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5 Things I Wish I’d Known Before I Landed My First Tech Job


One of the benefits of being 20 years into a tech career, mostly in Silicon Valley, is looking back at your individual history, studying the data, connecting the dots and telling a story that helps others on the same path.

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And while I’ve always looked at my career as an adventure full of opportunities to learn and explore, there are a handful of things I wish I’d known before I started my first tech gig.

1. Never underestimate your liberal arts education.

I studied history and diplomacy as an undergrad at Georgetown University, prior to getting my MBA from Duke University. I remember my family saying, “What are you going to do with that degree?” Truth was I saw myself as an international lawyer, jetting between New York and Paris. But, then I fell in love with technology. Instead of switching majors, I chose to cultivate a deep understanding of human nature and the art of negotiation. I was also flexing and toning my critical thinking muscles. What I couldn’t know was how much I’d use these skills, that I’d draw on this early training every single day of my professional life.

For example, after graduation I landed my first tech job at Gateway Japan. We were creating a way for bankers, academics and journalists to access information online, on a computer. We encountered so much resistance from our best clients. One even told me, “I’d rather thumb through a stack of academic journals to find an article than type words into a box on a screen.”

Humans are, by nature, resistant to change. I knew that from years of dissecting the past. So, I began piecing together historical bits of data, drawing conclusions and using storytelling — like any great historian — to help our clients understand the value of the change, or why they needed our product — and it worked!

2. Your best customers today will be the most resistant to change tomorrow.

I was still wearing my historian-critical-thinking cap when I moved on to Intuit. Almost immediately, I was met with that familiar resistance to change when we attempted to migrate accountants from their legacy accounting practices to our newer software solution.

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Instead of spending all our time trying to force change, we began marketing our new technology to new and forward thinking accountants. We focused on the change that would disrupt our business and their practices tomorrow. We didn’t lose sight of our best customers in the process; we just went forward cultivating new ones who were more receptive — at the time — and then created a migration path for those who would come around eventually.

3. It’s easier to tap into a consumer’s natural behavior than to force a 180.

Years ago, when I used Pinterest for the first time, I was blown away. It nailed the idea that it’s natural for people to pin things they’re interested in on a board. It didn’t create an entirely new way to save snippets of recipes and DIY projects. It took a known behavior, applied it to the digital world and grew dramatically as a result.

This is also why so many electric car makers kept the ignition key concept intact, even though that’s not how an electric car even starts. Tapping into existing consumer behavior to make new technology easier to adopt is critical. And, if there’s no existing behavior, build education, training or intuitive features (like swiping and scrolling on your phone) to make your new technology easy to adopt.

4. You have to create space for serendipity and then be receptive to it. 

As a Type A, results-oriented person, it was easy early in my career to focus on the punch list and, as I like to say, “GSD.” But, I’ve learned time and again that it’s just as important to take a break, step away from the project and interact with colleagues, customers and even people in different industries. These serendipitous moments can lead to creative breakthroughs and major bouts of inspiration, even if they take place during a walking one-on-one or standing in line. You never know when the magic is going to happen.

Early in my career at Intuit, while chatting over coffee, I casually asked a colleague, “What are you working on?” This was one of those pivotal points. He went on to tell me about a “top delighter project” that was consuming him. By the time we’d finished our coffee, we’d worked out the solution for migrating hundreds of thousands of customers to the new product I was launching. The moral of this story: Always be open to “chance encounters.”

Related: How to Become a Millionaire by Age 30

5. Flexibility is the new stability.

At Lyft, I often talked about how dynamic the ride sharing space was — and how it was driving extraordinary behavior change and disruption. Embracing that energy and harnessing it for our passengers, drivers and the business was critical.

Now, as CEO of Art.com, this is even more true as we build on our 18-year legacy. There’s no playbook for most of what we’re doing as we bring technology to bear on problems old and new. We’re creating solutions on the fly, innovating more deeply and making it easier for customers to express themselves. The pace of change is off the charts, but we’re in lock step.

Hindsight is 20/20, right? Collectively, we’re moving forward at warp speed in the tech space. But, maybe a look back, like this, can help change the course of your history.



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