Former Harvard Meditation Advisor Shares Steps On How Entrepreneurs Can Overcome Doubt

Doubt: It’s one of those one-syllable feelings that can feel catastrophic as an entrepreneur. About four in ten newbies and business owners experience this all-too-common emotion, but its ubiquity doesn’t make it any less challenging. According to former Harvard Meditation Advisor Kassi Underwood, the present moment has a lot to offer uncertain entrepreneurs—even if, in this very moment, it’s hard for you to believe that sitting with your doubt is the way to go. 

An author, podcaster, and entrepreneur, who holds a Masters of Divinity from Harvard, has come against her fair share of self-questioning. Below, she offers her perspective on what doubt actually is, why it may manifest more often for women and non-binary entrepreneurs, and what to do when you find yourself in the grips of this emotion. 

So, what is doubt? And why does it run more rampant among women entrepreneurs

Underwood has a simple definition: “Doubt is fear. It’s that simple,” she says. “A lot of things that we label with more complex terms are just fear. Guilt is fear. Doubt is fear. Doubt is, 'I don't know if I can do that,' which is another way of saying, 'I'm afraid I can't do this. I'm afraid.'” Mic drop, right? 

Understandably, this doubt (aka fear) doesn’t target all people equally. Women and non-binary entrepreneurs—and particularly those who are Black, Indigenous, and people of color (BIPOC) —are up against discrimination that makes the fear more readily available. Since women-founded startups receive just 2.3 percent of venture funding and the funding gap is even bleaker for founders of color, it makes sense that you may constantly be asking yourself questions like, “Can I do this?” and “Are the steps I’m taking leading me toward success?”

What’s more, as women, we may be more likely to question our leadership skills in the C-suite. “Those of us who grew up as girls are programmed with the beliefs that we should be quiet, or we're going to come across as bossy or rude or demanding,” Underwood says. “We're taught that we're not supposed to care about money, or that if we do that, we're a gold digger or we're too masculine. There are so many insults that come with being a female entrepreneur.” If any of this sounds familiar, know that your experience is normal (which is not to say it’s acceptable or fair that you have to deal with it.) 

Over time, systematic change like more funding going to women entrepreneurs will hopefully take the burden of doubt off all of our shoulders (or, okay, at least lighten the load). In the meantime, however, Underwood has five steps to help you approach doubt with mindfulness. So go ahead: Plug into the present moment. 

1. Meditate (for one minute!) in the morning to reduce your overall quantity of fear triggers

No surprise here! Diffusing doubt doesn’t start the moment you begin to feel uncertain; it starts the second you open your eyes. If meditating for 20 minutes feels daunting to you, never fear. Underwood has designed a one-minute, daily meditation that you can do in the morning to head off doubt before the day has even begun, so you have less “Ahhh!” moments later in the day. 

2. Identify and put words to your fear

“If a fear comes up, first of all, identify what you’re afraid of in the moment. Like, ‘I'm afraid that I'm going to send this email, and they're going to say no,’” Underwood shares. Once you’ve taken a pulse on what it is that has your heart racing, you can start working through it, which leads us to…

3. Identify the “lie you’re telling yourself”

“In fear, there's always a lie that I'm telling myself,” Underwood says. “One of the most prominent lies that women tell ourselves is, 'I can't handle that. If this goes to shit, I won't know what to do next.' And, of course, that's not true. You're gonna figure it out like you're a badass woman and you're gonna know in the moment, what to do next, but you can't solve a problem that's not even happening.”

Find your lie. 

4. Write out the worst-case scenario and the best-case scenario

Now that you’re holding your fear in one hand and your lie in the other, you’re ready to plan. “The next thing to write down is, 'how would I handle the worst case scenario with courage? What's that look like?' And then what's the best case scenario? What news do I want to create for myself, my life, and life in general?”, says Underwood. 

For example, if the worst-case scenario is that you lose a client, the best-case scenario may be that you now have an open slot for a cool new client that aligns with your values. Bam. 

5. Keep the fruits of this exercise nearby

“You can put some of those lines up on your fridge or in your office,” Underwood advices. “They will start inspiring you and help you cut through those moments of doubt. So you'll be in doubt, but you have already done the exercise. You're like, ‘Oh, right. I don't believe that anymore. Like I actually can handle this. Even if the bad sh*t happens, I can handle it.” You absolutely can!

Written by Kells McPhillips