Ep. 386 “Is this it?” – Reframing success before your next chapter

Estimated reading time: 14 minutes

Voted most likely to succeed at 17, Anna Lundberg has spent years asking what that actually meant – and whether it still matters. This episode traces the quiet question so many high-achievers carry but rarely say out loud: is this it? And reframes it not as a sign that something’s gone wrong, but as evidence that something’s ready to shift.

Key moments

[00:01:01] Going back to the roots – Why the question “what does success mean?” is at the heart of everything Anna does, and what prompted her to revisit it now.

[00:01:36] Most likely to succeed – What it felt like to receive that label at 17, the baggage it carried, and the school cultures that shaped Anna’s early relationship with achievement.

[00:03:11] The conventional success checklist – Oxford, PPE, a master’s, luxury marketing at a prestigious multinational: ticking the boxes and then stepping away.

[00:04:31] Three famous examples – Elon Musk, Sheryl Sandberg, and Arianna Huffington as case studies in what conventional success costs and what it prompts people to reconsider.

[00:06:33] UK stats that tell the real story – A third of workers report extreme stress, half say work is hurting their relationships, and work-life balance has finally overtaken salary as the main reason people change jobs.

[00:07:57] A brief history of our relationship with work – From Ancient Greece to the Protestant work ethic, the 9-to-5, and hustle culture: why these aren’t natural laws, they’re design choices.

[00:11:02] Seasons of success – Why success isn’t static, how it shifts with each chapter of life, and why feeling friction at a former finish line is not failure.

[00:13:00] Three responses when “is this it?” surfaces – Pushing through, blowing everything up, or pausing to redesign deliberately. Which one actually works.

[00:14:02] Neil Vora and Riz Ahmed – Two classmates who went on to very different kinds of remarkable lives, and what their paths prompt Anna to reflect on.

Key resources

• Anna’s Substack
• Book a free call with Anna: onestepoutside.com/call

Reframing success

So for today’s episode, I’m going back to my roots of the absolute core of what this podcast is all around. It’s a question I’ve been exploring in recent keynotes. And in fact, I have been since 10 odd years ago. And it’s the question and the topic that I’m exploring in my new weekly Substack. And it is, what does success mean to you?

So to go right back to the beginning – pretty much the beginning – in the year 2000, which sounds both futuristic and a long time ago now, I was voted most likely to succeed by my classmates. And I remembered that many years later, as I’ve started to question what success means, I’ve asked myself, what did they mean? Have I lived up to it? And does it even matter? And so that’s the question we’re asking today.

And it’s maybe a question that we rarely say out loud, but – is this it? Is this the success I’ve been working towards? Is this as good as it gets? Is this it?

So the 17-year-old me, I’m going to be completely honest and vulnerable here, would much have preferred to have been voted most likable or most well-rounded, I think there was another category. Most likely to succeed, as flattering as it sounds, to me was probably associated with some baggage from the all-girls school I’d gone to where I was teased for being – I want to say boffin, was that the word people used? A boffin, which was I guess a geek or a nerd. I studied less and less to try to combat that label. But there was definitely this kind of – is it tall poppy syndrome? You know, you shouldn’t stand out, you shouldn’t be too confident, you shouldn’t be good at what you do – which is a bit absurd as my mum used to say, given that it was a school that was meant to be for gifted children. But the culture in the American school that I went to for my IB in 98, 99, 2000 was very different, because there it was actually admired to do well.

And I did check those boxes. So I actually graduated valedictorian. I went to Oxford, I studied PPE, I did a master’s, and I continued to a very prestigious multinational company where I worked in luxury marketing. So I suppose that is success. If you are one of my classmates from 2000, you can tell me – was that what you meant by success?

In 2013, I took a sabbatical, travelled across South America for three months. I still talk about it a lot, so apologies if you’ve heard that many times. And I had a moment of realisation halfway through where I kind of disconnected from where I’d imagined myself ending up. And I called HR and my boss and I resigned.

And now, 12, 13 years later, I’m working for myself. I have a podcast – long running, top 3% apparently in the world. I’ve published several books. I’m living by the sea with my family. No prestigious job title, no household company name. I’m not an eight-figure founder. I’m not a world-renowned speaker. So again, classmates of 2000, are you still impressed? Are you disappointed? And the question for me – does that even matter?

So when I did this keynote a while ago for a tech conference, I took three examples which I felt were pretty well-known success stories in that world. The first one is Elon Musk. Multi-billionaire, pioneered electric cars, travel to Mars, AI, whatever else he’s doing – but 120-hour work weeks, controversial work culture, and a colourful, let’s say, personal life. So at what cost did he become the richest man on earth? Certainly successful by conventional standards and looked up to among many.

