A Hollywood producer who spent over a year following around early retirees has his own simple question to decide what’s worth his money — and what isn’t

Travis Shakespeare has an easy way to determine whether something is worth your money. Frederick M. Brown/Getty Images
  • Money is easy to spend, but how do you determine what’s valuable and what’s worth – or not worth – spending money on?
  • Emmy nominee Travis Shakespeare has a morbid answer – ask yourself how happy the purchase would make you if you were to die tomorrow.
  • He said thinking about your own death is the ultimate litmus test when considering whether something is worth your money.

Whether you’re a college student on a budget, starting a new career in a new city, or a working parent with people depending on you, it can be difficult to decide where to spend your money, especially when you feel you’re in need of a lot of things.

How do you determine what’s valuable and what’s worth – or not worth – spending on?

That’s exactly what Brandon of the Mad Fientist, who retired early at 34 and has found the concept of value to be harder post-early retirement, asked Emmy-nominated Hollywood producer Travis Shakespeare in a recent podcast.

Shakespeare spent a year directing the documentary “Playing with FIRE,” which follows a 30-something couple navigating the financial independence and early retirement, or FIRE, community and explores the trend through conversations with a dozen-plus early retirees.

Shakespeare, who lets value drive his own financial life, boiled down the answer in one question: “If I were going to die tomorrow, where will this land on my value scale?”

Shakespeare asks himself this regularly when he looks at something he may want or want to do. “I think the ultimate litmus test is to always think about your own death, which is a very stoic practice even though I wouldn’t have necessarily called myself stoic,” he said.

When he was younger, Shakespeare discovered a luxury safari website in Tanzania and promised himself he’d go someday. Fast forward to his 50th birthday, and he celebrated the milestone by fulfilling that wish, he said on the podcast. Despite the expense and opportunity cost – the idea that he could be investing the money instead – he asked himself, “If I’m dead tomorrow, which do I want?”

The answer was easy. “I was like, ‘There’s no way I want to walk off this planet without spending three weeks on the Savannah in Tanzania’ because that’s an incredible experience for a human being to be able to encounter,” he said, adding that it was 100% worth it.

He said it can sometimes be hard to stick to his concept of value when surrounded by the external pressures of the LA showbiz lifestyle. Take, for example, his affinity for clothes, which he doesn’t buy very often. Shakespeare agonizes over the difference between a $US75 pair of shoes and a $US400 pair of shoes because the quality of the products is drastically different.

But when it comes down to it, experiences outweigh material items. Shakespeare rented a tuxedo for the Emmy’s because he doesn’t own one.

“I’m too cheap to do it because I’m like, ‘No way! I can use that $US2,000 to go visit you [Brandon] in Scotland,” he said. “So I’m going to rent one for $US110 off the Internet instead. Nobody is going to notice. I mean they might, but I don’t care.”