Financial Lessons for Generation Y

Investment adviser’s new book offers tips on overcoming financial and emotional obstacles.

Young woman looking very serious
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Intergenerational tensions are nothing new, but delayed retirement for many workers and financial pressures on recent college graduates have raised the stakes for some in recent years.

In his latest book, "No One Ever Told Us That: Money and Life Letters to My Grandchildren," Boston-based investment adviser John D. Spooner offers unconventional wisdom for his grandkids and other members of Generation Y as they cope with heavy student loans, a tough job market and other financial and emotional stressors.

U.S. News recently asked Spooner for advice on standing out from the crowd, trading stocks and prioritizing investments. Excerpts:

Generation Y has received a lot of bad press about feeling entitled to things or unwilling to pay their dues. Do you think those stereotypes hold any truth?

Yes, I do, for a few reasons. Recently I was told by a boss that he asked a couple of the young people in the office if they could stay Friday night until 6:00 and finish a report; they said, "but I have plans for the weekend." This would be unheard of in previous generations. And parents complain to me about, "I have three children and two out of three I'm sending checks to every month."

[Read How Gen Y Is Overcoming the Economic Blues]

The younger generation has to figure out how to separate themselves from the crowd and get noticed in an increasingly anonymous world. When I'm looking at resumes, I like to see what jumps off the page; what makes you different from all of your cohorts?

How can Millennials stand out and show perspective employers they're the exception to those negative stereotypes?

Do something that's unexpected to get yourself on other people's radar. I got a young man a job with a big advertising agency in Boston, and the next week, on Monday morning, there was a little box on my desk. I opened it up and it was [a package of] small rectangular business cards. On one side was a picture of me in color that he had taken from The Boston Globe, and on the rear of the card was my name, my office phone number and a phrase from the book, which was "dare to be different." I said, 'If this young man went the extra mile and was creative, I will never forget this kid. He can come and call on me anytime. I'm going to try and help him or make calls for him.'

Also write a [thank-you] note [after an interview] because people don't write personal notes anymore, [so] they tend to keep them. It is much more special than a text or an email because [they] have something that's solid in [their] hands.

Generations sometimes disagree about who had it tougher: those who lived through the Great Depression, people coming of age now with high unemployment and high student debt, or the generation in between. Do you have any thoughts on that?

I told my kids I used to have to walk to school 5 miles each way uphill, and they would laugh because it was so exaggerated and not true. But I do think that this generation will be the first in American history to not exceed their parents. We're surrounded by noise 24/7 from social networks and the media that never stops. It influences people emotionally.

[Read: 5 Lessons From the Last Stock Crash.]

So, what can turn this around? Sooner or later, tough times turn to good times instead of fear and anxiety. We're a long way from that, but I think there will be a catalyst—whether it's a person or events—that gives people more hope. It isn't just four or five years of tough stuff. We've had maybe 13 years where things have been hard, so there's almost a generation of people who think nothing can be good ever again, which it will be. After a while, you can't just compare 'I had a tougher time than you do' or 'I'm having it tougher than you do.' Sooner or later, people are going to be forced to be more industrious.

What is the biggest financial lesson you hope readers take from your book?

I was taught by a mentor, who had bought my first brokerage firm, that it's possible to get rich in the stock market if you concentrate [and] don't diversify. He taught me about concentration instead of spreading your money out all over different asset classes, which is conventional wisdom. Pick one or two companies that you really believe in for the future—something that provides products that everybody is going to use forever. Concentrate on one or two companies that eventually you build up a big holding over the years. If I have any net worth it's because of those concentration periods. It takes a little intestinal fortitude to do it because bad markets come along a lot over the course of one's life, but if you believe in one or two companies, keep them.