Turning Risk Into Opportunity

I gave this talk at NERCOMP’s “Unite and Ignite Your Career” workshop for women on January 23, 2015. I also gave a slightly modified version of it at the Wonder Women Tech Conference in Los Angeles in February 2015.

Title Slide
About two years ago, I was having dinner with my husband and our two teenagers, and we started talking about college. At the time, our daughter was a junior year in high school, and as you might imagine, we were talking a lot about college. At dinner that night, my daughter asked me how I chose which college to attend. Before I tell you what I said next, you have to understand something about me:
Picture of a tricycle
I grew up in a small town in Rhode Island, in the same small town where my father was raised, and where his father was raised. I don’t exactly come from adventurous stock. So, at age 17, when deciding where to go to college, I applied to the best school within a 50 mile radius of home. Fortunately, it was a top-notch school (Brown University in Providence RI), and to this day, I’m grateful they accepted me.Yet, over my career, I’ve learned to be more adventurous and to embrace risk. In my talk today, I’ll share my career journey as well as my risk-taking journey. I’ll also share tips from other technical women about how they evaluate and embrace risk.
Picture of warnings at a sea cliff
When I was young, I evaluated opportunities by thinking of things that could go wrong, the potential downsides. What if I went far away to college, got sick & needed my mom? What if I didn’t have enough money to travel home for Christmas? Would I find a safe place to store my things over the summer? You get the picture.
Brown University
After graduating from Brown with a degree in Computer Science, I stayed on campus working with a research group as a software engineer. I had interned with them, & knew it was the right place for me. It felt comfortable to “shelter in place” and stick with what I already knew.It wasn’t a bad decision at all; I learned a ton, worked on some cutting edge technology, published research papers, and worked with really great people. I also met my husband while working there.
British Red Phone Booths
Speaking of my husband…I married someone who is more adventurous than I am. As he likes to say, he rescued me from the state of Rhode Island. We took a big risk, and moved to just outside of London, where I got a job at Hitachi Europe Limited, working on research similar to what I had been doing at Brown.
Golden Gate Bridge
However, the tech scene in England 20+ years ago wasn’t our cup of tea. (Pun intended.) So, we moved to the San Francisco Bay Area – the promised land for software engineers.I joined a startup called GO Corp, which was developing an early tablet computer. I was initially a software engineer there, and moved into project management. Yet, like so many startups, GO was not successful. From there, I joined another startup, Macromedia. I spent the next 12 years working there, growing my responsibilities to the executive level and starting my family.I then joined Adobe Systems when it acquired Macromedia. During this time, I started Adobe’s women’s initiative to provide career development opportunities and support to women across the company.
Karen speaking to a group of women
About three years ago, I decided to leave my corporate job to strike out on my own. Today, I am an advocate for technical women. I advise tech companies on how to attract more women and retain the female employees they already have. I also provide leadership coaching for women in the tech industry, I give talks, and I do a lot of writing.
Ferris Wheel
Did anyone notice a change in me? I went from being a risk-adverse young woman living within a 50-mile radius of my hometown, within the boundaries of the smallest state in the USA, to someone who lived and worked internationally, worked for startups, grew her career to the executive level, and then left that all behind to focus on her passion of supporting other technical women.What changed? Over the course of my career, I’ve seen the positives that can come from risk, and I now evaluate opportunities by looking at all the things that could go right. The upsides. And I’ve found myself saying yes to things that my younger self would have talked herself out of.
Seth Godin quote on failure
I love this quote. Yet I wonder if fail is even the right word. I don’t like to use the “f” word, the “failure” word. Let me explain.
Athentica logo
I left one thing out of my career journey. Last year, I joined an early-stage startup in online learning as the CEO. When I was being recruited, I looked at the impact we could have with our first product, the business we could build, what I would learn, and the ways I would grow my reputation and my network. Sure, there was the risk that we wouldn’t be successful, but I didn’t let myself focus on that. Instead, I looked at the upside and said yes.Well, it turns out things didn’t go according to plan; after just six months, I made the difficult decision to leave the startup. Did I fail? That’s not how I’m looking at it. I learned a lot about early-stage startups and pitching to VCs. I made strong connections with people working to improve online education. I led the development of the initial product offering. I worked with great people. So much good came from it. Notice I’m still looking at the upsides…
Quote about inner critic
How many of you have an inner critic helping you imagine worse case scenarios? What will people think of me if I speak up in that meeting? What if I ask a dumb question in email? What will people think if I advocate for a new technology?When we listen to our inner critic, we focus on the negatives, the potential downsides, the terrible things that could go wrong. We talk ourselves out of our confidence. And women tend to do this more than men.
