Thank you!

Graduation season is upon us, along with its signature mixture of excitement, relief, nostalgia, hope and anticipation for the future. (And speeches. Plenty of speeches.)

No matter where you are in the journey of a career, graduation season can serve as a career maintenance checkpoint, an opportunity to reflect on progress, remind yourself of valuable lessons and recommit to your most ambitious aspirations. It's a time to revisit the big questions that reoccur at every professional turn and transition, that new grads are just confronting: What lies ahead for me? How do I construct my career with purpose and define success on my own terms?

But while graduation season raises these questions about personal development for new grads and seasoned operators alike, the speeches often fall short of substantive answers. They impart lofty aphorisms, like “Do what you love” or “Follow your dreams” — messages that are loaded with inspiration but lacking in practical follow-through.

Here at the Review, we’ve been fortunate enough to speak with leaders whose advice goes deeper, whose tested tips can help you lay the tactical groundwork to chart your course. As we pored through their insights, we found one common thread: While there’s no one “right” way to forge a meaningful career, there are a lot of actions you can take right now to bring yourself one step closer to defining and reaching your goals.

In this roundup, we’ve gathered the principles and practices that have powered the careers of Silicon Valley’s best operators. We start out with big-picture thinking on defining and building a fulfilling career, then move into more tactical tips, like finding a mentor and taking charge during conversations with your manager. Whether you’re fresh out of the collegiate gate or on the cusp of another chapter in your career, we hope this advice helps you feel a little more confident as you embark on these next, brave steps.

1. Picture your career as a painting, not a ladder.

Zainab Ghadiyali’s story might sound familiar to recent graduates: Long before she rose up the engineering ranks at Facebook, became a Product Lead at Airbnb, and co-founded Wogrammer, she was a college senior — unsure of her path, graduating straight into an economic recession.

“During my senior year, I applied to over 200 jobs and got rejected everywhere,” she says.

When career growth is often presented as a straight, upward line, Ghadiyali’s story makes the case for another kind of career design: one that doesn’t follow a progression of titles, but rather chases after the call of curiosity. Ghadiyali’s circuitous path to Silicon Valley ended up imparting valuable lessons about the benefits of forging an unconventional career path.

Without a clear next rung to place her foot on, Ghadiyali set off in different directions to hone in on an interest in healthcare. She left the U.S. to work for the public health nonprofit the Foundation for International Medical Relief of Children, which took her to far-flung villages in India and South America. After close to a year, she decided to go back to the U.S. for grad school, to study health economics. Once there, she would eventually (and quite accidentally) wander into the hackathon that would lead her to interview with Facebook.

On paper, Ghadiyali’s moves after college might seem like a series of missteps leading her astray from her eventual path to tech. But by drawing excitement and curiosity as a throughline, the connections between apparently erratic transitions begin to emerge. That’s why Ghadiyali encourages people to instead think of their careers as a work of art.

“When you look at a painting from a distance, you see a larger, cohesive picture,” she says. “But as you approach the canvas, you see that there are, in fact, hundreds of separate strokes that make up that picture. Think about your career as a work of art — expansive, independent movements that incrementally reveal a whole.”

When we visualize a career ladder, we start putting ourselves in a box. Step back and see the painting — every experience adds a brushstroke to a bigger picture.

From early years traversing the globe, to her touchdown in Silicon Valley, Ghadiyali’s meandering journey recalls a line from Steve Jobs’s now-storied 2005 Stanford commencement address: “You can’t connect the dots looking forward. You can only connect them looking backwards. You have to trust that the dots will somehow connect in your future.” By centering curiosity, anyone can apply her takeaways to design a career that’s unique — and most of all, meaningful — to them.

Personal happiness and fulfillment aren’t the only benefits of taking the career path less traveled. As Ghadiyali notes, if you design your professional transitions around inquisitiveness, adaptability, and investing in a diverse set of skills, you can effectively future-proof your career.

“There’s no doubt that technology is changing the nature of jobs,” Ghadiyali says. “The jobs that will be even more valuable in the future will require a high level of creative problem-solving, empathy, communication and influence. Those are the qualities that we won’t successfully be able to train computers to do for a long time. That’s what will make you invaluable, no matter where you go, and always.”

To the young grad just starting out, here’s what I’d say: Don’t worry too much about building a resume. Focus on building your repertoire of skills, and most of all, on creating a really great life.

