, let's call that zero, in these terms, to being there's an MVP. There's something. There's a product that can be launched that you're going to graduate, if you will, to the next level of its journey into more maturity. That zero-to-one journey, for me, feels like there's a question about letting go because to create something like this, it's like your baby.

It becomes your baby. It's the baby of the founders, the architects, the engineers, the coder. It’s like everybody's. Yet the cycle, if you will, for a VC or for even companies that have to continue to iterate new things to be relevant, to be profitable, you have to move through that cycle and then let go.

I want to understand from your perspective. What's the mindset when you're coaching somebody? You're coaching an executive or somebody senior who you feel like is hanging on to that baby too long because they either don't know what the next baby will be or whatever the reasons. Let me get some thoughts from you. Have you seen that? Have you diagnosed that? Have you helped somebody?

You often need somebody potentially from the outside. This is why all founders need a coach because you get so into it that sometimes you don't realize you aren't letting go when you need to. On the flip side, that doesn't mean you're not allowed to have strong opinions. That's the duality of it. Sometimes, it's about, “I have this decision. I have this belief. I'm going to keep trying different avenues to see if this pathway is the right way.” That's okay.

You can have a vision, but realize that the steps along the way to get that vision may be different. That is the key in letting go. In my terms, I call it loving accountability. I always tell people, “I am in a judgment-free zone here.” I will call out when I see you holding on to something or making a decision that I don't think is potentially the best.

I'm always doing it from the perspective that I want to see you thrive and succeed. I also tell people that this is also my opinion. I'm not going to be hurt if you don't agree with me. Let's have a discussion about this. It's that quote about strong opinions loosely held. You can have a vision, and you potentially don't want that changing that much. You don't want to be waffling on what that vision is, but where you do need to let go is on the how.

The how can change, and if you're so stuck on how you're going to get to that vision that you don't see that there is potentially a much easier opportunity to get there. I see this with early founders a lot like if it's their first company. I have a founder I'm coaching. He has a great product in the developer productivity space.

He researched like, “How do you do traditional marketing?” It talks about you creating ads or you reaching out to people. You have a lead funnel, or you send, like, sales lead-gen type messages to CTOs potentially. I was like, “You're an engineer. A very senior engineer at a very well-known public company is your background. That is a differentiator. How many messages have you gotten on LinkedIn on a daily basis back when you were at your full-time job that you ignored because it looked like a sales pitch from a vendor?

He's like, “Oh, yes.” I was like, “What if instead you go and have a peer conversation with CTOs and say like, “I've been doing research around the challenges you're all facing around AI. I have some insights that I'd be interested in learning what you're doing. They are much more likely to hop on a call with you then.” Sometimes the coaching piece is showing people that just like the traditional right way to do things is not always the easy or smart way to do things.

When it comes to letting go, that process of letting go, is there something that you feel is a catalyst for more success? Again, in the VC space, for example. They invest in something. That's the baby, of course. They want it to succeed. Then when they start to see it succeed, then they are. Even before that, already looking out into the ecosystem for that next opportunity.

You could say that's more transactional, but again, that’s a bit of a negative way to look at it but it is transactional. It certainly doesn't seem like it's attached to it. I think that’s the differentiator. How attached is a wise level of attachment when it comes to how you bring something from zero to one? That's the lens I'm looking at it through.

The other thing you need to decide is, are you building this thing with an exit in mind? Are you building this thing with a desire to run it for another 10 to 20 years? There's no right or wrong between either of those. You can decide, “My desire is to build this. Very much like you were saying, the VC will see it succeed.

Tweet: Perfectionism is the enemy of progress. Build your MVP, launch it, and let your customers teach you how to refine it.

It'll try to go through an acquisition but also on the flip side, there’s nothing wrong with deciding. I want to build this and this is the thing I want to see how it runs for the next 10 to 20 years. Maybe I know I'm not going to make as much money because I'm not going to make an exit, but that's an intentional decision. That's coming at it from that place is where letting go ends up being important.

