Many years ago, I used to write annual birthday essays sharing the most important lessons I’ve learned over time. They were an annual tradition I cherished because it allowed me to reflect and consolidate what I think I know to be true.
Having a log of my learnings over the years creates the opportunity to capture a moment in time. And looking back on those moments shows me how far I’ve come.
So I’m getting back to it this year. My birthday is September 7th. I spent the weekend accumulating everything I could think of to get to thirty eight.
These are not lessons I think you should apply to your own life, they’re merely what has worked for me. Please read them as “advice to myself” rather than advice for you. But of course, if something resonates then please take it with you and remix it to fit your needs.
Here’s what I think I’ve learned about life, love, work, adventure, and more in my time on this planet…
On Relationships
(Marriage, Parenting, Friendship & Family)
One: Long term friendships compound in value with time.
New friends cannot understand who you once were the way a twenty year friend can. Going through highs and lows with someone by your side, knowing they will not abandon you, is priceless.
The fights and the bickering and the joyful six-hour dinners and the family trips and the long phone calls in times of need — they are irreplaceable. Don’t you dare let a friendship die that has helped you become the person you are today. If you’re both not done growing, then you’re not done growing together.
Two: Done right, marriage is the ultimate long-term friendship.
Ooh are there highs and lows in a marriage.
And all the more so for a marriage that starts early in life. Who do you think you are when you’re 21 years old? You’re wrong no matter the answer! When you start dating early in life, you have to figure out who you are together. And what a beautiful, brutal process that is.
Who am I? Who are you? Who are we? Are questions we’ve had to answer over and over. While that might sound a bit scary or threatening, I mean it in the most wonderful, beautiful, fall-apart-in-each-other’s-arms-and-then-put- each-other-back-together way possible.
Marriage is both one of the hardest and most valuable things that exists in this world. Nothing, I repeat nothing, has changed my life as much as dancing with the woman I married has. (Love you, Nicole)
Three: Being a father is one of the most exhausting and challenging things I have ever done. It is also, without comparison, the most rewarding.
Seeing my wife become a mother and flourish in that role. Seeing our boys develop into their own beings and personalities. Getting to heal my own inner world through parenting. All of it is beautiful and I am so grateful for it.
Four: My children do not deserve to live with the burdens of my past.
It is my job and responsibility to heal from my past so that they don’t have to. While my boys might have wounds from our relationship, they will not have the same wounds for the same reasons that I had.
Five: Conflict is not inherently bad or unsafe, it’s a tool for understanding.
I grew up in a household where there were two conflict modes: passive (most of the time) or over-the-top aggressive (brief moments). I learned that conflict was dangerous and it’s better to keep my emotions bottled up. In reality, conflict serves everyone involved when wielded well
Six: One of the most important skills in life is learning to say what you need.
It’s the scariest to say what you need in the relationships you care about most, because those are the relationships we’re most scared of losing. But those are also the exact relationships where it’s most important to be able to ask for what you need.
Seven: Relatedly, making clear requests gives you the chance to get your needs met.
Making a clear request can sound artificially stilted, but it works every time. Three steps work well:
- “I have a request. Are you willing to hear it?”
- If the person is willing to hear it, make the request clearly. If not, circle back later. “Would you be willing to do bedtime tonight so that I can go play basketball with my friends,” is an example of a request.
- Be as unattached to the answer as possible so that yes and no are okay. Every request requires a response and a clear one.
The key to all of this is for every person involved to exercise their full agency. The person making the request and the person responding. If the answer is no to the request, that has to be ok or else it’s a demand, not a request.
Eight: Non-violent communication, another little framework I’ve learned, is like a magic superpower for handling conflict.
- State the facts.
- Share your feelings.
- Name the underlying needs behind the feelings.
- Make a request (see above)
If you can’t tell, I’ve had to find ways around my natural conflict aversion by finding thoughtful ways to have hard conversations.
Nine: Rituals and traditions are rich ground for joy and hope.
Schedule them. Invite people in. Make them something special. Take marriage retreats. Create an annual fishing trip. Say yes to the annual camping trip. Build the holiday traditions with the boys. Have endless Sunday BBQs. All of it is life-giving. Lean into it. Enjoy it. It’s who I am.
