When does positive impact justify suffering?
A conversation with Alex McCann on finding meaning in work
Hey enoughers! Can I call you that? Enoughites? Enoughins? We’ll keep workshopping the name. Suggestions welcome.
Today we’re trying something new on the ol’ newsletter: an interview!
Today’s guest is a wonderful human you may have spotted around Substack: Alex McCann. Alex writes the newsletter “Still Wandering”, is the Founder of Rumbo, an AI career-coaching app, and has gone viral with a few of his essays, namely, “The death of the corporate job”.
His writing has gotten so much traction because he’s pointing to a struggle that a whole lot of people are experiencing right now: Corporate jobs, a mainstay of Western Society since the industrial revolution, aren’t working for us the way they used to.
Maybe it’s the mass AI layoffs, housing unaffordability, the “crisis of meaning” that haunts millennials’ dreams at night, or maybe it’s the metacrisis as a whole… but something is shifting. Many are finding an unshakable feeling of emptiness and disconnection in their work. And with job markets being so volatile, they’re wondering if this is even a “safe” path anymore.
A few weeks ago, Alex and I had a wonderful conversation, which he published on his newsletter here. You can view this conversation as part II, going deeper into some of these themes of work, meaning, impact, suffering, and enoughness.
Pro tip: when you read Alex’s words, read them in his beautiful British accent, which makes him sound much more intelligent than me and my Lawng Island tongue.
Awlright…let’s get into it!
David: Hey Alex! Welcome to my neck of the internet. Thanks for agreeing to come over and continue the conversation.
I’d love to start with your recent article, which broke down five subgroups of meaninglessness in work: Distance from impact, values contradiction, interchangeability, manufactured necessity, and lack of authorship.
It was SO good. My question after reading it: Is it inevitable that meaninglessness emerges in corporations as they scale?
Alex: I think yes.
To be honest, all of the subgroups get ticked by a lot of corporate work, as I understand it. But I think “lack of authorship” is the big one.
I’ve probably had 300–400 conversations with people suffering from career uncertainty. Maybe half are people in corporate jobs. And it’s always the first thing they say: “I don’t know what’s happening to the work I’m doing. I don’t see it. It gets passed on.”
So I think there’s something fundamentally human about needing to feel useful and seeing the impact of your work.
David: So, what direction do we take this? Does corporate work need to change to become more meaningful? Or is it a lost cause, and people are starting to look elsewhere?
Alex: I think it’s both, and it depends on where you sit.
Some corporate work can be made more meaningful. Shorter feedback loops so people see the impact of their work, smaller teams, more autonomy. But for a lot of roles, the structure itself makes meaning difficult. If your job exists to create a report that feeds into another report that informs a decision you’ll never see the outcome of, no amount of company culture work is going to solve that.
What I’m seeing in hundreds of conversations is that people are starting to take the question more seriously. They’re asking, “What problem do I want to work on?” rather than, “What company do I want to work for?”
It doesn’t mean everyone’s quitting to start a business. But they’re thinking more carefully about alignment between who they are and what they spend their time doing. And for a long time, they weren’t asking that question at all.
David: When we last spoke, we discussed how many of us choose our work from a wound rather than a scar. We turn to work thinking it might heal our traumas, but it just causes all sorts of issues, because it becomes a way of avoiding the actual work of healing.
I’m curious, how did that land for you? Where do you notice that showing up in your life?
Alex: Yeah, it was spot on the money.
So, earlier in my career, my mindset around money was completely different. My mindset around impact was completely different. I think I even said to my coach, Charlie, at that time, “I have to be a millionaire by the age of 30.” That was one of the first things I said.
And that’s characteristic of my relationship with money up until that point. And I think that would be one of the wounds that a lot of my decision to take this entrepreneurial path comes from.
It’s weird because I’ve grown up really comfortable. Not otherworldly wealthy, but never had to worry. And I don’t know where it came from necessarily, but I always remember having anxiety around money.
Since then, it’s developed into: what happens financially happens. I’ll be fine. I proved to myself in my last job that I could find opportunities that allow me to live at a standard of life I’m happy with. There’s no risk of me being homeless. I can come home, I have a great relationship with my parents.
And when I stopped focusing on money so much, I started focusing on: what’s the problem space I’m really interested in? Who are the people I’d really love to help?
