Habits – Grandpa Bob Encouraging Leadership

What I’d Tell a 21-Year-Old Now

My niece is turning 21 in a couple of weeks. That milestone prompted me to go back and read a post I wrote in 2013 called Advice for a New 21-Year-Old.

Reading it now, I still stand behind it. But a lot has changed in the world and in me since then. A 21-year-old stepping into adulthood today faces a different landscape than the one I was writing about then. After more than a decade of watching young people navigate it, I think an update is in order.

Back in 2013, I intentionally opened with drinking and gambling. Those are two of the classic threshold items attached to turning 21. Things the world suddenly says you’re allowed to do.

Turning 21 feels significant in part because it comes with new freedoms. New access. New choices. New opportunities to say yes to things that used to be off limits.

But if I were to distill what I want to say today, it’s this:

The most important part of turning 21 isn’t what you’re allowed to do. It’s what you’re responsible for doing with your new freedom.

On Drinking

Back in 2013, I wrote specifically about types of alcohol, mixing drinks, drinking water between drinks, and a few other practical things. The tips were fun, and I meant them. But what I was really trying to say was simpler.

Don’t let alcohol become the thing that teaches you who you are.

A 21-year-old can easily mistake access for maturity. Being allowed to drink is one thing. Knowing how to carry yourself is another.

If you choose to drink, stay in charge of yourself. Stay aware. Stay responsible. Don’t confuse recklessness with fun, or excess with adulthood.

There’s nothing impressive about losing control, hurting people, damaging your future, or building habits that begin as entertainment and slowly become dependence.

Freedom says you can. Wisdom says you don’t always have to.

On Gambling

Gambling is worth talking about, less for the casino tips and more for what it teaches us about life.

A lot of life will tempt you into thinking you can outsmart systems that were built to profit from your confidence. Sometimes that system is a casino. Sometimes it’s consumer debt. Sometimes it’s a flashy investment story. Sometimes it’s just your own belief that you’re the exception to every warning sign.

Understand the odds. Understand the incentives. Understand that some games were built for you to lose slowly enough that you keep playing.

That lesson applies far beyond cards, dice, and slot machines.

On Money

At 21, your income may still be modest. Your savings may be thin. But your financial decisions aren’t any less meaningful.

This is the age when you should begin learning how money actually works.

Learn how to live below your means. Save at least 10% of your income, always. Learn how savings accumulate and compound over time. Einstein called compound interest the most powerful force in the universe, and he was right.

Learn how debt can easily grow if you allow it. Learn how investing works. Learn what markets do over time. Learn what risk is and what it isn’t. Learn how compounding works for you, or against you.

Don’t hand the whole subject over to experts and decide this isn’t for you.

It is for you.

Nobody can make this investment in your understanding except you. It’ll take effort, time, and discipline, but the payoff will be enormous. The earlier you begin, the more options you give yourself later.

On Taxes

This is one area I would add much more explicitly today.

Taxes shape your paycheck, your investments, your business decisions, your home decisions, and your retirement decisions. They are one of the most powerful forces shaping the economy around you. Most people your age treat taxes like background noise. They are anything but background noise.

Learn how federal income taxes work. Learn how your state handles taxes, including property taxes. Learn the basic tax forms. Learn what withholding is. Learn the difference between deductions and credits (it’s a big one). Learn how capital gains differ from ordinary income.

Most importantly, learn how and why governments shift tax policy. You’ll find that it’s often less about revenue generation and more about encouraging or discouraging certain behaviors. When you understand this, the debates about tax policy start making a lot more sense.

You don’t need to become a tax attorney. But you do need to stop treating taxes as some mysterious thing that happens in the background while adults in suits handle it for you.

The sooner you understand taxes, the less often you’ll be surprised by them.

On AI and Paying Attention to the Future

This didn’t belong in the 2013 version the way it does now.

If I were talking to a new 21-year-old today, I’d tell them to learn how to use AI well.

Not as a crutch. Not as a substitute for thinking. Not as some fantasy weapon that will let you dominate the world.

Use it as a tool.

Use it to expand your access to knowledge. Use it to test ideas. Use it to get a rough draft or minimum viable product moving. Learn what a minimum viable product is and why it matters so much to growth.

