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22 Lessons on Life, Love, and Choosing What Matters Most

“Most people spend the first half of their lives collecting and the second half choosing what to keep. Now that you’re closing in on the top of the hill, which lessons learned and pieces of advice do you plan to always carry with you?”

A friend asked me this question on my 38th birthday. At the time, I didn’t have a good answer.

Looking back, that played a big role in why I decided to write as realizing I was still lost after 13,879 days of walking didn’t feel good.

Six years have passed since that conversation — high school and half of college. During that time, I’ve published 300+ articles, many of which are rooted in weeding out what matters from what doesn’t.

It’s helped.

I’ve spent the majority of 2022 offline because my eyes began to hurt. But I’ve been listening and taking notes. Here are 22 lessons the world — and the good people I’m lucky to have along with me for the ride — have taught me that I plan to carry with me from this past year.

1. The importance of play increases with age

“You don’t burn out from working too much. You burn out from worrying too much.” My friend Jeanette said that. It hit me hard.

2022 rained stress from all major corners of my life. The days I felt good though, were when I got outside and kicked a ball, chased my kids, or got kicked by my kids while chasing a ball.

That was my daily homework — fight to find pockets of fun.

Like relationships, the importance of play increases with age.

2. Choose the kind of noise you want in your life

When visiting my family, my kids were jetlagged and made a raucous at my parent’s house before the roosters woke up. When I apologized, my mom and dad said something that made a lot of sense — “It’s great noise!”

The world is loud and shows little sign of quieting down.

You get to choose the soundtrack to your life.

Get clear on what you define as the right kind of noise.

3. Listen to the teaching, not the teacher

My friend Conor made a video about this idea. Like him, I tend to think advice needs to come from someone who’s walked the path I want to go down, knows me inside and out, or has spent years studying a topic.

But that holds us back from interesting takes from surprising places. Good ideas come from everywhere. If something speaks to you, thank the person for sharing it and take it with you.

4. You’re allowed to disappear

“Your writing is a reflection of your living. Throw yourself into something else. You’re allowed to disappear.”

A friend said this when we were talking about the reality of making a pro-longed living online. I followed his advice. I threw myself into a ton of new situations. I taught a bunch at universities. I went from not knowing how to write books to helping three people who are doing a lot of good in the world finish theirs. I was finally able to travel home to see people I care about who have health issues. I fulfilled a life-long dream of buying a fixer-upper on the Mediterranean to hopefully watch my kids grow up in.

The best writing, or art of any kind, creates human connections. And that becomes harder and harder to do if you don’t prioritize connecting with actual humans — and that includes time with yourself.

The online world isn’t going anywhere.

If you need to, opt-out.

You’re allowed to disappear.

5. If you want to change the world, care for five people

The best moments of my life happened when I chose to keep my world small. That, and when I didn’t have my phone.

Ask yourself who you’re grateful for. But don’t stop there. Take it one step further by asking yourself the exact people you want to say your name when they’re asked who they’re grateful for.

  • Close your eyes and zero in on the five people who matter most to you.
  • Breathe them in until you can see every line on each of their faces.

This simple flip will give you tremendous clarity on what you need to do to ensure the people you love, love you back. 

6. Strength is saying “I’m scared”

My youngest kid has never been a fan of sleeping. But instead of waking up having to pee or because he wants to play, recently, it’s been because he’s scared.

One groggy morning, I complained to my wife about this. “Don’t we want our kids to tell us when they’re scared?” she replied.

Like Charlie Maksey alluded to in his hit book, The Boy, The Mole, The Fox and the Horse, “help” is the bravest word we can say.

7. The secret to a long life is found in differences

As you get older, the more the days begin to bleed into each other. To live a long life, you need to unlock new worlds. The fastest way to do this is by spending time with people who don’t look, think, or act like you.

Getting to know other people’s stories will always be the best way to better write our own.

8. Being unassuming is a superpower

“I wanted to speak up when clients thought one of the taller or more vocal members of my team was the owner of my company. But I learned early in my career just how powerful being unassuming can be. People speak freely with me. It builds trust. If you prioritize learning one skill, focus on suspending your ego.”

My friend Kevin Ervin Kelley, AIA said that.

He’s a good guy.

The world needs more people who don’t lead with their titles or feel the need to tell people how important they are.

9. True freedom isn’t tied to money

True freedom is much simpler than that. True freedom is having the courage to be yourself — while working to develop the stones to continually bet on yourself.

Money comes and goes. That curly-haired money-hungry vegan in the Bahamas is a good example of that. Plus, it has a funny way of chaining people to the pursuit of more, more, more forgetting that golden handcuffs are still handcuffs.

Follow people who can teach you to be monetarily wealthy if that’s your thing. 

But don’t forget to also develop into the type of person who stays true to yourself if you lose it.

10. Slow is smooth and smooth is fast

My wife took things slow when we moved this past summer. I didn’t. A month later, she was chipping away in our new apartment with a smile on her face, while I was laid up in bed with a thrown-out back.

Being a military brat, I often heard the phrase, “Slow is smooth and smooth is fast.” This summer while reading my friend Benjamin Sledge’s debut (incredible) book, “Where Cowards Go to Die,” I came across it again.

Then I looked at my wife.

And then I looked back at myself.

