Moving Beyond “Grateful” — Practicing Gratitude 2.0 as a Team

Like many of you, I’ve had a long-standing gratitude practice of noting daily reflections, affirmations, and writing thank-you notes as part of my routine. I thought I had it dialed in. But reading Cy Wakeman’s Life’s Messy, Live Happy challenged me to think differently.

Cy calls it Gratitude 2.0 and it’s not about listing only the feel-good stuff. It’s about evolving your awareness so that you can see everything as worthy of appreciation…even the uncomfortable, inconvenient, or downright painful. Not because it’s easy, but because it’s meaningful.

“If you are unable to count everything as a blessing… consider taking your practice to the next level,” Cy writes. She encourages us to not just cherry-pick the highlights, but to track all the moments that catch our awareness aka the whole of our experience.

I realized that my own gratitude practice had some hidden judgment in it. I was indeed “cherry picking” and only acknowledging the moments that were obviously “good.” But in doing so, I was missing out on some of my biggest growth opportunities.

Instead of asking, “What am I grateful for?”, I’m learning to ask, “What am I thankful for?” Thankfulness feels more open to me.  It’s less about labeling and more about accepting. I don’t always know why something is happening, but I can be thankful for it anyway. There’s a quiet wisdom in trusting that there’s always a reason, even if I can’t see it yet.  And I may never know the reason, and I’m okay with that.

What Does This Have to Do with Teams?

A lot.

Too often in team settings, we celebrate the wins and sweep the rest under the rug. We give shout-outs for closed deals, resolved problems, or heroic efforts.  But we avoid the messy stuff. Gratitude 2.0 invites us to change that.

Here’s how teams can apply this concept:

1. Capture More Than Just Successes.  Encourage team members to reflect on all meaningful moments and not just the ones that felt good. A missed deadline might have revealed a hidden process flaw. A difficult client call might have showcased someone’s grace under pressure. What caught your attention this week? What tested you, stretched you, or shaped you?

2. Work the Gap. Cy suggests highlighting what’s easy to be thankful for and then turning your attention to what’s left over. She calls this “working the gap,” and that’s where growth lives. In a team context, that might mean asking:

• What’s happening that we’re not talking about?
• Where are we judging or resisting?
• What would it look like to mine this moment for meaning?

3. Get Curious Without Judging.  One of Cy’s most powerful points is the call to stay curious and resist the urge to judge or label. That’s not easy in team environments where decisions need to be made, and performance is measured both individually and as a team. But when we create space for curiosity, we invite reflection instead of reaction.  We might ask:

• Why did this happen?
• What might this be teaching us?

4. Honor the Process, Not Just the Outcome.  True gratitude in teams isn’t about tallying up successes.  It’s about honoring the whole journey. When we can be thankful for how we’re growing together, not just what we’re achieving, we foster a deeper sense of trust, resilience, and belonging.

Gratitude 2.0 isn’t a performance.  It’s a mindset. It’s not about pretending everything is great. It’s about choosing to see meaning, growth, and value—even in the mess. And when we practice that together, our teams become more grounded, more self-aware, and more connected.

And I am thankful for you, my dear readers.  Every day.

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