Let’s normalize talking about failure 

I fail every day. Little failures, like picking the wrong line at the grocery store. Big failures that alter the course of my entire week. Some failures are so tiny, I barely think about them, while others are consequential enough, they stay with me for months.

I’m learning to lean into failure — maybe not in the moment, but in the aftermath. Failing usually means I made a decision and took a risk. When we fail, it often makes us stronger and more informed.

Can we normalize talking about failure? Because there’s so much to learn from those moments. I’ll share a recent example:

In 2024, after a short pause in our grantmaking, the Foundation announced new and rebranded grant programs. The shift from Tier 2 grants to Community Support and Legacy grants was intended to make it easier and faster to give support to local organizations. Making this change, we believed, would benefit those we serve and our staff.

Two years later, we’ve admitted out loud this change did not work. We’re saying goodbye to Legacy and Community Support grants and replacing them with the former Tier 2 program.

Those two years taught us that, despite our best intent, the process wasn’t easier. It was confusing, and it created more work for the organizations applying for grants — the opposite of what we’d hoped for.

Nobody likes to fail. It doesn’t feel great to say, “I was wrong,” or “This didn’t work.” Worse, though, is the feeling of sticking with a bad choice just to save face, or because making a change took a lot of work.

“Failing fast” — gaining insights from mistakes, rather than spending a lot of time perfecting an idea — can spark innovation and shed light on better options. Sometimes, what we choose not to do is one of the most strategic decisions we can make. In this case, failure told us that the old way of organizing our grants was more effective. Staying the course with a complicated grant program structure would only have hindered our work of empowering Alaskans to help each other.

We made a big decision when we changed our Tier 2 program. But the right decision came later, when we asked ourselves, “Is this really working?” and found the answer was no.

I want to hold onto this moment as an example to look back on, to remember that the biggest failure is not being willing to admit something didn’t work. Failure isn’t a wall that prevents us from going forward. It’s a door that can lead somewhere better, if we’re willing to open it.

Thank you for all you do,

Gretchen Guess 
President and CEO