Starting a New Career

So Good They Can’t Ignore You

Cal Newport · 2012

Newport’s argument is the useful one for anybody at the bottom of a new ladder: follow your passion is bad advice, because passion tends to be a result of competence rather than a precursor to it. People come to love work they are good at. Which means the first two years of anything new are supposed to feel unrewarding, and that feeling is not the signal to leave. It is simply what not being good yet feels like.

Writers & Lovers

Lily King · 2020

Casey is thirty-one, waiting tables in Boston, in serious debt, grieving her mother and six years into a novel nobody has asked for. King writes the humiliations exactly: the friends who have quietly given up and got proper jobs, the questions at parties, the landlord. It is here because it is the only novel I know that gets the specific combination of being too old for this and doing it anyway.

Shop Class as Soulcraft

Matthew Crawford · 2009

Crawford had a doctorate in political philosophy and a think-tank job he could not stand, so he opened a motorcycle repair shop. The book is his case for manual work as thinking rather than the absence of it, and it is very good on the satisfaction of a job where the thing either runs at the end or does not. Essential reading if the new career is a step down in status and you are braced for what people will say.

The Squiggly Career

Helen Tupper & Sarah Ellis · 2020

The practical British one. Tupper and Ellis start from the fact that the ladder is gone and careers now move sideways, backwards and diagonally, and then give you actual exercises: working out your transferable strengths, building a network from a standing start, describing a jump so it sounds deliberate rather than desperate. Full of worksheets, which is either the appeal or the drawback depending on your temperament.

The Bookshop

Penelope Fitzgerald · 1978

Florence Green, a widow of modest means, decides to open a bookshop in a small Suffolk town in 1959, and the town closes ranks against her with tremendous politeness. Fitzgerald is unsentimental to the point of bracing, and this is not a book where courage is rewarded. Read it as the honest counterweight to everything else here: sometimes the venture is right and the place is wrong, and that is worth knowing in advance.

Kitchen Confidential

Anthony Bourdain · 2000

Bourdain came up through New York kitchens the hard way and this is his account of what the bottom actually looks like: the hours, the burns, the hierarchy, the particular pleasure of being the newest and worst person in a room full of people who are extremely good. Profane and enormously entertaining, and underneath it a serious argument about earning a place rather than being given one.

Remarkably Bright Creatures

Shelby Van Pelt · 2022

Tova is seventy, widowed, and cleans an aquarium at night, which she took on largely to have somewhere to be. What she finds is a job she is good at, a giant Pacific octopus with opinions, and a reason to get up. Charming without being soft, and the best argument here that starting something new at an age when nobody expects it is neither ridiculous nor too late.