I hear the same question at least 3x every week in different forms:

“What jobs do you think I could be a fit for based on my background?”
“I want to pivot into Product, is that even possible?”
“Do I need to get an MBA first?”

Behind each of these questions is a deeper one that we’re actually trying to answer:

Is what I want even possible… for ME?

When you’re a high achiever looking at your next career move, you want to make the “right” choice. You want to be strategic, smart, set yourself up for success.

And when you're so good at winning, the idea of "failing" at something is... well, terrifying. (I get it, I used to have a crippling fear of failure)

Here’s what I’ve noticed after working with hundreds of generalists in transition:

We often confuse real constraints with limiting beliefs. And that confusion keeps us stuck.

Today, we’re going to get crystal clear on the difference. Because once you can spot what’s actually holding you back, you can do something about it.

Let’s Talk About “Real” Constraints

Real constraints are factual circumstances that reveal where to get creative — not where to stop. Think of them as parameters of the game, not barriers to entry.

The most common ones I see in career transitions:

• Legal requirements (like visas or certifications)
• Technical skills needed for specific roles (you can't fake 'em)
• Current market conditions (few open roles)
• Time-sensitive financial needs (cash is king)

Here’s the thing though — these aren’t necessarily roadblocks. They’re invitations to get strategic.

Let me give you an example:

When generalists tell me “There aren’t enough Product Manager roles that are open to career changers,” they think they’re stating a fact. But what they’re really saying is “I don’t see an obvious path from here to there.”

This is where it gets interesting.

Because yes, the path might not be obvious. You might need to:

• Build specific technical skills first
• Take a strategic intermediate role
• Build more specialized knowledge
• Create opportunities through strategic networking
• Get creative about how you position your experience

But notice how none of these are impossible. They’re just trade-offs that require time, energy, and effort — you have to decide if you're willing to make those tradeoffs or compromise on what you want.

The more convicted you are in your path, the more committed you'll be to overcoming the roadblocks that pop up.

The Silent Career Killer: Limiting Beliefs

Now we’re getting to the juicy part.

Limiting beliefs are the stories we tell ourselves that block action.

And unlike real constraints? These are 100% in our control.

The sneakiest part? They feel completely real.

Here are the greatest hits I hear consistently:

• “My skills aren't going to translate"
• “I’m too senior/junior to do that”
• “I don’t have the right experience”
• "I didn't make that much of an impact"

Reality check: These aren’t facts. They’re fears in disguise.

Here’s How to Tell the Difference

Real constraints force us to ask, “How can I work with this?”

Limiting beliefs whisper, “You aren't enough.”

Real constraints need strategy shifts:

• Fewer jobs in your target role? → Get creative with your approach
• Missing a critical skill? → Create a concrete learning plan
• Location/visa constraint? → Only focus on roles that match
• Ultra competitive role? → Stand out with unique positioning

Limiting beliefs need mindset shifts:

• “I’m not qualified enough” → “My experience is valuable to the right team”
• “My path is too scattered” → “My diverse expertise is my superpower”
• “It’s impossible” → “I am working on finding the pathway”

The magic happens when you start questioning everything you think is holding you back.

I see this all the time: The moment someone gives themselves full permission to go after what they want — really believing it’s possible — everything shifts.

Their energy changes. Their actions align. And suddenly, opportunities start showing up.

The Truth About Your Next Move

Every major career transition starts with a decision to believe it’s possible.

Yes, the market is competitive. You may need to learn new skills. It will take longer than you want it to.

But impossible? That’s only true if you believe it is.

Plan A only fails if you give up on Plan A.

If you’re ready to move past limiting beliefs AND learn strategic ways to navigate today’s job market, I created something for you.

The Generalist Career Transition Playbook is a free 5-day email course to help you kickstart your career transition into the dream role you can't wait to wake up for.

It'll help you unlock clarity, confidence, your unique story, and a Stand Out Strategy to become a top 1% candidate who gets hired... no matter how non-linear your path.

It takes 15 min/day to learn & implement. The goal: create new momentum.

Time to question your constraints, shift those limiting beliefs, and get back to thriving at work.

Let’s win together,

In case you scrolled to the bottom >> I just launched The Generalist Career Transition Playbook. Over 100 generalist leaders have used these strategies to get clarity & land interviews at their target companies. Get the free course.​

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