🎉👏 Welcome back to the third annual Unrutty Award spectacular, where we celebrate the biggest, best, worst, dumbest, and most memorable from my past year.
As always, we celebrate in March to give voters1 time to gain perspective before deciding. Plus, the Oscars occur the same week, so Hollywood’s in good company.
Without further ado, let’s enshrine this year’s winners and nominees.
The 3nd-Annual Unrutty Awards
My Best (and Worst) of 2023 in:

Media Awards

Best Book
🏆 A Short Stay in Hell by Steven Peck
Honorable nominees:
- The Good Life by Robert Waldinger and Marc Schulz
- The Halo Effect by Phil Rosenzweig
Read 31 books, for what little that’s worth.
I recommended A Short Stay in Hell to more people than I can remember (and even bought it for some readers, most of whom never lived up to their end of the bargain by reading it then sending me their thoughts, which was a valuable lesson). I mention the lessons from The Good Life to more people than any other book and it will probably have the most lasting impact on my life.
My recap of the winner: A Short Stay in Hell’ Made Me Rethink My Shorter Stay in Non-Hell
Best Movie
🏆 Whiplash
Honorable nominees:
- The Barkley Marathons
- Air
- Red Obsession
It was my second time watching Whiplash, but hey, the rewatch was more enjoyable than any first watch of the other nine movies I watched in 2023.
Best TV Series
🏆 The White Lotus, Season 2
Honorable nominees:
- Dave, Season 2
- Succession, Season 4
- The Bear, Seasons 1 and 2
- Hacks, Seasons 1 and 2
Kim agrees with the winner. She dislikes the runner-up, Dave, probably because she’s not a juvenile, self-involved, wannabe rapper.
Best Podcast Episode
🏆 12 – The Rube, The Dollop
Honorable nominees:
- Jeremy Giffon – Special Situations in Private Markets, Invest Like the Best
- J Balvin, The Really Good Podcast
- Toastmasters, Aristotle, and the Essential Art of Rhetoric, The Art of Manliness
- Protein — Everything You Need to Know, The Art of Manliness
- What Lifting Ancient Stones Can Teach You About Being a Man, The Art of Manliness
I laughed so hard listening to The Rube that I had to lean against the wall outside the supermarket.
Giffon got me wondering what he claims to be “the single most important question in the world,” Why do so many people spend so much of their time on things they don’t like doing?
The guy on the protein podcast was refreshingly frank (“Collagen, by any measure, is the single worst protein you could ever see.”). He motivated me to consume more protein, which has helped me feel a lot less sore. (See: Best (Non-Human) Addition to My Life.)
The Toastmasters guy made a compelling case for rhetoric that I shared with many readers.
The stone-lifting guy has a great story and pushed me to find bigger, heavier rocks for my own beach rock workouts.
PS: I did a way better job than previous years at reducing my consumption and taking notes on noteworthy episodes. Reviewing my notes, though, I’m surprised by how little I remember. Is taking notes worth the time? Do I need to review regularly?
PPS: I was also on two podcasts this year: Still Small and Grind Less, Flow More.

Experience Awards

Best Trip
🏆 Drakensberg and The Midlands, South Africa
Honorable nominees:
- Galiano with Claudia, James, and Teddy
- Cape Point road trip (Blog recap)
- Sooke Roberts reunion
Drakensberg memories: So much food, old people loving Zac, hikes every day, getting drowned in thunderstorm on the last day, Midlands meandering.
Notably absent here is a trip to Puerto Vallarta. (See: Worst Decision.)
Best Dining Experience

🏆 Ostrich egg omelet at Cape Point Ostrich Farm
Honorable nominees:
- Cathedral Peak Hotel buffet
- Galiano beach meals
- Foxcroft for Kim’s birthday
- Hussar Grill (multiple occasions)
- West End anniversary tour with Kim (poutine, nachos, Korean, Japanese dessert)
They didn’t have ostrich egg on the menu, but when we asked they said they could whip us up an omelet. So big, cheap, exotic, and tasty. Potatoes super crispy, too. Then we bought our own fresh ostrich egg to crack open and cook at home, which was a bucket list experience in its own right.

