Goals – Grandpa Bob Encouraging Leadership

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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What Is Happily Ever After?

The glass slipper fits perfectly. The prince takes Cinderella’s hand. The castle doors swing open, and as the camera pans out over the kingdom, the narrator’s voice declares, “And they lived happily ever after.”

The end.

What comes next?

Did Cinderella and her prince travel the world together? Did they have children who drove them to the brink of exhaustion? Did she struggle to adjust to palace life? Did they face illness, loss, or financial strain? How did they support each other as they learned to build their life together?

“Happily ever after” is a blank canvas. It conjures a series of images in our head. Successes we dream of, milestones we hope to reach, adventures we’re planning, moments of pure joy we can almost taste.

For some, happily ever after is a corner office overlooking the city, business-class flights to international conferences, and coming home to a modern apartment where everything has its place.

For others, it’s Saturday morning pancakes with kids mixing the batter in a cloud of flour dust or teaching their daughter to ride a bike. Quiet evenings on the porch planning their next camping trip.

Still others may crave a life of endless travel, vagabonding from place to place, sampling cuisine from every corner of the world as they go.

There are as many versions of happiness and fulfilment as there are people.

Social media tries to curate our happiness by showing us picture-perfect moments. Engagement photos against stunning backdrops, vacation snapshots from exotic locations (often peering over two perfectly poured wine glasses on a balcony), career announcements celebrating promotions and new ventures.

These snippets of other people’s lives create a happiness catalog. A collection of achievements and experiences that can feel like requirements for a well-lived life.

We may start believing that fulfillment looks like someone else’s Instagram story, someone else’s LinkedIn update, someone else’s holiday letter.

Seeking fulfillment by following someone else’s template is always a fool’s errand.

Sure, be inspired by someone else’s success. Maybe borrow a travel idea, or try something new. But their world operates differently than ours. Their values, circumstances, and dreams belong uniquely to them.

What brings them deep satisfaction might leave us feeling empty. What fills our hearts might seem trivial to them.

True fulfillment can only come from our own perspectives, our own values, and our own definition of what makes us, and those we love, happiest.

Real “happily ever after” is wonderfully messy and beautifully imperfect. It blends all the goals and aspirations we have with all the compromises and adjustments we’ve made along the way.

Goals that seemed essential in our twenties might be irrelevant in our forties. The dreams we never imagined decades ago can suddenly become our life’s new mission.

This evolution reflects an ongoing process of learning who we are and what truly matters to us. Independent of what we thought we would want…or what others told us we should want.

Happily ever after lives in the ongoing appreciation of what we’ve built and who we’ve become. Our story matters because it’s still unfolding and it’s authentically ours. It doesn’t need to resemble the someone else’s highlight reel.

The glass slipper that fits you perfectly will look nothing like Cinderella’s. Maybe it’s a hiking boot, flip-flops, a running shoe, or something very formal, made of fancy leather…or no shoes at all.

You choose.

And that’s exactly as it should be.

Photo by Ella Heineman on Unsplash – because one of my greatest joys is making breakfast for my kids and grandkids on a Saturday morning…a wonderful part of my happily ever after.

Pausing at the Halfway Mark

July 2nd is about a week away. That will be the 183^rd day of the year. The halfway point.

I usually think of the summer solstice as the halfway point since the days start getting shorter after that.

Either way, it’s a good time to reflect.

Think back to January. Back then, you were probably wondering how to shed a few of those extra pounds you gained over the previous two weeks.

While sipping your leftover peppermint cocoa on New Year’s Day, what goals or intentions were on your mind? Did you write them down? Did you share them with anyone?

Be honest with yourself. What have you done that moves you closer to achieving any of the goals you set six months ago? Even small steps count.

Do those goals still matter to you? Have you added new goals since then?

Whatever your answers, write them down. Pick one thing to act on this week to get back on track. Movement builds momentum, and maintaining momentum is the key to achieving any goal.

Don’t forget to celebrate. A new productive habit. A relationship strengthened. A busy season endured (every industry seems to have one).

These quiet victories matter. They deserve your recognition.

Halfway through the year, the invitation is simple. Reflect. Realign.

Begin again.

Side note: Consider doing this exercise with an even larger time horizon.

-What were your goals 10 years ago? 20 years ago?

-Are those goals still important to you?

-Have you made progress on any of them?

-What are your goals for the next 10 years? 20 years?

-What concrete steps will you decide to take over the next 6 months to make progress on at least one of your 10-year goals?

