The Strategic Guide to Breaking Your Career Plateau

 

View in Web Browser   Book a call with me    Get my Book  Hey, it’s Maya. Welcome to my weekly newsletter, where we talk about leveling up in your career, and becoming successful on your terms. If you’re looking to break into executive roles, check out my group coaching program, Success Builders. It will provide you with the strategy, mindset, and tools required to become executive-ready and get the promotion! I typically work with ambitious tech leaders who want to level up into Director, Sr. Director, and VP roles who want to increase their impact and influence.  Apply here.   I remember the day I decided to leave Microsoft.   On paper, everything looked great. Good salary, prestigious company, interesting work. But something was missing.   I wanted to be a VP, and despite my track record, it was clear this wasn't going to happen where I was. The path upward was blocked. Not because I wasn't ready, but because there simply wasn't an opportunity.   Many people told me I was crazy. "Just be patient," they said. "Something will open up eventually."   But here's what I knew: waiting for "eventually" meant settling for "good enough" instead of chasing "great."   Six months later, I was leading marketing as a VP at a fast-growing startup.   The Growth Ceiling is Real Let's be honest - sometimes there's simply no room to grow where you are.   Maybe you haven't seen a promotion in three years.   Maybe your manager has made it clear there's no budget for senior roles.   Or maybe the organizational structure means you're stuck unless someone above you leaves.   Whatever the reason, hitting a growth ceiling doesn't mean you're trapped. It just means it's time to grow in a different direction.   Why We Settle for Good Enough I get it. Change is scary.   What if the new role doesn't work out? What if you're making a mistake? Isn't it safer to stay where things are... fine?   But here's the truth: at the senior level, playing it safe is actually risky.   While you're settling for "good enough," your skills are stagnating. Your market value is decreasing. And those leadership opportunities you dream about? They're going to people who dared to move.   There’s one more problem no one talks about.   The longer you stay where you can’t grow, the more you believe it’s your only option. That it’s the best you can do. And that mindset block is the biggest problem because it makes you complacent. And in the long term it lowers your confidence.   That’s how you get stuck for 10 years.    The Strategic Exit Now, I'm not suggesting you quit on a whim. Every career move I've made - including leaving Microsoft - was carefully planned.   I’m suggesting that you make a strategic move. Make a plan that delivers the growth you are craving instead of hoping staying put will eventually pay out.   Being strategic means two things: First, you move for value. That could be a better title, higher salary, or greater fulfillment. Often, it's all three.   Second, you plan your exit. This isn't about storming out after a bad meeting. It's about deliberately designing your next career chapter.   Your 6-Month Runway The key to a successful transition is preparation. I always tell my clients to start building their runway six months before they need to take off.   Why six months?   Because you need time to: Evaluate internal opportunities (just to be sure you're not missing something) Research the market and your worth Update your selling proposition Start having strategic conversations Line up potential opportunities   This isn't about job hunting (yet). It's about positioning yourself for success.   Think Like an Entrepreneur This strategy is the reason I was promoted with almost every move I made in my career.   It wasn’t luck or even timing. It was 30% strategy + 70% mindset.   Here's the mindset shift that changed everything for me: I stopped thinking like an employee and started thinking like an entrepreneur.   Employees wait for opportunities. Entrepreneurs create them. Employees worry about job security. Entrepreneurs focus on market value. Employees settle for what's available. Entrepreneurs pursue what they want.   You might get a paycheck from a company, but your career? That's your business. And sometimes, growing your business means entering new markets. Your Next Steps First, you need to make a clear-eyed assessment: Are there real growth opportunities where you are?   Don't base this on hopes or maybes. Look at the facts: When was your last promotion? What's the actual path to the next level? Is there a concrete timeline or just vague promises?   Then, set a deadline.   If you see a clear growth path, great! Put a timeline in place and hold your organization accountable.   If not, mark a date six months from now on your calendar.   That's your runway. Start preparing for takeoff.   Remember: You're not a tree. You're not meant to stay rooted in one spot, especially if that spot isn't giving you what you need to grow.   Your career is your business.