If the COVID-19 pandemic has made you more anxious about money, you’re not alone. Over 75% of individuals are significantly more nervous about their personal finances and financial future, according to a Thrive Global original survey of 5,000 Americans. In these uncertain times, protecting ourselves from the harmful physical and emotional effects of money stress is more critical than ever — and hearing the financial stories of others can help. In this series, Thrive is asking personal finance experts, business owners, and other savvy professionals to reveal the hard-earned money wisdom they wish they could go back and give to their younger selves. 

Red Antler, the Brooklyn-based creative agency Emily Heyward co-founded, has been called “the nation’s most sought-after and respected brand-builder.” Before launching the agency that crafted the brand identities of V.C.-backed startups like Casper, Allbirds, and Boxed, Heyward began her career navigating the corporate ladder at advertising agencies.

She shares plenty of career insights in her new book, Obsessed: Building a Brand People Love From Day One — but when it comes to money wisdom, she admits she learned some lessons (about saving, spending, and recognizing her worth) the hard way. 

Here, Heyward shares with Thrive Global the money advice she’d give to her younger self.

On “lifestyle inflation” — a.k.a. spending more every time your paycheck increases:

Early on in the workforce, every time I got a raise, I’d very quickly adjust my standard of living. The second I’d start making more money, I’d start spending it. And I’m not talking about spending on rent. I started going out to dinner more, I’d buy more expensive cocktails, I’d shop, I’d do all the stuff you do in your 20s. 

Even though I felt that I was living fine on my entry-level salary of about $32,000, as I worked my way up and made more, it still felt like I wasn’t making enough money. Then later, when I started my own business and went back to making about the same as my entry-level salary (which isn’t uncommon for entrepreneurs in the early years of getting their businesses off the ground), it was a huge shock to the system. It suddenly felt like my whole lifestyle was off limits to me. 

If I had not immediately increased my spending each time I got raises in the past, and had maintained some kind of financial buffer, cutting back would’ve been an easier adjustment. 

On recognizing when your financial needs differ from your friends’:

During this time of starting my business, I realized I had to start saying no to a ton of things that I used to say yes to — especially as spending pertained to my social life. This was tough, because I was reaching an age where all my friends were starting to make more money and live a more lavish lifestyle, and I was suddenly taken off that track. Obviously it was for a very good reason — I have no regrets about starting my business — but those first couple of years were definitely an adjustment.

On realizing your value — and then asking for what you’re worth:

It wasn’t until I left my first job that I realized that going to the next place was a chance to have a big bump. I should have asked for more money more quickly at my first job. Now that I’m a boss and people are constantly coming to me asking for raises, I realize how much power great employees have. And rightfully so. I think that’s how it should be. But I don’t think I realized my value at the time.

Ultimately, I don’t want to lose great people on money alone, and I don’t want people to feel that they have to leave to get that big buck. There’s something terrible about the fact that loyalty almost gets punished. In other words, if you stay in a place for longer, you’re making less than the people who come in and negotiate when they start. That’s always a really helpful data point, too. You could say: “I’ve been here for this many years, and if I went somewhere else, I’d be making more.” And if you’re a boss reading this — I think this a good thing to be reminded of. You want to reward your longstanding employees who have stuck with you and grown with you and will continue to do so.

On why being generous pays you back dividends in well-being and happiness:

Sometimes when finances are tight, there can be an instinct to stop being generous. But I think that generosity should be the last place you cut back. Of course, if you cannot afford a birthday gift, you don’t have to buy one — you can certainly make one, or find another way to express your giving nature. But if you’re choosing between buying a gift for yourself or a gift for your friend? I’ve learned to prioritize the generous act, because it’s ultimately going to lead to greater abundance in your life. 

On how there’s more than one way to save:

I used to think, “I’m going to live in the moment and everything will work out,” which I totally recognize as a position of privilege. But over the years, my attitude about saving for the future has changed. I contribute to my 401(k) now, I’m happy to say. Thanks to my wife, we also put away money for our son. We’ve got to start somewhere with his college fund, even though he’s 15 months old. And although we do have money invested in the stock market, I’m very grateful that we don’t have all of our money tied up in stocks, especially at this moment. 

We’ve always kept a cushion in a savings account. Some people say, “Oh, that money in savings is not working hard enough for you.” But then something like this pandemic happens, and it’s nice to know that we have money that’s basically cash — easily available to us if something were to happen. My dog got cancer recently and I didn’t even question getting her the surgery that she needed, and it was incredibly expensive. I appreciated having money on hand to cover something like that, which I obviously never could’ve foreseen happening.


  • Alexandra Hayes

    Content Director, Product & Brand, at Thrive

    Alexandra Hayes is a Content Director, Product & Brand, at Thrive. Prior to joining Thrive, she was a middle school reading teacher in Canarsie, Brooklyn.