Quitting Doesn’t Mean You Can’t Start Again

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Screaming Yellow Zonkers Smith Rock

Me high above the Crooked River at Smith Rock on the aptly-named “Screaming Yellow Zonkers.”

Have you ever quit something you used to love? A job? A relationship?

Well, four years ago, I quit rock climbing. It was no longer fun for me, so I stopped after a decade going at it.

At the time, I was also cranking on my fledgling business and every day was intense. Keeping climbing in the mix felt like tapping a dry reservoir, not a release of pent up energy.

Kicking back around the fire after a great day outside.

Kicking back around the fire after a great day outside.

Enter mountain biking. Instead of static, cautious moves on a rock wall, I spent hours pedaling through wild areas and ripping down rocky trails. I was a control freak in my business, but I could hit a flow state on a bike. I shelved my climbing gear and spun pedals, initially near home and then all over once we hit the road in 2013.

I still love biking, but a funny thing has happened since we landed back in Portland two weeks ago – I’m stoked to climb again. And now I have two things I previously lacked in Oregon, our Sprinter and a flexible schedule to explore my backyard.

To kick off our Pacific Northwest spring/summer stay, we landed and I quickly turned around to hit the road with my friend Martin. Bachelor trip! Chelsea waved sayonara and went back to back to relaxing at home, exactly where she wants to be right now.

Martin at the top of Smith Rock.

Martin at the top of a climb at Smith Rock.

For me, five days in Central Oregon followed. I’d forgotten the easy nonchalance of a bro trip, the swing of pushing hard physically and then sitting around a campfire trading stories. With the van as base camp, we launched into days rock climbing at Smith Rock and a “rest day” mountain biking in Bend.

After 2.5 years traveling, I’ve found that I’m definitely calmer and more centered now that work doesn’t dominate my mental space the way it used to. (Martin even noticed.) The angst I used to feel climbing a hard route is still there, but to a much lesser degree. It was actually fun to be on my edge, teetering on a cliff, not just a fear-soaked experience.

Nothing like a trad lead to keep the heart rate high. Here I am on Spiderman at Smith Rock.

Nothing like a trad lead to keep the heart rate high. Here I am on Spiderman at Smith Rock. (Photo: Martin Tull)

I attribute this to happiness via subtraction, as these days I’m rarely doing things I dislike. The result is that I don’t hit decision fatigue, mental exhaustion, or frustration as often. I’m still working on curbing my road rage though!

Realizing my head is stronger while tied into a climbing rope is one thing. Translating that into appreciating being home for awhile is another game entirely, and I’m trying to apply my feeling of contentment to the (relatively) stationary life.

Smith Rock in all it's glory

Smith Rock in all it’s glory. This place should be a national park!

After all, I can do all the things I enjoy here, even if it doesn’t carry the cool factor of traveling to new places. We both want to be in one place to just hang out and not constantly be exploring distant realms.

My goal is to appreciate the Pacific Northwest for all the excellent fun it offers, whether in or around Portland. It just takes a new head space. As travel writer Pico Iyer penned, “Going nowhere is not about austerity so much as about coming closer to one’s senses.”

Onward!

Ryan tightrope walks the ridge on Indian Point, a calf-buster hike east of Portland with killer views.

Ryan tightrope walks the ridge on Indian Point, a calf-buster hike east of Portland with killer views.

Crowdfunding the Fair-Haired Dumbbell

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Hanging with the old Ford

In 2007, I was a fresh-faced engineer working my first job after graduation and a year of travel. Flush with cash relative to years of penurious living, I wanted to invest my money, and not in old project cars like the above.

My reading list at the time was full of books about Warren Buffett and other money managers. Armed with tactics, I thought I could beat the market. I spent hours each day poring over stock charts, pretending I knew what I was doing.

I didn’t. When the 2008 financial meltdown nuked the market, I got hammered with (most) everyone else. Unfortunately, I had to sell at the bottom to free up cash after quitting my job, locking in the losses. My brilliant wife held onto her stocks through the chaos and came out way ahead.

What We Do Now

Eight years later, my investing style is much different. We mostly invest in index funds and via the stocks of a few companies whose services we use and like (e.g. Amazon, Netflix, Apple). I prefer set-and-forget weekly or monthly auto-investments through Wealthfront. This allows me to rarely think about the market crashing, burning, or whatever strong words the news uses for a 1% daily change. THE SKY IS FALLING! BUY GOLD AND PALLETS OF AMMO!

We also invest in what we know: real estate. Specifically, real estate in Portland, refuge for water-starved Californians searching for sub-seven-figure properties.

The problem is that single family real estate is a long-term play and requires managing the property, finding tenants, and being actively involved. On the other hand, commercial properties require a ton of cash to access or you have to buy a generic real estate investment trust (REIT) that holds shopping malls in the Midwest or office buildings in Florida. *Yawn*

As an alternative, we recently invested in a fun, different building named the Fair-Haired Dumbbell that breaks ground soon. A local developer (and cool dude) named Kevin Cavenaugh from Guerrilla Development is the brains behind this idea. They’ve done other interesting, successful projects in Portland, and this latest will house creative professionals on Portland’s east side. Update July 2016: Here’s a take on the project by the New York Times.

A digital mockup of the proposed Dumbbell. Photo credit Guerrilla Development.

A digital mockup of the proposed Dumbbell. Photo credit Guerrilla Development.

Why Do You Care?

We invested because we support Guerrilla’s mission to keep Portland awesome/weird and not just build boring structures with no zing. The exterior skin is a pattern by an Italian designer. Crazy, ugly, cool? At least it’s different.

