The Iteration Point
The Iteration Point - a podcast about the moments that change everything. The pivots, the setbacks, the reinventions. The stories that don't fit neatly on a resume.
The Iteration Point
People, Passion, and Purpose: What Our Guests Taught Us About Work
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
After five conversations with people navigating career transitions, three themes keep surfacing: the people you work with matter as much as the work itself, staying hands-on is essential for certain personalities, and impact trumps income when measuring real success. In this look back at the first five episodes, Michael pulls together insights from Kim, Erik, Helder, Russ, and Shara to explore what actually makes work meaningful - and why the traditional metrics of success (salary, title, prestige) often work against us.
Welcome to the Iteration Point. I'm Michael Atkins. Over the past few weeks, I've had conversations with five incredible people navigating career transitions. A therapist who left corporate healthcare after 21 years, an artist and marketing professional turned technology manager, an engineer who's worked on everything from semiconductors to Amazon Echo devices. A business coach who helps startups find their footing. A technology veteran building a portfolio career in the age of AI. And as I've been listening back to these conversations, I keep noticing the same things coming up. Not the things you'd expect, like salary negotiation tactics or resume tips. Instead, what keeps surfacing are three deeper tooths about what actually makes work meaningful. Today I want to pull those threads together and share what I've learned from these conversations, about what really matters when it comes to work. So here are the three things that kept coming up across every conversation. First, that the people you work with can matter as much as the work itself. Second, that staying close to hands-on work, getting your hands dirty, is essential for certain people. And third, that impact and purpose mean more than income and titles when you're looking back on your successes. I'm going to dive into each of these, starting with the people you work with. Here's a clip from my conversation with Eric. We worked together at Earth Advantage, and I wanted to highlight some of his thoughts.
SPEAKER_04Yeah, just tremendous people at Earth Advantage. They're just really great, great human beings across the board. And it was a joy every day to work with them. It was a joy to work with the developers I worked with who were in their own separate companies as well. They were also really unique, special people. Uh, and I miss working with them as well. But, you know, life, life changes, and you, like you said, you pivot, you figure it out.
SPEAKER_03Eric didn't focus on missing the title or his projects. He talked about missing the people, the daily collaboration, the relationships you build when you're working towards something together. Here's a clip from talking with Helder.
SPEAKER_02I I was in at Plantronics for this long because of the great environment and the great people we had there. And when I went to Amazon, I was a little iffy about how it was going to be. Some of the smartest people I've worked with in my entire career, not just one or two, but all of them.
SPEAKER_03Helder could have gone anywhere with his skills, but he stayed so long in places because of who he was working with. And when he talks about what he's looking for next, it's not just about the technology. It's about finding great people again. Here's a clip from my time with Kim.
SPEAKER_00Really proud of the work my team was doing. Um, I felt I was a servant leader. They were doing the tough work, the important work of actually talking to folks, but I really felt like I was there to be able to help, you know, smooth things out for them, support them in whatever way they needed, because they had to be in a good space to be able to be compassionate and engaged and fully present with the members that they were trying to assist. Um, and that was great. And I felt really proud of that work, proud of what the team was doing and how they were helping folks.
SPEAKER_03Even in a management role, what lit Kim up wasn't the KPIs or the strategy meetings, it was supporting the people on her team so that they could do their best work. Here's what I'm taking from this. We spend so much time optimizing for the wrong things when we're evaluating jobs. We look at compensation packages and career progression and company prestige. But we we don't always ask is who will I be working with every day? Will these be people who challenge me, support me, make me better? Can I help elevate them? Because the reality is, if you're working with people you genuinely respect and enjoy, you can get through almost anything. And if you're not, even the best title and salary won't make up for it. The question isn't just what company or industry should I work for? It's who will I be working alongside. The second theme that kept coming up is this need to stay close to the actual work, to get your hands dirty. And what's fascinating is how career advancement often pulls you away from exactly that. Here's Helder's take.
SPEAKER_02I have to get my hands on it. And um, if I don't have an opportunity to get my hands on it, then I, you know, I'll do the job, but will I love the job is the difference, right? And I gotta be able to love it, right?
SPEAKER_03Helder has this deep need to be hands-on, whether it's solving technical problems, producing music, or restoring hot rods. And he's realized that just because he can also do strategic work doesn't mean that's all he should be doing. Getting into the weeds can be fulfilling sometimes. There was a similar sentiment expressed by Kim.
SPEAKER_00But I noticed over the past couple of years, um, as I you know moved further in my leadership path, it was pulling me further and further from the work that I really loved. Um, I never had a strong ambition to you know try to advance my way up a corporate ladder or anything like that. That's not what I was going for.
SPEAKER_03Kim got promoted into a management role that looked like a great move, and for a while it was, but it was pulling her farther and further away from what she was actually passionate about. All the meetings and operational work wasn't what drove her to get into this field in the first place. And here's the pattern I'm seeing. Traditional career progression often means moving away from the thing you're great at. You're a great engineer, so they make you an engineering manager. You're a great therapist, so they move you into operations. You're doing hands-on product work, so they promote you into strategy. And for some people, that works. Or if you really love the strategy side of things, paying your dues and the hands-on product work first is important to develop perspective that you can use at the higher level. That evolution can either be a welcome change, or can end up taking you away from the motivation that drove you into the field in the first place, and you end up in a deeply unsatisfying situation. I had this conversation with my father before he passed. He worked at a company where he tested circuit boards and fixed issues that came up. He enjoyed his work, he was good at it, and he was one of the most personable people you'd ever meet. He absolutely could have tried to move into management, but he told me that the trade-off would have been more stress and taking him away from the work he liked doing. I think there's a certain personality type, and Helder articulated this perfectly, that needs to get their hands on it, that need to be builders, not just managers of builders. So if you're in a role where you're being pulled away from the hands-on work and it's making you miserable, that's not a character flaw. That's a signal. It might be time to find a different path, even if it means stepping off the traditional ladder. The third theme is about how we measure success. And this one really challenged me. Here's Kim again.
