Clarity – Grandpa Bob Encouraging Leadership

Decision Time

A decision sits in front of us, waiting.

We turn it over in our head. We ask a few more questions. We look for one more data point. We check with another person whose opinion we respect. We wait for the timing to feel right.

And still, we hesitate.

We tell ourselves we need more information. More time. More certainty.

Indecision usually grows from very human places. Fear of being wrong. Fear of being blamed. Fear of choosing a path that can’t be undone. Fear of embarrassment.

Add decision fatigue to the mix and postponement starts to feel reasonable.

Meanwhile, the cost of waiting accumulates quietly. Teams stall. Momentum fades. Confidence erodes. What began as a thoughtful pause turns into drift.

Most leadership decisions are made without perfect information. Progress rarely waits for certainty.

So, what is our hesitation really telling us?

Sometimes, it’s a clear no. A request pulls us away from what matters most. We don’t like what we see, but we’re not sure why. Maybe a partnership doesn’t sit right with our values. In these moments, extended thinking isn’t searching for clarity. It’s searching for a way to explain our decision.

Other times, we hesitate because the decision stretches us. It introduces uncertainty. It raises our visibility. It asks more of us than we feel ready to give. Growth decisions usually feel uncomfortable before they feel right.

At some point, the data stops improving and the waiting stops helping.

Start small. Take a step that tests the decision rather than locking it in. Forward motion reveals new information…something thinking alone can’t.

A decision that turns out to be wrong isn’t failure.

It’s feedback.

And feedback points us toward our next decision.

“Whenever you see a successful business, someone once made a courageous decision.”
— Peter F. Drucker

Photo by ChatGPT’s new image generator, which is way better than prior versions of the tool.

Simplifying 2026, One Decision at a Time

Every December, I return to a familiar practice. I reread a few of my older posts, looking for threads that might help clarify my thinking about the year ahead. Last year, on the final day of 2024, I wrote a short post on my goals for 2025:

-Serve the quests of others over my own
-Offer insights and advice, not direction
-Push beyond my comfort zone and inspire others to do the same
-Bring the loaves and fishes, and trust God with the rest

I see that I longed for simplicity without mentioning it directly. I wanted more presence, more clarity, more intention, and a little less noise in a world that seems to generate more every year.

This week, as I listened to Tim Ferriss speak with Derek Sivers, Seth Godin, and Martha Beck about simplifying life, I realized this desire has been with me for a long time. More than a decade ago, I wrote a short post called Becoming a Chief Simplicity Officer, describing how organizations thrive when they remove friction and create clean intuitive paths so people can focus on what truly matters. The idea was straightforward. When systems run smoothly, people flourish.

It turns out this Chief Simplicity Officer role fits in life just as well as leadership. Someone needs to step into the work of reducing complexity, eliminating friction, and clearing space for the things that deserve attention. Someone needs to guard the essentials by shedding the excess.

That someone is me, and it’s you in your life.

From Tim Ferriss’s Podcast

Derek Sivers: Simple Isn’t Easy, but It Is Freedom

Derek Sivers says simplicity requires intention. It doesn’t appear just because we cut a few tasks or say no occasionally. It takes shape when we clear away commitments that no longer belong and choose what contributes to the life we want to live. He often talks about building life from first principles instead of living on top of default settings.

Every recurring obligation fills space that could hold something meaningful. Every dependency adds weight. Every unfinished task pulls at the edges of our attention.

What possibilities would rise if complexity stopped crowding the edges of your life?

Seth Godin: Boundaries Create Clarity

Seth Godin approaches simplicity through the lens of clarity. When you know exactly who your work is for, you stop bending your days around expectations that were never meant to guide your decisions. Clear boundaries turn vague intentions into choices you can actually live out.

Simplicity often follows sharper edges. Define your edges, and the path through each day becomes easier to walk.

Martha Beck: Choose Joy, Not Habit

Martha Beck speaks of simplicity in the language of joy. She tells a story from her twenties when she made a single choice that reshaped her life. She turned toward joy and stepped away from misery, even when the joyful path cost more in the moment. Joy has a way of clearing the fog. It cuts through distraction and highlights what brings life.

Her words invite us to examine the decisions we’ve kept out of habit or comfort. Some habits strengthen our soul. Others only multiply clutter. Joy reveals the difference.

Ten Simplicity Moves for the Start of 2026

These actions are small, but each one lightens the load. They remove stones from a shoe you may have been walking with for years without realizing.

