- Jean Kang spent a decade working in various roles and companies throughout Silicon Valley.
- She would’ve navigated her career differently had she known things like there are no ‘dream jobs.’
- Job-hopping, personal branding, and exploration were also crucial to her career development.
When I graduated from college in 2014, I thought I’d finally made it. Before graduation, I landed a role in Silicon Valley and was excited to start.
Looking back now, after nearly a decade of working at companies like Meta, LinkedIn, Pinterest, and Figma and hopping roles more times than I can count, I realize my early impressions were overly rosy — and a bit naive.
Silicon Valley taught me a ton and helped me boost my salary to more than I thought possible, but there are a few things I wish someone had sat me down and told me when I was fresh out of college.
These insights might’ve saved me from a few late-night spirals or could’ve helped me navigate my career a bit more strategically. They also gave me the courage to leave behind my $300,000-a-year job and build a multi-six-figure business on my terms once I learned them.
Here are five pieces of advice I wish I could’ve told my younger self.
1. Job hopping isn’t quitting
I probably would’ve laughed if you’d told me in my early 20s that switching companies multiple times within a few years would help me stand out. I assumed staying put and showing loyalty was the “safe” path.
Yet, in Silicon Valley, some of my biggest leaps in salary, responsibility, and growth came after I decided to hop from one role to another. This was especially true during market shake-ups, like mass layoffs.
When teams are rebuilding, they hire for high-impact roles that are often critical to moving the needle. If you’re still employed and apply for one, it sends a loud and clear message: “I’m confident, I’m valuable, and I’m here to make a difference.”
If I’d known that earlier, I would’ve pounced on opportunities sooner rather than waiting and hoping things would improve at a company that no longer fit.
2. Build your personal brand before you ‘need’ it
I used to think personal branding was a bit fluffy, but just under two years ago, I saw a void on LinkedIn for real, honest career stories. I started sharing my insights — what it’s like to be a program manager, the differences between project and product roles, and how to combat imposter syndrome — and people cared. Before I knew it, I had tens of thousands and now over 160,000 followers across LinkedIn, Instagram, and my newsletter.
My personal brand served as a jumping board for lucrative opportunities and increased my confidence. Brand sponsors started reaching out. Clients wanted me as a career coach. I realized that your name could carry weight outside your company — and that’s crucial when layoffs hit, or you’re considering going solo.
Had I started building my brand earlier, I could’ve leveraged it to negotiate better offers and land roles that excited me and made me feel less chained to any employer’s fate.
3. Your early career is about exploring
For the first few years, I beat myself up for not having a linear career path. I tried sales, account management, customer success, and program management. While it felt like I was throwing stuff at the wall and hoping something stuck, something magical happened.
Those pivots gave me a fuller understanding of how companies operate, what kind of work lit me up, and where I could deliver unique value.
Silicon Valley rewards curiosity. When I realized that program management was my zone of genius, my diverse skill set made me a stronger candidate for all sorts of roles.
If someone had told me early on that it’s perfectly fine — even advantageous — to experiment, I wouldn’t have wasted energy feeling guilty about my “lack of focus.” Instead, I’d have embraced my pivots as a strategy to discover my impact.
4. Your manager matters more than you think
Getting starstruck by big brand logos, flashy products, and employee perks is easy. I thought working at dream companies would solve all my problems and set me up for steady career growth.
Over time, I realized that your immediate environment — your manager and your direct team — plays a far bigger role in your day-to-day happiness and long-term development than the company logo on your résumé.
A great manager who champions your ideas, respects your time, and encourages growth can make an imperfect organization feel worth it. Conversely, a manager who sees you as a cog in the machine or doesn’t invest in your potential can make a dream company feel like a nightmare. I’ve now experienced both.
If I’d known earlier how critical the right boss is, I would’ve factored that into my decision-making more heavily, maybe asked more pointed questions in interviews, or trusted my gut when something felt off.
5. There are no ‘dream jobs’
Silicon Valley loves to hype “dream jobs” — the unicorn startups and tech giants everyone would love to join. I’m grateful I got to experience some of those “it” companies firsthand. For a while, it was exhilarating, but over time, I learned that no matter how cool the company or how impressive the perks are, there might come a day when you wake up and think, is this really it?
You may find yourself staying late to meet arbitrary deadlines, supporting products you’re not passionate about, or feeling disconnected from the outcomes. That doesn’t make you ungrateful; it makes you human.
Recognizing that even “perfect” roles can lose their sparkle gave me relief. This realization was a big reason I eventually left corporate life behind.
I feel blessed and want to pay it forward
I don’t regret my time in Silicon Valley. It taught me incredible lessons, gave me the financial runway to start my own business, and connected me with brilliant people, but knowing these five things up front would’ve saved me from second-guessing myself, feeling guilty about not having a perfectly linear path, and putting all my self-worth into a job title.
Today, as a career coach, creator, and solopreneur who’s replaced and surpassed her Big Tech salary, I can say that Silicon Valley is still a place of immense possibility — but go in with open eyes.
Jean Kang is the founder and CEO of Path to PM and a LinkedIn Learning Instructor who is paving the way for future program managers.
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