Best Adventure
🏆 The Four Corners Urban Hike. (Recap here.)
Honorable nominees:
- Going for a “shortcut” on a run in Pemberton.
- Running in Drakensberg and getting hit by a thunderstorm that destroyed my phone.
Most Memorable Moment
🏆 Sandy’s birth.
Honorable nominees:
- Finding Delicious Monster from McGregor, South Africa at Trader Joe’s in Bellingham, Washington.
- Getting hit by thunderstorm during my run in Drakensberg.
- Manako and Andrew rapping in Sooke.
- Da Bomb hot sauce knocking people down at the surprise Hot Ones party Kim threw for my birthday.
- The moron running into our car on the way to Alvina’s Halloween party.
- Pinning down Zac with two nurses at emergency while doctor tried and failed to get the bead out of his ear.
- Zac on Xmas eve scared to go to sleep, fearing Santa will say “Boo!” to him at night.

Decision Awards
Worst Decision
🏆 Not making a Mexico trip happen with Kim in the spring.
Dishonorable nominees:
- Rebalancing my investment portfolio in May. (No disaster, but would’ve done better by staying put.)
- Forgetting to turn off the hose at parents’, so it stayed running all weekend, leading to an email from strata council about excessive water use.
- Splitting out The Zag from The Unconventional Route(???).
Kim and I had the idea to take a “scouting” trip to Puerto Vallarta in the spring. My parents offered to babysit Zac. Don’t know why we didn’t.
Nice to see that two of the other nominees are acts of commission, rather than omission. Shows I’m putting into action what I’ve learned about regret. (See: Why You’ll Regret Living a Life of Minimizing Regret.)

Best Decision
🏆 Going to Drakensberg.
Honorable nominees:
- Being patient with South Africa flights.
- Buying tons of data so I can work from anywhere outside
- Putting Zac in shopping carts so he doesn’t wander around causing chaos.
- Not signing up for Virgin Active in the second half of the year.
- Moving newsletter to Substack, which earns rather than costs me money.
The unimpressiveness of this list tells me I have work to do on living up to that “Hard choices, easy life. Easy choices, hard life” quote.
Note to future selves: This award plus the previous indicate I ought to be more proactive and less cheap about planning trips.
Best Money Spent
🏆 $300-ish dollars a month (subsidized) for Zac’s Tuesday and Thursday daycare in Vancouver with Andrew and Sa.
Honorable nominees:
- $25-ish dollars on protein powder from Costco.
- $82 for inflatable plane bed for Zac, which worked like a charm.
- $3 and $10 for gas station vacuum and cleaning of mom’s car instead of doing it at home.
- $21 diaper wipe dispenser, which is much better than using bags.
- $10 chest buckle for Zac’s backpack so it stays on.
- $8 for Baabaa, the emergency replacement to Zac’s Sleepy, which he somehow lost in the airport immediately upon arrival in Cape Town.
- 9,000 ZAR a month for Talent.
Worst Money Spent
🏆 $150-ish in Short Stay in Hell copies bought for readers.
Dishonorable nominees:
- However much Kim spent to replace her wedding ring, which fell out of her pocket in Cape Town in February.
- $1,000-ish to get the bead out of Zac’s ear, which was necessary and hope will get refunded by insurance, but was still extremely unpleasant to pay.
Hoping to spark engagement, connect with people in my audience, and earn some karma points, I gave my favorite book of the year (see: Best Book) to a handful of readers. My only request to each of them was that they tell me what they thought of the book. Nobody complied.