Photo by Elliot Pannaman on Unsplash – why this image out of the thousands I could have chosen from Unsplash? My focus wasn’t on the stark, still, wintry vibe (although that’s nice). I was captured by the story it conveys. In my imagination, this person set out to cross the entire lake. Clearly, their chosen path wasn’t successful. Poor planning? Lack of vision? Who knows?

But the halfway point is a moment like this. A pause at the edge, where we get to decide if our goal still matters. If it does, it’s time to retrace, replan, and re-commit to accomplishing what we set out to achieve.

Two Steps Forward, One Step Back…

Is still progress.

Pick any project—it doesn’t matter if it’s something you’ve assigned to yourself or something your boss has given you. It could be a huge, long-term project, or something that should take less than a week.

Chances are, that project will turn out to be harder than expected. It will require effort that nobody saw during the planning process (whether planning consisted of a 5-minute conversation, or a multi-month series of meetings and discussions).

Here’s something else about projects: even when we’re given full ownership, most of us will try to find ways to make sure we’re not fully responsible for the outcome.

But no matter what, the project remains. We own it. We also own the goal of getting it done right.

“The man who moves a mountain begins by carrying away small stones.” – Chinese Proverb

Progress is made through consistent effort, one step at a time. Then another. Then another. It’s the steps toward the goal that matter, almost as much as the goal itself.

What if some of the steps we take are the wrong ones? What if we have to go back and redo some of our work? What if somebody sees us make mistakes along the way?

Each of these are (almost) guaranteed to happen.

Embrace it. Learn from it. Carry on.

Keep stepping forward. Learn along the way and give yourself permission to take a step (or two) back from time to time.

The progress you’re making is the reward.

Photo by NEOM on Unsplash

Process Over Outcome — The True Value of Life’s Challenges

The year spent training for a triathlon isn’t just about race day. It’s about the discipline, endurance, and self-discovery that come with each mile ran, every beach swim, and each grueling mile logged on the bike. The race is the goal, but the transformation to triathlete happens during the journey to the starting line.

What about Basic Training for the Marine Corps (something I haven’t personally experienced)? Recruits aren’t merely learning the basic skills they’ll need to be successful. They are becoming something entirely new…a Marine. The recruit is transformed into a Marine by the training process.

Consider a four-year college degree. It’s been said (not sure who said it first) that the main thing a recruiter learns about a college graduate is that they had to apply themselves adequately over a four (or five, or six) year period to get enough class credits to graduate in their chosen major. Each college graduates’ journey is different, and that journey is often as valuable as the classes they had to take to get their degree.

Even smaller experiences like a short hike, a long drive to visit family, or a phone call with a friend can offer more than just their immediate outcomes. They can provide moments of reflection, connection, and growth.

Life’s experiences are not just a series of goals to be checked off or memories to be cherished.

When we learn to enjoy the process and the lessons along the way, we gain something far more valuable: growth, understanding, and the ability to appreciate the transforming power of our journey.

Photo by Matt Howard on Unsplash

Embrace Your Unique Goalprint: The Power of an Ambition Audit

A little over a decade ago (time flies!), I wrote a post that introduced the concept of Goalprints. That post described a series of steps and questions that we should use to understand our unique Goalprint and determine if our lives are supporting (or not supporting) our goals.

I recently heard about the concept of an Ambition Audit… taking a step back to assess whether your ambitions are still relevant, achievable, and fulfilling. I realized that this concept complements the Goalprint exercise extremely well.

Here’s an updated post that integrates the Ambition Audit concept…plus I’ve added a handy cheat sheet that you can use for this exercise.

There’s a classic quote in business: “People who buy shovels don’t want shovels. They want to make holes or fill in holes as quickly and easily as possible.”

Chances are pretty good that you’re selling shovels to someone. Or maybe you dig the holes?

Either way, the planning, the shovel, the digging, and the hole itself are all merely steps along the way to achieving someone’s goals.

Are they achieving your goals? Maybe.

That all depends on whether you know what your goals are.

The funny thing about goals is that no one has the same goals. They may share some or agree on goals to pursue together. But no two people have the exact same goals.

Each of us has a Goalprint as unique as our fingerprint. It captures our passions, our dreams, and the specific goals we’ve laid out for our lives. Partially developed Goalprints live in our subconscious mind until we take the time to bring them into our conscious mind and fully define them.

Consciously defining our unique Goalprint isn’t easy. Nothing worthwhile ever is. But once defined, how do we ensure our goals remain relevant and truly reflective of who we are?

That’s where the Ambition Audit comes in—a powerful tool to regularly reassess and realign our goals with our evolving values and life circumstances. Combining the process of creating your Goalprint with an ambition audit ensures that your aspirations remain meaningful and motivating.