Another – Sheryl Sandberg. And when I said her name at this tech conference, I got some boos, which was interesting. COO at Meta, aka Facebook. I read Lean In back in the day, face of women’s leadership. And interestingly, after her husband’s death, her priorities shifted, she stepped down, and the script changed. So again, at what cost did she have that huge conventional success? And is she less successful now?

Arianna Huffington – one of my, I want to say, almost role models, certainly inspirations. She co-founded the Pulitzer-winning Huffington Post, but she famously collapsed from exhaustion and pivoted to founding Thrive Global. Again, success on the outside and a reckoning on the inside.

The pattern that I see there, with some okay pretty extreme examples, is that success was measured externally – by wealth, prestige, achievement. Almost never measured by what it costs: the stress, the health, the relationships, the presence. And so the question we’re sitting with, for me at least, is success really success if it means neglecting the very things and people that actually matter?

Okay, so let’s bring this down from the billionaire level to the everyday and look at some UK stats. A third of workers report extreme stress. Almost half say work is hurting their relationships. Two thirds are not able to fully be themselves at work – perhaps masking neurodivergence, sexuality, or simply personality. Over half are considering quitting.

Work-life balance, interestingly, has overtaken salary finally as the primary reason for changing jobs. But if you know me at all, balance is not a very useful goal. It’s a pretty misleading and contradictory term because work is a part of life, not separate from it. The zero-sum game framing serves no one. And yet clearly there is some kind of pull towards that flexibility – being more present with family, taking care of ourselves, and living a more nuanced life.

So the question becomes – are you successful if you dread those Sunday evenings? If you envy people who, at least on social media, seem to have more freedom than you do? And do you ask yourself quietly, as I did and I have done, is this it?

Okay, so at this point I like to go back into a brief history of our relationship with work. Just a little bit of context to show that these aren’t natural laws, they’re design choices. Ancient Rome and Greece – leisure was the ideal, work was for slaves. The Protestant work ethic came in some centuries later, where we could pursue virtue through industry. And I really see that being so deeply embedded in our culture and our psyche.

More recently – although it’s still quite recent – the Industrial Revolution brought long factory hours until Henry Ford, around 100 years ago, introduced the 9-to-5. Not out of altruism, of course, but out of efficiency. Then we have the digital age, with flexibility on the one hand but constant connectivity and pressure to be always on on the other. We’ve also had the pandemic, and of course the advent of AI.

Economist John Maynard Keynes predicted in 1930 that we’d be working 15-hour weeks by 2030. So we’ve got four years left to get there, with our biggest challenge being what to do with all our spare time. Instead, what do we have? Hustle culture. 996 – that’s 9am to 9pm, six days a week – celebrated in some cultures, formerly in China, as well as in Silicon Valley.

But there are counter-examples worth naming. Tim Ferriss back in the day – though the four-hour work week is pretty far off where he is and where the rest of us can be. We’ve had the four-day week movement gaining traction following Andrew Barnes’ experiment in New Zealand. Mark Randolph, co-founder of Netflix, shared in one of his most viral LinkedIn posts how he protected Tuesday date nights above everything – prioritising family and his relationship with his wife and children. And Eric Yuan, Zoom founder, delayed starting his company until his children were older and still regrets not having been as present as he’d have liked. So these aren’t naive idealists. They’re people who have questioned the default and designed differently.

I think my most personal thought that I want to bring to this conversation is this idea of seasons. I wrote about it recently on Substack, but it’s something I’ve talked about for years, since one of my friends prompted me to think about the fact that perhaps having a newborn baby was not the moment for world domination. And it connects really to this trend of women opting out of corporate – because success is not static. It changes as your life evolves.

If I look back and overly simplify: work hard, play hard 20s. My digital nomad years of freedom, adventure, beaches, luxury trips. Then settling down, taking the business more seriously, parenting young children. And now – school hours, making time for myself with sea swims, volunteering for school trips, but also building something sustainable that holds my ambitions, which are growing again now the kids are a little older.

Each version makes sense in its moment. None of them is wrong. But what perhaps felt like a finish line at the time started to become a bit more frictionful. And that’s not failure – it’s just a sign that it’s time to grow in a different way. To recalibrate.

The problem is not that you change – that’s totally normal. The problem is when you keep running an old script past its sell-by date because you never stop to ask whether it still fits.

