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The Most Generous Feedback

David Sherry
4 min read

The Most Generous Feedback

The past two months I’ve been testing what it could look like to build a unique type of community based around generous communication, brand and marketing.

In this incarnation…It totally flopped.

And to be clear, it was 100% because of my approach.

But I also received THE most generous feedback I’ve ever gotten on a project of mine.

I’ll share a snippet of that here:

The Most Generous Feedback I’ve Received:

“But when it comes to the community and this entire project over the past couple of months, I have to admit I have no idea what is going on here, or where this is going. I don’t know where this is going or really where you are trying to take me with this.”

This was bridged by some very kind words (before, and after), which showed that he only had my best interest at heart. I thanked him, refunded his payment and left feeling even more respect for this person.

Truly – this is the most generous thing someone has shared with me lately related to my work.

What this person share was thoughtful in that it had my best interests in mind by voicing the thing that others were maybe afraid to voice, even myself.

Sometimes the most obvious thing is the most avoided.

This happens at every level of society. And even moreso with ourselves.

As Ben Hunt says, “everyone knows that everyone knows that…”

The thing is…all of the learning happens when you make mistakes.

But only if you see them. And the faster you see what’s not working, the faster you can let go.

I remember pitching brands on being their full time photographer and getting rejected pitch after pitch. I remember the rejection and realizing that I needed to do something different… it was letting that path and series of mistakes drop away that lead to Death to Stock.

You see reality for what it is, so that you can drop what’s not working, which allows you to pick up something new.

The Seasons of Growth

My friend Chris has a book on the “seasons” of our lives. It’s the best book I’ve read on going through transitions. He uses the seasons as metaphors for different stages of growth.

“We don’t control the seasons, but we can cooperate with them.”

"The worst approach you can take when you're stuck is to try harder or hustle harder…We are failing the test of the fall season when we stay committed to strategies that aren’t working.”

“In the winter season, the action that keeps you stuck is to frantically try anything and everything. We feel isolated. In that isolation we return to old reactions to force a change..You’re not cooperating with your winter unless you see what you have not been able to see."

"If we are going to experience a true, non-hyped new beginning, it will only come after we release old dreams and destinations. In the spring season, we’ve fully owned that we can’t bring back old motivations.

In the spring season, we use what we learned in fall and winter to pinpoint the passion in us and become laser sharp with our actions.“

"Summer is a time to refill our tank, unwind and relearn how to enjoy what has been accomplished. We want to move through summer by relaxing and playing while we keep an eye on our foundation. "

I highly recommend the book as every one of us is in one season or another in different areas of our lives. This natural pattern of growth, action, stuck points, collapse, is all natural.

Link here:


So, how do you move forward/reflect when a path you take fails?

1. Recognize your intentions were good
There were many things I could have done better, but I truly cared about the people and the project itself. While intentions don’t make a great product, they help you recover quick because you had a type of purity about your attempt.

2. See Reality for what it is.
The longer you cover up what’s not working, the longer you stay stuck taking actions that aren’t moving your mission forward. Accepting that this path didn’t lead you where you thought it would is great because once you drop it, now you can move forward

3. Drop what’s not working
The faster you recognize that you’re simply continuing something for the sake of continuing it, the faster you can find forward progress that feels more natural and is more effective.

4. Wait for clarity on what the journey is for.
One thing I’ve seen time and time again with myself and with others is… to lead someone, or a group of people, you need to have some type of clarity on where you’re trying to go together. This sounds obvious, but without the North Star, it’s much harder to get momentum. I see most newsletters and blogs as journey’s that both the creator and the audience are going on. Without the leader of the journey as the guide, things break down, and both parties are left feeling lost.

5. Have courage to be vulnerable again.
By releasing what wasn’t working, you drop a lot of what you were wrapping your identity around. To drop a lot of what you had wrapped your identity around takes courage, because suddenly you’re out there without the comfort of the “certainty” you felt when you had that armor on, even if it was weighing you down…”

To get back out there, and try something new takes courage, but not as much as making the decision to keep growing instead of shrinking away into the comfort of the known.


All of this leaves me optimistic because by finding what doesn’t work, you’re now more like to find what does.

And, by dropping what was forced, you’re able to pick up what is natural.

xx David