Read about Zainab Ghadiyali’s lessons from her circuitous path to Silicon Valley.

2. Nurture your rookie spirit. It will serve you for your entire career.

When you have fewer bullet points on your resume than everyone in the room, it’s easy to feel daunted. But don’t be discouraged by inexperience — executive advisor and bestselling author Liz Wiseman makes the case that as a rookie, you have more to bring to the table than you think. (And even for those who are further along, revisiting the rookie mindset provides a powerful perspective reset.)

In 1990, Wiseman was promoted to manage the training department of her first job out of business school, at a mid-sized startup called Oracle. She was 24 years old. “I didn’t really know what I was doing. All I knew was that this was a grown-up job and I wasn’t quite grown up yet, but no one seemed to be bothered by that but me,” says Wiseman. “My real value didn’t come from having fresh ideas. It was having no ideas at all. When you know nothing, you’re forced to create something.”

Since her early days at Oracle, Wiseman has dug even deeper into the powers of the rookie mindset. While researching her book Rookie Smarts, she studied how inexperienced people handled tasks, then compared their performance to people who have been doing them for some time. Here’s what she found:

Experience creates blind spots and scars. “With time, we obviously gain knowledge, wisdom and more data points to inform our power of intuition. We build confidence and networks, but we're also creating blind spots,” Wiseman says. When your mind recognizes a pattern, it tends to stop innovating, and to reach for what it already knows. “We stop seeing new data points or contrary points of view.”

Furthermore, the more experience you gain, the more likely you'll have some bad experiences that will continually remind you of your mistakes. “I have a whole set of scars that remind me not to do things that didn't seem to work out well the first time,” Wiseman says. “Sometimes those scars are valuable lessons learned. But other times, they keep you from taking risks.”

Experience can fuel fear. “If you envision a really steep learning curve, it starts in a phase of ignorance, this really gentle part of the curve. This is where, even when we're given important and hard tasks, we can say to ourselves, 'How hard can this be? I can do that,'” says Wiseman. “It's only when we start to dig in and become more aware that we realize how hard something is. As we gain more experience and familiarity, we start seeing the gap between what we can do and what the people around us can do. We start to panic.”

The most powerful form of learning comes when we're desperate. When we have no choice but to learn.

“Where rookies really outperform is when the work is innovative in nature,” she says. “Rookies learn a lot faster than people with experience because they are desperate and uncomfortable. When we get comfortable, that's when we start to teach and mentor other people.” But it's also where people slow down and stop contributing as much.

But you don’t have to lose your rookie luster over time. “As I looked at top performing rookies, I found this really interesting type of person: the perpetual rookie. These are people who are successful professionals, leaders, entrepreneurs with years of mastery who, despite that, maintain their rookie smarts — their ability to think and approach their work as if they were doing it for the first time,” says Wiseman. As she investigated the attributes of perpetual rookies, Wiseman identified several traits they have in common:

So how do you gain the valuable insights of experience, while keeping your rookie smarts? It’s all about consciously cultivating your perspective. Wiseman spoke with Bob Hurley, founder of the surf company Hurley, which eventually sold to Nike. “He said that at every juncture of building his business he had no idea what he was doing, and it turned out to be an advantage,” she says.

When Hurley finds himself stuck in a rut, he thinks back to something that happened many years ago, when he was hitting the waves at Huntington Beach. He ran into Wayne Bartholomew, the reigning world champion surfer at the time, who said he preferred surfing with beginners because they gave him energy. “So Bob told me, 'Now when I have bad days, I go out and surf with the amateurs,'" Wiseman says. "He spends his time talking to them, hanging out with them, and he says it revitalizes his point of view.”

Read more of Wiseman’s research on how you can execute like a rookie, at every point in your career.

3. When you make tenacity a part of your identity, it can help you tune out the naysayers.

If you have an ambitious idea, it can be hard to know how and whether to act on it. And while graduates receive plenty of advice on pursuing passions, that well-intentioned counsel often falls short of tactical steps, failing to help grads connect the dots between where they are and where they strive to be.

Dennis Crowley is here to make “Follow your dreams” more concrete — and he discusses the one career principle he drew on to turn his aspirations into action.

Since he was in grad school, Crowley had been grappling with one big idea: a product that understands how users move through the world so well, it can deliver timely, personalized tips. It took over a decade to make the idea a reality. (Today, that reality is called Foursquare.) So what helped Crowley persevere over ten years and numerous hurdles? He chalks it up to tenacity.

