Everyone fails now and then—it’s just part of life. But what about failing over and over? Is that ever a good thing? It turns out, it can be, if you’re in the right situation.

Listening to a podcast after a tennis tournament, I hoped to learn why failing can actually be beneficial. The podcast featured Astro Teller, head of Google’s X division, where big, bold ideas are encouraged, and failure is celebrated—literally, with bonuses. At Google X, the aim is to think big, because even if you fail, you’re pushing boundaries, and there’s no real personal financial risk—it’s all Google’s money.

But what about the rest of us, who don’t have the safety net of a multibillion-dollar company? There are times when taking big risks and potentially failing repeatedly might still make sense:

1. When You’re Using Other People’s Money: Like politicians during a shutdown or companies during a risky venture, using other people’s money can buffer you from the consequences of failure.

2. If You’re Born into Wealth: For someone like Bill Gates, who came from a family of means, the risk of dropping out of Harvard to start Microsoft was mitigated by his family’s wealth and connections. He knew he had a safety net.

3. When It’s Not Your Own Money on the Line: Consider venture capitalists and startup founders using investors’ funds to try bold ideas. They can afford to take risks because personal loss is minimal.

4. When You’re Older and Have Experience: Age and experience can bring a certain respect and acceptance for repeated attempts and failures. Plus, as you get older, you might feel you have less to lose by trying something new.

5. If You Have a Supportive Partner: Having a partner with a steady income can give you the buffer to try out new ventures. When I left my job to focus on Financial Samurai, knowing my wife was still working and we were covered financially made it easier.

Repeated failures in these scenarios can be stepping stones to massive successes or invaluable learning experiences. While not everyone works in an environment where failure is rewarded, recognizing when and where repeated attempts are acceptable can lead to significant personal and professional growth.

So, should you fear failure? Not necessarily. Sometimes, those repeated attempts, even if they end in failure, are exactly what you need to find your path to success.