When we are about to take action, and we say, “This might not work,” — literally speaking the phrase — we do a few things.

One, we relieve tension. We accept that there’s some level of risk in what we’re about to try, and that there are no guarantees.

Two, we embrace some level of experimentation. A curious mindset. A posture of, “let’s see what happens.”

Saying, “This might not work,” is a powerful tool, whether said to ourselves or aloud to a group.

But what happens when we think these words? How does it affect our ability to act?

How long can we hold the tension of, “this might not work,” before running back to safety? Are we able to face uncertainty, or do we avoid risk at all costs?

Because what it might cost is something new and remarkable.

Discovery lies on the other side of what might not work. Dare to risk it.

I try not to repeat myself in what I post to this blog.

But in thinking about this today, I also recognize that some things are worth saying more than once.

From your particular vantage point — what you see, what you experience, and what you believe — what’s worthy of repeating?

What must we say again and again … as many times as it takes to know it by heart?

It’s easy to critique. Easy to say, “You’re wrong.”

It’s much harder to be enrolled in finding solutions.

* * *

We don’t need more fault-finders. We need more problem-solvers who are willing to contribute.

There is no path to greatness that is without some portion of failure.

The question is not about how we can avoid failing.

The question is about how we can fail better.

It’s not that we try to fail. We certainly don’t aim for it. But we can think of it more as unpleasant medicine rather than a terminal condition.

Through failure we learn. Without risking it, we haven’t yet come alive.

During a luncheon, a priest once told me he had said a prayer — years earlier — to bless all his future meals so he wouldn’t need to say grace anymore. (He was joking.)

* * *

At times, we take action in a definitive way. We take care of things “once and for all” with lasting effect.

Gratitude doesn’t work this way. Gratitude is ongoing.

It’s not to be “taken care of” like an item on a to-do list. It’s a practice that enriches us the more we embrace it.

The hardest thing I did yesterday was a twenty-minute drawing.

Every mark on the page hurt. I felt like crying. Literally.

But I kept with it. I had committed to twenty minutes of drawing, and I was going to do it.

It was not joy. It was not leisure. It was not the beauty of creativity flowing through me — or at least it didn’t feel that way.

It was struggle. It was resistance. It was the frustration of, “This is not working the way I want it to.” It was self-doubt and self-loathing.

But I continued.

And I made something.

And I’m better for it.

And the part about me being better has very little to do with how the drawing looks.

* * *

The creative thing you resist with such fortitude can be a rewarding struggle for you, too … but you cannot turn away when the going gets tough. You must bear it and see it through.

A grinding, clanging sound let me know it was time to take my pressure washer to a repair shop.

I remarked, “I’m surprised it broke. I only use it for a few hours, two or three times a year.”

The technician replied, “Well, that might be part of the problem.”

While some equipment degrades after each use, other tools work better when they’re put to work regularly. Let them sit idle, and instead of preserving them, they fall into disrepair.

Is this a lesson that relates to body, mind, soul, spirit, and creativity? You bet it is.

Let’s not let ourselves fall into disrepair.

Imagine a therapist who knows you only by what you’ve googled.

All she has is a list of what you’ve entered into the search box. Every search … for the past five or ten years.

What would she learn about you?

How might she advise you?

Write the story you want to read.

Paint the painting you want to see.

Invent the sandwich you’d most like to eat.

Open a business where you’d love to be a customer.

Little by little, build the world you want to inhabit.

If I close my eyes, I can recall flavors from a meal I had nearly twenty years ago.

In the work we do, what flavors and experiences can we create … that will be remembered years from now?

What can we bring to the world — no matter how small — that’s simply too good to be forgotten?

There are lots of reasons to delay making a decision. Maybe we don’t have all the information. Maybe the conditions are fluid. Maybe we don’t feel ready to commit.

But many times, we delay because we’re afraid. We’re worried about a bad outcome. We’re worried that we’ll look stupid. We’re worried that we’ll have regrets.

