'I Can't Shake the Feeling That I'm Failing'
An essay and video conversation on failing well and succeeding poorly, in collaboration with writer David Roberts
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Success looks different depending on where you start. In this collaboration, I’m exchanging essays on success with writer , who comes from a background of generational wealth and whose writing explores with candour how privilege, obligation, and personal ambition intersect. We approach success from very different life experiences. Despite our differences there’s a similarity to the questions David and I are trying to answer about advantages, disadvantages, social mobility, and how money influences our notions of success. My essay is below and a link to David’s essay follows.
I’ve been working lately on a column considering the changing landscape of media and the fact that so many media friends and colleagues are now setting up camp here on Substack. What it means for culture has been on my mind as the slide of legacy media has rapidly escalated over the last two years and comes to represent something bigger. A collective unravelling, and perhaps a remaking. If we’re lucky.
My desire to write about it emerged from the same sense of bafflement that led me to start Peak Notions a few years ago – the sense of something large and inscrutable, moving too rapidly toward us to adequately process the totality of what we are looking at. Too big and suddenly too close to make out anything but flashes and inklings. As someone who lives online as much as in material reality, and who recognises that the two are so entwined, for both better and worse, that they cannot be understood in isolation from one another, I wanted to make a place devoted to finding sense in it all.
When I think about success these days, this is where my mind goes right away as someone who has worked in media for over a decade and is watching conceptions of success within my own industry be unmade at an unprecedented rate. It’s not clear to me what constitutes success anymore but it feels like something I should be clearer on, given how much time I spend thinking about it. Especially, when you begin your life in one sphere but find yourself later living in another.
Aged four. If you’re wondering why everything is brown, it’s because it was Limerick in the nineties (a bad era for décor). Also every adult smoked. Indoors.
Nobody around me had serious money when I was a child. Anyone I considered rich was not really, I would realise later, when I somehow found myself ill equipped for the environment of an elite university and then spending time around London media people who did come from wealthy backgrounds. Our neighbours were not wealthy, it turned out. They just had a big, damp-smelling dog and an out-of-tune piano, which I considered a very monied object to own.
As a child, I didn’t know anyone who lived an intellectual life or had much time to think about ideas. Everything was too imminent. There wasn’t time for abstraction when my mother was weeping on the stairs over an electricity bill she couldn’t pay or my father, drunk again, was trying to shoulder the front door in while we waited on the police to cajole him into leaving. Or stuff him into the back of a squad car as the neighbours watched through twitching curtains.
I thought I would like to be a writer, but hadn’t even a vague sense of how one might do that. My mother encouraged me despite everything. It’s because of her that I have consistently ended up in rooms that people like me are not usually allowed into. This has felt like success. Triumphant. Like slipping a knife between the ribs of fate. Yet, the lack of belonging I feel in these rooms feels like failure.
2019, standing on Coco Chanel’s famous staircase at 31 rue Cambon in Paris, before a private tour of her apartment that I will remember forever. I was a successful beauty editor at this time. This would be one of those rooms I felt like a fraud in…
I left university after finishing my doctorate in philosophy (which I wouldn’t recommend to any poor kids who would like to have money when they grow up!) to work in an industry that has been dying since long before I entered it. I wrote for newspapers and magazines in Dublin and then in London and found myself in an industry whose conception of success – perhaps like the wider conception under which my generation has laboured since stumbling into a post-crash adulthood – was outmoded from the very beginning.
Millennials have a distinctly uncomfortable relationship with success, or at least the conception of it inherited from our parents. It’s a definition that entails career and financial stability, home ownership and parenthood, and which demands a life rooted in community and family. It is an impossible definition for most of us to relate to, let alone realise, in this fragmented era. The result is a generation of people who both look and feel like failures according to the imposed standard, and who are collectively cynical in the face of this ill-fitting conception of a good life (even as we castigate ourselves for falling short of achieving it). We are a generation obsessed with our own lost potential. Attempting to remake the definition of success not merely into something that is achievable under the restrictions imposed upon us, but into something we can peaceably live with. Something that won’t keep us awake at night.
Nowhere is this more obvious than among people who are emerging, wounded and self-recriminating, from the rubble of legacy media. Many of them are turning up here on Substack, nursing career-long wounds and the rhetorical questions of parents who gave them every opportunity and now can’t quite understand why their job hopping forty-year-old son or daughter lives in a house share or can’t seem to settle down. It’s the world we live in. I often wonder how, along with my difficult upbringing and my accursed millennial status, my time in academia and my chosen line of work may have impacted – or perhaps warped – my conception of success.
Graduation day, when I received my doctorate in the philosophy of psychology from Trinity College Dublin. I did not feel successful here. I felt triumphant, exonerated, weirdly angry, and pretty tired. It took a lot to get to this moment.
Because I don’t feel successful. I can’t shake the feeling that I’m failing. Like that large, inscrutable, too-fast-too-close change occurring in both media and culture, I can never quite land on a satisfactory position. It is a perpetual job of work to manage this murmur of mediocrity within yourself. In exchanging essays on success with someone who shared this feeling but had a very different route to arriving at it, I’ve gained some useful clarity on my own situation. That I too carried a legacy – but one to cast off rather than protect and augment. One to disprove, destroy and divest from. Very much not to live up to. It helped to be reminded that I felt the weight of my mother’s ambition for me, and still do, nine years after her death. The unpayable debt to her that I will always carry and am grateful for. The rooms I can’t relax in. It is a comfort to remember that this discomfort is merely a link to where I come from. It is the tether of memory. It keeps me from floating away.