If you fall into that decision, then you're like, “I need to let go of this. It's being sold.” When you're starting something new and looking at the zero-to-one piece, you should be pretty clear about what your end goal is. From a financial transactional perspective, people will tell you that your end goal for creating a business is to sell it and then start the next thing because that is how you will get more money.

I am not disagreeing with that. At the same time, this goes back to what we were talking about earlier. You also get to decide what your version of success looks like.  If your goal is not to go make millions and millions of dollars and it's not about playing the game and you started this thing because you're passionate about it. You want to run it for the next 10, 20, or 30 years until you retire. There's also nothing wrong with that. That is the thing that people don't talk about.

I'm thinking about somebody reading this and applying it, as we always do, to their own lives or to their own situations. The question is a fundamental one and one that you can ask at the beginning. Best at the beginning but can be asked at any point along the path is, what is my true intention? That will answer or at least lead to what you're bringing out, Jossie. If your true intention is, “This is something I want to grow and be a part of and it's going to be my calling and my purpose for the next whatever many years,” you ought to know that at the start.

Versus, transactionally speaking, what I want to do is create something successful that I can sell so that I can then leverage it to create the next thing in order to be able to sell that as well. As we wrap up here, I want to ask you about something that's related to resilience. Here's how I want to tee this up because you're the perfect person to incubate this idea with. I watched a video of Jensen Wong, who everybody, I'm sure at this point knows, CEO of NVIDIA, giving a speech to a group of Business School grad students at Stanford. This high-end business graduate group.

He starts out saying, “Congratulations. You all should feel very proud of yourselves. I'm sure that you have high expectations,” as you would imagine, and he makes a joke, because to be able to pay the tuition at Stanford is a big deal. He goes, “You probably have high expectations,” then he literally pulls the rug out from under them because the next thing he says to them is, “In my experience, people with high expectations have low resilience.” You might have seen that clip. I'm not sure if you have.

I did not see that clip, but it is something that the research very much aligns with.

Say more about that. I may come on to say a little bit more about what you said next.

Building A Muscle For Hard Truths

When you've been so successful and you're a high performer, you don't build the muscle for accepting negative feedback or negative things happening because you're so used to things just succeeding for you. That is a muscle that needs to be built. It's one that often high performers don't get to build because it's not happening to them often. From a very neuroscience perspective, when something negative shows up, our amygdala gets hijacked.

We go into fights. It takes at least 30 minutes, if not on average two hours, for our thinking brain to turn back on to be able to process the negative thing that happened or occurred. I was just talking to people about receiving feedback, and I always tell people, “The biggest piece of advice that nobody gives about receiving feedback is the skill to say ‘I need to think about this, and I'll come back to you tomorrow.’” Everyone's being taught, like, “You need to learn emotional resilience and all this stuff.” Your brain literally shuts down.

I haven't heard a word you've said since you told me. I suck.

High performers, and especially the higher up you go, the more successful you get, the more cushy the life gets. The harder the fear of the fall can be. That is the other piece. If you've constantly been going in this upward trajectory, this fear of falling can be hard. I say that this is one of the challenges with the world, especially the tech industry prior to a few years ago, which had been going up and to the right since like 2009 or 2010. We have a whole generation of people who've never lived through a crash. Having been through the dot-com crash, where 25% of this valley got laid off during that time. We didn't have social media crying and screaming about it.

What was Puppets.com or Socks.com?

Pets.com.

Some of us remember.

The 2008 financial crash, I come at this as we're most likely going to have a crash. We're most likely in the middle of a crash. We're most likely going to get over it like every other crash we have looked at financially. Yet I have friends who'd started in the industry after that and never having had to build the resilience of going through that. Since it's been so long since the last one, and now social media is so much more than it ever was back then. There's all these compounding impacts to this.

It's more than a 30-year-old company, and they suffered a lot. He says, “When my team comes to me and says that they've gone through something or something's gone wrong, I applaud it.” The last thing he says to this graduate group, he says, “I wish you ample amounts of pain and suffering.” Can you imagine being in this seat to hear this modern-day Steve Jobs say that?