So if you are asking that question – is this it? – whether it’s at the initial step out of corporate or now in your business, is this it? It’s not a crisis. It’s just a signal. It means that you’ve outgrown something, or perhaps your expectations were too high, or were wrong for what actually matters to you. And this is evidence of growth. It’s not failure.

Okay. And there are a few typical responses when the question surfaces. You can push through and ignore it – and that works until it doesn’t. Usually, let’s be honest, ends in burnout or a bigger, messier crisis later. A lot of people in the Deloitte burnout data I’ve looked at are here.

Or you make a dramatic change – quit everything, move to Bali, become a yoga instructor, blow it all up. Sometimes necessary, often perhaps an overcorrection that recreates the same patterns in a new container.

Or the third way – pause, examine the underlying scripts, redesign deliberately rather than reactively. It’s not burning your life to the ground – although sometimes that’s necessary, or even forced, or even desirable – but starting small if you can. Gently questioning whether the inherited scripts still serve you, and exploring how success might look differently in your next chapter.

And this is what this podcast, and all my work, has really always been about.

So coming back to where this began – in 2000, in my yearbook. Neil Vora was my co-nominee for most likely to succeed. And we’ve recently got back in touch. I created a WhatsApp group for my year because it was 25 years. The incredible Neil was one of Time’s world’s most influential rising stars recently. He is a powerful advocate for preventing future pandemics. He is amazing. Really important work.

And then there’s Riz Ahmed, who is an actor and rapper. He has an Oscar, an Emmy, and was named by Time as one of the most influential people in the world back in 2017. He and I studied Middle Eastern politics together at Oxford University. So we did the same degree – but the comparison ends there. And it’s just interesting. I say it’s a bit tongue-in-cheek, but it’s hard not to see examples like that and think, oh wow, could I have made different choices? Have I not fulfilled the potential my classmates and teachers saw? And again, you can beat yourself with that stick, or you can recognise that you’ve made certain choices. It’s never too late, I think – the most successful entrepreneurs start at 35 or 45 either way. And you can take these things as inspirations rather than measures.

I don’t think I’m going to win an Oscar or an Emmy. I don’t think Time is going to put me on any particular influential list. But I shouldn’t be so hard on myself. We can think about how we want to measure things in the future, and also just really celebrate other people’s choices – personal and professional – and recognise them for what they are: their choices for them, not you. They may have come at a cost you weren’t willing to pay.

And I think what matters is living in a way that feels right for you – and feels right for you right now. Not performing success for people who voted on it when you were 17.

I also did a supper club recently where something came up that I hadn’t really voiced in that way before. When I was asked how you know if you’re performing or not, what I came up with was this: would you still do this if nobody was watching? Are you doing something just to impress your classmates, to get on a list, to have XYZ? Or are you intrinsically motivated – you love what you’re doing, it’s meaningful to you, it’s the right thing for you, for your family, for this season?

So I guess the question “is this it?” can be answered in two ways. One – yes, if you’re happy, fulfilled, living in alignment with what matters. Then yes, it is it, but it’s not the end. It’s a continuous journey. Or perhaps not yet, if you’re not. And that’s data in itself.

If you are on Substack, by the way, I’d love for you to join my 25 subscribers there. I’m very intentionally writing just for the joy of writing rather than to build a following. So that’s an exercise in itself of focusing on what matters rather than getting caught up in external metrics. If this conversation is interesting to you – and in particular if you’re not so much on the train of starting a business, but rather drawn to these bigger philosophical, meaning-of-life questions – Substack could be a great thoughtful space for you. You can find me there as Anna Lundberg, Anna S.E. Lundberg.

Again, as ever, if this episode landed for you, if you’ve been quietly asking this question yourself, I’d love to hear from you. If you get my emails, just reply – I’ll always answer. Find me on LinkedIn. And if you’re an independent expert specifically facing these types of questions, something new is coming very soon. Watch this space.

Massive congratulations to Neil and to Riz. And to you, if you are similarly hugely successful in conventional ways – this is not in any way to take away from your incredible achievements. I want to encourage you to reflect on what really matters to you. By all means, pursue those big goals – the Olympic gold, the Times list, the New York Times bestseller list. But do it with your eyes wide open, knowing why you’re doing it, what it means to you, and how things won’t necessarily fall into place magically just because you have the next XYZ thing.

Hope you found this interesting. Next week we have the usual interview episode, and then let’s see what we have for you next month. See you then.

If anything in today’s episode resonated and you’re at the moment where you’re questioning what’s next – whether that’s how you’re working, what you’re building, or whether the life you’ve designed still fits – I have a limited number of free clarity calls each month. You can go to onestepoutside.com/call. Come and have a conversation.