Here are the seven steps for creating and living your personal Goalprint, enhanced with the principles of an ambition audit:

Step 1: Define Your Passions

List the five things you are most passionate about and describe how you plan to center your life around these passions over the next five years. Are you willing to focus your life on this list? If not, maybe these aren’t really your passions.

Ambition Audit Tip: Regularly reassess these passions. Life changes, and so can the things that drive you. Ensure your passions remain true to your current self.

Step 2: Plan Your Experiences

Define at least seven things you plan to experience over the next ten years. This isn’t just a wish list—commit to these experiences. How many involve your top passions?

Ambition Audit Tip: Review this list annually. Are these experiences still aligned with your passions and values? Adjust as needed to keep your goals relevant.

Step 3: Financial Goals

Money isn’t everything, but it does make the world go around. Write down how much money or assets you plan to set aside for major expenditures in one year, five years, ten years, and twenty years. What income do you need to hit these targets? Start saving now.

Ambition Audit Tip: Revisit your financial goals periodically. Ensure they support your passions and experiences. Adjust savings and investments to stay on track.

Step 4: Define Your Future Self

Describe what you plan to be in one year, five years, ten years, and twenty years. This can be personal, professional, or anything else. Remember, being something is different than just where you choose to work. Make sure your future self supports what you’ve listed in the first three steps.

Ambition Audit Tip: Reflect on your future self regularly. Is this vision still inspiring? Does it align with your evolving values and circumstances?

Step 5: Align with Your Spouse

If you have a spouse or partner, compare, and discuss your Goalprints. What do you have in common? How will you accommodate and support each other’s Goalprints?

Ambition Audit Tip: Periodically revisit this conversation. Life changes, and so do relationships. Ensure your Goalprints remain compatible and mutually supportive.

Step 6: Hold Yourself Accountable

Commit to fulfilling what you’ve laid out in your Goalprint as you make decisions in your life. Define success on your own terms and stay true to your goals.

Ambition Audit Tip: Set regular check-ins to review your progress. Adjust your goals and actions to stay aligned with your ambitions.

Step 7: Annual Reassessment

Repeat this exercise once a year. Your Goalprint will change and grow over time—if you have the courage to let it.

Ambition Audit Tip: This annual review is your built-in ambition audit. Reflect on the past year, reassess your goals, and realign them with your current values and circumstances.

Your unique Goalprint, coupled with regular ambition audits, will guide you toward a life of purpose and fulfillment.

How about that cheat sheet? This is something I didn’t include in my original post, but I’ve had a few people ask me if a template or form exists. So, here’s an initial template that you can use. Just copy and paste this form into your favorite word processor and use it to capture your answers. Remember, there are no wrong answers in this exercise.

Personal Goalprint & Ambition Audit Template

Name: ______________________________
Date: _______________________________

Step 1: Define Your Passions
List the five things you are most passionate about and how you plan to center your life around these passions over the next five years.

Passion: _______________________________
• Plan: _______________________________
Passion: _______________________________
• Plan: _______________________________
Passion: _______________________________
• Plan: _______________________________
Passion: _______________________________
• Plan: _______________________________
Passion: _______________________________
• Plan: _______________________________
Ambition Audit Check: Are these passions still true to your current self? (Review annually)
• Yes / No
• Adjustments: _______________________________

Step 2: Plan Your Experiences
Define at least seven things you plan to experience over the next ten years. Remember, these aren’t visionary fantasy goals. These are things you actually plan to do in the relative near term of the next decade (remember, decades go by quicker than we realize).

Experience: _______________________________
• Plan: _______________________________
Experience: _______________________________
• Plan: _______________________________
Experience: _______________________________
• Plan: _______________________________
Experience: _______________________________
• Plan: _______________________________
Experience: _______________________________
• Plan: _______________________________
Experience: _______________________________
• Plan: _______________________________
Experience: _______________________________
• Plan: _______________________________
Ambition Audit Check: Are these experiences still aligned with your passions and values? (Review annually)
• Yes / No
• Adjustments: _______________________________

Step 3: Financial Goals
Write down your financial goals for major expenditures at different stages.
One Year
• Amount: _______________________________
• Income Plan: _______________________________
Five Years
• Amount: _______________________________
• Income Plan: _______________________________
Ten Years
• Amount: _______________________________
• Income Plan: _______________________________
Twenty Years
• Amount: _______________________________
• Income Plan: _______________________________
Ambition Audit Check: Do these financial goals support your passions and experiences? (Review annually)
• Yes / No
• Adjustments: _______________________________

