31 Lessons I Wish I Had Learned Before I Was 31

Chris —  April 3, 2013

Today I turn 31 years old.  I’ve learned a few things….mostly the hard way.  Here are a few lessons I wish I had known before about the three things that take up most of my thoughts: God, Girls and Growth.


1.  Girls want to be asked out.
A few years back I realized that, due to a string of crises, I hadn’t been on a date in years and I didn’t have anyone to ask out.  I bit the bullet and signed up for online dating.  Lo and behold, there were dozens of beautiful girls, just waiting to be asked out!  Many of them I knew and had never realized it would be possible to date them. The truth is, they want to be in a relationship, too, and were just waiting to be asked out!


2. It is better to be rejected than to regret not trying.
When I started seeing a counselor, I told him about a girl I’d had a crush on for years.  She was so beautiful, funny and kind that she scared the daylights out of me!  My counselor told me to ask her out, and wouldn’t drop it until I did. The date itself was horrifying. I learned I could do it, and I swore I’d never again get in that cycle of fear and regret. 

3. Birds of a feather flock together.
Know a girl who seems just perfect, but she’s unavailable?  Get to know her friends!  Wonder why you keep dating terrible hateful human beings? Do they seem to be all alike and hang out in the same places?  The old adage is true! Birds of a feather flock together.  Find out where a good one flocks, and you’ll find more just like her. (Unfortunately, they’ll probably be friends. Play it cool.)

4. Never trust a profile picture taken at an odd angle in a car.
Here’s a hard earned lesson from the alternative universe of on-line dating: If someone is taking a picture at an odd angle that doesn’t make any sense, they’re hiding something.  Trust me.

5. Do something free on the first date.
Chances are you will go on a fair number of first dates.  Wait to do something fancy until you think she’s worth keeping around.  It also forces you to be creative. This increases the chance of making great memories!

6. Judge by fruit.
I could put this one in any section, but I’ll keep it here.  Like John the Baptist said, judge a tree by its fruit.  You can’t have a relationship with “the person I think she could become someday.” You can only have a relationship with the person she is today.  The best predictor of future behavior is past performance. 


7. Jesus is the smartest man who ever lived.
Of all the things I have learned from Dallas WIllard it is this: you can trust Jesus to mean what he said because he’s smart. From The Divine Conspiracy:

“…can we seriously imagine that Jesus could be Lord if he were not smart? If he were divine, would he be dumb? Or uninformed? Once you stop to think about it, how could he be what we take him to be in all other respects and not be the best-informed and most intelligent person of all, the smartest person who ever lived?”

It’s just that simple. And totally life changing.

8. God pretty much gives you what you ask for.
In 2009, I applied for an internship that was meant to be done in conjunction with the MAGL.  I got into Fuller, but not the internship.  Another member of my MAGL cohort was in that internship program.  We both had incredibly similar experiences, and are now in similar situations regarding our careers.  I got a lot of the things I was looking for, plus the chance to live in Austin.

The fact is God doesn’t give me what I want when I ask for it. But I am learning, despite my anxious ways, that God always gives me what I need, when I need it.  The funny thing is, more than not, it’s what I ask for.

9. Serve people you disagree with.
I grew up among a group of Christians that knew we were right and everyone else was wrong.  We were “biblical”.  Other groups use words like “gospel”, “spirit-led” and “apostolic” to mean the same thing.  While we’ll never agree on everything, this “us vs. them” attitude is toxic and more importantly, un-Jesus-like.  Be a blessing to those with whom you disagree with, and walk in the tension between loving and approving.

10. God doesn’t care what you do.
I have spent most of my 20s suffering because I didn’t know what to do with my life.  I once heard Randy Harris say that if you take off in any one direction, you’ll find a place so dark that you can bring the light of the kingdom of God.  Years of frustrations could have been avoided if I just picked one thing and went for it.

11. Homeless drug addicts are just people.
I spent the summer of 2002 working with homeless teenagers. We played pool, ate picnic lunches and shared stories.  Over time, I began to realize these were just people, many of whom I really liked.  In fact, I’ve met a few homeless drug addicts that were more humble, down to earth and plain likable than many of the “successful” suburbanites I know. When you pass one on the street, keep in mind they are just people. That is all.