Work and Career Awards
Best Failed Initiative

🏆 The Pump.
Honorable nominees:
- The Unfollowables Series. Decent reception. Surprised at how few people wanted to be interviewed.
- Life Workout Plan.
- Twitter.
- Trying to connect with fellow creators.
- Following up with participants from earlier challenges. I sent dozens of emails to people I went above and beyond to help in earlier challenges. Only a few even bothered responding.
I went into the year with grand visions of The Zag becoming a virtual gym for your comfort zone: a source of ideas, exercises, inspiration, accountability, and community for constantly challenging complacency in rewarding ways to develop your own, unique, sexy status quo. I launched the first month in August and only seven people were interested.
Favorite Content Created
🏆 Sooke Ones, Pt. II
Honorable nominees:
- I Found Info-ligion
- Rut-ology 101
- How to Get the Advice You Need But Don’t Want to Hear
- The Untold Marshmallow Story
These are my personal favorites. I truly have no idea what readers’ favorite was. I did a survey during the year, which included asking my most engaged readers what their favorite post was and everyone had a different answer.
Favorite Concepts Devised
🏆 Be useful.
Honorable nominees:
- Maximizing anti-regrets instead of minimizing regrets.
- APEX (Afford Patience, Explore the Extraordinary).
- Flip-flopism, my new info-ligion.
- Snakes and ladders decision making.
Tangentially related: In January, I named 2023 “Arnold” in honor of Schwarzenegger. During the year, I came to believe that being useful is the most important driver of well-being. Then, at the end of the year, Arnold come out with a book titled, Be Useful.
Best Zag for The Zag
🏆 [None]
Honorable nominees:
- Go back to school for a Master’s and PhD to earn credibility and learn from intellectuals.
- Write a book.
- Get a job.
- Make it a virtual gym for your comfort zone.
- Develop a daily accountability model similar to My Body Tutor.
- APEX (afford patience, explore the extraordinary) as an alternative to FIRE.
- Help people find their calling, like CliftonStrenghts but based on personality science, feedback, and other evidence.
Once I realized The Zag wasn’t working as I’d hoped, I spent the rest of the year trying to figure out what to do next. Still looking.

Personal Achievement Awards
Greatest Milestone
🏆 August 2023: Sandy born.
Honorable nominees:
- December 2023: 10 years since the dinner that brought Kim and I together.
- April 2023: 10 years since my “pretirement”.
- March 2023: Launched The Zag.
Greatest Blessing
🏆 Getting daycare for Zac for two days a week in Vancouver.
Honorable nominees:
- Having parents around in Vancouver to help with childcare.
- Talent, our nanny in Cape Town who is our best yet.
- Grocery delivery: Walmart in Vancouver, Checkers in Cape Town.
- Zac potty-training himself in February.
- Finding a family nurse in Vancouver thanks to Carla and Nadia.
Funny how everyone says kids are the greatest blessing in life, but all my greatest blessings of the year were things that relieved the challenge of raising them.

Greatest Headache
🏆 Finding a home in Cape Town.
Honorable nominees:
- Finding a sublettor in Vancouver.
- Zac’s slow and picky eating.
- Tech issues: OneDrive not working on my OS, emojis breaking on both my sites, page speed.
- The bead in Zac’s ear.
Biggest Bummer
🏆 The Zag not working.
Honorable nominees:
- Finding out we’re having another boy. Kim and I will never know what it’s like to have a daughter.
- The inconvenient location of our place in Cape Town at the end of the year.
- Kim’s pre- and post-birth physical issues.
- Google’s updates cut The Zag’s traffic in half.
- Getting only 22 responses to the survey I sent to 700+ of my supposedly most engaged subscribers.
I had high hopes that making The Unconventional Route a pure travel blog and putting all the personal development content onto a cool new site, The Zag, would make things clearer to readers and Google and help both sites grow. Nope.
Biggest Change of Mind
🏆 Relationships are important. → Relationships matter most.
Honorable nominees:
- I’m on the brink of breakthrough professional success. → I’m at an unbreakable brick wall.
- I eat enough. → I need more protein.
- Consuming information I later forget is a waste of time. → Consuming content that supports the values of my “info-ligion” subconsciously pushes my behavior in the right direction. (Read: My post on finding info-ligion.)
- Reading fiction helps most. → Reading stories helps most. (Read: The easier alternative to learning the hard way.)
- Means are meaningful → “The mean is an abstraction. The reality is variation.” (Read: The End of Average by Todd Rose.)
- Drivers of business success are well understood. → Business success is strategy, execution, and luck. (Read: The Halo Effect, Best Book nominee.)
- Most of who we are is genetic. → Most of who we are is random chance. (Read: What I learned from Innate by Kevin Mitchell.)
- Mindfulness is about finding calm and perspective. → Mindfulness is an exercise to physically change how your brain processes emotions. (Book: The Emotional Life of Your Brain.)
“Yeah, yeah,” I thought when I heard the authors of The Good Life (see: Best Book) say on podcasts that it all comes down to relationships. But I read the book anyway. And I’m glad I did. It opened my eyes to just how essential relationships are.
Greatest Awakening
🏆 Internal monologue. (See tweet above.)
Honorable nominees:
- I have hazel eyes. I always thought they were brown, but when I was googling whether the word “hazelnut” was named after the color or vice-versa, Google presented me with images that looked a lot like mine.
- My investment performance isn’t as exceptional as I thought. I found a mistake in my calculations. I’m barely outpacing the S&P500. Not bad, but special.
- Much of my audience are takers. They found me by Googling for free content and will take whatever they can for free. They won’t pay for anything or thank me in any other way, even by offering testimonials or responding to surveys.

