The metaphor often used to describe entrepreneurship is the one attributed to LinkedIn Co-Founder Reid Hoffman – you know, the one about someone jumping off a cliff and building an airplane on the way down?
Kimber Lockhart, Stanford alumna and CTO of healthcare provider One Medical, has another that draws on her personal experience as an amateur circus artist. Imagine standing on a platform 20 feet up, clutching the trapeze bar with both hands for the first time. Just as you get ready to hop off the edge, you take a deep breath and – oops – glance down.
That’s the moment Lockhart likens to the instant an entrepreneur decides to commit everything to launching a startup. Just after college, with little money in the bank and an offer to work at a prestigious consulting firm, she instead decided to co-found a tech company with a classmate who shared her passion for entrepreneurship.
“There’s a lot that could go wrong here,” Lockhart recalled thinking at the time. “What if this fails and nobody will hire me afterward? … What if I run out of money?”
Things worked out in the end. The startup grew and was acquired two years later by Box, where she spent the next five years and rose to a senior engineering role. She then went on to head engineering at tech-driven healthcare provider One Medical and is now its chief technology officer.
Yes, Lockhart is ambitious and always eager to grow as a leader. But she’ll be the first to admit she isn’t fearless. For one, she says she’s scared of heights. And yet, she still trains regularly at the San Francisco Circus Center.
“Take note of what learning feels like, so when you’re feeling it, you know you’re moving in the right direction.”
To overcome those times when she feels the emotional tension build – whether that’s under the big top or beyond – Lockhart reminds herself of four mantras that help her mitigate fear and keep things in perspective:
1. Separate the feeling of fear from the logical assessment of risk.
When she stood there on the trapeze platform, Lockhart’s acrophobia kicked in big time. But the truth is, the instructor attached safety lines to both sides of the harness around her waist, a giant net hung below, and countless people had done exactly what she was about to do, without incident.
Similarly, when she decided to be an entrepreneur, her fears of the startup failing were legitimate. But the risk wasn’t as bad as she thought at the time: She held plenty of jobs in college, including some that required real grunt work. And having graduated with a computer-science degree from Stanford, she would still be a competitive candidate for openings at software firms throughout the valley if her venture flopped.
To learn why you should venture boldly, watch: Taking Smart Risks While Not Following the Same Path.
2. In the moment, success can be indistinguishable from failure.
Before Lockhart’s startup was acquired, it was courted by several companies seeking to beef up their portfolio and services. This was in 2009, at the tail of the Great Recession, when prospects for even the strongest suitors seemed shaky.
In the end, Lockhart and her co-founder went with the company that seemed like the best fit culture-wise, not the one that offered the most money. They weren’t sure they made the right choice at the time. But in hindsight, it’s clear they made a good decision. That company was Box, now a leader in the document-management space.
To hear Jeff Seibert, Lockhart’s co-founder at the time and former senior director of product at Twitter, explain their color-coded decision-making process, watch Look for Culture Fit.
3. Careers are not straight-line sprints.
Lockhart is a visual person and likes to sketch out what’s in her head. And when she charts the trajectory of her career thus far, it isn’t a vertical line representing a succession of promotions stemming from her first job. Instead, her professional path looks more like an ascending staircase, where each step represents a tangential pursuit of a particular aspect of her previous role that excited her more than others.
She calls this “perpendicular career growth,” where you explore an area that you’d like to have a greater specialty in, regardless of what that might mean for your general career path.
“An example might be a product manager who writes a book on the latest effective use of social media, or an engineer who teaches part time at a coding academy,” she explains. “This isn’t part of their job description. It’s not going to get them promoted. But it’s a way for them to use an interest that they have to make a bigger impact on what it is that they’re doing.”
To understand how your career path can take unexpected twists and turns, watch The Clarity Morality Provides.
“There’s a lot that could go wrong here. What if this fails and nobody will hire me afterward? What if I run out of money?”
4. Lastly, realize what learning feels like.
The pursuit of knowledge seems cast in a warm glow, like the low ray of sunset beaming onto the head of a college student reading at a table. But think about it, whether it’s studying for a final, skiing for the first time or figuring out how to work with a new colleague in the office, how does it really feel in the moment – frustrating, confusing or even scary?
“Being able to recognize when that emotional tension is actually learning has helped immensely to shape my journey over the last few years,” Lockhart says. “Take note of what learning feels like, so when you’re feeling it, you know you’re moving in the right direction.”
To appreciate why the angst that accompanies learning is worth it, watch Astro Teller, CEO of Alphabet’s moonshot factory, X, in Pro-Learning, Not Pro-Failure.