Use it to make an idea more tangible. Use it to model possibilities. Use it to iterate faster. Use it to tighten your thinking by forcing your vague idea into something clearer and more real.

An idea in your head can feel pretty smart. The moment you try to express it, structure it, test it, or build it into something visible, you’ll begin to see its strengths and weaknesses. AI can help accelerate your thinking process.

A lot of people are afraid that AI will eliminate jobs, upend industries, and leave ordinary people behind. That fear is understandable. But the larger pattern is nothing new.

History is full of major technological shifts that changed the economic framework people were living in. Industrialization changed everything. Then electricity. Then assembly lines, cars, computers, the internet, and smartphones. Each wave brought creative destruction. Old methods faded, old jobs shrank, new opportunities appeared, new leaders emerged.

AI is doing the same thing now. And the people who will thrive aren’t the ones who wish the old way would come back. They’re the ones paying attention to where the world is going, and responding.

Pay attention to what’s becoming easier, faster, cheaper, more valuable, or more scalable. Pay attention to which skills are fading and which ones are growing. Then adapt. Learn. Position yourself well.

That’s a far better response than fear.

On Health

At 21, most people feel almost invincible. That feeling can fool you into thinking poor habits are free. They aren’t. They just send their bills later.

Make physical activity a normal part of your life. Build it into your routine so deeply that you miss it when it’s absent. Walk. Run. Lift. Stretch. Work outside. Stay active in ways that make your mind and body stronger, more capable, and more durable.

Healthy habits pay real dividends over time. Energy, mobility, resilience, mental clarity, confidence, longevity, and quality of life. These aren’t accidents. They grow out of a disciplined and consistent approach to taking care of yourself.

If you build a strong base now, your future self will thank you.

On Faith

A 21-year-old may or may not have ever been meaningfully exposed to faith. Some were raised around it. Some were barely around it at all. Some were exposed to a shallow version of it and walked away before they were old enough to examine it for themselves.

But by 21, your openness to faith is your responsibility.

Faith should never be reduced to pretending. You don’t need to manufacture certainty where you still have questions. But you should stay open enough to seriously consider that life is more than work, pleasure, achievement, money, and survival.

Ask the bigger questions.

Why are you here? What is good? What is true? What does it mean to live well? What does it mean to love well?

These are foundational questions. If you ignore them, you’ll still build your life on some kind of answer. You just may not realize it.

Faith has a way of changing the scale of everything. It changes how you think about suffering, success, failure, purpose, love, forgiveness, responsibility, and hope. It gives context to things that otherwise feel random, hollow, or purely material.

Stay open. Read. Ask. Listen. Seek out serious people of faith, not just loud people with opinions.

You don’t have to have everything figured out at 21. But you’re old enough to begin seeking honestly.

On Learning from Good People

Find good people and pay attention to them.

Look for people whose lives make sense up close, not just people who look impressive from far away. Find people who have built something solid. Who work hard, keep their word, love their families well, handle money responsibly, and have endured difficulty without becoming cynical.

Ask questions. Watch what they do. Learn from their patterns.

At 21, you’re old enough to choose your influences more deliberately than ever before. Choose wisely.

On Freedom

Turning 21 brings new freedom. But freedom by itself is only raw material.

What matters is what you build with it. You can use it to drift, indulge, imitate, and react. Or you can use it to build capability, health, wisdom, faith, discipline, and a life that stands up under real weight.

That’s the better use of it.

The world tends to celebrate 21 by pointing to what you can now do.

I’d rather point to what you can begin becoming. That’s where the real opportunity is.

Happy Birthday, Isabella, from your favorite uncle.

Photo by Shai Pal on Unsplash

The Rocks, A Higher Gear, and Campfires

In 2013, I wrote a short post called We Are All Mountain Climbers.

The idea was simple. If you look closely at life, you’ll see that everyone is climbing something.

A career. A relationship. A difficult time in their lives. A personal challenge.

Life has a way of placing mountains in front of us. Or maybe…we’re just good at finding them.

As I wrote back then, the climb only makes sense from the inside. Watching others or hearing their stories are no substitute for taking it on yourself.

