Career planning and goals: How to measure success on your own terms

Success isn’t just a number

Let me take you back to my early 20s. Fresh out of college, full of ambition, and totally ready to conquer the world. I landed my first “real” job at an eLearning company and decided to prove myself by working 60-hour weeks. I thought I was crushing it. Promotions, good money, gold stars from my boss—I was checking all the boxes.

But then, real life slapped me in the face. My relationship started falling apart, and my daughter—my reason for doing all this—asked me, “Why are you always working?” Talk about a gut punch.

That’s when I realized that success, for me, doesn't mean climbing the corporate ladder or burning myself out for a bigger paycheck. It means creating a life that feels good—one that aligns with my career planning and goals and lets me thrive. Since then, I’ve sworn off overtime (seriously, not a single hour) and stopped chasing titles. And let me tell you, I’ve never been happier.

So, how do you measure success without the paycheck being the end-all-be-all? Let’s talk about six ways to figure that out.

1 | Find joy in your work

Let’s start with the big one: Do you actually like what you do? No job is perfect (hello, endless email threads), but there should be moments when your work feels meaningful. Like you’re contributing to something that matters.

For example, I once coached someone who traded their high-paying corporate job for a sustainable fashion business. They took a pay cut but finally felt proud of their work. Now, they wake up excited to tackle their day—and isn’t that what success should feel like?

Ask yourself:

• How does your work fit into your career planning and goals?

• Is it bringing you closer to the life you want?

If the answer is no, it might be time to reevaluate.

2 | Become your best self

If you’re not learning or growing, you’re stuck—and no amount of money can fix that. Success often means challenging yourself. Pick up a new skill, say yes to a big opportunity, or step back to figure out what you really want.

I have a friend who left a senior role to go back to school for mental health counseling. Not a traditional move, but for her, it was the ultimate growth opportunity. Now, she’s thriving in a career she loves.

3 | Live on your terms

Let me be real: boundaries are my non-negotiable. After those 60-hour weeks nearly wrecked my life, I learned how to say no (and meant it). Success, for me, means shutting the laptop at 4:30 p.m. and being present for my family.

Quick boundary-setting tips:

• Decide on your “off” hours: Pick a hard stop for your workday and stick to it.

• Say “no” gracefully: Try, “I’d love to help, but I don’t have the bandwidth right now.”

• Block personal time on your calendar, even if it’s just an hour to read or relax.

• Don't just think about achievements when setting your career planning and goals. Consider how your career impacts your life outside of work. That’s balance.

4 | Make a difference

A true mark of success should include what you gain, yes, but also what you give. Maybe you’re mentoring a colleague, streamlining a messy process, or helping clients feel supported. Whatever it is, those small wins often add up to something bigger for you. Feeling pride in yourself has true value.

A friend of mine, who works in customer support, once helped a client navigate a really tough situation. They sent her a thank-you note saying she’d made their day. She told me, “That’s when I knew I was in the right career.”

Your turn

As you evaluate your career planning and goals, think about your impact. What’s one thing you’ve done recently that you’re proud of? It doesn’t have to be huge—sometimes the little things matter most.

5 | Build your tribe

Work is better when you like the people around you. Full stop. Success means having a team you trust, mentors who inspire you, and colleagues who get you. And if you have to fly solo? Build a network of people who will cheer you on.

One of my favorite career moments wasn’t nailing a big project—it was mentoring a junior colleague. Watching them grow into a leadership role was more fulfilling than any title I could have earned.

Think about this

Who in your professional circle supports your career planning and goals? Got it? Now, how can you strengthen those relationships?

6 | Shape your path

Let’s talk freedom. Can you choose your projects? Work remotely? Take a mental health day without guilt? That’s success, my friend.

A freelancer I know recently turned down a high-paying client to focus on flexible work that let them spend more time with their family. For them, freedom mattered more than cash.

Reflection time

Does your job:

• Let you prioritize what matters to you?

• Align with your career planning and goals? If it doesn’t, what small steps could move you toward a career that does?

Success is personal

Here’s the thing about success: it’s not one-size-fits-all. It shouldn't require climbing the ladder, working overtime, or impressing other people. It should be defined by building a career—and a life—that feels right for you.

So, what do your career planning and goals look like? Write them down. Reflect on them. And if you need a nudge in the right direction, check out the Career and Business area of my website.

Because at the end of the day, real success isn’t just about making a living—it’s mostly about building a life you’re proud of.

What does success look like for you? Write it in the comments below.

Next steps

• Visit the Career and Business area for resources to help you plan a career that fits your lifestyle, not the other way around.

• Find and lower your expenses this month (and keep them lower) with our 30-Day Challenge: Lower your expenses.