It's true, though. It is true. I reflect back on my life, and I forget if I mentioned this, my mom passed away after struggling with Alzheimer's for eight years. I had to basically remotely caregive for my mom, and my dad was suffering from serious mental health issues while trying to do this. It was a hard point in my life. Even when challenging moments come up, I can look back and be like, “If I made it through those eight years, or well in the nine years, if I can make it through that, I can pretty much handle anything that comes to me.”

That's one part of it. Another part of it is also self-belief. One of the reasons I don't have fear as much, and not to say I don't get fear sometimes. We are humans, but where I come back to is I 100%, in my soul, believe I can make money. If coaching fell apart as a practice tomorrow because AI became amazing coaches and somehow you never needed a coach again. I'd figure out a different way to make money. I truly believe in my resourcefulness, in my ability to adapt, change and do something new. I believe that's where resilience starts. It is not like you can make up for some terrible event happening and pain and suffering. What you have control about starting now is developing that belief.

Our company WorkWell does a lot of research on resilience, but in the end, if there's one thing you could point to from the standpoint of the species, like the human species, but every species on the planet. It's this capacity for adaptability. That's the reason we're here. Darwin wrote about it a long time ago, “It's not the survival of the fittest.” It's not his quote. Because the fittest, the strongest, the smartest, the most intelligent are not the ones that survive. It's those that are best able to adapt to their changing environment. That's why we're here. We're the legacy of that. That is us.

If you don't believe that you truly have the ability to adapt to almost any environment, you're lacking the most important part of the equation to begin with. As you said, the belief that you'll be okay because you have what it takes to be okay. There's also an element of people wanting to avoid pain.

Somebody once called it the false evidence appearing real or something. I've been taught that it's more anticipation of pain. When we anticipate pain, that's what fear is. We're thinking, “There will be pain associated. If I lose my position, my job, my business goes down or my business changes.” Whatever it might be. The fear is that I'll experience pain.

Yes, and for very logical folks, which a lot of technology leaders are, it's twofold, but it's not wanting to feel that emotion and/or never having been taught how to feel emotions. I resonate with that one because after my mom passed away, it took me eight years before I fully processed and let myself feel the grief from that. I went on a vacation to visit my best friend, and I ended up crying on and off for a week.

I said that was like one of the best vacations I've ever taken in my life, despite the fact that I spent my evenings crying because I allowed myself to feel. Again, in the corporate world, those are those mushy things. Those are not important to deal with. If you're having feelings, you tamp them down. If you learn how to process your emotions and let them flow through your body so they are not stuck, you're going to thrive so much more and be willing to take action.

It will certainly not have you repeating a pattern of avoidance because this is how we respond to those things is a distraction. Our bodies are great at that too. It’s a separate topic, but our bodies will conveniently find ways to grab our attention as opposed to dealing with the emotion. This wonderful old book by Dr. Sarno is his last name. It's called Healing Back Pain.

There will be links to Jossie's website and the work that she does as a coach and lots of other things and anything else that we've made reference to in our talk. This book in particular is also good to include because it's a book about how our bodies and minds are very clever at distraction so that we don't have to feel those emotions.

All of a sudden, you've got a low back spasm, and your back goes out, and you can't stand up for hours. You can't work for a couple of days. That's, by the way, the most common reason for a missed day of work, and you go, “What's that all about?” This structure, the car accident, or the whiplash. What is it?

Often, it's just a stuck emotion. It's literally your mind keeping you from dealing with something. “The mind is a trickster,” John Kehoe once said. It's an interesting thing to try to hack what's going on inside between your ears and mine. Jossie, I have loved this conversation. I feel like I literally could continue talking to you. Maybe we'll just do part two of this.

I would love to. I feel like we have so many more things that we could talk about, too.

Our audience will often ask for that. That's great. There'll be a few postscript words for me. Stick around for that, folks, but for now, I want to thank Jossie for everything she shared. I took copious notes. I thought of so many great things that you did share. I look forward to the next time that we get to chat. Thank you.

Me, too. Thank you.