There was another part of the metaphor that mattered even more.

Many of us start the climb with backpacks full of things that make our journey harder than it needs to be. Old resentments. Lingering disappointments. Criticism that stuck with us longer than it should have. Sometimes we even carry baggage that belongs to someone else.

Years later, I came across a Buddhist parable that gave a new wrapper to this idea. It described people walking through life carrying large boulders. Anger. Ego. Grudges. The suffering didn’t come from the boulders themselves. It came from choosing to pick them up.

In 2015, I wrote about riding my mountain bike.

Whenever a hill approached, I had a habit of shifting into an easier gear before the climb even began. It felt like preparation. It felt like the smart thing to do.

One day I tried something different. Instead of downshifting, I shifted to a higher gear and pushed harder.

To my surprise, I climbed much faster than before, without bonking like I thought might happen.

Sometimes growth means discovering we’re stronger than we realize.

That experience raised questions I still ask myself.

Where else in life do I downshift before the hill arrives?

Am I protecting myself from difficulty…or underestimating what I’m capable of?

Recently, I read a post by Tim Ferriss about the “self-help trap.” He described sitting around a campfire one evening with a small group of close friends, the kind of unhurried night where the conversation slows down enough for truths to surface. He found himself thinking about the fire, and then realizing the fire wasn’t the point. The people sitting around it were.

He described how easily we can become so absorbed in optimizing ourselves, tracking progress, chasing improvement, climbing toward our next summit, that we lose sight of why we started climbing in the first place.

Summits will eventually fade. Our achievements will blur with time. Recognition disappears quicker than we expect.

Perhaps the real work of self-improvement is simpler than we think.

The rocks we’re carrying were never necessary.

The hills we fear are usually smaller than we imagine, or remember.

And the fire, the one worth tending, isn’t the one powering our ambition. It’s the one we gather around with the people we love.

Photo by Marc Zimmer on Unsplash

Six Questions at the End of the Day

For the next two weeks, I’ll be doing something new.

Marshall Goldsmith is encouraging people to ask themselves six questions every day. That’s the whole experiment.

Six questions. Asked at night. Answered honestly.

They all start the same way:

Did I do my best to…

The questions don’t ask what happened to me today. They ask what I did with today.

During his webinar introducing the experiment, Mr. Goldsmith referred to the Rigveda, an ancient poem from India that he described as being thousands of years old. He just mentioned it and moved on.

I had never heard of the Rigveda, so down the rabbit hole I went after his webinar ended.

The Rigveda is a collection of hymns. A lot of it is about everyday things. The sun rising. Fire. Breath. Life continuing. There’s a sense that daily life matters. That how we live each day counts.

People have been trying to figure out how to live a good life for a long time. Way before self-help and leadership books. Way before webinars and podcasts.

St. Ignatius of Loyola comes to mind. He developed something called the Daily Examen. It’s a review of the day. You look back. You notice where you were grateful. You notice where you fell short. You think about tomorrow.

Different times. Different traditions. Same basic ideas.

At the end of the day, pause and ask, “How did I live today?”

Goldsmith’s six questions fit right into that pattern.

Did I do my best to be happy today?

The question hits differently when the day is already over. I can see clearly whether I purposely enjoyed the day or just rushed through it.

Did I do my best to build positive relationships?

Now I’m thinking about the way I spoke to someone. Whether I listened. Whether I gave someone my full attention.

The questions are short. The reflections take some time.

Goldsmith describes happiness as “enjoyment with the process of life itself.” Happiness lives inside the day. It grows out of our engagement with what’s already in front of us.

The writers of the Rigveda seemed to understand that. Ignatius understood it too. They’re asking us to pay attention to our life and actively engage in it.

I’m only a few days into this experiment. Nothing dramatic has happened. No big breakthroughs.

But I know I’ll be answering these six questions later. I move through the day with more awareness. I catch myself sooner. I stay present a little longer. I think twice before reacting.

It’s a small shift…but small shifts repeated over time shape our lives.

Thousands of years have passed since the Rigveda was written. Centuries since Ignatius taught people to examine their day.

Our modern life looks very different, but the question remains the same.

How did I live today?

Here are Goldsmith’s six questions:

–Did I do my best to set clear goals today?