Ten: Everyone wants to be in community. Every community needs an organizer. Be the organizer.
Most everyone wants to be invited to something amazing. Most everyone really does want to be seen and heard and appreciated and understood. And most everyone struggles to open up until they feel safe.
I have wanted to feel belonging and community my whole life! The only thing I’ve found to scratch that itch is to be the one to bring people together.
Perhaps that means there’s no other way for me to fit in. Perhaps that’s part of why I was put here… to bring people together and help them feel safe to finally be seen.
Eleven: Food is a gateway to the soul.
Preparing food is an expression of love. Sharing food is an act of belonging.
When these things come together with a group of humans around a table eating a home cooked meal prepared meticulously for the express purpose of making them feel loved… that is when people begin to let their guard down. It’s when they begin to finally — FINALLY — open up to the possibility of opening up.
With the right question at the right table, friendships can go deeper in three hours than they can in everyday life over ten years. Create those tables.
On Work & Calling
(Entrepreneurship, Leadership, Coaching, Wealth)
Twelve: So far I have seen almost no correlation between the experience of wholeness a person has in their life and any measurable sign of “success” they have achieved.
Wealth, audience reach, network, number of employees… these are all tools. Money solves for needs, but it does not provide wholeness.
Success and wholeness are on two different and unrelated vectors. If I can have everything, I want both. But if I can have only one, I want wholeness.
Thirteen: We can solve almost any problem in 90 focused minutes.
It takes the right environment, with the right conditions, and the right people. Seeing this at work in my coaching has been the closest thing to a superpower or wielding magic.
Fourteen: Most people don’t struggle with what to do. They struggle with the emotional cost of doing it.
Most of the time I observe people looking for “the answer” to their problem. And most of the time I find that they already know the answer, but they don’t like it for one reason or another.
Usually that’s because there’s an emotional cost they’re not willing to pay. Change happens when the cost of not doing it finally becomes higher than the emotional cost of following through.
Fifteen: You can be kind and also get results.
Too often these things get pitted against each other in popular lore. No one is kind 100% of the time, but I also know many leaders who are kind more often than not while also building remarkable lives.
The next time someone preaches to you about being a jerk to get results, just know that there are plenty of examples that prove otherwise.
Sixteen: Hard things feel hard; that doesn’t mean I’m broken.
I have been public speaking since at least college, perhaps longer. Every time I’m scheduled to go in front of an audience, the same thing happens:
- I get anxious.
- I procrastinate on my slides.
- The night before my talk, I stay up longer than I should practicing and editing my presentation.
- About an hour before I go on stage, my stomach ties itself in knots and my underarms sweat.
The only way to make it stop is to go on stage and do the thing. Within five minutes, the energy flows and I feel amazing. This roller coaster of emotion has never changed despite giving hundreds of talks and workshops.
If I had told myself a story that something was wrong with me the first time it happened, I never would’ve had so many opportunities I’ve valued. If you’re scared, that doesn’t mean you’re broken. It might just mean you’re doing a hard thing.
Seventeen: Electoral politics is a popularity contest.
It was once a foregone conclusion that I’d run for president someday. In reading endless presidential biographies, I grew a reverence for the office and a belief that it is one of the most sacred roles one could hold.
Letting go of this idea has brought me more peace than I would’ve anticipated. Politics is a game of progressive compromise on one’s morals. It shouldn’t be that way, but it is. Now I act and allocate attention accordingly.
Eighteen: The news serves partially to scare you into inaction.
News overwhelms me with so much information that I feel helpless to solve the scope and scale of the problems in the world. The paralyzing nature of it fuels our desire to consume more, which fuels the business model of news.
Bonus: Real change happens human to human.
It happens in our communities. If you have found a vein of work that will change lives (which I thankfully have through coaching), then go as deep as you can with as many humans as you can and change lives.
If I have to choose between shallow reach or deep work with a few, choose the deep work. Trust that everyone else will do their part too.
On Mind & Heart
(Faith, Mental Health, Psychology, Wisdom, Learning)
Nineteen: Books are the best invention in the history of humanity.
Twenty: Having needs is not a flaw or a weakness.
