Essay Archive

Get new thought-provoking essays that question the status-quo
(and question questioning the status-quo).

Prefer audio? I read the essays and I created a podcast feed. It’s like an audioblog.


31   Internalized Capitalism and Intentional Communities

24  Reflections on 30+ Hrs of Mediated Conversation with ISTA Leadership


30  Why You Should Date Your Friends


17  A World Without Politics


5    This is why I don’t believe you

28  Life Is Already Full

15   How the Military Prepared Me to Live in Community


21  Boundaries Can Heal When Love Cannot

14  Saying Sorry Is a Privilege

30  Spiritual Gaslighting: Why Sexual Predators Love Tantra
24  A Practical Guide to Taking Back Your Power from Social Media
15   You Don’t Owe Me Your Body, I Don’t Owe You My Heart

8    Stop Expecting Life to Be Awesome and It Will Be

31   Uncertainty in the Age of Coronavirus


6    A Pragmatic Guide to Trust

2     We Fucking Need Each Other

22  I miss blogs.
15   You Can’t Be Nice to a Narcissist

2   Back in the Saddle: 2018 Annual Review


21  Tell the Truth

1   Before You Read ‘The Way of the Superior Man’ Read This

4   The Surprising Foundation of Every Great Relationship

20 The Day Life Coaches Replaced Best Friends
13  To my Overachieving Friends, Whom I Love Dearly [Poem]
6   Art Isn’t Dead, We Are

30  What It Means To “Leave Someone Better Than You Found Them”
16  Everyone Believes in God
2    You Don’t Have Time for Art [Poem]

25  Loving All The Parts
18  Why Nerds Are Happier
11   The Difference Between Having Needs & Being Needy
4    2018 Ultra-Light Travel Guide: My Gear & Mindset

28  The Reason It’s So Hard To Find Happy Relationships on Dating Apps
21  The Problem with Liberalism (From A Liberal’s Perspective)
14  17 Creative Ways To Be Lonely
7    How Modern Marriage Is Making Us Lonely

28  You’re Not Trying To Debate, You’re Just Being a Dick
21   Stop Looking for “The One” and Do This Instead
7     State Change vs Transformation

31   The President America Needs, Not the One It Wants
24  Why Sex Workers Should Replace Dating Coaches
17   I Want You To Like Me [Poem]
10  5 Simple Ways to Have More Intimacy with your Friends
3    On Public Shaming and the Death of Civilized Discourse


27  Consequences Create Motivation: 2017 Annual Review
20  The 10 Kinds of People Who Leave Annoying Comments on Facebook
13   Why Narcissists Love Spiritual Communities
6    7 Ways I Use Minimalism On My iPhone

29  5 Mistakes People Make When Writing On the Internet
22  Dear Men in Glass Houses
15   I Don’t Care You Got Engaged
8    The Ten Commandments of Boodaism
1     The Key to a Peaceful Divorce

25   Most People Are Stupid (What George Carlin Taught Me About Happiness)
18   Just Feel the Pain
11    The Confronting Reason You Haven’t Been Able to Do That Thing You’ve Been Wanting to Do for a While
4    It’s Okay to End a Good Relationship

3   I’m Cycling from Vancouver to San Diego [2-Month Sabbatical]

26 You Can Always Walk Away
19  Relationships Are Really Really Really Really Really Fucking Important
12  Dating Beyond Gender
5    I Wish We Would Stop Saying “You Can Have It All”

28  I Would Fall In Love With My Ex-Wife Again In A Heartbeat
21  What I Believe Makes America Great 
14  The Self-Righteousness of Minimalism and Vagabonding
7    The Magic of Slowing Down

31  The Subtle Shift That Causes Friction in Long-Term Relationships
24  A Minimalist Love Song [Song]
17  You’re Busy Because You’re Afraid to Change Your Life
10  A Religion of One [Poem]
3    Why Men Shouldn’t Be Threatened by Feminism

26  Why Nuanced Conversation About Consent Is So Hard
19   5 Awesome Fucking Reasons Straight Men Should Take It Up The Ass
12   Why I Love and Hate Being Friends with Entrepreneurs
5    An Ode to Space [Poem]

29  How To Transform Jealousy Into Excitement
22  In Defense of Millennials
15  The Most Un-Romantic Marriage Advice Ever
8   The World Is Inside You [Poem]
1    You’re Not a Bad Person, You Just Have Great Taste

22  I’m Triggered That You’re Triggered
15   4 Relationship Lessons From 4 Years of Marriage
8    Why Understanding Privilege is Essential to True Consent
1     Why Tantra and Polyamory Don’t Mix

25  The Fetish of Consistency
18  How To Travel Indefinitely With A Normal Backpack
11   The Purpose of My Travels
4    I’m Not Changing a Damn Thing in 2017


28  2016 Annual Review
21   A Minimalist Christmas Poem
14   The Unexpected Reason I Can Afford an Adventurous Life
7     5 Reasons a Feminist Is Sexy

30   It’s Not Okay To Be Silent Anymore
23   I’m Afraid of Being Gay
16   Art is Disagreement
9    On Being A Man [Poem]
2    The Hardest Thing About Professional Blogging

26  I Promise, It’s Not Lame to Ask A Woman for Permission
19   Traveling Sucks Too
12   Communication Is My Fetish
5    What Music Is Really About

28  This Is For Me
21   In Defense of Pick Up Artists
14   The One Question No One Asks On A Date (But Should)
7     Loneliness Is My Spiritual Practice

