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HOW-To: Go From Penny Pincher to Breadwinner

As a creative, there’s a good chance you hate talking about—or, well, even thinking about—anything to do with money or investing.

The latter is always a particularly daunting subject, and if we’re being honest, as creatives, we’d all rather just be creating. But it’s a conversation we all need to have—so at HOW Design Live 2023, longtime programming partner Ilise Benun and Fidelity Head of Content Jennifer Barrett had it.

As we work behind the scenes on programming HOW Design Live 2024, here are four big takeaways from their inspiring and empowering session “Good With Money,” designed to help you be just that.

Overcoming Investment Paralysis

Right out of the gate, Barrett made a critical point: There’s no shame in feeling a lack of confidence around your finances, especially since so many of us were never taught about subjects like investing growing up.

Many of us thus suffer from investment paralysis—we think we’re not good enough at math; we don’t know anything about the market or how it works; we tell ourselves we’ll invest when we really start making money; and on and on. We give ourselves a million excuses for not investing. So look inward and deconstruct yours. If, say, you’re not investing because you’re not “good with money,” Barrett advises asking yourself a key question: What would it take for you to feel like you are good with money? Write out a list, and soon enough, you have a plan that you can research and put into action. 

For those who say they’ll eventually start investing when they start making more money, “a lot of people believe you need to make money in order to invest,” Barrett said, “but really, you need to invest in order to make money. It’s backwards.”

Analyze your excuses, and you’ll soon find yourself poking holes in them and taking proactive steps toward a new financial future.

Investing 101

Barrett and Benun challenged another misconception we tend to have about investing at large: “It’s a pretty common belief that we need to save for a rainy day and save for retirement,” Barrett said. “And we forget about all those decades in between. Investing is more than just investing for your retirement—it’s really investing for all the things you want in those decades before.”

Reframe your thinking around investing. When Barrett did, she decided to put a pool of money into the market. She wasn’t fully confident about what she was doing—but she had to start somewhere.

Timing Your Moves

Barrett began with some initial research and started investing money in three different exchange traded funds that were essentially index funds. “You end up getting coverage across most of the market,” she said. 

There was only one problem: This was the beginning of the Great Recession in the late 2000s. Terrified, she called her mom, who is a successful self-taught investor. Her mother showed her a chart of the S&P 500 from its inception—with its various regular ups and downs over time—and imparted a critical lesson: You don’t want to panic sell when it’s in a dip. She didn’t, and today her investment has tripled. 

“[My mom] said, number one, it’s time in the market—not timing the market.”

After starting with index funds, Barrett then began investing in individual stocks.

“One of the most important things you can do is just get into the game, and then learn as you grow,” she said.

Avoiding the Gender Cliche and Forging the Future

Barrett said that when you look at surveys of parents, they still are more likely to talk to their daughters about how to spend smartly—but when they’re talking to their sons, the subjects are about how to build credit, how to invest, how to generate wealth. “And those are very different messages.” She added that in the media, articles for women tend to focus on penny-pinching, saving for a splurge handbag, and so on. Barrett says it’s time for a shift—and that reframing your mindset around investments and finances can be cathartic.

“Think about what it is that you want. And what you need to do to get there—growing your income, growing your wealth, whatever it is that you need to do to afford the life that you want. It’s really expansive in the way you think about your financial capabilities and the possibilities for your life.”