5 Lessons Learned From My First 5 Years of Working

Originally published on Medium.

I wish I could tell you that I had strategically charted out my career path from the very beginning—that, upon graduating Stanford, I knew exactly what I wanted to do; managed to successfully maneuver my way into doing it; and am now climbing a perfectly vertical ladder.

But in reality? Nothing could be further than the truth.

Instead of launching myself onto a beautifully straight trajectory, I stumbled and fell and explored and soared—a lot. At my lowest points, I was paralyzed by moments of doubt and insecurity, and the feeling that I’ve somehow utterly failed at life. During my high’s, I felt like I was on top of the world—able to dream and achieve anything I wanted.

There are a million things I’ve learned in the five years I’ve worked since graduating—and a million and one things I’ve yet to discover.

But here are my top 5 lessons:

1. It’s important to know what you’re doing and where you're going—but much more important to know who you are.

At and after Stanford, I’ve always been so focused on “doing.” In many ways, that’s the way American society works—we do and do and do, often to the brink of exhaustion and detriment of our own health. We pair our identities so closely to our jobs, that the loss of the latter so often triggers the loss of the former.

Instead of focusing on building character, we focus on building mirrors. We are constantly obsess with our own reflection, thinking that if we see a failure in the mirror, the world must see one too.

I can’t recall how many times after graduating that I’ve felt this way. No matter how hard I worked, I never felt like it was enough—I could always be doing more, going further, moving faster. In my quest for something to climb, I often felt disenchanted, even when I made it to the next step. Like so many of my peers, I was a hamster on a wheel—except I didn’t even feel like I knew what I was doing half the time. The other half, I was just trying not to fall off.

But in the midst of this chaos, I realized something—I was focusing on the wrong thing. What I do can and will change. But to focus on building character—that’s the most difficult (but rewarding) job of all. I am so far from being the person I want to be in so many ways. However, while careers and circumstances will change, conviction, authenticity and substance will always need to be my guiding compass.

2. The best roads in life are the long, confusing, winding ones you don’t understand until you’re on them.

I love old towns because they’re often filled with winding roads. Unlike the clean, paved roads that make up so many suburban American neighborhoods, these foreign villages are often crisscrossed with paths that are unmarked, unlabeled and simply not straightforward. While walking them, you may stumble upon a delight you didn’t realize existed, or an adventure you didn’t expect. Because of this, I think they’re the best.

Life, in every way, is very much like this — full of twists and turns, and surprises that simultaneously threaten to overwhelm and astonish you. But for some reason, we’re trained, as children, to expect a straight path ahead.

In high school, I was given a simple directive: get good grades, go to a good college and get a good job. That will ensure never-ending happiness, right? It sounds na?ve now, but back then, I truly believed it—perhaps why I found myself disappointed after when I realized there is so much more to life than that.

My career path to date has been anything but straightforward. There have been countless of times when I’ve truly envied some of my peers who went into more structured fields (not to say these paths are easy—quite the contrary!). Instead, I found myself in a variety of roles, companies and locations, exploring many different interests and passions—product design, tech, operations, marketing, growth, public relations and counting.

I don’t regret any of it. Having a diverse set of experiences has given me clarity on what I’m particularly strong at and where I want to go next.

3. The grass is greener where you water it.

Choice. That is something my generation is often said to have plenty of. While we certainly don’t all have access to the same opportunities—unfortunately, the idea of privilege is very real—there are, on the whole, more ways we can choose to live our lives. We can get a full-time job with benefits or freelance. We can marry, date or stay single. We can live in the U.S. or abroad. We can reinvent ourselves constantly, changing our looks, careers and location.

In the early years of my career, I grew enamored with the idea of choice. I fell into the tempting belief that the “grass is always greener on the other side”—when in fact, it truly is green where you water it. How many times have I left a job, only to find that the same problem exists in the one I just took? Or to leave a city to realize that home is a state of mind, not only a physical location?

It’s easy to always seek something new and answer the Siren’s call—without realizing that you’ve just left your steady ship for something that’s simply an illusion.

I’m not perfect—there are still many times when I longingly look at something else, wishing I had it. But now that I’m slightly older, I realize there is something to be said about seeing something through the good and bad, and not shying away from a bit of pain.

4. You should never apologize for being human.

Now, don’t get me wrong—I am completely onboard with being professional. As an employer or employee, you should be on time. Be respectful. Keep your promises. Commit to only what you can deliver. Keep your calm, even in the face of conflict. Etc.

But when did we create a culture in which people always have to apologize for being human? Over the past years, I’ve seen apologies for everything at work—apologies for having a sick child, going on bereavement, not checking email on vacation, feeling ill or not going to an after-work event because of prior family commitments. I, too, have apologized for everything under the sun—including bad weather, bad food and circumstances that were clearly out of my control.

But now, I finally realized — it’s okay to be human and to own your human-ness.

It’s okay to not always be 100% perfect and 500% "on" all the time and 1,000% robotic-like. There will be days when I exceed expectations and days when I need some time to myself—and that’s okay.

Being human is a gift — we should never forget that.

5. Never say never because then, it most definitely will happen.

Growing up, I harbored a lot of “never’s” in my head. I never would live in Silicon Valley. I never was that interested in tech. I never would fall completely in love with New York City. I never would actually get around to pursuing an MBA.

And then—all these things happened. But even more than that, they happened in totally unintentional and surprising ways. Yes, I worked hard, but I found myself learning things I never even knew I could learn.

But all of this reminded me: Oftentimes, the best things in life are the things you really thought would never happen—and then, through some crazed power of the cosmos, they do.

I still have a lot of doubts in my mind. Can I actually become an entrepreneur and start my own company? Can I become the leader I hope to be? Can I make a meaningful impact that will last beyond my lifetime?

All of these dreams will take hard work. But at least, now the “never” is gone. Instead, I say: “Bring it on.”

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Over the past five years, I realized that every individual does have a unique path. There is no “right” answer, and there never was. We are not robots, programmed to only think a certain way or do certain things—but flesh-and-blood humans with ideas that have completely revolutionized the world time-and-time again.

I am more excited than ever to help shape the technological revolution that’s rapidly transforming our lives. But I’m also excited to help keep the humanity in the choices we make.

It’s been five wild, exciting, highly transformative years—and I’m ready for what’s next.