The Top 15 Lessons I Learned in My 20s

Age 19: Last Call Weekend at Skelletones // Grand Rapids, MI // 01.09.2009 //

Age 19: Last Call Weekend at Skelletones // Grand Rapids, MI // 01.09.2009 //

Lesson 1: Don’t Worry About What You Can’t Control

Worrying about something you can’t control isn’t going to change the outcome. Instead, think about what you can do with the tools and skills you have. There are things you can control (i.e. how you respond to a tough situation) and things you can’t (i.e. how others respond to a tough situation). You save time, energy, and stress when you know the difference.


Lesson 2: There is Always a Solution

And more than likely, it doesn’t look like the first image that pops into your head. To find an even better answer, start by making a list of barriers (what’s blocking you) to define the problem. Use as much detail as possible. Next, make a list of solutions; write down everything you can think of, even if some of them are not currently possible. The more solutions you can think of, the more creative they will become. Tough problems often require creative solutions, and you will become very creative if you push yourself to think of 50+ solutions to an issue you are solving. Once you start generating A LOT of ideas, the challenge is reframed, and it turns into a game; the barriers which once caused anxiety become obstacles you want to overcome. Eventually, you’ll find your solution, because there is no situation too difficult to be void of a practical solution.


Lesson 3: Set One Goal for the Day

On my least productive days, I’ve made to-do lists with more than 20 items on them. It’s intimidating; where do I start? When everything’s important, nothing is a priority. Each morning, you should know the one thing you need to accomplish that will bring the most value to your day. Everything else is icing on the cake.

(See my 4 Corners Time Management diagram on p. 102 of Age of Agility)


Lesson 4: Fail Often

When you fail, you learn where your skills are and where you need to improve. Failure is really only feedback. We all fail and we all need to fail if we ever want to grow and get better at something. What’s important isn’t the act of making a mistake—that’s only 10%—the 90% that matters is how you respond to it. If you can learn from every failure, it will be well worth the embarrassment, money lost, or stress it may have caused you.


Lesson 5: Read More and Read Diversely

In the fall of 2008, I added reading to my daily routine. Before then, I couldn’t stand it. I was a slow reader and I had a hard time focusing on a block of text (I write more about my struggles in Age of Agility). What helped me was reading along with audiobooks. In 2009, I challenged myself to read 100 books in a year. I’ve been reading at least 100 books a year since. This year, I’ll reach 1,000 unique books (follow me on Goodreads).  

I’ve also challenged myself to read a wide variety of books: fiction, nonfiction, pulp “airport novels,” classic literature, poetry, plays, memoirs, biographies, business strategy, religious texts, anthropology, sociology, women & gender & cultural studies, philosophy (so much philosophy), psychology, physics, biology … you name it, I’ve read, am reading, or will read about it. Here is my reasoning: the more diverse your knowledge, the better you will be able to make connections between ideas. On top of that, I’m more confident mingling with strangers at events, because whatever they're interested in, chances are, I’ve read something about it. And it allows me to ask questions, so I can learn more about the person and whatever they’re interested in.


Lesson 6: Spend Less

Dave Ramsey said it best: “We buy things we don't need, with money we don't have, to impress people we don't like.” Most people are terrible at managing their money (I was one of them). Now, I’d rather buy cheap blue-jeans and drive a used car than buy something I know I will never truly appreciate.


Lesson 7: Avoid Debt (Including Student Loan Debt)

Money is a huge source of stress. When you’re stressed, you can’t think straight, you make poor decisions, and worst of all, you stop enjoying life. If you use a credit card, don’t spend more than what you can pay off. And if a credit card is too big of a temptation to overspend, get rid of it. You can do everything with a debit card nowadays. 

Now for the elephant in the room: college. Education is changing. Don’t go to college unless you know it’s going to be a worthwhile investment (and you get to define “worthwhile,” because everyone goes to college for a different reason—here’s my blog post that goes into more detail). Chances are, you’ll be paying on your student loans for the next 20 years—a study from the OneWisconsin Institute finds that it takes graduates of Wisconsin universities 19.7 years to pay off a bachelor's degree and 23 years to pay off a graduate degree. 

If you do decide college is for you (hurray!) look into all your options. There are grants and scholarships, and you can always ask your employer to help cover your education costs. Also, community college is a smart way to save money—you can always transfer to your favorite university later (transfer students with good grades have a higher acceptance rate than high school seniors with good grades). 


Lesson 8: Never Pass Up an Opportunity to Learn Something New

Age 25: Sammamish 1/2 Marathon // Redmond, WA // 03.07.2015 //

Age 25: Sammamish 1/2 Marathon // Redmond, WA // 03.07.2015 //

Take advantage of every opportunity to learn, even if there is no clear correlation to your future goals. 