Being raised in a culture of conformity and restriction, and emerging into a working environment that generated a huge incentive to signal success while the industry falls apart around you, I eventually came to associate success with autonomy. In a world which limits us, tells us who we are and demands the impossible, I decided that to be successful is to be free. And yet outsider status (sometimes in my case, elective) can confer a feeling of failure and exclusion. Of being parallel to what happens and not a part of it. As can being a member of a generation of people who work hard and aim high (as they were taught to) but always seem to feel that they’ve just missed it and the thing has already happened without them. I continue working to find a way to feel that I’ve done well with what I was given. To forgive myself for what I am, and what I’m not.
And so off to work we all go on that internal locus of evaluation the stoics taught us to nurture. To find value in the self rather than looking out toward a world whose priorities are blatantly radically misaligned. And yet I’m conscious of the likely impossibility of achieving this. The Sisyphean battle of feeling valuable in a culture which has a limited conception of success and an unrealistic standard of it. I think about those parts of us that only become real when other people can see them too. I suppose the tragedy and optimism of a Sisyphean endeavour is that it begins again the next day. We can keep trying.
Read what David Roberts has to say in this link to his essay on success
And take a look at his Substack newsletter, Sparks from Culture by David Roberts, for frank and accessible essays on the morality of wealth, class and capitalism. David is a writer who routinely (and thrillingly) says the quiet part out loud.
We recorded this 23 minute video to discuss our relationships with success.
Very interesting. I have often wondered too about what constitutes success and assumed it highly subjective. It's probably not as subjective as I think it is, though.
I think I have quite a low bar for what constitutes success but also quite a clear conception of what I think it is. I am certainly often accused of being an underachiever and I am well aware that I do not like being in charge of things or having too high a public profile. I’ve run two organisations & it was just very stressful and sucked the joy out of life. I’ve had a large social media following & it consumed my life and I deactivated my account.
I find a lot of satisfaction in keeping my life small and simple & this has frustrated some of my friends and family who think I could do more with it - be more prominent, make more money. Some have accused me of being afraid of success and attributed this to low self-confidence, but I’m not convinced by that. I just don’t think not being rich and famous is something I’d regret on my deathbed. I certainly wouldn’t regret having not spent more of my life working.
I once had a particularly excruciating interview that I didn’t realise was one. I had assumed a wealthy philanthropist wanted to have lunch with me because he was having a CSJ problem he wanted my advice on but actually he wanted to know if I wanted to do anything big with my life that he would consider worth funding. He fired questions at me about my goals, aims and ambitions until, in the end, I got very overwhelmed and shouted (yes, literally), “I just want to be left alone to write things!”
I think that moment really distilled for me what my understanding of success is. I want to be left alone to write things. And earn just enough money from writing things to do that. Ideally, in a tiny cottage by the sea. With Labradors. I could earn enough money to do that by writing for other people, but then they’d edit me and also give me topics to write about and I don’t want either of those things.
And then there’s the care work thing. For 17 years, I was a care worker helping elderly and disabled people live fulfilling lives with dignity and I loved that job. I very much enjoy meeting people in this context of supporting them to achieve what they want to achieve. It’s incredibly rewarding. I think that the consulting I do for people in danger of cancellation fulfils that need in a different context. It’s ideal for me because I am working with others but also have autonomy and an independent role at the same time.
I think the closest I get to the most common understanding of success in my field is that I want the thinkers whom I most respect to know who I am and respect me. I have achieved this. There are four people who I consider to be my most respected thinkers and the most influential on my own thinking and they all now know who I am and respect my work. This makes me very happy.
Here is the Helen recipe for what I would consider a successful life:
1) Being able to write about the things I want to write about and earn enough money from this to cover my living expenses.
2) Spending part of my time working with others but in an independent consulting/supporting capacity, not a leading one.
3) Not working too much! Having time to explore various hobbies. At the moment I am learning Old Norse and to read and write in runes.
4) Having my thinking & principles respected by the people whose thinking & principles I respect.
5) Having a small cosy home by the sea and near forests and rivers, and a small cosy family to share it with me that includes a dog.
Both of you have more or less said that comparing yourselves (in whatever metric) to others is a mistake. It is in fact a recipe for misery. There will always be people who outflank you in most if not all categories. That’s the way it is. So what? In this respect, you can’t change the way it is. Therefore, for happiness, you must change your perspective.
In a highly stratified society like the UK, people with imposter syndrome will feel awkward. People who don’t give a damn will be accepted for themselves on their own terms.
I am Irish. I came from a middle-class family in so far as that had any meaning in 1950 in Ireland when I was born. I qualified as a veterinary surgeon from Trinity College Dublin in 1974 and migrated to the greater opportunities of London. I practiced there for 45 years and then I sold up and moved to Somerset where I now live. It never crossed my mind to value myself by comparison with anyone other than myself yesterday.
I am lucky enough to have a very close and supportive family and one of the things that gives me pleasure is that very many of my veterinary staff are still happy to meet me for dinner when I go up to London, which means I did something right by them.
My life has not been all roses and success. I have been robbed, cheated on, disappointed and occasionally very broke, but you know, if life was one success after another, there would be no fun at all in that.