Every human being on the planet has needs of all kinds, including love, belonging, safety, and wellbeing. These are universal and should be welcomed. Some of us learn to neglect our own needs in order to stay safe and belong in our family systems. Unwinding this is hard but worthy work.
Twenty-One: We all need support, reassurance, and recognition.
While we can learn to be ok without them, it’s not sustainable to move through life without the support of loving people around us. It’s ok to ask for support. “I need help” is a sign of inner strength.
Twenty-Two: Opening to love is a scary process, especially when you’ve not felt loved before (even if you were in fact loved).
First is learning that love exists. Then that love can be safe. Then that we can only love others as much as we are able to love ourselves.
And then there is the long, dark, deep work to actually learn to love ourselves. I wish I had a better playbook to share on how to do that, but my process has been a winding, unclear path.
Twenty-Three: Belonging starts with shared stories.
The fundamental units of belonging are understanding and acceptance. To be understood for all that I have experienced and to still be welcomed and accepted is the root of my desire for belonging. Knowing that what I have been through or done does not cast me out from the community I long for gives me peace and hope.
Creating venues for people to share our stories together has become a path to belonging for me and others.
Twenty-Four: Vulnerability is a super power.
It’s the only way to achieve belonging. It’s the best and most authentic way to lead. One can be vulnerable and strong. One can be vulnerable and not emotionally dump on others. One can be vulnerable and respected.
Perhaps being vulnerable is the only way to be respected and appreciated in a way that actually feels whole.
Twenty-Five: When I start thinking I’m dying of something – some horrible illness, or ache, or pain – it’s usually a sign that I haven’t processed my negative emotions and instead buried them.
Rather than obsessing and going down a rabbit hole about my health, the key is to go back to what happened just before I started getting afraid I was dying. Whatever that event was is probably the thing I haven’t processed yet.
Twenty-Six: Poetry, memoir, and fiction have become some of my greatest teachers.
I no longer search for books, essays, and other resources that tell me what to do. Poetry, memoirs, and literature allow me to take my own lessons away from every story or verse so that I can apply it to my life in a way that’s meaningful to me.
Settling into the comfort and trust in myself to take what I need has allowed me to let go of prescriptive teaching or outsourcing my agency to an expert or guru.
Twenty-Seven: The Catholic Church has built me up and also let me down terribly.
At a time when people most needed community (COVID), I felt cast out of my own faith community by a priest practicing an archaic form of faith. This is a reminder that a given person’s experience with any organization is only as good as they person representing the organization.
What I found on the other side of leaving our church home was a deeper spirituality and connection to God. I found that I could be with God anytime and anywhere. I’ve now boiled my faith down to three things:
- Prayer and 1:1 connection to God
- Making every effort to foster the fruits and gifts of the spirit within my own soul
- Aspiring to live in such a way that if someone found out I was Christian ten years after meeting me, they’d think more highly of Christianity as a result
Twenty-Eight: When I feel lost or scared or sad or anxious: go into the yard, take your shoes off, stand barefoot in the grass, and look up at the big beautiful sky.
Hold one hand over your heart and one hand over your stomach. Recite all the good you have done this day. Pray to be filled with faith and hope and peace and love and kindness and wisdom. Thank God for every little blessing you can think of this day.
Cry the tears of gratitude or fear or sadness you wouldn’t let yourself cry when someone was looking. And when you are done, go back inside and see what might have changed. 99% of the time, you know things will be ok.
Twenty-Nine: Internal family systems therapy has changed my life.
It has taught me to grieve, to process and understand my anger, and to dig out of that deep well I go to when it feels like everything might as well end right now.
It has helped me heal, helped me open to love, helped me share yourself with the people I most love. It has helped me transform my life. And all it took was the courage to seek out the methodology that most works for me.
Bonus: Being aware of other people’s emotions is not the same as being aware of your own emotions.
They are separate skills. I have a superpower in recognizing other people’s emotions thanks to my hyper vigilance, but I’ve had to work very hard to feel my own emotions. Learning to fully feel my own emotions (even the “bad” ones!) has changed my life.