12. Find a Church you can be a part of without being dishonest.
Once upon a time I was broke and took a church job.  I had nothing in common with the people there and a different vision of what a church should be.  I couldn’t shake the feeling that I was pretending to be someone else and lying every Sunday.  It ate me up inside.

I made the decision I’d rather feel honest than get paid by a church.  I miss somethings about full time ministry, but I sleep like a baby.


13. Healthy people get counseling.
In 2006, I applied for a leadership position with a Christian ministry.  After reading my personality profiles and hearing my stories, they responded “Chris, we like you.  We also think you are very broken right now.” They proceeded to call a counselor in my hometown, and schedule an appointment.  Over the coming months, I would sit and tell my stories, and leave exhilarated.  It gave me the opportunity to pull back from my current physical and emotional state, and see it in the grand narrative of my life in Christ.  Even today, I share the stories of the first few lessons I learned in those sessions.

I’m not sure why we still have a stigma against counseling.  As far as I’m concerned it’s like a good diet or regular exercise routine: Counseling is something that healthy people do.

14. Ask for help.
Once, while trying to unlock my door with my hands full, my roommate came up behind me. He stood there, waited and finally said “ask for help.”  Once I did, he opened the door for me.

This is so simple it hurts: Life is easier when you ask for help AND people want you to ask them!

15.  Cultivate the ability to do nothing.
In today’s culture, everything is always on and always changing. Even laid back people can have trouble taking a break.  Just try it this week, it’s harder than it sounds.

If I could master and teach others one principle, it would be the Biblical idea of Sabbath.  This means a lot more than taking a day off.  It means shaping your week and your community so that you can spend an entire resting and re-creating.  Can you imagine anything for restful or inspiring?

16. Learn how to be cocktail smart.
Two realities of cocktail parties: (1) What you do isn’t that interesting, and (2) Everyone likes to talk about themselves.  If you want to come across at suave, funny or just kind, make it a goal to know a little bit about everything.  Keep just enough random knowledge in the back of your head you can ask informed questions that will get people talking about themselves.

17. Be on the constant look out for mentors.
Experience isn’t the best teacher – other people’s experience is! A few older, wiser men and women have opened up their lives, listened to my stories, and shared theirs.  They gave advice when needed, and occasionally, direction.  No matter what you think you know, you will come across situations you don’t know what to do with.  That’s why we need mentors.

18. Cars are not better than bicycles.
Most of 2010 was spent riding a bicycle.  Without a car, I had to plan ahead, calculate my commute, as well as food and supplies I would need.  I spent two hours outside every day and didn’t need to schedule exercise.  I slowed down, and learned what my city is really like.  I had to limit the radius of my life. I was as healthy and organized as I have been.

There are a few things like avoiding rainstorms and buying groceries that are easier now that I have a car.  But not many.

19. Spend more time asking questions.
The clichés are true, “the older you get, the more you realize how little you know”, and “people don’t care how much you know until they know how much you care.”  I love my own voice and am naturally terrible at asking questions.  When I realized this in college, I printed out a list of icebreaker questions and carried them in my wallet for special occasions.  People want to talk about themselves.  It’s a great way to make a friend and learn a thing or two on the way.

20. You cannot be good if anything if you try hard enough.
For four years of college, I tried to be a music teacher.  Try as hard as I might, I could never pick up on the ear training, the sight reading or any of the other real skills needed.  I’ll never be tall and athletic enough to play basketball.  I’ve given up on astronaut and Nobel Prizes as well.

As I get older, I’m finally sorting out a few things I love and can do well.  I’ve given up on the other things, and I’m okay with that.

21. Punk rockers either sell out or die alone.
I’ve always been a contrarian and loved winning a good argument. I guess that’s why I was so attracted to the punk rock, DIY, “stick it to the man” worldview.  While it’s been fun sticking it to the man, I slowly picked up on the fact that if you’re always picking fights and proving points, people will eventually stop listening to you.  There is also something I’ve found more exciting than arguing: working together to come to a meaningful compromise.

22. Pick a few important books that you will read every year.
Groucho Marx famously said “Outside of a dog, a book is man’s best friend. Inside of a dog it’s too dark to read.”

