Will This Make You Proud?

This morning at the Nasdaq Entrepreneurial Center, I shared a question during a session on focus and prioritization:

“Six months from now, will I/we be proud that we invested our time and energy on this project?”

It sparked a lot of engagement, and I think that’s because it actually contains two questions:

1. Is this worth doing?
   Does this initiative deserve our focus at all? Will it create impact, growth, or meaning that lasts? If not, why pour time and energy into it?

   Example: launching a new product line may stretch your team, but will it create long-term differentiation? If yes, that’s worth doing. If no, maybe it’s a distraction.

2. Could I be doing more so that I am proud of this?
   If it is worth doing, am I showing up fully? Am I bringing the energy, creativity, and commitment that will turn this into work I can look back on with pride?

   Example: if you’ve committed to running a half marathon, are you showing up to train consistently, or just hoping pride will show up on race day?

Why These Questions Matter

The first question is about choices; it’s a way to filter out distractions so we focus on what’s truly significant.
The second is about commitment; it’s a way to make sure sure we don’t just go through the motions, but actually stretch ourselves to deliver something meaningful.

Together, they turn a simple project filter into a growth mindset.

Not Just for Work

While I framed this in the context of business projects, the same questions apply to wellness goals — physical, spiritual, mental, social, emotional.

• Is this worth doing? Is this habit, practice, or goal aligned with what I want to build in my life?

  • Example: committing to weekly dinners with your family might not show up on a work calendar, but six months from now it’s the investment you’ll be proudest of.

• Could I be doing more so that I’m proud of this? Am I putting in the effort to make it real, not just aspirational?

  • Example: deciding to meditate is good, but creating a daily practice is what will bring pride when you look back.

We don’t often give ourselves the chance to feel proud of progress in these areas. But we should. Pride isn’t just a nice feeling; it’s a catalyst for momentum.

A Challenge for You

Look at the projects or goals on your plate this week and ask both questions:

1. Is this worth doing?

2. Could I be doing more so that I’ll be proud of this six months from now?

Your answers may surprise you.

A Milestone Mindset

Leadership is really a series of intentional choices, choices that help improve clarity, resilience, and impact. These two questions are filters that anyone can use to focus on what matters most, and to make sure the work (and the life) we’re building will be worth being proud of.