Choose your own adventure in Silicon Valley

In 2013, I spoke at SheCodes, a conference for women in technology held in Silicon Valley. Many of the attendees were recent college graduates or in the early stages of their tech careers. This is the talk I gave.


The story of a career path isn’t just a resume that lists out companies and positions and dates. It’s also about the transitions. Those major forks in the road that force us to make a choice on which direction to go next. They emerge from time to time, and sometimes catch us off guard. That’s certainly true here in Silicon Valley, where we have a high concentration of people working in the same industry, moving fast, taking risks, and innovating.

Today, I’d like to offer up my own career path as a case study in transitions. I’ll be doing a reading of a Choose Your Own Adventure style story I’ve written about my professional journey in Silicon Valley.

For those who don’t know, Choose Your Own Adventure is a series of children’s books where you assume the role of protagonist and get to make choices at key points throughout the story.

Let’s begin!

Chapter 1

It’s 1991. Six months ago, you graduated from Carnegie Mellon with a B.S. in Technical Writing, moved to Silicon Valley, and started your first job: writing user manuals at IBM. It’s the middle of a recession and you feel lucky to have a job at all. But it’s a mixed bag.

My business card, 1991

On the plus side, you have your very own office, which your mom keeps telling you is highly unusual for an entry level employee. You like your coworkers and the benefits are good. The hours are sane.

On the minus side, you’re just not that excited about the work. Rather than explaining how to set up complicated enterprise databases, you wish you could make them less complicated in the first place. You want to be a user interface designer, and use multimedia to make software fun and engaging. You’re not at the right place to do that.

What do you do?

A. Focus all your energies on quickly finding a new company and job that you’re passionate about.

B. Stay at IBM and look for things to do that relate to your longer term career goals.

I chose B. Let’s see what happens next.

Chapter 2

IBM is not where you want to be forever, but you’re staying put for now. Leaving your very first job after only six months won’t look good to prospective employers. And good luck finding them — very few companies are making the kind of software you’d like to design, and the ones that do want people with experience. So you focus on what you can do to make your current situation better over the next couple of years.

One thing you do is make friends with the Human Factors department where the usability professionals are and volunteer your writing skills. You write specs for the UI designs they produce. You copy edit all of the user-facing error messages in the software.

Second, you start taking video production classes on the weekends — reimbursed by the company — and that leads to a work assignment to create an instructional video.

Before you know it, you’ve been at IBM for two years and have more relevant experience under your belt. So you decide to start looking for your next job.

It takes nine months but you finally get an offer as an associate producer at a small multimedia agency in San Mateo. You wouldn’t be a UI designer, but you would be working directly in multimedia, on interactive CD-ROMs.

What do you do?

A. Take the new job.

B. Keep looking for a UI design position.

I chose A. Let’s see what happens next.

Chapter 3

The new job is awesome! It’s a small company — just 50 people — so it’s way different than IBM. You can wear jeans and T-shirts to work, and you have beer bashes every Friday!

You’re responsible for managing all aspects of a project: schedules, budgets, project assets, resource allocations, client relationships.

My business card, 1994

The work seems to be a really good fit with your ability to organize, and you’re gaining confidence in dealing with important clients like Apple and FedEx, and leading cross-functional teams without authority.

You also learn that technical writing is a highly transferable skill. You use it all the time to write release notes, client memos, and once again, UI specs. It’s more stressful and more hours, but also more rewarding.

After a year, you get promoted to Producer. Now you’re training and mentoring associate producers. And then one day in May 1995, something surprising happens.

America Online (as it was called back then) acquires your company. The stock options are generous, and everyone’s excited about the possibility of becoming fabulously wealthy, because AOL is doing very well. But work-wise it’s a bit of an adjustment.

My business card, 1995

Just when you were getting really comfortable in your role, everything changes. Your projects and clients are eventually phased out. AOL sites aren’t as interesting to produce as CD-ROMs. You miss the old days.

But it’s the #1 consumer technology company, and you think one day the country might be spending as much time on AOL as they do watching TV.

What do you do?

A. Pursue a transfer to AOL headquarters near Washington, D.C. and hope you’ll be happier there.

B. Find a better place for yourself among the many choices in Silicon Valley.

I chose A. Let’s see what happens next.

Chapter 4

You’ve got mail! And you’ve got golden handcuffs.

There’s enough at stake that you’re willing to relocate to stay at AOL. So you start talking to contacts at headquarters. You make good progress. You start telling your friends in D.C. that you’ll be moving there soon.

And then two weeks before Thanksgiving in 1996, you fall victim to AOL’s very first round of layoffs. 300 people. No one saw it coming. You’re shocked. You’re hurt.