SPEAKER_00I needed a pep talk a few days ago because we just got done doing our taxes, and I'm like seeing what I made on my W-2 last year, and I'm like, yeah. I I'm like, well, how did I? And I just walked away. How how could I? And yet I had to remind myself that, but I it but it needed to happen, and a dollar amount does not define me, and I am building a new business.
SPEAKER_02Here's the thought along the same lines from Helder. For me, one of the things that's also super important, not enough for me, not enough for me to love it. I need to know that what I do is having an impact on the world around me, impact on people, on individuals, or even a large group of individuals, right?
SPEAKER_03But it's gotta be able to make the world better somehow. Helder isn't just looking for interesting work. He needs to know it matters, that it's having an impact beyond just generating profit for shareholders. And when that impact isn't there, the work loses meaning for him. There was an interesting take from Shara on how continuous learning opportunities right now are key, especially with AI gaining traction.
SPEAKER_01I have to mention that I forget where I read this recently, but there's an opportunity cost now to being in a corporate job that doesn't let you learn AI. Um, you know, for the last six months or so, I've been diving into various AI tools, um, cursor and cloud code, um, looking into open claw. And yeah, it takes some time to kind of figure out all the tools and the landscape. Um, the tools for promoting your business, um, doing websites, GEO. I mean, there's just a lot of learning. Uh, and so anyone who's not doing that now is going to be behind. So it's kind of risky to have certain full-time jobs if if they're not the right one.
SPEAKER_03I think what she's getting at here is that the stable corporate job with the good salary might not actually be the safe choice anymore. If that job is keeping you from learning, from staying hands-on with emerging technologies, from developing skills that will matter in five years, then the security it offers might be an illusion. So when we're measuring success, we can't just look at today's paycheck. We have to ask: is this role investing in my future? Or is it merely extracting value, but not giving me the opportunity to grow into work that I love? Russ had a great exercise he runs his clients through.
SPEAKER_05If you take a piece of paper, throw it landscape, and just put three columns on it. Um, and in the first column, what do I do really well? Right? What do I just what when something needs to get done? What is it that people come to me looking for? What am I world class at, if you will? Second column, what do I love? Not just what I love to do, but just what do I love? Um, you know, trees, cars, attics, you know, uh buildings, architecture, landscaping, what take your pick, right? What are the things that I just love? They energize me. And the third column is a little more challenging. It's what is the combination of those two that people are willing to pay for?
SPEAKER_03What I love about Russ's framework is that it starts with what you're great at and what you love, and then asks what people will pay for, not the other way around. We often start with what pays well and then try to convince ourselves that we can learn to love it. But that misaligns our internal value with external compensation. Here's what I'm realizing. We've been conditioned to measure career success by very specific metrics: salary, title, company prestige, upward mobility. And those things matter. I'm not going to pretend they don't. We all have bills to pay. But what these conversations have shown me is that those external metrics can actually work against us. They can keep us in roles that look successful but feel hollow. They can make us afraid to make changes that would actually make us happier. Kim said something that stuck with me. I have much to offer this world. That's her mantra. And when she's measuring her success by whether she's offering what she has, her coaching, her presence, her ability to help people, that's when she feels fulfilled. When she was measuring it by her salary and title, she felt misaligned. So the question becomes, what are you optimizing for? And is it actually what matters to you? Because I think a lot of us are optimizing for things that society told us mattered, or that mattered to us 10 years ago but don't anymore. And we haven't stopped to re-evaluate. So here's what I'm taking from these conversations. People matter. More than we give them credit for when we're evaluating opportunities. Ask yourself, who will I be working with? Do I respect them? Will they challenge me? Make me better? The hands-on work matters. If you're someone who needs to get your hands dirty, don't let career progression pull you away from that. There's no shame in wanting to stay close to the work. In fact, there's wisdom in it. And impact matters. More than titles, more than income. Ask yourself, am I using what I'm world-class at? Am I making a difference in a way that feels meaningful to me? Or am I just collecting a paycheck? These aren't easy questions, and they don't have universal answers. What matters to you might be completely different from what matters to me, or to any of the guests I've talked to. One more thing. These three things, people, hands-on, work, impact, they're all things that AI can't give you. AI can help you be more productive. It can automate tasks. It might even replace certain roles entirely. But it can't give you the feeling of working alongside people you respect. It can't give you the satisfaction of getting your hands dirty and solving a problem yourself. And it can't tell you what impact means to you. Those are fundamentally human questions. And they're the questions worth wrestling with. This podcast has been a great iteration in my life, and I'm excited to announce that I've landed in an opportunity that starts in a few weeks. So the podcast will be transitioning to a different format and a schedule that's still to be determined. I'd like to thank all of you for listening and engaging with me and my guests. And if you haven't listened to the full conversations with Kim, Eric, Halder, Russ, and Sarah, go back and check them out. Each one has so much more depth than I can cover here. Thanks for listening to the Iteration Point. I'm Michael Atkins. We'll see you next time.