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.
Grandpa Bob Encouraging Leadership 
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