The germ of tenacity, he explains, can be as much about a great idea as one’s self-identification with it. “Sometimes you just have to build it to prove to yourself that it works or doesn't. It’s as much about if and why it works, as your agency in it,” says Crowley.

His first experiment, Dodgeball, was initially just a city guide, where users could write reviews of places they’d been. This was around 2000; the guide wasn’t mobile, and crowdsourced content was still relatively unheard of. In fact, everyone in the space told him it couldn’t work. “People said it's a bad idea,” says Crowley. “I lulled myself into thinking the same. So we didn't build it.”

So what changed? Quite simply, this product was something Crowley himself wanted to use. The idea stuck in his mind, needling him, and he had to see if it could work. “To build it was almost like fulfilling a need to express myself. So that was the project I learned how to code for. I taught myself out of one of those big ‘Learn to Code in 30 Days’ books,” he says. “Personally, it was fulfilling. Externally, it wasn't a huge success. A couple of thousand people used it.”

But it laid the groundwork for Dodgeball Version 2.0, the prevailing version when Crowley founded a company by the same name in 2004. “I was on the product and engineering team of Vindigo at the time, and we would say, ‘Wouldn't it be crazy if you could see where all of your friends had been? You wouldn’t have to read the reviews — you could just go to the places they’d been.’"

Again there were naysayers, and again Crowley knew he needed to see if it could be done the way he would do it — and if anyone else wanted to use it. “I wanted this thing to exist. I thought, ‘It doesn’t seem like anyone else is going to build this, so I’ll go build it.’”

If after several turns in your career and life, you return to the same idea, pursue it. Your creation is as much an act of self-expression at that point.

Around that time, as fate would have it, Crowley and several of his friends were laid off. “We were trying to find each other around the city,” he said. They had a need, and the time and skillset to meet it. “We wanted a way that you could just check in at an East Village bar and that's how you would know to go find someone. Looking back the idea was there, we just needed a community to form around it.”

Dodgeball introduced the world to the concept of “checking in,” and it turned out, lots of other people wanted it. “I thought, ‘If only ten of my friends use this, it's fine because it helped us.’ We found that if you can build something that you're interested in and your ten friends are really into, there's a good chance that their ten friends will be into it, and their friends as well,” says Crowley. “My lesson is that you’ll need more than yourself eventually, but not much more. Don’t give up until you can go after it with at least ten friends.”

Read more of Crowley’s takeaways on tenacity here.

4. Before you reach out to a potential mentor, be specific about what you want out of mentorship.

You’ve probably heard a lot about the benefits of mentorship, the not-so-secret ingredient to a successful career. But the process of actually procuring a mentor can feel more inscrutable.

Luckily, First Round’s own Whitnie Narcisse has distilled mentorship down to a science. After studying 100 mentor-mentee matches in First Round’s Mentorship Program, and she’s extracted the best advice for people starting to search for and build relationships with mentors.

Whitnie Narcisse at the First Round office.

Her first tip: When it comes to reaching out to potential mentors, don’t say the word “mentor.” Because the word can be so loaded with pressure, nearly all of the mentors that Low surveyed identified the use of the word as the number one reason they were disinclined to talk to someone.

Instead of asking “Will you be my mentor?”, try this email template:

Hi, I’m trying to get through [XYZ specific situation or challenge]. I’ve heard from several people, [names of respected mutual connections here], that you might be able to provide some insight or direction in this area. Might you have time to meet for 30 minutes over coffee?

Throwing out the shorter slot demonstrates sensitivity to their busy schedule, and that you won’t waste their time. If the conversation is good, it’ll last longer than 30 minutes or lead to follow-up conversations. And always buy them coffee.

You’re going to get someone to take you more seriously if you can be really granular about what you want to accomplish — it makes them feel like they have exceptional expertise and are being proactively sought out, says Narcisse. Steer clear of broad requests like, “I’m looking for direction in my career…” but don’t get too surgical either, i.e. “I want introductions to these five people…”

You want to be very clear and explicit about why you targeted this person. Do enough homework to briefly explain why you’re looking for guidance relevant to their experience. That way, you don’t have to use the word “mentor.” Instead, you're inviting them to apply their considerable knowledge on something they’ll find intellectually engaging and impactful. That’s how people want to feel — not that they’re taking on an additional obligation.