What do you do?

A. Take full advantage of the outplacement services and land a new job before the end of your severance pay.

B. Apply to graduate school. After six years, you're ready for a break from working.

I chose B. Let’s see what happens next.

Chapter 5

AOL did not make you fabulously wealthy after all, but you can pay for graduate school. Harvard has a master’s program in educational technology that appeals to you. You would love to design high-tech tools for learning. So you spend all of December getting your application together.

Next, you teach yourself HTML and look for contract work at one of the many dot coms cropping up in the area. You reach out to your professional network, which is difficult because LinkedIn hasn’t been invented yet.

One of the better known dot coms in the valley is Netscape. AOL hasn’t bought it yet — that’ll happen in a couple of years. A former coworker is there and helps you land a contract for 10 hours a week as a web producer.

Once you get your foot in the door, you see there’s tons of stuff going on, and it becomes very easy to grow your assignment into 40 hours a week. Especially when you let them know that you have a writing background in addition to producing.

The editor of the Netscape home page has gone on a six-week leave, and they ask you fill in for her. So for a short time in 1997, you’re responsible for what gets seen daily on the most visited page on the World Wide Web.

And more good news: you get into the program at Harvard, and at the end of the summer, you leave Silicon Valley for grad school.

Fast forward a few years

After earning your master’s degree, you talk to some educational software companies in Boston and New York, but you decide it’s too big a step backwards in salary.

So you move back to Silicon Valley and in 1999 become employee #9 at a startup that will remain nameless.

Chapter 6

It’s 2001, and you’ve been at the startup for two years. You’re Executive Producer, a fancy title for a role that combines project management, UI design, and content production.

One day, the CEO calls everyone into the conference room. After two rounds of layoffs, this can’t be good. It’s amazing how quickly things have turned: 150 employees at the beginning of the year, now down to 50 in July. Morale is at an all time low.

But a new job is hard to come by these days. In fact, some friends of yours have made the national news for organizing daily outings for young adults who are out of work in Silicon Valley. They call it Recession Camp.

In the conference room, the CEO announces that for the next six days, everyone will be working for minimum wage. Then after that, everyone will be taking three weeks of mandatory vacation. If you don’t have enough to cover it, you’ll be taking some days without pay. During that time, the company will be seeking another round of funding to stay afloat.

And there’s more: the company is asking everyone to come in and volunteer for free during mandatory vacation. Each employee has to fill out a form stating that they understand everything that’s just been explained, with a checkbox to check if they plan to volunteer. Everyone on your team has checked the box.

What do you do?

A. Check that box and volunteer. Be a team player and help the startup in its time of need.

B. Buck the trend and use your mandatory vacation as focused time for a job search.

I chose B. Let’s see what happens next.

Chapter 7

In late July, 2001, you get a phone call from your boss. Tomorrow the company is shutting down, and there will be a meeting at 9 am. You tell her, “Sorry, I can’t make it. I have a job interview.”

Two weeks later, you land your dream job: UI designer at TiVo.

My business card, 2001, front and back

You can’t believe all those hours of watching TV all your life have finally paid off! Of course, it was your other qualifications too, but you’re still pinching yourself.

Once again, you discover that technical writing is a transferrable skill. You’re writing UI specs again, this time for designs that you created. You also learn that your producer skills come in handy — you’re bringing more formality to the design process, and your efforts are appreciated. All that, plus you’re finally focusing your career on UI design and growing your skills in that area, learning from smart colleagues.

For four and a half years, you’re in a state of Flow, the term coined by that psychologist whose name you can’t pronounce. Basically, it means you’re fully immersed, fully energized, and loving what you’re doing.

And then one day, you get a call from a recruiter.

He’s with a public company that’s been in the news non-stop for the past couple of years. About 5,000 employees. You use their product everyday, many times a day, and it makes your life better. Same with everyone else you know.

You can’t imagine ever leaving TiVo, but you have to admit you’re curious about this other place. So you interview and get an offer to join their user experience team.

What do you do?

A. Accept the offer.

B. Stay at TiVo.

I chose A. Let’s see what happens next.

Chapter 8

Well, it turned out to be that classic choice of big fish in a small pond, or small fish in a big pond with free gourmet meals.

My business card, 2005

Moving from TiVo to Google feels like moving from a small town to the big city. And like any big city, it takes a while to figure out how to get around and feel at home.

You always knew that the role of UI designer can vary from company to company. At TiVo, you focused on interaction design: flowcharts, wireframes, and specs. Other designers handled the visual design: colors, branding, typography, and the delivery of pixel perfect layouts.