And then I thought, “Huh.”

11. The sole purpose of finding your power is to share that power with others

My friend Kim said that.

I wish more people thought like that.

I wish more people acted like that.

12. The words we read become the world we see

Environment affects behavior. This is not only true regarding our physical world, but also the online one. If you’re surrounding yourself with messages and attitudes that bring you down twenty-five hours a day, change your diet.

This is not the same as ignoring the problems in the world. 

It means you pick your battles. 

Use what pisses you off as fuel to right what you feel is wrong with the world. Just make a point not to drown yourself in it because the world has buckets of it. 

Activism demands focused action.

13. You can never tell someone how much they mean to you enough

This past year I taught a lot of shy and reserved people storytelling and public speaking skills. Months later, a few students told me that even though they have a lot of teachers, I was their teacher.

That one sentence — which took them a few seconds to say — keeps me going.

Pick up the phone.
Physically write a letter.
Go see people in person.

Silent gratitude is selfish.

If you appreciate someone, tell them.

14. The best decisions are those that create the most future options

I’ve had to navigate situations of late where there wasn’t a positive outcome. Choosing between two negatives sucks. But when it happens, train yourself to map out which one could potentially create the most future options.

Then remind yourself that decisions are defined by what you do after making them.

15. Being welcoming is a seriously attractive quality

Having recently moved, I was back to having to make new friends again. I’ve gotten better at it as I’ve lived in a dozen different places, but asking people I don’t know to hang out still terrifies me.

Fortunately, I didn’t have to make the first move as a few people at our kid’s school went out of their way to make my wife and me feel included.

We all feel like outsiders at some point in our lives. Few qualities are more attractive than going just a little out of your way to make other people feel comfortable.

16. If you want to know how you feel about someone, say goodbye

Want clarity on who you want in your life? Imagine your life without them.

Sounds morbid, but give it a shot.

  • Who are the first people you reached out to when covid came on the scene?
  • Who are the handful of people you drop whatever you’re doing when they call?
  • Who are the people you never want to say goodbye to?

Hold these people tight.

We don’t always get to choose the last time we get to say goodbye, but in the meantime, we do get to choose how often we say hello.

17. Like the best stories, the best friendships are full of challenges

Some of my closest friends are people I have consistent fun with. But for the most part, my closest friends are the ones who’ve stuck with me when others would have bailed and vice versa.

Challenges tie people together. If I’ve learned anything in life, it’s that when things are going wrong, very few people do everything right. Cut people some slack. It’s in doing hard things and sticking by people during hard times that creates meaning.

If you felt like you weren’t there for a friend when they needed it in the past, apologize and don’t make the same mistake in the future.

Like most of these points, this one is just as much for me as it is for you.

18. Discover people for yourself

This past year I’ve gotten to know a few people who I was initially skeptical of because of something I read online. 

It turns out, some of these same people have been amazing at checking in on me and my family at times when I needed it and have been generous without asking for anything in return. 

I’m glad I suspended judgment long enough to get to know these people for myself. 

There are parts of all of our stories that don’t represent our entire story.

19. There’s a lot of value in imagining a beautiful future

My wife said that. It came up when discussing how most films of the future are dystopian in nature — the world is burning, everything is on fire, and everyone is against each other.

Take the time to imagine a bright future. 

And I’m not talking about envisioning your ideal future self — but your ideal future society.

A future with hope.
A future where people think of others.
A future rooted in community.

It’s hard to build the future we want to see if we don’t know what that looks like.

20. Enjoy the benefits of age(s)

I’ve never been someone who’s looked forward to getting older. But this past year, I felt a shift and I began to embrace middle age. And the primary reason for this is I’m surrounded by age groups that define the entire human experience.

  • My kids teach me the value of patience and how to find a reason to laugh after crying. 
  • My thirty-year-olds friends teach me about how to navigate the new world we live in. 
  • My sixty-year-olds friends teach me about the parts of the old world that are worth keeping. 
  • My eighty-year-old parents and friends teach me about what really matters. 

No matter your age, spend time with people younger and older than you.

They’ll teach you how to better see the world. 

21. Lead through storytelling

Halfway through a project I was working on this past year, the 88-year-old founder of the company I was doing work for, passed away. I never got a chance to meet the man, but the design firm that contracted me told me loads about him. The one that stuck with me the most though was his ability to lead through storytelling. 

Whether you’re a corporate leader, start-up founder, parent, teacher, or any other kind of leader, steal this philosophy. 

When someone screws up, set your baseline to talk about a time you did too. 

When times are tough, set your baseline to talk about other challenges you or other people have been through. 

When times are good, share the stories of those who made that happen.

Stories are the world’s strongest bridge. Collect yours. But don’t only do it for yourself, do it to let others know they aren’t alone.

22. Never leave a bedtime story unfinished

Speaking of stories, my proudest accomplishment this year is even if my kids fell asleep before I was finished reading their bedtime story, no matter how tired or stressed I was, I read every word anyway.

My kids go to bed with a belly full of stories. And I go to bed knowing I’m the type of person who doesn’t cut corners on the things that matter most.

Choose one thing you have total control over and do it exceedingly well.

Actually, screw that. 

Just choose a life of stories. 

Thank you for reading.
My best to you and yours.
 —  Michael

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