-Did I do my best to make progress towards my goals today?

-Did I do my best to find meaning today?

-Did I do my best to be happy today?

-Did I do my best to build positive relationships today?

-Did I do my best to be engaged today?

h/t – Marshall Goldsmith

Photo by Jonh Corner on Unsplash – looks like an awesome spot to think about these questions.

Always Improve Your Position

A few days ago, I was listening to Jocko Willink speak about the quiet discipline behind Brazilian jiu-jitsu. I’m not a jiu-jitsu person, but one idea landed for me. It’s a truth I already knew but had never heard spoken so simply:

Always improve your position.

In jiu-jitsu, nothing happens all at once. A submission arrives like lightning, but only to the untrained eye. What looks like a sudden victory is really the final expression of dozens of subtle movements that came before it. A hip shifts. A grip tightens. An elbow gains an inch of space. Most of these moves go unnoticed. Each small adjustment creates a little more room, a little more leverage, a little more advantage.

I’ve always believed real progress works this way. It’s rarely dramatic. It’s quiet and patient. The accumulated effect of showing up, learning something new, adding a bit more care, and preparing a little more than required.

Breakthroughs rarely come from a single moment of inspiration. They come from the quiet work no one sees. The thoughtful practice that sharpens your skills, the trust built over months of ordinary conversations, the time spent learning before making a decision. When opportunity arrives, it looks sudden to others. To you, it feels like the next logical step.

This truth showed up clearly for me after a derecho tore through our property on Father’s Day weekend a few years ago. Ninety-mile-per-hour winds knocked down at least thirty trees across multiple acres. When I walked our land the next morning, everything felt broken and overwhelming. The cleanup looked like a project that would take months. I didn’t have months to devote to it.

But I did have mornings. So, I decided to work for an hour and a half every day before work. I cleared a small section each morning. It was incredibly slow. I dragged branches, cut trunks, chipped debris, split firewood, and made countless trips to our local dump. Small steps, small progress, one morning at a time.

Over the course of a year (maybe more), I worked my way across our entire property. Along the way, I cut in new hiking trails and removed a number of unhealthy trees. What started as a mess became a healthier stand of trees and a network of paths that look like they’ve been here forever.

Out of destruction came a daily habit that changed my life. I still work outside every morning. Clearing brush, trimming trees, expanding trails, building chicken coops, restoring a rustic barn. All in small ninety-minute bites. It’s like a time-lapse video created through countless quiet mornings of small improvements.

The pattern I saw on my land is exactly what Jocko described on the mat. I didn’t need a grand plan or a burst of superhuman effort. I needed to improve my position every day, just by a little.

Improve your position today, even by an inch, and tomorrow becomes easier. Improve it again tomorrow, and the day after that reveals options that didn’t exist before. You don’t need surges of motivation or dramatic reinvention. You only need the willingness to keep moving, always improving.

Careers grow this way. Trust grows this way. Faith deepens this way. Families strengthen this way.

Progress won’t always be linear. Some days distractions will pull us off course, or setbacks will undo work we thought was finished. All of this is part of the journey. Even then, the way forward still comes through small steps. Imperfect, uneven, but the work of always improving our position remains the same.

We improve our position slowly, almost without noticing. That’s enough. Tomorrow, we’ll improve again. Then one day, we’ll find ourselves able to take a step that would have felt impossible a year ago.

Focus on the next inch. The miles will take care of themselves.

Photo by Walter Martin on Unsplash – a great rendition of my early morning work environment for at least a year.

When Fires Become the Work

Ask someone how their day went, and odds are, they’ll say, “Busy.”

Dig a little deeper, and you’ll hear about the fires they had to put out, the urgent requests from their boss, or the upset customers they had to talk in off the ledge. Everyone’s racing from task to task, reacting to whatever pops up next.

What you don’t hear—at least not often—is someone saying, “Today I worked on our 30-day goals,” or, “I spent the afternoon exploring how AI might streamline our operations,” or, “I studied what our competitors are doing better than we are.”

Most people are caught in an infinite response loop. The big questions get pushed to tomorrow, especially if the boss isn’t asking about them anyway. And often, he’s just as busy reacting to his own list of urgent problems.

