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Advice / Succeeding at Work / Getting Ahead

5 Quick Tips That'll Help You Get Better at Taking Risks

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Early on in my advertising career, I was considering taking a marketing role at a major food brand. But, as I scanned the lengthy list of requirements in the job description, I thought to myself, “I don’t check off all these boxes.” Feeling somewhat defeated, I closed the posting and didn’t think much about it—until recently.

At Cannes Lions a couple of months ago, one of the speakers on a panel, advertising legend Charlotte Beers, shared the troublesome statistic that women need to feel that we meet 100% of a job’s qualifications before we apply. Men, however, only need to feel 60% qualified before hitting “send.”

In other words, women are less willing to take risks on themselves.

My experience job hunting, as well as my work as the President of Berlin Cameron, a creative and experiential agency, got me thinking about the psychology behind this phenomenon. In the past couple of years, I’ve had the opportunity to work with and get inspired by a number of female entrepreneurs. I’ve also served on the board of empowering organizations like Girl Up, and have started a division at Berlin Cameron called “Girl Brands Do It Better” to advance female founders.

And even with many of those I’ve met and worked with, how to take that first risky step has crept into conversations, and I wondered why.

I wanted to explore what sort of advice, or change in mindset, might help women to embrace their risk-taking side. So, I set out to discover what it takes to make that leap and dare to begin. I talked to experts, career coaches, and brilliant women who’ve launched companies across industries to find out how to get inspired and ignite new ideas.

Here’s what I learned:

1. Believe in Your Vision

Mentally investing in your own future is key.

“When people are stuck, it means that they are not connected enough to the end vision. If you think about a goal to run a marathon, the more connected you feel to that end vision, the more motivated you’re going to be,” executive coach Suzannah Scully, who’s worked with companies like Apple, Sephora, and Airbnb, told me.

She added, “If you have some limiting beliefs in your mind as to why this wouldn't work out, explore those beliefs and figure out why you think it's not going to work. I love the expression that a belief is just a thought you’ve had over and over again. It doesn’t mean that it’s true.”

2. Think Small

Any time you’re about to make a big leap, whether it’s putting together a deck to secure funding or working on an important pitch, the end result can be overwhelming. Setting small, easily achievable goals is one way to jump-start yourself.

Lisa Sun of the functional fashion line Gravitas agrees: “Set a goal every two weeks, even if it’s small things like opening a bank account for your business. After 10 weeks, you’ll be able to look back and have accomplished a lot.”

3. Check Perfection at the Door

Anytime you’re starting something new, the pursuit of perfection can be paralyzing.

“Choose action over perfection,” says 100 Days Without Fear founder Michelle Poler, who speaks all over the world about overcoming fear. “Women are perfectionists, and we have to let go of that desire to be perfect. We’re too afraid to fail ourselves—but when we don’t even try, we fail ourselves even more.”

You’re going to have failures, but try to learn from them and move on rather than chasing the impossible.

4. Find Your People

The importance of building a community’s crucial to opening your mind to take a risk.

“Surround yourself with others who are doing it—ask for help, don’t get stuck in your mind, and research, research, research. It’s one thing to have a great idea, it’s another to do the work, build out a business model, and thoughtfully go for it,” says Ashley Sumner, the co-founder of the female-focused co-working space Quilt.

Part of this is not being afraid to share your ideas and get feedback from others. “I’ve never had it come back to haunt me that I shared what I was thinking or previewed an idea with someone,” explains Katie Fritts, the founder of the luxury underwear subscription service Underclub. “If anything, it’s held me more accountable to do what I say I’m going to do.”

5. Make Fear Your Personal Force

No matter what stage you’re in in your career, fear’s going to be omnipresent. But everyone I spoke to agreed that it can be a great motivator.

“My job has been an exercise in flexing those muscles that I don’t usually flex,” Evvie Crowley says of the digital lifestyle publication, The Caret, she co-founded and launched this year. “I have an entrepreneurial drive, but it’s underneath a lot of insecurity. The best way for me to get over my paralyzing self-doubt is to keep pushing to make it a viable brand.”

Dee Poku Spalding, the founder of WIE Network and The Other Festival, added, “The first time you take a big leap of faith and it works is an incredible boost to your confidence. That gives you the confidence to do it again.”

After talking with all these women who’ve overcome the barriers that tend to hold us back, I’ve come up with a couple of insights of my own: Women are naturally good connectors who embrace community, as well as listen to and support each other.

So when it comes to taking risks, we’re a lot more equipped to do so than we think.