The Real Reason Your Goals Keep Failing (And How to Actually Achieve Them)

You've set the same goal three times now. Maybe it's "become more strategic" or "build executive presence" or "transition from individual contributor to leader". You know what you need to do. You've read the articles, taken the courses, made the plans.

So why hasn't it happened yet?

Here's the truth most career advice won't tell you: your goal isn't failing because you don't know enough or because you're not working hard enough. It's failing because achieving it requires you to become someone you haven't learned to be yet. And that's a completely different kind of work.

The good news? Once you understand this, everything changes. Because you can absolutely become that person - you just need to approach it differently than you've been approaching traditional goal-setting.

The Identity Gap: Why Knowing What to Do Isn't Enough

Think about the last time a goal kept showing up on your list month after month. Maybe it was delegating more effectively, speaking up more in meetings, or building strategic relationships outside your immediate team. You probably knew exactly what you needed to do. The problem wasn't knowledge.

The problem was that doing those things felt inauthentic, uncomfortable, or simply wrong. That discomfort is your current identity pushing back against your goal. And here's what makes this tricky: the identity that got you to where you are today might be the exact thing preventing you from getting to where you want to go.

For instance, maybe you've succeeded by being the person who always delivers flawless work. That identity has served you incredibly well - until your goal requires you to delegate imperfect work to others.

Or perhaps you've built your reputation on being the technical expert who solves hard problems. That works beautifully until your goal requires you to think strategically rather than technically.

Your current identity isn't wrong; it's just incomplete for where you're trying to go. You can't force yourself to achieve goals that contradict who you believe yourself to be. You have to evolve the identity first.

Three Identity Shifts That Make Goals Achievable

1. From "The Person Who Does It Best" to "The Person Who Enables Others"

If your goal involves any form of leadership - leading a project, managing people, influencing without authority - you'll need to make this shift. The challenge is that your current success probably comes from being excellent at execution.

Here's how to evolve that identity: start measuring your success differently. Instead of tracking what you personally accomplished today, track what you made possible for others.

• Did someone on your team solve a problem without your help? That's a win.

• Did you create space for a colleague to showcase their work? Another win.

Try this: identify one task you do really well. Now pick someone you could teach it to. You're not just delegating a task - you're practicing a new identity.

2. From "Deep Expert" to "Strategic Connector"

Early in your career, going deep in your domain is exactly right. But at some point, your goals shift. That requires adding breadth to your depth.

Start showing up in spaces adjacent to your expertise. If you're in product, attend some commercial planning meetings. If you're in operations, ask to join conversations about customer strategy. You're not there to be the expert - you're there to understand how your expertise connects to other parts of the business.

The shift happens when you start asking questions like "How would this impact the customer experience?" or "What's the competitive angle here?" instead of only speaking to your specific domain.

3. From "Problem Solver" to "Opportunity Creator"

Solving problems feels productive because every problem you solve gives you immediate feedback that you're valuable. But if your goal involves innovation or strategy, you need to become someone who creates opportunities.

Protect time for non-urgent thinking the same way you protect time for urgent deadlines. Block two hours a week where you're not solving anything. You're exploring, connecting ideas, asking "what if" questions. Treat this time as sacred as you would a client meeting.

The Courage to Feel Inauthentic

Identity transformation always feels fake at first.

When you first delegate something you could do better yourself, you'll feel irresponsible.

• When you first speak up in a strategic conversation outside your expertise, you'll feel like an imposter.

• When you first let a problem go unsolved to focus on opportunity creation, you'll feel negligent.

That discomfort isn't a sign you're doing it wrong; it's a sign you're growing. You're supposed to feel inauthentic when you're becoming someone new. Eventually, the new behavior stops feeling like pretending and starts feeling like you.

Making It Practical: Your 30-Day Identity Experiment

• Week 1: Identify the gap. Ask: who would I need to be for this goal to feel natural? Write down three qualities that person would have (e.g., "someone who trusts others to deliver").

• Week 2: Pick one micro-behavior. Choose the smallest possible action that aligns with your new identity. So small it feels almost silly.

• Week 3: Practice in safe spaces. Find low-stakes situations to practice your new identity. You're building the muscle memory without risking high-stakes failures.

• Week 4: Reflect on what's shifting. Notice what feels different. That discomfort is data - it shows you where the old identity is still fighting for survival.

The Goal Behind the Goal

Your goal isn't actually about the outcome you wrote down. It's about becoming the kind of person who can achieve that outcome naturally. Once you become that person, the original goal often becomes almost effortless.

The goals you keep not achieving aren't failing because you're not capable. They're failing because they're inviting you to grow into someone you haven't yet learned to be. The question isn't whether you can achieve your goals; it's whether you're willing to become the person who makes those goals inevitable.

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About the Author

Karin Wellbrock is a leadership coach and Partner at Kay Group K.K. Japan. Based in Asia for the past 17 years, she works with leaders across regions who navigate multi-cultural teams and cross-geographic responsibilities. Karin specializes in helping professionals bridge "the knowing-being gap" by focusing not just on what they should do differently, but on who they need to become.