31   Fighting Against Something Also Supports It
24  There’s No Such Thing as a Failed Relationship
17   You’re Perfect Just the Way You Aren’t
10  How I Define a Successful Relationship
3    Don’t Follow Your Heart

27  We’re Unhappy Because We Try to Win a Shitty Game
20  I’m Afraid of My Truth
13   Love + Drugs
6    On Personal Branding and the Addiction to Self-Importance

29  My Wife Is Not My Therapist
22  Yes I Would Be A Good Dad, and No I Don’t Want To Have Kids
15   Insecurity as a Gateway to Connection
8    The Death and Rebirth of My Marriage
1     Ego Makes Intimacy Possible

25  Breaking the Gender Code
18  This is Me, This is Enough
4    How the Manifesting Generation is Collectively Killing Our Self-Esteem

27  Here’s a New Way to Look at Life Purpose
20  5 Things I Wish They Told Me When I Started Life Coaching
13   Bernie Is My Girl
6    Lonely Is The New Normal

30  I Hope You Give Up On Love
23  How Your Addictions Can Be Good for Productivity
16  Why Most Relationship Experts Are Completely Wrong About Polyamory
9    Your Life Is Always on the Right Track
2    I’m Afraid My Wife Will Die

3    February Sabbatical: Why I’m Taking One Month Off

27  The Real Reason People Join the Military and Go To War
20  The Simple Key To Relaxation
13   The Secret to Happy Relationships I Learned From Jesus
6    Why Artists Fail, Go Broke and Die Unfulfilled


28  30 Ridiculously Simple Ways To Make Your Life Better
21  2015 Annual Review
14  How To Get a $65,000 Loan Back From Your Friend
7    5 Simple Questions To Find Creative Work You Love

30  Jesus Loves Orgasms
23  You Don’t Need To Save The World To Feel Like You Made A Difference
16  I’m Struggling Not To Sell Out
9   Having an Intention vs Needing a Strategy
2    What I Mean When I Say I’m in an Open Relationship

26  The Inconvenient Truth About Legacy
19  How To Find Your Passion Instantly
12  Running Out Of Money As An Adventure
5    Virtual Exchange Program: Geography Class for the 21st Century

28  All Emotions Are Created Equal
21  What To Do When I Die
14  How Indulging Perfectionism Makes Me A Better Writer
7    All Perspectives Are True

31   Life Is a Carnival of Experience
24  Life is Like an Art Class
17   Maybe You’re Not So Fucking Special
10   Are You Really In Control of Your Life?
3     A Goal Is Something You Don’t Want To Do

27  The Most Frustrating and Beautiful Day of My Life
20  On Breaking Up
13   You Don’t Want It Bad Enough, and That’s Okay
6    4 Habits of Highly Effective People Who Are Never Satisfied

29  How To Touch Someone’s Heart
22  The Benefits of Comfort and Security for a Creative Life
15   An Encyclopedia Contains No Wisdom
8    All Affirmations Are False

25  The Audacity of Giving Yourself Permission
18  Doing Your Best, Even When It Sucks
11   On Art and Making Money
7    Love is Either a Daring Adventure or Nothing At All
4    The Joy of Missing My Wife

27  On Earthquakes and Feeling Helpless
20  The Real Difference Between Traveling and Vacationing
13   The Commodification of People
6    The Beauty of Distraction-Free Reading

30  Personality as a Substitute for Courage
23  My Wife Talks to Elephants
16  Gurus Are Just Like You
9    You Don’t Need To Figure Out Where Your Life Is Going
2    Why I’m Never Ever Buying a House Again

23  I Don’t Own My Wife
16  Why Athletes Make Terrible Husbands
9   My Life in Four Minutes
2   The Sexiest Thing You Can Do For A Lover In Bed

26  The Wisdom of Paula
19  Please Stop Believing People Who Say You Are Fucked Up
12  Create, Ship, Repeat
7    Hail To The King
5    3 Things I Wish People Knew About Open Relationships


Everyone Has Money Problems (And Why That’s Reassuring)
What If Every Day Was Sunday?

On Writing

3 Rules Not to Live By

When It Might Be Time To Fire Your Therapist
Your Personality Is Bullshit
6 Things I Realized About The Naval Academy After I Got Out
Please Believe In Me
My Relationship Sucks, and So Does Yours (Sometimes)
Stay on the Train
Being Married is Killing My Relationship
The Peculiar Reason That Men (and Women) Are Afraid Of Deep Relationships
Why Sex Educators Struggle To Talk About Money
My Wife is a Terrible Piano Player


7 Things Musicians Wish Club & Bar Owners Knew
The Profound Importance of Courage
Everything I Write Is Bullshit
The Biggest Myth About Dating
How Allowing Yourself To Feel Horrible Might Change Your Life
Doing What You Love Won’t Make You Happy
The Beauty of Trial and Error
3 Myths About Dating at The Naval Academy


The Secret to Having Amazing Hands
Letter from My Unborn Son
The Paradox of Happiness
On Being Superman
Understanding Your Masculine and Feminine Side
The Bad Habit I Took Away from the Naval Academy
Why You Need to Struggle
A Letter to Parents on Christmas


The Secret to Getting More Tips and Happiness in the Service Industry
38 Things I Wish They Told Me at The Naval Academy
What I’ve Learned About Happiness


10  This World, Again?