Body & Lifestyle
(Health, Energy, Taste, Routines)
Thirty: Sleep, diet, and exercise are the key to everything.
Anytime I start wondering what’s wrong, or feel like I’m never going to achieve my goals, or that I don’t have the energy for something…then the key is to first ask:
- Have I been sleeping eight hours a night?
- Have I been eating whole foods?
- Have I been getting at least 30 minutes of good exercise a day?
If the answer is no to any one of these, I should fix that problem before obsessing about some other imagined problem.
Thirty-One: Going to sleep is the hardest skill of all.
I have struggled with sleep my whole life. Since before my memory took hold, there has never been a time when sleep felt safe.
Still, sleep is the key to my longevity and wellness and sustainability of all that I do.
I deserve rest. I deserve an environment that allows me to rest. I deserve to feel safe and loved and supported. And I deserve to keep working on it at the soul level until I can finally lay my head on my pillow and go to sleep without the fear that has been with me since I was a boy.
Keep trying. It will be worth it.
Thirty-Two: When I start drinking more than one cup of coffee a day, it’s usually a sign I’m masking fatigue and trying to make up for a lack of sleep.
Using caffeine as a way to power myself to do more than I have energy for is a sure path to burnout over time.
I function best with no caffeine, but if I’m going to drink it, I should be taking a 30-day break at least once every six months. If I’m trying to be superman, perhaps it’s time to lay down some responsibilities rather than drink more coffee.
Thirty-Three: Looking good changes how I feel.
A nice haircut, a new outfit, a piece of jewelry that has meaning and purpose. Getting up in the morning and getting dressed like I’m going out into the world (even if I’m not) changs the way I feel and look at myself.
Plus, what I wear is a chance to share my personality without ever speaking a word. Let your style reflect your inner world and let the haters keep walking.
Thirty-Four: World class body workers help integrate the pain and challenges of the past
A massage therapist who can hear and understand that you have been abused and then create an environment of safety is a gift.
A chiropractor who knows anatomy and physiology better than most orthopedic surgeons is a gift.
A cranio-sacral therapist (I didn’t even know this was a thing that long ago) is the other half to a great psychologist or psychotherapist.
Great body workers do for the body what a therapist does for the mind. Without integrating my body and mind, true change does not and cannot happen.
Thirty-Five: When it comes to my health, don’t read the internet.
If I think something is wrong, go to a doctor and tell them what I think is wrong. Ask them specifically for diagnostics to find out for sure.
When the results come in, don’t look at them. Schedule time with your doctor and look at them together.
If you don’t trust your doctor to be the source of truth on this, find a new doctor.
The internet is where anxious souls go to convince themselves to have a panic attack because they are dying. You either are or you aren’t, so go find out rather than looking it up online at 12:30am.
World & Adventure
(Nature, Travel, Creativity, Culture)
Thirty-Six: Time in nature is always healing.
Whether it’s an hour in the garden, a couple hours on a hike in Forest Park, a full day hike outside of Portland, or multiple days on a river or mountain, I have never come back from time spent in nature and away from technology and regretted it.
The formula from The Nature Fix seems to be the perfect prescription for me:
- Two to four hours every week
- A full day every month
- 72 hours two to four times a year
But the 72 hours outside seems to be most critical – it’s what resets my nervous system.
Thirty-Seven: Some of the most interesting people I’ve ever met are full of contradictions and complexity.
I love hip-hop and peaceful inner wholeness.
I am a huge fan of Jordan sneakers and also deeply believe in sustainability.
I love college football and equally love reading an obscure book from 30 years ago.
One week you can catch me fly fishing in a canyon covered in sunscreen, dirt, and sweat and the next you can find me at one of the best restaurants in Portland enjoying a great meal with a group of friends having deep conversation.
You can’t put me in a box. And I don’t want to put you in one either.
Thirty-Eight: Travel has unlocked parts of me I was scared to know.
As a young person, I only left the country one time to Brazil on a mission trip in high school.
At first, travel beyond US borders felt scary. Now I revel in the learning that will come from being uncomfortable.
Travel has taught me more about myself than any number of books or courses could.
That’s all I have for you this year. I hope you found something to make you think a bit deeper today. If you enjoyed this, would you consider:
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