Woman gazing out of window
Here’s another thing about our gender. There’s a NASDAQ report about women’s appetite for investment risk, which show women tend to be more risk averse. While women and men do not differ in their perception of possible gains or losses, women tend to be more pessimistic that it’s going to pay off.
Woman in front of 3 doors
So, what’s a woman to do? Even though I’ve come a long way on being more optimistic and looking at the upsides, I still want to make sure I’m pushing myself to take the right risks. After all, not taking risks can also be risky. So, I’ve started collecting stories from technical women about how they evaluate and embrace risk…Let me tell you about 4 approaches.
Plate of pancakes and fruit
How many of you know of Goldiblox, an engineering toy for girls? The founder of Goldiblox, Debbie Sterling (another woman from a small town in Rhode Island), got a degree in engineering from Stanford and began her career. But she wanted to do something bigger, something to encourage young girls to pursue engineering. She had a regular “Big Ideas Brunch” with friends who encouraged her to pursue her ideas, to take risks, to create the prototype of Goldiblox, to find a manufacturing partner, to launch a Kickstarter campaign to raise funds to create the products. And soon after launching it, she won an Intuit Small Business award which gave her an ad slot at the SuperBowl, and she even had a Goldiblox float at this year’s Macy’s Thanksgiving Day parade.
Pie chart financial report
Let’s move on to the second approach. You know how financial advisors recommend a balanced portfolio of investments. Depending on your investment goals, they might recommend 10% money market, 40% fixed return investments, 50% equity investments. These numbers may change depending on your goals and where you are in your life, but this portfolio approach is a good way to balance investment risk.I have a friend who wanted to make a career change from engineering to product mgmt. She was inspired by an article she read about keeping one foot on the ground when taking on a new risk. Don’t change everything at once. So, she stayed at her company and pursued the new career path.   Sure, it was risky to leave a job she was good at, but she mitigated the risk with a balanced approach. E.g., Same company, benefits, commute (10%), joined a new team but brought with her a strong internal reputation and cred (40%), and the risk was would she be able to master the new job responsibilities (50%).
Paper prototype
Now for the third approach. We create software prototypes all the time to test ideas, get feedback, and learn. Guess what: you can also use this approach to run experiments on risk you’re considering.A former co-worker of mine decided she had to make a change. She’d joined a Bay Area software company right out of college, and before she knew it, 10 years had passed. She enjoyed what she was doing, but wasn’t feeling fulfilled. She was wondering if she should join a non-profit/NGO instead. And she had always wanted to live in a large city like NY. She decided to take a sabbatical and validate two things: living in NYC and working for a charity she cared about. She volunteered to do an unpaid internship for the charity, and moved in with some friends in Brooklyn. And she loved it. She ended up taking a full-time role at the charity & moving to NYC.
Women riding bikes
Last but not least, it’s important to surround yourself with people who support you and encourage you to take risks. People who won’t think you failed if something doesn’t work out. People who can point out to you when you need to move on from something and look for the next opportunity. This picture is of my friends from college, who are my advisors. We’re about to go on a bike ride on one of our annual weekends together.
Woman facing three doors
But why even bother embracing risk? Why bother with a Big ideas brunch, a balanced portfolio approach, prototyping your life, or a personal advisory board?
Blockbuster Video Store
How many of you have heard of the Innovators Dilemma? The dilemma is relying on prior success to keep you successful in the future. That what has worked for the company before, what has fueled growth, will continue working in the future. Think Kodak in the age of digital photography. Blockbuster in the age of Netflix.
Marshall Goldsmith quote
What’s the equivalent of the innovator’s dilemma for an individual? “What got you here won’t get you there.” It can be risky to not take risks, to stay where you are, to keep doing what you’re doing.
Karen's family
This is my family. I’m the short one.Remember that story I shared at about joining an early stage startup? As I reflect on it, I think that one of the best outcomes was that my kids saw me take this professional risk. And, they know I’m doing just fine, even though it didn’t work out. I hope they’ll think back on this time when they need to evaluate options in their future careers. I want them to be able to take a risk—to take on a stretch assignment, to move internationally, to switch jobs—and not be held back by the fear of all the things that could go wrong. I want them to focus on the upsides, not the downsides.And I wish the same for each of you, the next time you need to make a decision that might feel risky.
Picture of Karen
Thank you!