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I've got to add this to my personal list of favorite episodes from the show. I love talking to Jossie. If you'd love a part two of this conversation, please let us know. You can just email us at Team@WorkWelllabs.com or Team@AdamMarkel.com if you prefer, and with comments, questions that you might have for Jossie and I. You can always do that as well. We'd love to answer those for you.

I felt like she and I are simpatico. I loved what she shared about how it is that we often are getting in our own way from fear, but this particular type of fear that she described that leaders have. The fear of that fall. The fear of the possibility of that fall and the pain that's associated with that is one of those things that does really get in the way.

She shared some insights about feedback that it is a requirement of any entrepreneur, any leader, any executive that we develop this muscle. A muscle for negative feedback. Think about that for a second. If we don't, then we are less resilient than those that have. That was this concept that Jensen Wong shared with the business student graduates at Stanford University.

He's saying to them, “You have high expectations and that's probably going to be your biggest issue. That's going to be the thing that could, in fact, get in the way of your success,” because they haven't yet developed that muscle for negative feedback. From a neuroscience standpoint, they'll seek to avoid experiencing anything but success.

That's not the road of most leaders. It's not the path that we're on as human beings in so many respects. To the extent that we've just been able to avoid adversity or others around us have helped us create and curate, if we could use that word here, an environment where we don't have to deal with a lot of negative feedback.

It might be that's kind and that was compassionate and empathetic and all those good things. Yet it might have also set us up for failure down the road because we won't be able to deal with it. We won't know how to overcome it quickly. We won't have the self-belief that we can adapt and move forward based on that, that we will not just survive it, but will thrive in spite of it.

Since we lack that self-belief, that may impact our confidence in that moment and may contribute to us not being able to make the best decision possible, to be able to pivot, in other words, in the moment without feeling weighed down by that issue of low resilience, low adaptability, or low appetite even for adversity. I know it sounds funny to say that because who wants to have an appetite for adversity and yet resilient people know that they've been able to overcome things.

When those things happen, they're not devastating. In fact, they are often a catalyst for growth. I love this conversation and love where we tracked it and how we also looked at the mindset of somebody that can move from zero to one in terms of incubating an idea and getting it to that MVP. That minimally viable product stage to then be able to learn what is needed and pivot again in order for that product to make it to the marketplace, to scale even, and to ultimately lead to an exit.

We also tracked a first-tier question, a valuable question, first domino question, if you will. What's your true intention when you start something? Is your true intention to exit? Is it your true intention that the thing that you're creating is something that you're going to eventually let go of, graduate and let go of so that you can then move on to something else and work through that same very seamless process?

That's a question we ask at the beginning. It's better to ask it anytime, even in the middle, I suppose. If you don't ask it at all, then you're lacking a certain clarity that will help you to be able to move without resistance. Ultimately in business, or in anything, we need to move as resistance-free as possible. When we let go of our attachment to things, when we let go of our fear, when we are able to feel our emotions and express our emotions and not try to avoid our emotions.

All these things create a more resistance-free existence for us, life for us, and experience in everything that we do. This among many things we discussed. Super appreciative to Jossie for that conversation. If somebody you know would benefit from hearing this, please share this episode with a friend, a colleague, a family member, etc. Again, let us know your feedback. As always, I want to just thank you for your time. Thank you for your presence on the show.

Even though we don't get to see each other, I can feel you all out there reading. I'm so grateful for our community, this expanding group that are the people that are leaning into the Change Proof principles and soon, the re-culture principles. Which is something we'll be talking about. Thanks so much, as always. Ciao for now.

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About Jossie Haines Jossie Haines spent 25 years in software engineering leadership, including leading an Emmy-winning team at Apple and creating the VP of Engineering role at Tile. She is now an executive coach for senior tech leaders, coaching them through the moments that matter most — new roles, team turnarounds, building something from scratch, high-stakes transitions — so they succeed in the role and drive real impact. What sets her apart: she can get into the technical weeds, drive 10,000-foot strategy, and coach the mindset shifts underneath.