A mentorship relationship should be mutually beneficial. As you get to know your potential mentor, start to evaluate whether this person is a good fit for your growth.

The ideal experience gap is 5-10 years. That far out, the mentor is experienced but can still remember what it felt like to be in their mentee’s shoes.

To make sure you’re both investing time and energy into a productive match, ask yourself these questions:

Finally, don’t limit yourself to just one mentor. It’s important to have a number of perspectives to bring to bear on the biggest challenges you face. You might not have full-on mentorship engagements going with a handful of people, but it’s good, as a mentee, to have two to three other seasoned operators in your life to consult. You want to socialize important questions, collect responses, and then triage.

You might call this your Personal Board of Directors, and consider treating these relationships the way a company might interact with its board. Narcisse built a personal board of directors for herself over the last several years, and it’s become a major source of insight and strength in her career.

The handy thing is that you can ask your primary mentor for introductions to others in their network who might be able to illuminate different topics, angles or solutions for you. For example, one mentee had three areas she wanted to tackle with her mentor, and one was management. Instead of trying to offer advice himself (as a relatively new manager), he introduced her to a woman who was a tier of leadership above him to provide greater perspective.

“Everyone has blind spots, not just those who are less experienced,” says one mentor. “I always ask my mentees to have a couple other mentors who specialize in areas where they need to succeed but where I’m weak. I also have a list of 4-5 folks who I always recommend. It’s also a good idea to ask several mentors the same question to hone in on the right answer or you.”

Read more of Whitnie Narcisse’s advice on what makes mentorship work.

5. Take ownership of your career by proactively managing your manager.

For many, graduation means swapping grades for 1:1s, 90-day check-ins and the all-important performance review. At first, you might be tempted to let your manager take the lead on these meetings. But at the end of the day, those conversations are meant to serve your growth, and you should feel empowered to proactively shape the conversation.

Russ Laraway has made a career of helping managers and direct reports generate regular, meaningful dialogues that help talent (that’s you) feel supported. Many people, especially young people, experience what Laraway calls “the ants-in-the-pants” feeling of wanting to get promoted or leave the company. “People are often surprised, though, that they can grow toward their dreams and stay put in their current role. That’s why it’s so helpful to have regular career conversations that take into account both your short and long-term plans,” he says.

Laraway designed a framework for career conversations around three key components of a career path, to help direct reports solidify their career goals and managers better support their direct reports. While his framework was originally written for the manager’s perspective, we think there’s power in flipping the script and viewing his framework as a tool for managing up — advocating for yourself and ensuring that you have the career conversations with your manager that you need to advance.

To that end, we’ve adapted his advice for you, the direct report. A brief note from us: If your manager already follows a similar framework, that’s excellent. If she doesn’t, find ways to raise these topics of conversation with her at your next 1:1. At the very least, take the time to reflect on these questions and articulate your goals to yourself.

Here’s Laraway’s framework on the three career conversations you must have with your manager, adapted for direct reports:

1. Discuss your key motivators.

Once you feel that you and your manager share rapport, open up to your manager about what you value and what drives you.

Laraway recalls a conversation he had with a direct report, who shared with him why she switched from cheerleading to swimming while she was in high school. She said that when she swam, she felt gratified seeing her lap time diminish with every practice. “It became clear that she deeply valued hard work leading to tangible outcomes,” says Laraway. “It established for us a shared, textured understanding of what she cared about, what brought her to this point and what I, as a manager, could do to make sure that she was still feeling motivated.”

2. Share your lighthouse and put it into focus.

“You might think that you don’t know what you want to be when you ‘grow up.’ That’s a common apprehension,” says Laraway. “But I’ve never had a person who couldn’t tell me about their dreams.”

Start by visualizing your dreams to yourself. “None of it should be time-bound — no 10-year plans. What would you be doing at the pinnacle of your career, when you’re feeling challenged, engaged and not wanting anything else?”

That’s vision is your lighthouse, blurry and fuzzy in the distance. “Now what a manager is really useful for is helping you bring that lighthouse into focus. We want to see the paint chips. We want to see the red tiles on top. We want to see the seagull perched on it. So in order to get that level of clarity, we've got to ask a few more questions,” Laraway says.