When I was 21, I was lucky to have a business mentor. During one of our weekly coffee sessions, I began talking about one of my classes I was struggling with: it was boring and it all felt like review. My mentor responded by telling me to focus on how the professor was teaching the class. He said: If the content is boring or review, tune into something else, like how the professor is delivering the information because there is always something to learn in every situation. Ask yourself, what’s working? How would you improve upon it? (Thanks, Andy C.)

Finally, not every lesson comes in lecture form. If you’re observant and ask questions, you can learn something from everyone, even if it’s what NOT to do.


Lesson 9: Move Outside the Classroom, Get Your Hands Dirty

Classroom learning (or in-person learning from a master), self-education (reading, listening to podcasts, reading blogs, going on manic Wikipedia clicking rampages), and hands-on experience all play a role in a well-rounded education. What’s missing in most education is the hands-on portion, which is arguably the most important part of learning. When you can, find ways to put your learning into action so you can see how it applies to real-world situations. 

I learned my best lessons through hands-on experimentation, like starting a company at 18 (and having it fail), being part of a business apprenticeship program at 24 (where I was able to work alongside brilliant people at huge companies), publishing a book at 27, and taking a second stab at starting a company at 28 (ten years later, I’m more prepared, and I'm always learning!).


Lesson 10: Stop Complaining

Don’t bring issues to a supervisor unless you have solutions. 

Besides, the world is beautiful—be thankful there are tragedies in this world you will never experience. Be thankful for what you do have. Be still. Enjoy the moment. (And again) Be thankful. Our time here is short. Don’t let all your time pass without fully enjoying the human experience.


Lesson 11: Getting Drunk Isn’t Worth the Hangover

Not only do you run the risk of doing or saying something you regret, you lose an entire day. There are healthier, safer, and less expensive ways to blow off steam or bond with friends.


Lesson 12: Be Kind (even if you think someone doesn’t deserve it)

Everyone you meet has something they are working through. This is why I try to be especially kind to people who are rude, because there is a real struggle at play in their hearts, and their body is only responding as any of ours would. Be kind, and part of being kind is 1) knowing when to stick with or pull out of a project, and 2) knowing when to close the gap or distance a friendship. Be patient, and when you can’t be patient, be kind.


Lesson 13: Everything is a Gift

When someone offers help through time, advice, or funding, it is a gift. They are going out of their way to help you for the sole purpose of making you a strong or better human being. It is not something you are entitled to, it is truly a gift, and one you can give back to others. If someone has helped you, the best way to thank them is to help others as they have helped you.


Lesson 14: Always Do Your Best

Always do your best. Always. You cannot buy integrity, you cannot buy years of knowledge, you cannot buy a skill, and you cannot buy your reputation. These are all things you build, and always doing your best is the quickest way there.

This is YOUR best, not someone else’s. Every person is on a separate path leading to their own unique goal. Never compare yourself to others, because their goal is not your goal. Your pasts are just as different as your respective futures. When your paths cross, always do your best, and encourage them to do their best. If you find that your half-hearted effort is as good as their best, be patient and lead by example. Your focus should always be on doing YOUR personal best.


Lesson 15: Respect Others Because You Respect Yourself

Respect is something that is earned. Before someone has earned your respect or after they have lost it all, treat them with decency because of the respect you have for yourself. When you are rude, cruel, mean, disengaged, or hold a grudge, you are only hurting yourself—you hold yourself back from your own progress. Whatever you do, do it respectfully, because how you treat others starts with how you treat yourself.


Age 28: Atlas's first birthday // Lake Nokomis, Minneapolis, MN // 08.04.2018 //

Age 28: Atlas's first birthday // Lake Nokomis, Minneapolis, MN // 08.04.2018 //

**Bonus Lesson 16: Never Sacrifice Your Values** (W/ A SPECIAL ANNOUNCEMENT)

In my opinion, one of your most important values should be loving and respecting yourself (the whole put-your-oxygen-mask-on-first-in-an-airplane cliché). You shouldn’t wake up every morning hating your life for any reason at all, but especially if it’s due to your job. If this is you, take time to start looking for work that supports your lifestyle, grows the skills you are interested in, and gives your life purpose. This is one of the most important life lessons I’ve learned so far (at 28), and that’s why it is the topic of my next book in the Age of Agility series, Meaningful Work: Discovering your purpose, achieving your ideal lifestyle, and growing your talents in your perfect career. 

If you have any comments or want to share your story, send me an email here

More than luck,



Andrew J. Wilt is the author of Age of Agility, a book that addresses the skill gap between school and work. He can be reached at and on Twitter @andrewjwilt