Response mode is easy. You don’t have to choose what matters most. Just deal with what’s in front of you. There’s no time for stepping back, rethinking the process, or preventing tomorrow’s fires today. You stay busy. That way, you can tell yourself you’re still needed.

And when the day ends, you can point to everything you handled and feel like you earned your paycheck.

But the real questions are:
Did you move any of your monthly, quarterly, or annual goals forward?
Do you even know what they are?

For many, the answers are no and definitely no.

Working in the business is the default. It’s safe and familiar. It keeps your hands full.

Working on the business is different. It takes time, thought, and courage. It means facing questions without clear answers. It means exploring new tools, unlearning old habits, and imagining better ways to serve your customers.

No fires today? Is your boss on vacation? Sounds like an easy day.

But if no one thinks about what’s next, if no one is asking what should change or improve, and if no one is steering the ship, that ship will eventually drift. Maybe into a storm. Maybe into the rocks.

And no one will notice until it’s too late.

So, ask yourself:
Are you steering, or just responding?

Side note: These questions apply outside of work. If we’re not actively steering in our personal lives, we can just as easily find ourselves in a storm we could have avoided, running aground on some rocks, or drifting aimlessly out to sea.

Photo by Amir Saeid Dehghan Tarzejani on Unsplash

Garbage In, Garbage Out: Your Focus Defines Your Success

“Garbage In, Garbage Out” doesn’t just apply to computers—it applies to your life. The people you spend time with, the content you consume, and the habits you build shape your future. Want better results? Choose better inputs.

“You are the average of the five people you spend the most time with.” – Jim Rohn

“You are what you repeatedly do.” – Aristotle

“Show me your friends, and I’ll show you your future.” – John Kuebler

“Your life is controlled by what you focus on.” – Tony Robbins

The old phrase, “garbage in, garbage out” doesn’t only apply to computers and databases. It applies to how we live our lives.

Our inputs—the people we surround ourselves with, the information we consume, and the habits we cultivate—shape our outcomes.

If you spend time with amazing, imaginative, productive, and adventurous people, chances are you’ll start adopting some of those same qualities. At a minimum, you’ll develop personal goals that push you to emulate those qualities in your own way.

On the other hand, if you surround yourself with negative, self-destructive, bitter, or complacent people, their mindset and behaviors will slowly seep into your own life. Even if you think you’re immune, habits and attitudes are contagious.

Small Choices Compound Over Time

Consider this simple example.

If you exercise at least three days per week, you’ll see progress. Do it five days per week, and your results will be even better.

But if you instead have the habit of drinking a large chocolate shake for lunch every day, the impact won’t be immediate, but with time you’ll notice a negative shift in your health and energy levels.

Neither of these changes happen overnight. But over months and years, they define who you become.

Our small choices create big results.

The Status Quo Trap—It’s Hard to Change

It’s obvious that if you run toward a cliff, ignoring all the warning signs, you’re in for a big fall. But in real life, it’s rarely that clear.

Like the boiling frog who doesn’t realize the water is heating up until it’s too late, many people stay in toxic environments, bad habits, or unproductive routines because the declining results are slow and gradual. It doesn’t feel urgent—until suddenly, it is.

Our Inputs Dictate Our Outputs—So Choose Wisely

Our mind works like an algorithm. What we feed it shapes what it returns to us.

If we constantly consume negative news, gossip, or toxic social media, our mindset will reflect it.

If we surround ourselves with people who challenge us to grow, read books that inspire us, and engage in meaningful conversations, our perspective will shift toward productivity and fulfillment.

The good news? We choose. And by making intentional choices, we set the trajectory for our future.

Challenge: Take an Inventory of Your Inputs

For the next week, pay attention to what’s influencing you. Your environment, the content you consume, and the habits you engage in.

Who are the five people you spend the most time with? Are they making you better?

What are you reading, watching, and listening to? Is it fueling growth or draining your potential?

What small habit could you start today that would improve your future?

The inputs you choose today will shape who you become tomorrow, next year, and a decade from now.

Your choices matter. Make them count.

Photo by William Topa on Unsplash

Are You Willing?

