How Gratitude & Humility Helped This Serial Wellness Entrepreneur Overcome 2 Financial Traumas

Portrait of Sheryl O'Loughlin

Image by courtesy of Sheryl O'Loughlin

With an estimated 67 percent of Americans at least a little anxious about paying the bills, and 58 percent worried they won't have enough money for retirement, it's becoming increasingly clear that being financially well is an integral part of overall wellness. Of course, money management isn't one-size-fits-all, so we're talking to people from all walks of life to find out how they achieved a healthy relationship with their finances. We hope it empowers you to live a life Well Spent.

Sheryl O'Loughlin has long been a pioneer in the clean-eating space. Formerly the CEO of Clif Bar and Plum Organics, a company she started, she is currently at the helm of Rebbl—a popular line of superfood-packed beverages.

O'Loughlin is also an author, a mom, and an incredibly spirited entrepreneur. Despite her successful career in business, O'Loughlin has faced painful financial hardships and found ways to navigate them with grace and integrity. In this candid conversation, she shares the lessons she's learned on the other side of a bankruptcy scare and house fire, lends advice to aspiring entrepreneurs, and dispels one financial myth that cripples a lot of women, in particular.

What does financial well-being mean to you?

For me, it's about making sure our family's priorities are being met and getting very clear on what is important to us. Of course, that includes the basics, but it also includes the ability to have fun and do things where we're learning, traveling, and eating healthy food. It's being able to have that, embracing it, and being grateful for it.

What has your financial journey looked like up to this point?

Have you ever heard the term "bag-lady syndrome"? There's a theory that over time women have developed this fear that money will go away and we'll be stuck with nothing.

For me, I know that very feeling came from my childhood—I had a single mom and saw how challenging it was to not have money. Quite frankly, this way of thinking is what led me to going into business in the first place. It was a hard decision for me because I was so into social justice and changing the world, so I ended up feeling like I did a deal with the devil by going into business in order to make sure I secured my financial future early. (My whole life changed when I discovered that there could be a way of doing business that could really help to create this kind of change in a much more sustainable way. That was an amazing little journey in and of itself.)

Your money is not your identity. Your house is not your identity. You are your identity. Your relationships are your identity. That’s what most important.


But I built up a certain amount of financial security over time, and it felt good. Then my husband started a company that we turned into a family business, and it blew up. We lost everything we had. We were in so much debt—we had a lot of people following us and credit card companies following us. We almost went bankrupt. It was a really scary, scary time for a while. Here I was, designing my life in order to avoid this bag-lady syndrome and it still happened—which was a good lesson in the fact that things are just out of our control sometimes.

We've been working our way back on track from that, but it really has been an up-and-down journey along the way.

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Tell me more about that time. What tips do you have for people who are going through a low point like this and feel lost and helpless?

The company was called Blue Sky Family Club. It was a great concept—all about healthy food and creative activities for kids. But the building we leased was so big, and it cost around $20,000 per month. When it didn't work out, we did everything we could to try to negotiate our way out of this thing, but we couldn't. So imagine your money has all gone away and you have this $20,000/month on top of it. This was happening right around the time when I started Plum Organics. I can't begin to tell you how stressful that was, trying to run a company when you're trying to hold your shit together.

For us, it helped to take a pragmatic approach. We deal with things step by step. If you start thinking too far ahead into the future, it starts to become overwhelming and you can't take the steps that you need to do to get there.

An example of that is that during our tough time, we had to move out of our house immediately. I know so many people whose identities have been so wrapped up in their house that to walk away from that is nearly impossible. That just digs you into a deeper hole and creates more and more fear. It's just a pragmatic thing. "What do I need to do in this moment? What do I need to do in the second moment?" Eventually, you'll get there and you'll be able to see your way into a new future, but you can't do it if you're holding on too hard to what you think your identity is all about. Your money is not your identity. Your house is not your identity. You are your identity. Your relationships are your identity. That's what most important.