So that’s probably my most poignant example of moving from operating from a wound to operating from abundance. And it’s been a really interesting journey to notice the different feelings along the way.
David: That financial scarcity seems to be so common today. I notice that even for people who aren’t struggling to make ends meet, there’s still the fear of losing it all and finding themselves in that position. It seems to be what stops people from leaving jobs where they’re unhappy. Even though they have the privilege, it seems like they’re functioning from fear of losing it.
Alex: I think you’re right. And I’ve had the same observation speaking to people.
Obviously, in some cases, it is a real worry. It’s legitimate. But often, the reality is much less dramatic than people make it out to be.
I also think people hear advice in hyperbolic terms: “I made this leap,” “I took this jump,” “I took all the risk, and it paid off,” “capitalism rewards risk,” “fortune favors the brave.” That narrative is largely perpetuated by social media.
What you don’t hear is the nuance: you don’t have to go immediately. There’s no rush. You can take your time. Think of a plan. With sufficient information, through reflection and research, you can diminish the risks.
People think things are more binary than they actually are. There are more roads available. What happens if you scale things back for six months, save some runway? Dedicate an hour an evening to researching opportunities, understanding how your experience uniquely positions you, networking, playing around with numbers?
Maybe it’s not an hour, maybe it’s 20 minutes, and you wait 12 months. But you’re not stuck. You’re not doomed in your current predicament forever. People tend not to think like that. I don’t think I have enough experience with the problem to fully understand why, but that’s what I’ve noticed.
David: You’ve talked to a lot of people with career uncertainty who are unhappy, especially in corporate. Have you talked to many people who are happy?
Alex: I live with one.
My dad is there. He’s an example of somebody who is extremely happy, successful, fulfilled. I’ve been really lucky that from a young age, I know exactly what it looks like. He’s an engineer. I have memories going to Heathrow Airport—he was the chief engineer for Terminal 5. So we go there all the time whenever we go on holidays. And he’ll say, “I remember doing this thing I built,” and he can see it. It’s such obvious pride.
It’s interesting: with my dad, and with entrepreneur friends of mine, there’s something with enoughness. A clear line, knowing what enough means.
My entrepreneur friend just had his first kid and lives out in Cyprus. He’s making really good money. He could make a lot more, but he’s said: These are the hours I’m going to work. I’ll work really hard in those hours. The rest of the time is for my kid. I’m leaving a lot on the table, but that’s the tradeoff. I’d happily pay the excess money I could be making to spend time with my kid and engage with family.
So that’s another example. It’s helpful to have a clear conversation with oneself about what enough looks like.
David: Let’s talk about that. If you’re unhappy at work, is it just an enoughness thing? Like, if your expectations of what was “enough” were lower, you’d be happy?
Alex: You’re exposed to so many more opportunities to compare today. A hundred years ago, the average person’s frame of reference for success was geographically limited. Now, the smartest people in the world are figuring out ways to bombard you using algorithms and social media with, “You’re not good enough. Here are people who’ve done amazing things, and you could be aiming higher.”
There’s a balance. I absolutely advocate for people to aim high, but by the laws of distribution, not everybody can achieve the 1% goals. So we need a conversation about valid and realistic expectations, and not making people feel like they’re not enough.
In one of your articles about enoughness, you mentioned your wife having a strong innate sense of enoughness. I have a similar thing with my partner. Success for them doesn’t look like millions of pounds or a huge business. It looks like helping people they see every day and being engaged with their work. These things are still valid. And society tells people it’s not valid.
So that’s one thing. Another thing that our mutual friend Simone Stolzoff talks about in The Good Enough Job: Enoughness is vague. Are we speaking about enoughness financially? Enoughness in terms of impact? And if it’s impact, how do you measure impact? Intensity? Breadth? It becomes tricky to measure. So the concept of what is “enough” gets vague.
Rutger Bregman talks about the type of work that has net positive impact. If you can honestly say your work ticks boxes—net positive to society, expansive rather than extractive, not exploiting anyone—then I think wanting more, being ambitious, is healthy.
Whereas if you’re in jobs that are, “how can I take from other people, funnel that into one person, make the shareholder richer, climbing over people”, then you have to question: is the pursuit good for society?
Because ambition is powerful. I think ambition is good. It builds cities and countries and great technology. But it has to come from a place where you can argue your work is net positive.