He suggests that managers and direct reports go through these three questions for focusing the vision, only after you both understand the dream:

Laraway shares the story of an employee, Jane, who articulated this lighthouse: To own and operate her own spirulina farm.

This woman had also noted in her life story conversation that the happiest she ever was in her career was when she “built something from nothing” at a former employer, so this vision was aligned with what she valued most. Knowing her wildest dreams helped Laraway place her in a position that would deliver experiences that would compound and prepare her for where she was headed — even if she was in a different industry currently.

“We were working in digital ads at the time at Google. Together, we were able to take the right actions given her vision, and advocate for her to get training that would be valuable for her as an entrepreneur,” Laraway says.

3. Create a career action plan.

Once you’ve talked about your ideal vision, Laraway recommends that you and your manager co-create a detailed action plan that outlines exactly how you’re going to reach that vision for yourself. Think of it as a roadmap to self-actualization. He shares three important pit stops your roadmap should include:

Your action plan should outline steps that your manager can take to develop your current role to move you in the right direction. “A lot of times when we think about career, we’re a broken record, stuck on: what's next, what's next, what's next. People are hungry to know what their next job will be, or when that next promotion is coming,” Laraway says. But if you feel like your manager has your back and is investing in you, then that can help reduce those “ants-in-the-pants" feelings.

It should also outline how you can enhance your network. Who do you want to reach out to, to help you get to where you want to be? Your manager can help here, too. “This can entail everything from helping set up informational interviews to being their sounding board to help pressure-test a direct report’s thinking,” says Laraway.

Finally, it helps give shape to your immediate next step. If you’re explicit with what the next step or role will be, your manager can help advocate for you to make a lateral or vertical move, or give you goalposts to hit on a quarterly basis. Your manager can help set you up on the next, logical path en route to your dreams.

6. You’re allowed to quit when you’re unhappy. But make sure you’re not quitting because you’re impatient.

For much of our time in school, we're are taught how to prepare for getting a job. But when it comes to quitting a job, we’re left without a compass to navigate those feelings. This reality often comes as a rude awakening to new graduates. As the workforce evolves and more people increasingly change jobs, we almost need to become experts at quitting itself and knowing when to do it.

“At my first job at Microsoft, I would get migraines all the time because I knew things were suboptimal and needed to change,” says Ellen Chisa, now the co-founder and CEO of Dark. To help her evaluate what, exactly, needed to change, she reflected on where her feelings were coming from.

You might have a lot of different feelings that make you want to quit — antsiness, an unsettled stomach, FOMO, envy, dread. Make sure that these aren’t impatience in disguise, says Chisa. Impatience is common when you’re just starting out at a new job. In contrast to genuine unhappiness, impatience can be acted on productively, and is often quelled over time.

So is your desire to quit coming from impatience, or something deeper? Ask yourself these questions:

“Sure, there are sometimes reasons to leave a company after 8 days because it was sold to you entirely differently during the interview process, or it’s a clear mistake," says Chisa. "But the more common flip-side is that you might hate a new job for the first three months or even a year only to have it actually turn into what you wanted.”

She’s spent a lot of time studying and speaking to fresh graduates who are just joining the workforce. It turns out that most people simply have a very tough first year. “They aren’t used to sitting in a chair all day. They’re used to cram cycles, not a sustained cadence of things to do. It can be really disillusioning,” she says. “And the ugly truth is that this isn’t just about recent grads. Every new job environment has a different cadence, different demands, personalities that might make you want to quit, no matter where you’re at in your career. That first year can be brutal and deceiving.”

When you start feeling unhappy in your work, you owe it to yourself to get specific about changes you could make for it to get better, and to develop your own innovative solutions and experiments to try. No matter how warm and fuzzy the culture, your co-workers and boss are not therapists, says Chisa. It's not their job to respond to your discomfort.

“You'll succeed if you get yourself to focus," she says. "Figure out and write down exactly what kind of work you want to do. Is that valuable to your current company? If not, keep looking. If so, what argument can you make to your boss to pivot in that direction? You’d be surprised how many mature professionals haven’t really thought about this with any depth or rigor.”

Read more about Chisa’s advice on the magical benefits of the quitter’s mindset here.

Have you considered taking your next career step in the startup world? First Round’s community of companies include
Snackpass, Astorian and Glide — and many are hiring now. Access our exclusive list of opportunities with the referral code gradwisdom.

Photography by Bonnie Rae Mills

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