Moving the Goalpost: How to Be Proud of Where You Are AND Ambitious About Where You’re Going

You start out with I’ll be satisfied when I get that promotion. You get promoted, and then you think… I’ll be happy when I reach six figures. Now you make great money, but your mind jumps to, I’ll know I’ve made it when I have my own office.

Despite reaching all your (self-imposed) milestones, you still feel like you aren’t “there” yet. No matter how much you accomplish or how quickly you do it, your mind persists in constantly moving your own goalposts.

It’s a common qualm for high achievers.

If you’re a constant goalpost-mover (guilty) it can even happen before you reach the goal. When you’re close, and you’re pretty confident it’s going to happen, the once coveted thing is no longer the goal anymore. You’ve already set your sights on the next thing. The result is, you never pause to soak in how far you’ve come, costing yourself the intermittent pride, gratitude, and resolve that comes with achievement.

I’ve struggled with this for decades. Over time, I’ve learned that being proud of where you are and being ambitious about where you’re going aren’t mutually exclusive; the two can coexist (with some work).

Here’s what I’ve found helps:

Write down your goals.
Having the goal in writing makes it more concrete, which in turn makes the “I did it” feeling more real. Further, if you continuously write down your goals, you can look at your results over an extended period of time. Recent achievements often don’t feel as exciting; the work is still fresh, the challenges are still present, and the results are new. Yet if you look back at your goals from ten years ago, you’d likely swell with pride. You’re probably aware of how far you’ve come in the last year (it was a lot of work!) but it’s easy to lose sight of how far you’ve come in the last 10 years.

Mark the occasion.
When I first crossed the six-figure mark, I bought a $150 lamp I had been eyeing for months. The purchase felt a bit frivolous, but I bought it anyway to mark the occasion. Many years later, I still look at the lamp and smile. It’s a physical reminder of how far I’ve come. It doesn’t have to be buying something — take a trip or go out to a great meal and take a picture. Give yourself a reminder that you’ve ticked off an important goal. Otherwise, you’ll forget.

Define more significant goalposts.
If you’re changing your goal every week, you’ll exhaust yourself. The feeling of achievement will never be significant and new goals will cease to be exciting. If your job gives you weekly, monthly, or even quarterly goals, consider setting longer-term markers for yourself. Maybe it’s a promotion, a salary threshold, or even a work-life balance achievement, like being able to take Fridays off. The more substantial the goal, the greater feeling of achievement. But don’t wait until you’re making millions in passive income to celebrate; aim for something realistic in the next 6–12 months.

If you’re a high achiever, you’re probably accustomed to ‘congratulations’ and ‘good job.’ Your accomplishments are likely recognized at work, in your industry, and by your family. Yet until you learn to be proud of yourself, it will never feel real.

Never stop creating ambitious goals; that behavior got you to where you are! At the same time, grant yourself some praise. Recognize that your ability to celebrate (even for a moment) will give you the energy you need to keep going.