Any other specific financial steps that helped you get out of that time?

We didn't have any money to put into savings. At that time, it was really just about getting through and stripping our lives down to the basics.

The other thing we've done is we've always met with a financial planner. You have to have the right one, but they can really help you to see beyond what you can do in the short term to what you can do to set yourself up for the future. When this all happened, our kids were 5 and 8. As we started to work our way through it, we thought, "What do we need to do for our kids in terms of putting a little more money away for college? What do we need to do to bring our 401(k)s back on track?" We started to open up to, "What is the bigger picture here, and how do we make our way toward it?"

What guides how you spend money today?

A couple of things. First, a purchase has to fit with what our family goals are, and it has to be something that will make us truly happy for a long time. If it does, we buy it and feel really grateful for it. Then, we let go and think, "This is good. We made the right decision for us."

What tends to happen is that people can get sucked into a cognitive dissonance, like "Should I have done that? Oh my God." But it's done. Enjoy it. Soak it in.

You have to go out there and be really bold with your choices, but at the same time, you have to balance it with humility.

Last year, we lost our house in the California fires. "Things don't matter. It's only stuff" quickly became our mantra. But we lost everything. I'll fricken' tell you, when I get something now, I have so much appreciation for it, and it just makes me smile.

For example, my husband bought me this necklace, and he was like, "You deserve this necklace. It's something to make you happy." I look at that damn necklace every single day, and I can't tell you how happy it makes me. It's a stupid little thing, but I just feel the gratitude of it, knowing how easily it can go away.

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Are you guys back in the old home now, or is it completely destroyed?

Oh, it's gone. The wildfire took out half of the neighborhood. There are literally no houses there. We're lucky that insurance is paying for the temporary home we're living in nearby while we rebuild the old one. In probably about a year or so, we'll be able to get back in there.

This is where I go back to gratitude. We feel so lucky because we have good insurance. A lot of people were renters or had shitty insurance companies that didn't come through like ours did. Blue Sky was scary. This was just a pain in the ass—something we had to get through.

How do you talk to your kids about money?

When we were going through the Blue Sky thing, my older son was 8 years old, and we had to talk to him about what was happening. We tried not to make it scary, but we told him we were going through a hard time and we had to be careful with our money. Then—this was the cutest thing ever—my son got his piggybank, took out 35 cents, gave it to my husband Patrick and said, "I want to be an investor in Blue Sky." Now he's a senior in high school and applying to college, and I'm like, "Dude, you have to share that story in your essay."

Transparency is an important family value to us. Balance that with making it so your kids aren't afraid can be a hard thing to do sometimes. But it's all about supporting them so that they're not afraid.

What advice do you have for aspiring entrepreneurs?

A couple of things. First of all, one of the things we learned with Blue Sky is that you need to know what your personal risk level is and what you can withstand. One of the big mistakes we made there was we took on way too much financial risk, way more than our family could deal with, and we were self-funding it.

With Plum, I knew it was venture risk, so there's a downside of that with lack of control, but at the same time, there was security knowing that if it blew up, which thank God it didn't, my family wouldn't go down with it. You just have to understand that life is uncertain, so be pragmatic about what you can take on.

One of the things I talk about a lot is bold humility: You have to go out there and be really bold with your choices, but at the same time, you have to balance it with humility so that it doesn't become hubris.

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What's one money tip you would give to your younger self?

Given that I had bag-lady syndrome, I think it would be don't be so afraid. There'll be ups and downs throughout your life, but it will be OK. A lot of times we live in fear about the things we don't know, the uncertainty and the complexity of the world. We try to control and hold on, but we can't. We can have the best intentions, but things happen. It will work out. Somehow it will work out.

This interview has been edited and condensed.

Also, establishing a regular meditation practice can drastically improve your health, and so can choosing the right foods. Ready to learn more about the power of food? Register now for our FREE Functional Nutrition Webinar with Kelly LeVeque.

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