Let me tell you a story about a CF…

Lehman Brothers hired me in 2001, when I was 27 years old and living in California. So, I packed up my stuff, moved to New York City, and started a new life.

I had been a Coast Guard officer, a blue-collar guy, making around $45,000 a year. Now I was going to be a Wall Street guy. Lehman hired 300 associates, and I was one the 80 in sales and trading. It was awesome.

One night, a good friend put together a dinner with some other Wall Street guys at a Brazilian steak house. It was one of the fancy restaurants in town, and I didn’t know what to expect.

After a ton of food, they brought the bill which we were splitting 12 ways (even though the other guys ordered wine and desserts). My portion came to $80. And I thought, “How am I going to afford to live in New York?”

I had never paid that much for dinner in my life. Up until that point, I might eat out once a week at a cheap Chinese spot, where dinner for two cost $15.

Everyone else thought $80 was no big deal. And it was painful for me. I wasn’t a jerk about it, but the meal really stressed me out, and I’m sure it showed. I was tight with a buck, and I probably wasn’t much fun to be around at that dinner. I was too worried about how much it would cost.

You know what that means? I was a CF. (Don’t ask me what CF stands for—you can figure it out.)

The irony here is that I probably had the most money out of everyone at the table. Partly because I saved like crazy. And partly because I’d bought a condo when I lived in California, and it had doubled in value. So, there I was, in my late 20s, with a net worth around $200,000, and a big new job on Wall Street. But I could not enjoy spending $80 on dinner with friends.

Make the Pie Bigger

Don’t get me wrong—saving money and living below your means is good, especially early in life. You can tolerate cheap stuff in your 20s and 30s. But you also want to focus on ways to make more money. And that might mean overhauling your life—new job, new clothes, new everything—like I did when I started at Lehman.

And once you’ve earned some money and built up your wealth, you had better enjoy it. Maybe not when you’re 35, or even 45. But by the time you are 55, you should enjoy your money.

One of the reasons I launched my new podcast BE SMART is because I’d read all the personal finance books, I’d listened to all the guidance out there, and I’d concluded that it was… not smart.

It’s just a bunch of people telling you to give up every little luxury. It’s people saying that the way to wealth is to downsize your life, give up coffee, and leave bad tips. The whole industry is built on teaching you to be a CF.

None of these “gurus” talk about getting a raise, or switching careers, or starting your own business. They don’t teach you how the markets work. And they don’t show you the smartest ways to invest the money you save. It’s just tips ‘n tricks for slicing the pie into smaller and smaller pieces.

BE SMART is a podcast about making the pie bigger. It’s about living a life that is both abundant and free of financial stress. And it’s about getting the answers you want about your money.

That’s why I’m hosting a LIVE Q&A for listeners on Monday, November 15 at 1pm ET. And I’m reserving a spot for readers of The Jared Dillian Letter, too. So, please check your inbox for a link to this LIVE video event on the morning of November 15. You can also shoot me your questions ahead of the event by clicking here.

Jared Dillian