Cancel one subscription that no longer serves you. Even a small change can create a surprising sense of clarity.
Choose one non-negotiable time boundary and honor it. Maybe evening email and scrolling limits or a weekly focus block on your calendar. Small open spaces accumulate over time.
Simplify one recurring decision. Automate it, template it, or eliminate it entirely.
Pause one habit you maintain out of inertia. Give yourself a week to assess its value.
Identify one activity that consistently brings joy and schedule time for it this week.
Unsubscribe from three email lists that add noise instead of value.
Clear one surface you see every day. A calm space refreshes the mind.
Revisit your goals from last year and carry forward only what still matters. Release the rest.
Decide who you are working for. Clarity about your audience sharpens the work you choose to do.
Ask yourself one grounding question: What do I truly need to live the life I want? Let your answer shape what stays and what goes.

Looking Back at 2025 and Forward Into 2026

My goals for 2025 were aimed at deeper alignment with the things I care about. They served me well and opened my heart to possibilities I never would have imagined. I’ll carry these goals into 2026 (and beyond).

For 2026, I’m adding one specific goal to my list. I started working on this goal a few months ago, and it’s pushing me way outside of my comfort zone. While it’s a personal quest (and not one that serves the quests of others over my own), I believe it will serve others on their journey. I’ll be bringing the loaves and fishes and trusting God to do the rest. I’ll share more details later.

A Closing Invitation

Simplicity grows as unnecessary weight falls away and clarity rises in its place. You don’t need a title or a plan to begin.

You only need to choose.

Choose clarity.

Choose boundaries.

Choose joy.

Choose to be the Chief Simplicity Officer in your own life.

Let this be the year you simplify your days and rediscover the freedom and clarity that come from intentional living.

Photo by Paul Earle on Unsplash

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Permission to Conclude – and Get Started

A friend called recently. He’s been running his own business successfully for over a decade. Things are going well, really well. That’s why he reached out.

He wanted to talk through some ideas. Usually when I get these calls, it’s because a business owner is thinking about making a major change. Maybe selling, maybe acquiring another business, maybe just trying to get unstuck from a rut. But this wasn’t that kind of conversation.

He explained that his team is doing great work. His own role had evolved into mostly business development and handling occasional fire drills. Lately, there haven’t been many fires. The business is running so smoothly that, for the first time in years, he has time on his hands. Unexpected free time.

That’s usually a good thing, right?

He thought so too at first. He ramped up his business development efforts (always wise to add growth fuel to a business), and then he did something else. He stepped back and watched. Observed. Assessed.

For the first time in a while, he was able to look at the processes and tools his company uses with a fresh set of eyes. The eyes of an outsider.

That’s when he saw the gaps.

Not because things were falling apart. But because, with a little perspective, he realized how much better things could be. He saw inefficiencies, opportunities for automation, outdated systems, and new tools that could transform how they operate.

His brain lit up. Ideas started flowing. He made lists. And more lists. He started thinking through what needed to change, planning what to build, what to retire, and how to bring the team into the improvement process.

That’s when he called me. Not for help solving the problems, but because he suddenly had too many ideas and plans.

He’d become overwhelmed by the possibilities.

So, I asked him: What would it take to give yourself permission to conclude the brainstorming, the planning…and begin?

He paused.

As the boss, no one else was going to tell him to stop generating ideas and to start work on executing them. There’s no urgent deadline forcing a decision. No one asking for a status update. The machine is humming along, profitably. But he can see how much more potential is just sitting there waiting to be tapped.

We didn’t talk about his ideas or operations at all. We talked about how to decide. How to identify the vital few initiatives that would make the biggest difference. How to involve his team. How to get moving.

We talked about starting, and how starting builds momentum.

Our brains love ideation. There are no limits, no constraints. It’s energizing to imagine improvements, design new systems, and sketch out possibilities. We feel smart. We feel alive.

But our minds? They get restless. We lie awake at night, spinning. We second-guess ourselves. We get caught in the loop of “what if” and “maybe later.”

That’s where permission to conclude enters the picture.

It’s the quiet decision that says: “I’ve thought enough. I’ve explored enough. I may not have a perfect plan, but I have enough to begin.”

It’s the green light we must give ourselves. To start, to build, to test, to course-correct.

It’s a commitment. Not to perfection, but to movement.

To gain clarity through execution. To action that reveals what thinking alone cannot.

If you find yourself spinning with ideas, take a deep breath.

Give yourself permission to conclude.

And start.

Photo by Isaac Mugwe on Unsplash – the rider has no idea what lies ahead…only guesses, maybe some visualization of what could be lurking around that dark corner. The only way to find out is to start and figure it out along the way.

h/t – I learned about the concept of the “vital few” over 20 years ago from MAP Consulting. A simple yet powerful realization that we can only work on a few things at any one time. Choose the vital few, work on them, then move to the next set of vital few items after that.