The Woman Who Makes Financial Planning Easy—Even For Millenials Who Were English Majors (2024)

On Monday, there was a debate on the front page of The Wall Street Journal’s “Personal Finance” section over whether or not students should be required to take financial planning courses in college. Why all the bluster? Because the U.S. is ranked 14th in a 2015 global study conducted by Standard & Poor’s Ratings Group and others, with Americans logging an average financial literacy rate of 57 percent—and many would argue a presidential election was just decided because a large swath of the people in this country feel financially disgruntled. Between navigating student debt and figuring out 401(k)s, “adulting,” as these oft-referred-to life skills are sometimes called, ain’t easy. Not to mention, tax season is officially upon us. Cue the screams and the fainting!

Fear not, we’ve enlisted the help of Alexa von Tobel, the founder and CEO of LearnVest, a company that offers an affordable way to get a financial plan together that’s so straightforward even English majors can understand it. “I came up with the idea for LearnVest because when I graduated from college, I had all of these personal finance questions, and there wasn’t a financial planning resource that spoke to me,” explains von Tobel. “They’d have drop-downs with questions like, ‘How many years have you been working?’ And ‘none’ wasn’t an option! I’d just started my job, and all of the places I visited were asking questions about big stages of life, and not two of them really catered to mine.” She set out to create what she short-handedly refers to as the TurboTax for financial planning. She eventually sold the company to Northwestern Mutual in 2015, although it continues to operate as a separate unit, and von Tobel is still the CEO. She’s appeared as a correspondent on the Today show, Good Morning America, and Bloomberg among others, penned the book Financially Fearless, and going forward, she can add Vogue finance guru to her lengthy résumé, because from here on out, she’ll be opining on all of our biggest money concerns on a regular basis. Before her column kicks off next week, we asked this entrepreneur who seems to have all of the answers some tough questions about everything from launching a business and balancing career and kids to grappling with the gender pay gap. Find out what she had to say below, and be sure to check back soon for her first column.

Leading a company of over 400 people, you obviously have a very busy schedule. What are some of your time-management tricks—especially as you’re also a mother to a one-year-old? In previous articles, you’ve talked about waking up early and eating the same thing for breakfast and lunch. How long have you been doing this for? Do you still do this? Are there any new tricks of the trade that you live by?

Probably one of the biggest tricks I live by is that everything’s better if you exercise. I really mean it. Monday through Friday, I have a pretty regimented schedule. That means waking up early, ideally between 6:00 a.m. and 7:00 a.m., and working out, either in a class with best friends or on an elliptical where I power through emails.

I also tend to eat the same thing for breakfast and lunch, mainly because it’s easy: Breakfast is Greek yogurt and a cup of coffee, and lunch is a piece of fruit and a salad. The reason I do this is because it takes the thoughts off my plate. It’s what I’ve always done, and yes, I still do it. It allows me to be mentally prepared for when life is changing and I’m making bigger decisions, by preserving my decision-making power for things that matter as opposed to what I’m going to eat. You’d be surprised how paralyzed you can be when someone asks you what you want for lunch. It can take me two to three minutes to answer, and I just don’t need that energy expended there. I’m a prolific note-taker, and I’m a big fan of the power of now—if you have to do something, just get it done right then and there rather than putting it on a list. I am also human, and sometimes I have weeks when everything doesn’t work properly, and on those weeks I just juggle.

Another trick I really love and that helps is writing letters to my daughter whenever I am away overnight about why mommy works . . . it goes straight to an email address I set up for her for later; it serves as a journal of sorts. This helps me stay connected to her in a bigger way, even when we are apart, as that is honestly the hardest part of being a working mom.

You’ve also talked before about how important your mentors have been to you—especially the ones who have told you that you need to work harder. Do you think it’s important for everyone to have mentors, and if so, why?

I’ve had incredible mentors who have pushed me. Pushing sounds like someone’s been tough on me, but what I mean is, these are people who inspire me, who said “you can do it” and “you can go farther,” and when I look back, some of the people who have been crazily important to my life have been my mentors: Ann Kaplan, Lee Barba, Theresia Gouw. They were all on my original LearnVest board. I created a safe space by saying, “Push me harder; I want us to go our absolute farthest,” and people didn’t feel like I was going to break. I have outgrown—and continue to outgrow—all kinds of awkwardness as an entrepreneur, and that’s because I let people around me know they can give me tough feedback.

What has been the hardest part about being a working mom?

Being a working mom. It’s really hard. And the toughest part is that there are days where you just question whether you’re making the right decisions. You want to be in two places at once and it is not easy— it’s just that simple.

How has being a mom changed how you work?

I’ve always worked smartly and efficiently, because I wanted to set the tone for the whole company. Probably the biggest thing that has changed how I work is that now, I sprint out the door at 6:15 p.m or 6:30 p.m. to put my daughter to sleep. Luckily I live a block away, so I can be there for bedtime and then get back on later. Barring work travel, that is the one thing that I am unbending on. We have this new little routine: My daughter likes to go through my purse. And so right when I walk through the door, I give her coins—she gets pennies, nickels, dimes, and quarters—and we put them in each of four little piggy banks. If you ask her what she’s doing with the money, she’ll say “saving for college.” I do believe that good habits for your financial life are made early.

What’s your biggest tip for balancing career and family?

Here’s my biggest tip for balancing career and family: Clean the slate. If you are obsessed with your job and you really do love it and it fulfills you in every way, everything works. If you hate your job, it does not work. Because I love coming into this office, and I love the people I work with, and I love our mission, and I love bringing financial planning to America, and it means so much to me and it runs so core to my value system, it makes this constant juggle possible. If you can find a way to love your job or do something that you do love, you will make it all work, because you don’t come home depleted. That’s not to say I don’t come home every once in a while exhausted, but there’s a big difference between exhausted and depleted.

Do you and your husband share household duties as much as possible? Is this ever a struggle? Do you believe in a second shift, or do you think if you and your partner have an understanding, domestic duties can be evenly split?

I have the best husband in the world. Cliff Ryan is the best thing that’s ever happened to me. We both have very big careers, but he is definitely the CEO of our house, and he helps me with everything. There are days when I do more, and there are days when he does more, but we are fundamentally a team.

I know LearnVest is meant to help the 99 percent learn about financial planning and how to manage their money. With this in mind, what do you think is the biggest challenge facing women from all financial backgrounds under this new presidential administration? And what should we do about it?

I can’t stress enough that one of the big things that I learned from this election, regardless of party, is that America spoke. If you take away someone’s dignity with their wallet, because they don’t feel like they can pay their bills or have their jobs or be fundamentally fulfilled by being able to put food on the table—something I thought about for a long time—the world breaks. If you do not feel like you can provide for your family, what happens is the fed-upness that we saw in this election. LearnVest is bringing financial planning to the 99 percent. I absolutely believe with all my heart and soul that if we can help fix America’s wallets, we can change the country.

What advice do you have for young girls? We know the gender pay gap and the tampon tax exist. What would you say to young girls and women who are just beginning to enter the workforce, who feel like the deck is stacked against them?

I always tell people to dream big because no one else is going to dream for you. When I get to mentor—and I often do because I’ve been really fortunate to connect with mentorship programs where I get to sit with 14- and 15-year-olds—that is one of the things I tell my mentees. This one great 13-year-old girl said to me, “I want to be a lawyer.” And I said, “Why not a Supreme Court justice?” It’s my life strategy: Shoot for something that is way harder, and work your butt off for it, and if you only end up halfway there, you’re going to end up in this really great spot anyways. If you don’t, you’re negotiating against yourself and your dreams.