Coolest New People In My Life
🏆 Sandy.
Honorable nominees:
- Xavi.
- Peter and Bella in Cape Town.
- Alex and Rika in Vancouver.
- Ali and Lorena in Vancouver.
- Many of the readers I talked with.
- Some fellow writers/creators I talked with.
I made a concerted effort to engage more with people, especially readers and people working on similar things as me. The conversations I had were mostly energizing. I still long for something more—someone who challenges me in the right way and who I can challenge, too.
Best Non-Human Addition to My Life
🏆 Morning protein.
Honorable nominees:
- AI dictation.
- Periodic runs around Lion’s Head.
- Lifting super heavy rocks at the beach.
- Phone camera that works.
- Items from best purchases.
I recovered quicker and some of my nagging pains went away after I started taking protein.
I’ve been tossing rocks on the beach for years. Trying to pick up and flip super heavy rocks has been a fun addition.
Both of these additions came thanks to podcast episodes. (See: Best Podcast Episode.)
Best Thing I Quit
🏆 Dealing with crappy public WiFi.
Honorable nominees:
- [Can’t think of others.]
So much more efficient and stress-free to buy a ton of data and tether with my phone. This way, I can work from beaches and parks anywhere in Vancouver.
Best Monthly Challenge

🏆 The Show-er (Daily demonstration of appreciation to Kim)
Honorable nominees:
- Funth
- Networkout (proactive reaching out and engagement with peers).
- Inhumentoring (30 min tinkering with AI for 100 days straight).
Best Deep Dive
Honorable nominees:
- Generosity
Innate by Kevin Mitchell (my recap here) was my favorite book on the topic of how we’re pre-wired, then random chance makes us who we are. I also liked The Emotional Life of Your Brain’s look at how much of our emotionality depends on how our brains are wired, but how we can re-condition those pathways with mindfulness exercises.
Most Consistently Rewarding Activity
🏆 Picnics at Kits Beach in Vancouver.
Honorable nominees:
- Picnics at Saunders.
- Writing (even though others’ reception of it hasn’t been rewarding).
- Sunsets from our balcony in Cape Town.
- Early morning volleyball games at Camps Bay.
- Day Trips: Dageraad, Bellingham, Elgin, Delta, Cape Point.
- Father-son adventures with Zac: Clifton, bike trips, parks around Vancouver.

Family Awards
Zac’s Favorite Things
🏆 Sleepy and then Baabaa, his security blanket stuffies.
Honorable nominees:
- Telling everyone who asks his age, “I’m five!”
- Baking and offering make-believe cookies for everyone.
- Playing baseball by hitting berries and rocks and other sticks with a stick.
- Holding a stick, making a “Brrrr” noise, and pretending to cut trees, bushes, and grass.
- Dame tu cosita. (4.5B views?!!)
- The Duck Song.
Sandy’s Favorite Things
🏆 Zac
Honorable nominees:
- Milk.
Zac’s the only one who can make Sandy laugh. Sandy loves Zac.
Kim’s Best Business Idea
🏆 Website facelifts
Honorable nominees:
- Vintage jewelry
- Retreats for women
Spoiler: New and even more exciting idea(s) coming in 2024! More than ideas, too…
Best Photo of the Year
🏆 Proud big brother

Honorable nominees:







What Do You Have to Celebrate?
What are your best, worst, favorites, greatest, and biggest from the past year?
Whatever they are, they deserve to be celebrated and recorded so you don’t forget them and learn from them to have even more to celebrate in years to come.

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