Try several jobs in your 20s, then commit to one
Writer Jack Raines says keeping every door open gets less valuable each year, so sampling work beats collecting credentials.
The Prof G Pod with Scott Galloway · Are You Saving Too Much Money? | ConversationsJack Raines, the 29-year-old writer of the Young Money newsletter, was speaking with entrepreneur Scott Galloway, who asked him to say more about an idea Raines has written about, that keeping career options open loses value over time and that avoiding experimentation can lead to a midlife crisis for people who committed to the wrong path too early.
Raines put the alternative this way: “you can take several shots on goal in basically every facet of your life when you’re young.”
In his account, optionality is most useful in the 20s because switching is easier. A smart and driven young person can get a starter job and get up to speed in a year or two, and single life leaves more room to move. As earnings rise and debt and obligations accumulate, that flexibility narrows.
He described two ways people waste it. One is collecting credentials without deciding what work they want, the banking to private equity to business school track that can drift into consulting or a hedge fund. The other is deciding too fast, like starting medical school at 22 without considering what doctors do every day, then reaching the early 30s with debt and a decade spent on a path that more thought at 21 might have avoided.
The better use, Raines says, is to “try a job for two years,” see what fits, and pivot if the outlook is poor or the work is a bad match. A few tries build, in his phrase, “a Swiss Army knife or generalist” set of abilities. From there, the question becomes how to apply those abilities to “the one thing that can compound.”
He allows one clear exception. A 24-year-old who finds work to be good at and enjoy should commit. Otherwise, Raines says, it is way better to have “tried a few things and found something” to commit to at 27 than to “commit to the wrong thing at 23.”
Questions people ask
How do you try different jobs without looking unreliable?
Look for roles with skills that carry over, like writing, selling, analyzing numbers, or managing people, rather than narrow credentials. Short stints read better when each move has a clear reason, such as seeking more responsibility, a different industry, or work you found you do well.
How do you know when you have found the thing worth committing to?
Raines points to fit and performance: work you are good at, enjoy, and can see improving over time. Outside his advice, career counselors often add outside evidence, such as strong reviews, growing pay, and mentors willing to invest in you.
Does this work if you want a career that requires years of training?
It is harder in licensed fields like medicine or law, where training is long and costly to abandon. Even there, shadowing, internships, and conversations with working doctors or lawyers can test daily fit before borrowing heavily for school.