Some books are fun. Other books are helpful. Some, you know that you will hold as close as your dearest friends.  After the Bible, I have three such books.  M. Scott Peck’s The Road Less Traveled (“once it is accepted, the fact that life is difficult no longer matters), Thomas Cahill’s Desire of the Everlasting Hills (“Did Jesus make a difference?”), and Dallas Willard’s The Divine Conspiracy (learning from Jesus how to lead my life as he would lead my life if he were I).

I try to reread these books every year or two, and hope to find other such dear friends along the way. 

23. Be happy with your body, but not satisfied with your health.
Every year or two I decide to hit the gym and change my body.  I stress out about diet and spend a lot of time sore.  Eventually, I give up or get busy.

The fact is that I still have the same body shape I did as a little kid. I’m not overweight, but I’ll never be a body builder.  Slowly, I’m becoming okay with this.  What is important to me is that I stay in good enough shape that I remain healthy and strong as long as I can. There’s a lot to do.

24. Keep a to do list.
Truly, truly I say unto thee: If you want to accomplish something, write it down.  The days when I keep a to do list I am more effective, energetic and sleep better.  The days I don’t, I’m constantly wondering what I’m missing. Don’t even worry about having a great system.  Write stuff down, cross it out, and watch your life come together.

25. Hold yourself to a higher standard than you hold everyone else.
It is good to have high expectations.  But if you don’t try harder yourself, your just a jerk.  This is a problem for people who are thoughtful or insightful, and know how to discover flaws in people or systems.  Get your own stuff together, then you can throw stones.

26. Learn how to say what you want to do.
This is my biggest flaw.  When people ask me “what do you want to do?” I clam up and freak out.  My mind is flooded by a million failures of my past and hypothetical crises of the future.  The fact is, if I’m not aiming at a target, I’ll never hit one.  People can’t help you if they don’t know what you’re trying to do. Until I can master this, I’ll be stuck where I am.

27. Learn to verbalize your emotions.
When dealing with a heavy bout of depression, a counselor gave me a list of 100 emotions.  My homework was to pick five emotions and write a letter to God every day telling him why I felt that way.  In time, I learned how to say what I felt.  Once I put a name to what I was feeling, it suddenly became smaller.  Eventually, it seemed like blinders fell off, and my panoramic vision returned.  Until you name your emotions, then they are just unsettled feelings that can control you.  In naming them, they become issues to be approached and handled.

28. When doing something you’ve never done before, don’t do it alone.
In 2009, I ran a marathon.  I had never done anything athletic, and mainly sought it out because I was unemployed, bored and poor.  I threw on a pair of shoes and went for a run.  Eventually, I worked my way down to a 10 minute mile and a 4:30 marathon.  However, in the mean time I made things overly difficult and injured my knee.  Every time it aches I am reminded how much better things would have gone if I had gotten some help learning how to run.

29. Make a plan. Then work it.
That marathon was the most organized I’ve ever been.  I eventually found a training schedule.  I knew how much I had to race and when.  This is what is called a “keystone habit,” and it inspired me to organize other elements of my life as well. Whatever you want to accomplish, write it down, then write a deadline, and then write a plan of how to get there.  It won’t be easy, but it is that simple.

30. Automate your giving, savings and your bills.
Growing up, my family had a lot of financial difficulties.  I am slowly learning how money works.  Here is the most important thing I’ve learned so far: Give first, pay your future self second (savings) and your bills third, then make your budget.  Automate this with your bank so you don’t have a choice.  When the winds blow and the waters rise, you’ll be glad you did.

31. Get a hobby.
So many people burn out from a job, ministry or even relationship.  They invest all of their time, work obscene hours and derive their entire sense of self worth from it.  The problem is that jobs don’t last for ever, and ministries have struggles. Even your significant other cannot bear your entire weight.  Yes, I know we should find our worth in God.  We also need to have something we enjoy doing, develops a skill, gives us down time, keeps us social and rounds us out as human beings.  Take cooking lessons, sign up for a bicycle race, build something or join a book club.  Just do something that’s not your job.

Which resonates most with you? What do you wish you had known at a younger age?

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