A better plan is to decide to decide. To not worry about making a smart decision, but to be smart about how we’re making the decision. To be smart about our process, knowing that we can’t fully control outcomes.

If you have all the data* — and the clock is the only thing that will change between now and the moment you make a decision — it’s time to decide.

While you’re at it, trust yourself. Trust your ability to think through things, and your ability to handle whatever happens, good or bad.

---

*Note: Gathering “all the data” might not even be possible. Almost always, we’re called to make decisions based on incomplete data. And even so, sometimes more information is not helpful.

“We took away the complaint box, and we haven’t had a single complaint since!”

Just because we don’t hear complaints doesn’t mean everyone is happy. Silence is not an indicator of contentment.

Can we be brave enough to listen to honest feedback from those we seek to serve? Even to solicit such a response? And can we be humble enough to accept where we’ve gotten things wrong?

“You believed in me when everyone else did too.”

That phrase isn’t special or endearing.

* * *

Our greatest teachers and mentors are those who seek us out when we are in darkness. The people who see good in us where others don’t.

What’s beautiful about this kind of relationship is that it’s personal. It’s one to one.

Gurus and influencers gain followers by the millions, but meaningful connection does not exist at scale.

Seeing a diamond in the rough and putting faith in someone who has been overlooked — that happens one at a time, and any of us can do it.

If you’re going to apologize to your audience by saying something like, “Sorry this message is so long,” then before clicking “send” or before you deliver your address, check the text.

• Have you included extraneous information?

• Are you repeating what people already know?

• Is there a simpler way to say what’s needed?

• Is any of the messaging more about you and your ego, rather than what best serves the audience?

If any of these are true, then don’t apologize … or do the valuable work of editing.

Suggestion: choose the latter.

“Which finger can I bite for it to hurt the least?”

I heard someone use this phrase to refer to a situation where all the options were painful.

The words resonated. Sometimes, all we have are flawed choices, and it’s our job to pick the best, imperfect path.

Even if she loves to play the clarinet, even if first chair is sick … during a concert, the conductor’s job is to conduct. Not to play her favorite instrument, but to conduct the orchestra.

Regardless of our preferences, there are times when we are entrusted with a role. In those moments — particularly when it relates to leadership — the success of the group hinges on our willingness to step away from our preferences and to step into the role that we’ve been given.

When we’re not being creative — rather, when we’re not expressing our creativity — we experience discomfort.

There’s an unease that builds when we don’t attend to our inherent need to create.

We’re creative beings, but being creative is not enough; we have to do creative.

In ways that are unique to each of us, creativity seeks us as a conduit. Let it happen. Create the conditions for it to happen. Even if that flow is more of a trickle or a drip, let creativity have its way.

* * *

Creativity calls for expression. Actively help it when you can. And when you can’t, at least get out of its way.

Whatever you do, don’t stifle it.

New shoes. New car. New house. New membership. New tech.

For any of these things: is it comfort or convenience? Utility or façade?

There can be a lot of good reasons to get new things. But if it’s solely for show, how much is it going to cost you … to tell yourself the story that you want to hear?

Yesterday, my wife and I hiked around a local lake. It was an amazing, hour-long walk along a beautiful, wooded trail.

But ten minutes into the hike, we noticed something: we were walking really fast. This wasn’t our intention.

We laughed. We had blocked off a few hours. There was no need to rush; we had all the time we needed.

So we slowed down. We soaked in the moment.

An empty calendar does not a vacation make. More than anything, our frame of mind sets the stage for experiencing rest and connection.

If no one is asking for your advice, one of two things may be happening.

One, people don’t trust your expertise or judgement.

Or two, people don’t see you as someone who is willing to offer advice.

* * *

If you’re someone who seeks to help others, part of your role is to communicate that desire through your kindness, your generosity, and your commitment to being present to others and sensitive to their objectives.