Career Off-Roading: How Not Planning My Future Led Me to Google

I graduated college back when dressing as a Spice Girl constituted a culturally relevant Halloween costume. At the time, it seemed like my friends and I fell into two camps: those who had a career path already paved out for themselves, and me.

I didn’t know what I wanted to do with my English major. I didn’t know where I wanted to be in five years. I wasn’t even sure what I wanted for lunch on any given day. I was completely up in the air while everyone else had hit the ground running.

These days, of course, I’m a real adult — as in, I wear a lot less flannel and gothy eyeliner, I no longer max out my credit cards on frozen pizza bagels, and I’m a functioning member of society with a job.

It’s even a job I really love. I’m the creative lead and content writer of a small team at Google, working on a mobile app.

Most people interpret this as me having my life figured out. After all, no one simply stumbles into a position building products at an influential tech company. You’re supposed to strategize, think things through, and map out each step carefully, right?

But here’s the truth. Between you, me, and the two other people reading this (Hi, Mom and Dad), I didn’t get this position through careful career planning.

Instead, I practiced career off-roading.

Meaning, I somehow missed the clearly laid out highway to success and ended up making a lot of abrupt turns and unplanned detours in my professional life.

Google Maps for Careers(TM) didn’t exist back then.

Just like real off-roading (says the person whose main experience with it is accidentally jumping a curb once), career off-roading can be exciting and fun, but also bumpy, risky, and downright uncomfortable.

And believe me, I know about uncomfortable. I’ve spent most of my working life getting used to the feeling.

Where we’re going, we don’t need roads.” — Doc Brown, 1980’s Philosopher

Before my current job, I spent nearly 15 years in advertising. And it was anything but a smooth time period.

I started looking for my first writing gig right after the dot-com bubble burst, when most ad agencies were busy laying off instead of hiring. After hustling and searching for over a year, I finally found a junior copywriter position. I was ecstatic…until 9 months later, when the agency said, “Whoops, just kidding about that job,” and laid off me and a good chunk of my coworkers.

By 2005, I had a perfectly adequate job writing newspaper ads and radio spots. But, I still felt compelled to pursue a position as an interactive copywriter — or “iCopywriter” as they so quaintly put it back then — at a notoriously tough agency. This was right before digital advertising had really come into its own, so for all I knew I could have been kissing my career goodbye. I was nervous. I knew nothing about this interactive stuff. But I did it anyway.

Fast forward 5 years, to me at an ultra-creative, ultra-competitive advertising boutique. By then, I was a digital-only creative director, and comfortable with that status…until I came into work way too early one morning. Since I was the only one around, the CCO asked me to write some TV spots for a major client meeting happening in an hour. I was terrified. But I did it anyway, mainly because I had no choice.

Did I write awe-inspiring works of genius? Of course not. But the experience built my confidence, and for the rest of my ad career I bounced between digital and traditional projects.

I could go on and on describing bumpy moments like these, but it’s probably enough to say that sticking to set career plans was never my forte.

Wheeeee! My advertising career!

Even so, I was unprepared for the moment an ex-coworker contacted me and said his team at Google had an open position that he felt suited me. I agreed to come in and meet the team, and was immediately impressed by their passion, innovative ideas, and ambition to create something from the ground up. But, I also quickly realized that this job would require me to walk away from advertising, develop an entirely new set of skills, and go fully off-road instead of merely flirting with small lane changes.

How could I possibly be considering this? I wasn’t some girl who just graduated college and needed a brand-new career.

That’s what my brain said to me, at least. Screamed at me, actually. It reminded me that, while this may be a dream job for anyone who can actually pay attention in a meeting for longer than five minutes, for me it seemed liked an odd, potentially disastrous fit.

As my brain rationally explained all of this to me, every other part of me took over and said, “Shut up. You know you’re taking this job.”

So, having no clue about product development nor how I’d survive as an emo creative type at a tech company, I turned the wheel and careened off my old career path. And somehow, it’s worked out.

Obviously, I’m not recommending anyone abruptly quit their jobs, face the great unknown, and yell, “Come at me, bro!” I’m also clearly glossing over all the hard work, tough interviews, and challenging situations I went through. But I believe continually changing course and not mapping out my career’s future has actually helped me build a particular set of survival skills.

1. It made me open to all the possibilities happening around me. If I had a concrete plan to only be a traditional copywriter, or a digital one, or to only work in advertising, I might have missed out on all the opportunities that came my way over the years. I’d only be willing to look at the ones that fit my very rigid end goal. Now I know my next good move can come from anywhere — whether that’s in tech, back in advertising, or in an industry or avenue I never considered before.
2. It taught me to rely on my instincts. If my future is already plotted out, every move I make needs to be justified, rationalized, and part of a larger strategy. But without any of that pressure on me, I can silence all the external noise and give my instincts a chance to take over. I’ll know when an opportunity is good because it just feels right. And I’ll also know when an opportunity isn’t good because something feels off about it.
3. I learned to adapt quickly and think on my feet. Because my career isn’t set in stone, it could change at any moment. If I only knew one way to be (I’m an advertising person only, I only do TV spots not apps, and so forth), I wouldn’t last very long. So I’m always ready to quickly evolve my skills and working style for different types of jobs, environments, and business needs.
4. I’ve trained myself to recover quickly. Some career changes I make happen, but others happen to me. Layoffs, failed projects, and other career trials are inevitable. However, learning to adapt quickly also helped me figure out how to bounce back fast. The more time I spend whining, feeling sorry for myself, and licking my wounds, the more I’m missing out on all the new opportunities coming at me.
5. I lost “the fear.” The fear of change. The fear of messing up my life with one career decision. The fear of what other people think. The fear of getting fired. The fear that I’m making a huge mistake. The fear of dying alone while whispering, “Rosebud.” All of these anxieties have gone away — or at least become much less overwhelming — because I know I can’t ruin a future I haven’t decided on yet.

Looking back, it’s funny to think about how much fear ruled me when I was fresh out of college. Because when you think about it, I’m still a little bit like that girl. I’m still figuring things out. I’m still not entirely sure what my next move is. I still have no idea where I want to be in five years.

How exciting is that?