Secondly, the Dumbbell is one of the first buildings in the country to use crowdfunding for part of its financing.

To do this, Kevin and Guerrilla Development worked to create an SEC-approved “Regulation A” offering. Basically, it’s a Kickstarter-style way to fund $1.5mm in equity in the Dumbbell. This allows someone to invest as little as $3,000 and get an 8% return from a chunk of the building profits. Certainly $3k isn’t chump change, but where else can you invest in a building for so little?

Sound intriguing? Check out Guerrilla’s investor page or watch their fun video about the project and why they crowdfunded it. We believe in this project and have recommended it to a number of friends. (Heads up that due to SEC regulations, this is only available to people who live in Washington, Oregon, California, Massachusetts, Virginia, and Washington D.C.)

I don’t benefit from writing about this, but merely love that crowdfunding opens commercial real estate to people who otherwise wouldn’t have access to it. I think (and hope!) we’ll be seeing a lot more of this type of financing structure in the future.

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Dig this kind of article? Email me if you’d like to hear more about how we invest, what services we use, and other financial-related writing. If you’re into it, I may write more like it in the future.

Holding $50 USD each (in Laos currency) with my buddies Keif and Blythe in 2005. #poortravelingstudent

Holding $50 USD each (in Laos currency) with my buddies Keif and Blythe in a trip overseas in 2005. Yep, my shirt says COLLEGE and I wore glasses back then. #poortravelingstudent

A First Date in Prague

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Meeting in Prague

Today is special. Ten years ago to the day, Chelsea and I met for the first time.

In Prague.

At the time, I was studying abroad in Gothenburg, Sweden. (Ok, mostly having fun.) Chelsea had just moved to Portland. Through an introduction from her brother, my college roommate, she and I wound up chatting online, then Skyping.

An offhand comment from me about traveling in Europe resulted in her booking a plane ticket to fly across the Atlantic for a first date. It was my bushy fro that wooed her.

I know, I know - I'm a serious charmer.

I know, I know – I’m a serious charmer.

We united in a square in Prague and kicked off a month journey through red-roofed Czech villages and Croatian islands with spectacular views and free house wine. Just in case we didn’t hit it off, Chelsea brought shirts emblazoned with FUN, the theme of the trip. She also brought fake buck teeth and temporary tattoos with sayings like Girl Love to embarrass me.

Turns out that we liked each other.

Two months later, she was back in Portland. Meanwhile, I took the Trans-Siberian Railroad across Russia with my brother. (A story for another day.) Then Chelsea soldiered through a long trip to meet me in Beijing to kick off our second date – 2.5 months exploring the far reaches of SE Asia from China to Thailand.

Top of a holy mountain somewhere in SW China.

Top of a mountain somewhere in SW China.

Let’s just say traveling together 24 hours per day is a quick way to get to know someone. We decided life together would be fun, so I got on a flight to Portland and moved in with her.

Since then, the saying about time flapping its wings has proven true. We’ve worked hard on businesses, dug into a community of friends in Portland, and built a life together. There were small trips, all woven into a busy work, social, and city life. The end of 2013 was major life shift when we headed out on a “four month” van trip that continues to evolve and has transformed how we aspire to live.

Alright, you caught me - this one is from a day exploring Vietnam by scooter. Everyone needs a pink umbrella while scootering...

Wait, that’s not our van! Exploring Vietnam by scooter in 2006. Pink umbrellas for rain protection are mandatory.

We get along well, even in a small space like a van or pedaling thousands of miles together, but we’re not perfect. There are fights, misunderstandings, and moments when she tells me to go for a run or force-feeds me to send my Hangry Alter-Ego (NARG) into retreat. (Check out my Happy Wife Happy Life post for tips on keeping it together on the road.)

Still, I figure we must be doing something right. When I think about it, there’s one thing that’s the bedrock of our successful partnership:

We never stop learning, or more importantly, being open to what the other person is learning.

It’s as simple as that. There are books about the five love languages, techniques on non-violent communication, and plenty of expensive therapists available. For us, continuing to learn, exploring the world, and growing keeps life interesting and aligns us on a path together.

Hanging with our favorite lambs at Farm Sanctuary.

Hanging with our favorite lambs at Farm Sanctuary.

To celebrate our ten year anniversary of meeting with a fitting gift, I dug deep into our photo collection. First, I picked over 1,000 photos of the two of us, starting April 5, 2006. Shots of us laughing, hiking, hanging with friends, doing handstands, wearing hats sideways, riding bikes, and all the fun of 3,650 days as a couple.

Then I made a photo mosaic with Mosaically using those photos to create a big print to surprise Chelsea. The shot I chose is a goofy one from our wedding day wearing those original FUN shirts. When you look at it from afar, it’s a portrait of the two of us. Upon closer inspection, it’s a 1,000 tiny moments we’ve spent together.

One of my favorite shots, now built from 10 years of fun moments.

One of my favorite shots, now built from 10 years of fun moments. (Here’s the original.)

After all, what is a relationship but a compilation of the moments shared with someone you care about? When I look at this print, I think of not just the times Chelsea made me smile, laugh, or feel special. I also dream of the expanding landscape of our lives, how many more adventures we will have, and how much we’ll learn and explore together. We’re just getting started.

Chelsea, thanks for being my life partner. Here’s to filling the next mosaic with many more photos of us sporting temporary tattoos or doing handstands. I love you.

I finally found a place to use a dorky wedding photo! It's amazing what those photographers can talk you into...

Yesssss – I finally found a place to use a dorky wedding photo! It’s amazing what those photographers can talk you into.