The “Risk-Averse” Label Hurts Women — Here’s How We Can Change It

By Chief Boss Lady Ambika Singh

When discussing gender disparities in the workplace, most advice and solutions often come down to a common sentiment: women need to take more risks. Male-dominated industries create environments where the fear of failure is significantly lower for men, so men are perceived as bigger risk-takers. This in turn makes women seem less likely to take risks, which has a huge impact on their professional development. This is why women are less likely to negotiate their salaries or ask for promotions, and tend to over-credential themselves. When pitching to VCs, it’s why women are more likely to play it safe, while men “pitch the dream.” The way we as women feel about risks can make us seem more hesitant when compared to men in the same roles. Because of this, women tend to be labeled as more “risk-averse,” which isn’t actually true.

In reality, women are taking equal risks to men, if not more. These risks just aren’t as visible. Across all aspects of professional development, women are unfairly left steps behind. We have to fight for the opportunities handed to men, like salary negotiation. For men applying to jobs, negotiating salary is standard procedure. For women, negotiating salary is usually seen as risking an opportunity we’ve already fought to secure. If we take the risks needed to reach the same starting point as men, we’ll be hesitant to push our boundaries further in a position we already had to earn. Women aren’t “naturally more cautious,” but have more of a fight to reach equality. 

The risk-averse stereotype is really harmful to buy into. Risk-taking is a leadership quality we as a society admire. Pegging women in general as more risk-averse supports the bias against women as leaders. It creates a huge double standard when female leaders take risks, whether it’s in their personal careers or for the company. People embrace the Steve Jobs “fail without fear” attitude. When women adopt this, it’s seen as reckless instead of a strategy for success. A powerful woman who takes risks doesn’t align with our expectations for her, so it creates a bad connotation. We wait for her to fall back into our gender norms, and are quicker to classify her risks as failures than we are men’s. Fostering risk-taking attitudes for women is crucial for women to be seen as leaders. 

Of course, this is easier said than done. Risk-taking is scary. Whether or not women are comfortable taking risks, in order to achieve workplace equality we need to be taking the kind of risks that will put us on the same playing field as men. How can we make big risks more approachable for women? Here’s my advice: 

1. Take Baby Steps

Taking risks doesn’t have to be a decisive, all-or-nothing, roadblock. Manage risk by thinking about everything in incremental steps so it doesn’t feel as intimidating or monumental. Breaking things down into smaller steps gives you more opportunities to change things if they go wrong. Instead of jumping off a cliff with your risk, take things one step at a time. When something goes wrong, take a few steps back to fix the error, and a few steps to the side to change your approach so you don’t fail again. Breaking things down gives you a realistic and achievable route to your goals. You can think things through and figure out how everything connects rather than getting overwhelmed by the big picture. Throwing yourself off a cliff isn’t a surefire way to accomplish anything. Walking down into the valley, one step at a time, is much more realistic. Try moving into ideas slowly. Maybe say it out loud in the shower. Then if it sounds good, tell a friend you trust. It feels good to let ideas out! You don’t need to dive off the deep end to reach your goals.

Instead of jumping off a cliff with your risk, take things one step at a time. Breaking things down gives you a realistic and achievable route to your goals.

When I started Armoire, I didn’t go in with the thought “I’m going to start a company today!” because that’s a scary statement and not very helpful in outlining how I was going to get there (not to mention an unrealistic time frame for myself). Instead, I broke things down into smaller steps— outlined what needed to be done to actually start a company and how I could take those tasks one at a time. When our website broke or an investor turned us down, our plan wasn’t doomed. We could fix what needed to be fixed, and approach the task from a different direction.  Taking baby steps helps mitigate the risk associated with bigger goals and makes you think through realistic routes to these goals. 

2. Only Deal With What You Can Control

Planning for big-picture problems out of your control isn’t doing you any favors. If you only plan for the vantage you can see, you’re not overwhelming yourself with how big and scary failure could be. It’s exciting to think of where your idea can lead, but then your mind tends to wander and next thing you know, you’re worried about things that won’t affect you for five years. Planning only for realistic next steps helps you avoid getting bogged down in the big picture.  

