Book review: The Pinstriped Prison - burnout and feeling lost
- Phil McAuliffe
- Jul 7
- 7 min read
Updated: Jul 7
What if your dream job turned into a golden cage? Lisa Pryor's 'The Pinstriped Prison' speaks about the hidden cost of success and explores how high achievers can end up stuck in careers that lead to disconnection and burnout.
Hello friend
I want to share a book with you that changed my life.
It’s called The Pinstriped Prison by Lisa Pryor. Originally published in 2008, a friend gave me a copy in 2017 — and I’ve been thinking about it ever since.
If you’re a fellow overachiever, this book might feel uncomfortably familiar. You may see your own story reflected in its pages: high performance, prestige, and a creeping sense of feeling lost and disconnected.
‘The Pinstriped Prison’ by Lisa Pryor
The book is about the trap overachievers can find themselves in working in corporate jobs that they hate.
Pryor details the pathway into the trap, which is characterised by making decisions based on what others think that the overachievers should do, rather than explore what they’re interested in.
The overachievers did well at school. They got good results in their final year and – possibly ignoring their interest in other fields – they acted on advice to not ‘waste the high marks’ and applied to university courses like medicine, law or commerce at prestigious universities.
Their decisions to do so were partly based on the social cachet that such courses and universities have, as well as the possibility of landing a high-paying and/or glamorous job after university.
Once at university, the overachieving student is surrounded by more overachieving students who want the same career. Competition intensifies to achieve the best results and get the best attention. Indeed, Pryor writes of how some organisations are woven into the fabric of some degrees, with law firms, accounting firms, banks and management consultancies sponsoring student clubs and subsidising.
These organisations use every opportunity to make working with them a joy and the way to embark on a life of wonder, awe and impact.
The overachievers want in. They set their sights on landing one of these jobs and do what they need to do.
The trap snaps shut
Once the job has been landed at a prestigious law firm, accounting firm or management consultancy, Pryor writes of the heady first year, in which everything is shiny, new and wonderful. The rarefied air smells sweet and the view from the windows from the upper floors of shiny office towers is amazing.
The life of a student in which instant noodles are a staple becomes meals at nice restaurants. Money flows into their bank accounts.
Boo hoo, right? Poor little rich kids. This sounds like such an ordeal.
Pryor writes that the overachiever has fallen into a trap laid by snappy marketing, FOMO and the overachiever themselves.
While the money is good, the work is boring, and the days are very long. Time off is rare.
Indeed, a memorable quote from an investment banker in London said to a group of prospective overachieving recruits is on the back cover of the book:
‘In your investment banking career, you should only have two holidays. One for your first wedding and one for your first heart attack.’
In work environments like this, relationships and connections outside of the workplace suffer. Frames of reference can narrow to the point that the world becomes work and work becomes the world.
With increasing salaries come increased costs: housing, cars, holidays and clothes. Eventually these costs can then extend to covering school fees at expensive private schools.
A lifestyle based on what success should look like has been created and must be maintained. The only way to maintain it is to continue to work hard, even if the overachiever and those they love are miserable.
Leaving the job or the industry to find oneself means putting everything and everyone at risk. It’s easier to grit one’s teeth and knuckle down, right?
While Pryor does not say it in her book, I’ll say it here:
The road to loneliness and social disconnection is paved by the words, thoughts and actions that keep us in places and spaces where we feel trapped and respond by gritting teeth and doubling down.
A look beyond the spin
Pryor methodically unpicks the spin that characterise the promotional materials that organisations use to entice overachievers to work with them. Words and concepts like ‘dynamic’, ‘fast-paced’, ‘exciting opportunities’, ‘work/life balance’, ‘impact’, ‘flexible options’, ‘diverse workplace’ and ‘client focused’ are scrutinised.
Behind the spin, she shows that the reality is that there is a lot of often boring work and unrelenting expectations to deliver that work within unrealistic deadlines. When this is the workplace culture, the workplace always wins (ie: the work is done to a high standard within impossibly tight deadlines) and the worker loses (ie: they’re the one who’s doing the impossible). Pryor critically analyses workplace diversity (which seems to be tokenistic) and the reality of being a woman in misogynistic workplaces and the impact that having children has on a career.
If you're feeling lost and burned out, you need to read it
While written in the days before burnout was widely spoken about, ‘The Pinstriped Prison’ is all about burnout and feeling stuck, lost and frustrated in our jobs. It also speaks to the power of belonging and what we will do to feel that we belong (even if it’s contrary to our own interests).
If a human places their worth and worthiness for love and belonging on factors outside of themselves, then there’s a risk – no, a danger – that once they enter these highly-prized and prestigious workplaces, they will fall into the trap of being gaslit that they’re never doing enough or being enough. They are hamsters running in the wheel to constantly prove that they are worthy.
Pryor describes how high achievers can have developed a thirst for external validation through school, university and their careers that can never be quenched. They feel that they thrive on deadlines and pressure. They see these as opportunities to perform and receive more praise. The create and then thrive on competition – seeking promotions, accolades and opportunities to showcase awesomeness.
The employers love and exploit it. The overachiever becomes lost.
Whenever we chase external validation, what we receive is never enough. And then when we achieve ‘success’, it feels hollow or anti-climactic. The thrill of a promotion lasts moments. There’s never enough money because someone else has more. The drive to perform to please someone else is relentless.
The result is that we become disconnected with our authentic self, those most important to us and our communities because we’re so consumed with what’s next and getting the next hit of external validation.
There’s a rich vein of content right here. We’ll be coming back to this topic soon.
How the book supported me
Though I worked in the Australian Public Service (including in diplomacy) - not the corporate sector – I saw the same dynamics the Pryor describes at play. I experienced the same pressure to prove myself, the same hollowing-out of identity, the same gnawing sense that I had become disconnected from my true self in the hope that I would fit in.
Pryor’s book gave language to what I was feeling: the numbness, the exhaustion, the quiet despair. It helped me realise that I wasn’t broken, but that I was simply caught in a system that rewarded performance over authenticity.
Reading it was the beginning of coming home to myself. I needed to know who I was behind the job title.
I highly recommend that you read this book if you work in the professional services and you feel that you’re wearing golden handcuffs and that you’ve sleepwalked your way into a rut.
Where to find it
Given its age, you may not be able to find ‘The Pinstriped Prison’ in your local book retailer, especially outside Australia.
However, you can buy the book through your preferred online book seller.
Further resources
You may find these episodes of the HUMANS:CONNECTING podcast interesting if the concepts raised in this review spoke to you:
A quick ask
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That’s it for this review
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Until next time, be awesomely you.
~ Phil
Important:
All views expressed above are the author’s and are intended to inform, support, challenge and inspire you to consider the issue of loneliness and increase awareness of the need for authentic connection with your self, with those most important to you and your communities as an antidote to loneliness. Unless otherwise declared, the author is not a licensed mental health professional and these words are not intended to be crisis support. If you’re in crisis, this page has some links for immediate support for where you may be in the world.
If you’re in crisis, please don’t wait. Get support now.
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