A photo illustration of a woman's hand holding a credit card.
  • Anne Lester is the former head of retirement solutions for JP Morgan Asset Management.
  • Lester managed billions of other people's money but often maxed out her own credit cards in her 20s.
  • She said she had to make more "friction" between herself and spending money to curb her bad habits. 

I was 26 with my life crammed into three suitcases. I had just finished an internship in Tokyo and was flying to Italy to move in with my boyfriend. I was in the final round for a great job and was excited to start my new life. I walked up to the counter and handed my one-way ticket to the agent. The man frowned at my comically large bags and heaved them onto the scale.

"Sumimasen," he said in Japanese, "the allowance is one normal-sized bag. You need to pay a fee for oversized luggage."

"How much?" I asked.