There are going to be a million more little problems between where you are now and the distant, looming thing you’re trying to problem solve for. When we were trying to figure out what kinds of items our members would actually want to rent from Armoire, we weren’t trying to figure out how we were going to scale operations when we grew. We focused on the problem at hand— what to buy that would benefit our members in the moment, and how to then show them these things we thought they would like. By the time we reached where we are now, with over 40,000 garments, we were better equipped to solve our scaling problem than we ever would have been in those early stages. We have a team of talented operations leads who completely changed the way we organize our ever-growing inventory. Their solutions were way beyond our reach when we were just starting out. We solved for what we could control, and found the tools we needed to reach the big-picture problems along the way.  

Planning only for realistic next steps helps you avoid getting bogged down in the big picture.

Trying to deal with problems out of your control is a dead end. Realistically, those problems might not even be the ones you’ll end up dealing with when you get to that point. Great companies die in stages where they’re over-analyzing problems so far out that nobody knows what they’ll look like. Problem solving within the vantage you see keeps you focused and confident in your ability to tackle the problems that arise. 

3. Find Boss Ladies Who Take Risks— Win or Lose

Finding mentors who have succeeded in the goals we’ve set for ourselves makes our goals seem more achievable. They prove that risk-taking does pay off. Female mentors help bring down the “boys-club” dominating so many workplace environments. They provide advice and support in unwelcoming environments.


Risks are more complicated for prominent women in male-dominated industries because they become figureheads. When they fail, they fail harder. Their failures are remembered more and assigned more significance because they’re unfairly cast as representatives for an entire gender. When women do amazing things, it’s seen as breaking the mold, while men are just confirming our expectations of them. If it’s inevitable women’s failures will be more prominent, use this to your advantage and prove you are capable of taking big risks. Having female mentors and leaders are so important because it gives you someone to pattern-match to, whether it’s win or lose. Seeing powerful women who try their best and fail is just as important as seeing those who succeed. Risks don’t always work out, but they can teach you a valuable lesson. It’s a risk to be seen as a figurehead for an entire gender, and by no means a fair burden, but when you rely on a network of powerful women it elevates women across the board. 

4. Lean into Risk — It’s Is A Good Thing 

Despite the downside, the fear of risk has its advantages, regardless of gender. Risks force you to stop and think through the best-case scenario, the worst-case scenario, and the middle, often more realistic, scenario. These worst-case scenarios are usually pretty unlikely (you’re probably not going to get fired by asking for a raise, despite what you tell yourself) and allow you to think through the flaws in your plan. The ability to think through scenarios is what makes women better suited for C-Suite roles. Leaning into your fear of risk isn’t a bad thing, it’s what helps you strive for perfection. It’s also a good reminder that risk-taking doesn’t have to be reckless and impulsive. Taking calculated risks encourages you to reach big goals without feeling like you’re putting it all on the line. 

Leaning into your fear of risk isn’t a bad thing, it’s what helps you strive for perfection.

5. Mitigate Costs Associated with Risk

One of my favorite things about Armoire is the ability we create for women to try styles they would never buy. I love it when members share their new willingness to branch out, or that their style looks completely different from when they first started renting. We help our members take fashion risks in an approachable way. Rental makes the costs associated with risks less devastating because the model encourages trial and error. For members, there’s nothing to lose by choosing a color they wouldn’t normally wear. If they end up with something they don’t like, they haven’t lost any money or time. Armoire mitigates the costs associated with “failures,” so these risks seem a little less risky. Members start with a color they wouldn’t normally wear, then maybe a style. Before long, their wardrobes are more colorful, more vibrant, and more uniquely themselves. Rental makes us more comfortable with taking risks, but what it’s really doing is changing our idea of risk itself over time. 

When fear of failure decreases, risk-taking doesn’t seem as scary. Most of the time, these risks result in success— our members end up loving things they never thought they would. Our members have completely inspired the way I think about risk myself. If we can mitigate perceived costs associated with failures, we can change our idea of risk completely. When risk-taking becomes more palatable, it eventually becomes a part of our daily routine. 

If we can shake the fear of risk-taking with our wardrobes, we can easily translate this into our professional lives. As women, we should get used to taking risks that put us on the same playing field as men. From there, we can become more comfortable with the big risks that successful men are celebrated for. The notion that women are more risk-averse is preventing us from being seen as leaders, and ultimately holding us back from equal-pay, promotions, and c-suite roles. As women, we have the tools, skills, and support we need to change the stereotype — so get out there and start taking big risks and remember we have your back. 


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