All that matters is learning what you believe in…

“I know this now. Every man gives his life for what he believes. Every woman gives her life for what she believes. Sometimes people believe in little or nothing, and yet they give their lives to that little or nothing. One life is all we have and we live it as we believe in living it and then it’s gone. But to surrender what you are and to live without belief is more terrible than dying—even more terrible than dying young.” –Joan of Arc

Joan of Arc lived less than twenty years. Yet she fought for her beliefs and made a huge impact on history. She died for her beliefs at an age when many are just beginning their life’s journey.

She knew what she believed in. She knew what it meant to sacrifice for her beliefs. Ask anyone who serves or served in the military, a first responder who runs into a burning building to save others, or a newly formed priest who has answered God’s call. These are just a few examples. Each of them know what it means to sacrifice for their beliefs.

Sometimes our beliefs emerge quietly without our knowledge. We go through life, making seemingly inconsequential decisions about what we will and won’t do. We decide who our friends are, and how much we will let them into our lives. We decide when to listen. We decide how honest we will be with the world around us.

We establish habits for living our life, and we go on our merry way.

Do you know what you believe in? Really? Do you know what you believe to be true? Do you know what is important in your life?

Have you made the quiet time in your life that’s necessary to consider these questions?

What if it turns out that the things you believe in aren’t manifested in the way you live? Are you willing to change your habits? Are you willing to eliminate the things that don’t support your beliefs? Will you support your beliefs in the way you live, and the way you work with others? Are you willing to make your beliefs the centerpiece of your actions in everything you do?

Joan of Arc was right. One life is all we have, and then it’s gone.

Where are you in that one life? Is it too late to examine your beliefs and change the way you live?

The answer is clear But, it won’t become obvious until we make quiet time in our lives to reflect. When we do, we find it’s never too late to examine our beliefs and change our life.

Every day is a new beginning if we choose to make it so. It doesn’t matter what happened in the past. It doesn’t matter who wronged you. It doesn’t matter if you had a terrible childhood. It doesn’t matter if you’ve missed opportunities in the past. It certainly doesn’t matter if you failed in the past.

All that matters is learning what you believe in. Then, deciding what to do with that new knowledge, starting today.

The only question is: Are you willing to find out?

h/t: Matthew Kelly

Closing Your Eyes to See More Clearly

Have you ever tried brushing your teeth with your eyes closed, or in total darkness? I’m sure you’re asking, “How hard can that be?”

Give it a shot and you’ll find out.

Would you be able to find the toothpaste? How about your toothbrush? The sink? Now for the tough part. Can you put the right amount of toothpaste on the toothbrush?

Maybe you mastered all of that, and even brushed the proper amount of time. Are you sure you’re spitting in the sink? Did you put the toothbrush back where it belongs? How about the toothpaste?

You (should) brush at least twice a day. Multiply that by your lifetime of days, and that’s a lot of practice. Your brain should do it automatically…and it does until you eliminate one sense (sight in this case). Then it gets a lot harder.

So hard that you may find all your attention focused on that one simple task. For that moment, you will be fully present. No distractions. Only a laser focus on trying to figure out how to get the right amount of toothpaste on the toothbrush without making a mess.

Our brains are amazing. The biggest consumer of calories within our bodies. So, over millions of years of development, our brains have found ways to disengage (in the interest of energy conservation). Once our brain establishes a pattern for an activity, it flips the “auto-pilot” switch and rests.

Think about all things you do in a day without thinking. Or, maybe all the things you do while thinking too much. What if you approached each one a little differently?

Commute to work a completely different way. Shop in the opposite direction (admit it, when you go to “your” grocery store, you usually go in the same direction). Put your shoes on starting with the other foot.

Put a penny next to your smart phone. Pick it up instead of your phone when you get that urge to check your messages. A penny for your thought. Maybe you can give those pennies to a charity. Since this is for your favorite charity, what if you put a $20 bill there instead? That habit of yours may actually help someone else.

Which brings us back to the original premise. Brushing your teeth in the dark. Try it. You just might see things a bit more clearly.

Here’s the kicker. If you brush in the dark for about a week, it will become second nature to you, and (you guessed it) your brain will once again go on auto-pilot. Time to switch it up again!