But at Google, you’re doing both interaction and visual design for your project. But mostly visual design, given the nature of the websites you work on.

It doesn’t take long for you to figure out that you enjoyed your day to day responsibilities at TiVo more than at Google. Your former VP at TiVo has approached you about returning.

But you love Google as a company and you’re excited about its future. And over the past 18 months, you’ve taken notice of another role at Google that you might be partially suited for: product manager. Your producer background is relevant. And so is your design background, because Google PMs sometimes do the interaction design work you’re skilled at. But you don’t have the prerequisite Computer Science degree.

What do you do?

A. Return to the job you loved so much at TiVo.

B. Pursue a transfer to Product Management at Google.

I chose B. Let’s see what happens next.

Chapter 9

Although you lack a CS degree, you believe you’d make up for it in other ways. You know from experience that your prior skills always come in handy when you switch careers.

Before you officially apply for a transfer, you make sure that the VP of Product would support you joining her organization, and line up internal references.

The interviews are tough. You know it’s a stretch. But you get the job. The experience reminds you that exceptions can be made, and it never hurts to ask.

My business card, 2007

As expected, you’re able to leverage your design and producer skills. But there are many other aspects to the job that are completely new to you and you’re feeling totally out of your comfort zone.

You work very hard, learn a lot, and do fine, but after three years your gut tells you that you’re never going to be a rockstar PM. You’re exhausted and miss the state of Flow that comes from immersing yourself in a design challenge.

Around that time, you find out about a UX opening at a startup. Their three-person interaction design team is made up entirely of former TiVo designers. They’re creating a pen-based tablet for college students. A chance to be a designer again and work on educational technology, but it would mean leaving Google. And you swore you’d never return to a startup after that last one.

What do you do?

A. Leave Google and join the startup.

B. Stay at Google and transfer back to a design role.

I chose A. Let’s see what happens next.

Chapter 10

You part with Google on good terms, letting them know you appreciated the opportunity to give product management a try. Now you’re happy to be designing again full time in a role that feels more like TiVo.

The startup is young and hungry, so everyone’s working long hours, including weekends. Not ideal, but you won’t be doing that forever — just until the product is launched.

Nine months go by and then one day, everyone is called into the conference room.

The startup has decided to sell the hardware portion of the business and focus solely on software for existing platforms. You get why the decision was made, but you came here because you were intrigued by the possibilities of the hardware. So this is a huge disappointment.

But if you leave before a year, you’ll have no stock options. And that hefty signing bonus you got? You’ll have to pay it all back.

What do you do?

A. Stay four more months until your one-year anniversary. You worked hard, so don’t leave money on the table.

B. Find another job ASAP. Being engaged in your work is more important.

I chose B. Let’s see what happens.

Chapter 11

It’s early 2011 and interaction designers have never been more in demand. When you’re not at the office, you’re immersed in your job search. You’ve talked to a dozen companies of all sizes. The choices are overwhelming.

Eventually, you decide you’re not going to another startup. You need work/life balance. And after your three-year design hiatus at Google, you want more recent projects for your portfolio. You risk having nothing to show for your efforts if the next startup pivots or folds.

So you target established consumer technology companies with a presence in Silicon Valley. Google is one of them, of course. And since you enjoy designing for consumer devices, maybe Android would be a good place for you.

One appeal of returning to Google is you wouldn’t be starting from scratch. You already know hundreds of people and the company’s culture. Also, rehires get to accrue vacation at the rate they were before. That would help your work/life balance.

But you’re not going to officially apply unless you’re sure you’d actually go back. You didn’t burn bridges before, and you don’t want to now. A few of your favorite designers from over the years are now working on Android. You schedule an informal lunch with them. Afterwards, you feel pretty confident that this would be a good fit. So for the third time in your life, you go through the Google interview process. You get the job.

You resign from the startup two months shy of your one-year anniversary and take a few weeks off to recharge before joining Android.

I still haven’t gotten around to ordering business cards, but I never miss an opportunity to get new work swag, like this Squishable Android.

Your prior Google experience helps you ramp up quickly. And once again, you’re able to put all of your skills to use: not just interaction design, but writing and project management too. Your impact is broader than ever: you’re not only designing for Android, you’re teaching others how to do it.

You finally found your place at Google. After six combined years there, you get your first promotion: the difficult jump from senior to staff designer. People start coming to you for career advice. You help them with their self assessments. You talk to them about what it was like to switch careers at Google.

One day in 2012, your manager tells you about plans to significantly grow the size of the design team. He asks you if you’d be interested in taking on a manager role.

There it is, another fork in the road. This one you’re happy to see, and you feel ready for it. You say yes and begin a new chapter.

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