As I say that, I’m thinking about Musk. Watching his descent into madness, I’m trying to pinpoint where it went wrong. At the beginning, it was clear he was concerned with the good of the world. And there’s no question he didn’t think about what enough looks like.
So maybe even if all the criteria are ticked for net-positive work, not having a relationship with enoughness is still dangerous. Interesting. I’ve never had to think about it before.
David: Yeah. I don’t know.
Alex: What do you think? It’s such an obvious example. Someone who probably set off with good intentions, didn’t temper expectations, and now there’s an argument he’s done more harm than good. I don’t know.
David: Enoughness is interesting to me because even what you described—impact, measuring it—can come from scarcity, woundedness. Like, “I will be enough if I have enough impact.” It seems like Musk has been very attached to being “the hero”, in addition to being attached to power and wealth.
What if enoughness is more of a state of being? I am enough. I don’t need impact, grand purpose, or meaning in my work in order to be enough. And then from “I am already enough,” okay… what is the work I feel called to do? And impact, and money are emergent properties of coming from enoughness.
Alex: Let me ask you this, because this is really interesting.
Say someone is totally focused on impact, not money, status, or power. Why is it a bad thing to not feel like you’re enough in that scenario?
Maybe it’s tougher for the person who battles never being enough. But maybe that’s the sacrifice they make to have world-changing impact.
Versus someone who says, “I’m not going to engage with that ambition. This is what enoughness looks like for me, and I’m going to feel better”, but the world misses out on impact left on the table.
So it’s worse for the person but better for the world. Do you see what I’m saying?
David: Yeah. Great question.
The question I’m asking is: Where is there suffering? Let’s take the scenario where I need to have impact in order to feel like I’m enough. And the world benefits from the impact, even though I’m suffering.
Where else is there suffering? Is the impact coming at the cost of patience with the people around me? At the cost of empowering people around me because I need to be the one credited with having impact? At the cost of my family? How many times have we seen people with incredible impact who built extremely toxic environments around them?
The suffering never just stops with that one person.
Alex: Yeah. The example that comes to mind is Ralph Nader, the guy who campaigned for seatbelts, famously a bit of a dick to everybody he worked with. But if you think about how many lives he saved with seatbelts, on paper, it’s hard to argue the sacrifice wasn’t worth it.
He probably suffered, people around him suffered. But you look at it from outside and say: was it worth it? A lot of people would say it was.
David: I think it creates a false dichotomy: either you have to feel like you’re not enough and have positive impact, or you have to feel like you’re enough and then you give up on impact.
But what if Ralph Nader felt like he was enough and still felt seatbelts were really important in the world?
Or what happens if Elon Musk felt like he was enough, he didn’t need more money, power, or reputation to feel whole, and yet he still believed in solving the energy crisis as an important gift from his heart to the world? What if he put all his wisdom and skills and effort and hard work into it. Sleep under the desk, fine…but with an open heart instead of a closed heart?
Alex: What if. I really like that. I’m going to sit with that.
David: Alright, last question for you. Tell me about the impact you’re hoping to have with Rumbo. What is the product, who is it for, and what are you hoping it can do for them?
Rumbo is an AI career coaching platform, and the core idea is simple. Before you start looking at jobs, you need to understand yourself. What you care about, what you’re good at, what problems interest you, and what the market looks like for someone with your specific combination of those things.
That sounds obvious, but almost nobody does it well. The standard career advice process goes straight to job listings and CV tips. People end up in roles that look fine on paper but feel empty within six months, because they skipped the foundational work of figuring out what they were looking for.
We built Rumbo to do that foundational work. You go through assessments, get a personalised report that helps you understand your patterns and motivations, and then work with Maya, our AI coach, to turn that into a strategy that accounts for your financial reality, your risk tolerance, your constraints.
It’s for anyone at a point of career uncertainty or transition. The impact I’m hoping for is that fewer people waste years in work that doesn’t suit them because they never had access to quality career guidance. Rutger Bregman talks about the smartest and most ambitious people ending up in jobs that don’t contribute much to the world, and I think that’s largely a guidance failure. People don’t lack talent or ambition; they lack the infrastructure to make better decisions about where to direct it.
David: That sounds like it could have incredible impact on the world AND relieve a lot of suffering. I’m pumped about what you’re building man. Thanks so much for the conversation. It’s always a pleasure to unpack this stuff with you.
Alex: Cool, man. It was such a pleasure. I really enjoy these conversations.