Step 4: Define Your Future Self
Describe what you plan to be in one year, five years, ten years, and twenty years.
One Year
• Personal: _______________________________
• Professional: _______________________________
Five Years
• Personal: _______________________________
• Professional: _______________________________
Ten Years
• Personal: _______________________________
• Professional: _______________________________
Twenty Years
• Personal: _______________________________
• Professional: _______________________________
Ambition Audit Check: Is this vision still inspiring and aligned with your values? (Review annually)
• Yes / No
• Adjustments: _______________________________

Step 5: Align with Your Spouse
If applicable, compare and discuss your Goalprints with your spouse or partner.
Common Goals:
• ____________________________
• ____________________________
• ____________________________
Supporting Each Other’s Goalprints:
• ____________________________
• ____________________________
• ____________________________
Ambition Audit Check: Are your Goalprints still compatible and mutually supportive? (Review annually)
• Yes / No
• Adjustments: _______________________________

Step 6: Hold Yourself Accountable
Commit to your Goalprint by reflecting on the following:
Decisions Made in Alignment:
• ____________________________
• ____________________________
• ____________________________
Challenges Faced:
• ____________________________
• ____________________________
• ____________________________
Successes Achieved:
• ____________________________
• ____________________________
• ____________________________
Ambition Audit Check: Set regular check-ins to review progress. Adjust goals and actions to stay aligned.
• Date of Next Review: _________________________
• Adjustments: _______________________________

Step 7: Annual Reassessment
Repeat the entire exercise once a year. Reflect on the past year and realign your goals with your current values and circumstances.
Reflection:
• What has changed over the past year?_______________________________
• How have your goals evolved? ____________________________________
• What new passions or experiences have emerged?_____________________
Ambition Audit Check: Ensure your Goalprint is dynamic and reflective of your true self.
• Date of Review: _______________________
• Adjustments: _______________________________

By using this template, you can create, evaluate, and adjust your personal Goalprint, ensuring that your ambitions stay relevant, achievable, and fulfilling. Embrace your journey of introspection and realignment to lead a life of purpose and fulfillment.

Seven Steps to Creating Your Goalprint

People who buy shovels don’t want shovels…

There’s a classic quote in business:

People who buy shovels don’t want shovels. They want to make holes, or fill in holes as quickly and easily as possible.

Chances are pretty good that you’re selling shovels to someone. Or, maybe you dig the holes?

Either way, the planning, the shovel, the digging, and the hole itself are all merely steps along the way to achieving someone’s goals.

Your goals? Maybe…that all depends on whether you know what your goals are.

The funny thing about goals is that no one has the same goals. They may share some, or agree on goals to pursue together. But, no two people have the exact same goals.

Each of us has a goalprint as unique as our fingerprint. It captures our passions, our dreams, and the specific goals we’ve laid out for our lives. Partially-developed goalprints live in our subconscious mind, until we take the time to bring them into our conscious mind and fully define them.

Consciously defining our unique goalprint isn’t easy. Nothing worthwhile ever is.

Here are the seven steps for creating and living your personal goalprint:

1. Define five things you are most passionate about, and how you plan to center your life around these passions over the next five years. Not willing to focus your life on this list of passions? Maybe these aren’t really your passions.

2. Define at least seven things you plan to experience over the next ten years. A quasi-bucket list, only with a ten-year horizon. Notice this isn’t a list of seven things you want to experience, rather a list of the seven things you plan to experience. How many of these involve the things you are most passionate about?

3. Money isn’t everything, but it does make the world go around. With this in mind, write down how much money or assets you plan to have set aside for big ticket expenditures (i.e., home purchases, kids’ college, retirement, something you were passionate about in item 1, etc.) in one year, five years, ten years, and twenty years. What income do you need to hit these targets? Start saving now, if you haven’t already.

4. Define what you plan to be in one year, five years, ten years, and twenty years. This can be personal, professional, or anything else you define as what you plan to be. Keep working until your “what” supports what you’ve listed in the first three steps.

5. If you’re blessed with a spouse, or a soon-to-be-spouse, compare and discuss your answers in the first four steps above. What do you have in common? Are your goalprints compatible? How will you each accommodate and support your spouse’s goalprint in the coming years?

6. Hold yourself accountable for fulfilling what you’ve laid out in your goalprint as you make decisions in your life. Enjoy defining success on your own terms.

7. Repeat this exercise once a year.

Unlike fingerprints, our goalprint will change and grow over time. That is, if we have the courage to let it.

____________________

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