Do You Want to Run a Business, Or Do You Just Hate Your Job?

One week to go at the engineering office!

Ten years ago, I left my safe engineering job and swam into the dark waters of self-employment. No steady paychecks, no health insurance, no 401(k) matching. Just me, a degree I owed money on, and adult anchors like a mortgage. I’d taken zero business classes and didn’t know a P&L statement from a TPS report.

Coolly, a steely-eyed Texas Gunfighter, I assessed my unique position based on my skills, what I enjoyed doing, and what the world needed. Success soon followed, along with a shiny Camaro.


Another day in the trenches of Office Space.

If there’s one thing I’ve learned in 10 years of self-employment, it’s that nothing is easy, but the end result surrrre looks nice. Whenever I hear “you’re living the dream,” it always makes me think: do you want the uncertainty and headaches of building a business, all with no guarantee of success?

Along the way, I went from coveting the lifestyles of certain people in my life and in the media to realizing that, whoa, behind that curtain in Oz lies so much work, worry, and stress. Trade offs, always.

To dispel any notions of overnight riches, here is the real story of my journey. It’s full of doubt, mistakes, inch-by-inch progress and plenty of setbacks. YAY! I begin as a morose engineer and (eventually) claw uphill to a place where I run my own business and am lucky enough to have the time and money to choose how I spend my days…but first, shit gets real.

Choosing to spend my time in places like Glacier National Park!

The Unvarnished, Damn-That-Sucked-Sometimes Path

After college, I strap on a backpack and leave the country for the first time, exploring the world for a year. Small-town Idaho boy on the loose! (I live on savings from working multiple jobs through college.) I gain more self-reliance than during my four years of college, plus traveling is FAR more interesting than differential equations. Unfortunately, it doesn’t pay much…(Ok, anything.)

Along the way, I meet Chelsea in Prague and follow her to Portland. I get a full-time job as an engineer. Two months into the job, I’m miserable. Forlorn in my cubicle, I stare at my pictures of exploits in 35 countries. Two weeks off per year?! If I’m lucky, I only get 4,680 weeks in my entire life!

The entitled millennial in me wants freedom and money, RIGHT NOW. C’mon world, I’ve done nothing to earn it, but I want it. No, I deserve it.

First date with Chelsea! If I can do a handstand, there’s no way working full time is necessary.

I start reading books like The Four-Hour Work Week and blogs about self-employment. (My reading list from those days is a study in cracking a code: real estate investment, entrepreneurship, The Millionaire Next Door.) The gears start whirring. I’m working long hours and downing Subway sandwiches at my desk. Meanwhile, Chelsea is starting a real estate career. Supportive partner to the core, she says, “Hey, talk to James, the finance guy in my office.”

James advises me to keep my sweet, secure engineering job. I’m earning $55k/year right out of college, far more than I’ve ever made. It’s 2007 and the housing market is teetering and everyone in the industry can feel it.

Advice be damned! I get a lending license. I have zero finance training, but I want to become the Green Lender, the sustainability finance dude.

I’d totally trust this guy with my money! I mean c’mon, he’s got a green shirt, rides a fixed gear bike and has big hair. #trustworthy

Friends are my first marks; somehow, I don’t screw things up TOO badly. I do a deal here or there on the side for a year, focusing on my own personal projects on my computer’s second monitor. (Alt-Tabbers out there, let’s just say I was quick on the draw.)

The condo market in Portland peaks. We’re sage investors, so we buy a condo. “We’ll flip this and buy a house next year,” we tell ourselves, toasting our good fortune. The condo drops 40% in value. #realestategeniuses

Mid-2008, I leave my engineering job. Adjustable rate mortgages explode like time bombs, flak spraying the markets. Whatever – I’m SO stoked to quit.

The market crashes. There are approximately zero point zero clients buying homes. Whaaaat am I gonna doooo?

I’m no dummy, so I focus on core business development strategies: rock climbing and biking. For months, I avoid doing the work to get started, living on savings. Road trips to beautiful places STILL don’t pay much, it turns out…

Thinking deeply about business development in the City of Rocks.

Hard at work on my business plan with my friend Don on a ride around Crater Lake.

A Journey to the Dark Side of Business

A college roommate and I are both casting about for business ideas. We start a tech consulting business (neither of us are qualified). One of our favorite biz names includes “Techasaurus Rex.” (Sigh.)

We shutter T-Rex when my roommate finds a multi-level marketing (MLM) business called LocalAdLink, which aims to compete with Google AdWords. With a failed MLM in college, surely I’ve learned there is no such thing as easy money and that MLMs are shady and sharky.

I jump into the MLM full-force. Craigslist posts, recruiting, “ground-level opportunity…” All the bullshit. We make a few dollars, mostly from other people joining. (Rule #1 about most MLMs: the product is secondary. It’s all about recruiting people to sell the product for you, a pyramid paying people at the top. Gimme a P, gimme an O…PONZI SCHEME!)

After a month or so of this BS, my biz partner finds another, shinier “opportunity” called Lightyear Wireless. It’s another MLM. Chelsea, the far more intuitive one in our partnership, sees right through it. No way am I jumping into this one – c’mon Dakota. Dean’s list engineering student, world traveler… Common sense says that…

Headlong, I dive into recruiting for Lightyear. This one goes well; recruiting is easier, money to be made. Ground floor opportunity again, baby! (It’s always ground floor.) It’s a cold winter and I’m working in our uninsulated condo. Curled at my feet is an archaic cat Chelsea rescued from the street. Her name is Annie and she’s the sweetest, most decrepit kitty ever.

Annie spends the last days of her life asleep by the space heater, croaking out meows for a pat. Her waning moments parallel the sunsetting of my MLM days. I read a professor’s article about MLMs and email him. He confirms my theory that I’m not actually putting efforts into a real business. That small nudge is all it takes.

Me and old Annie hanging out. (Side note: No way I’ve ever had so many pics of me sitting in office chairs in one blog!)

The Only Way to Make Money is to Create Value

I realize there is no easy way to make money without hard work and that it is time to buckle down and create value. It’s a hard lesson, and I feel stupid and embarrassed. Why don’t they teach these lessons in school instead of trigonometry?! I’m also lucky to only waste a few months of my life on MLM scams. To anyone considering them, here’s my odious advice: move on immediately.

My timing is unreal. The housing market collapses and the government rescues big banks. Not to worry: all my old engineering colleagues are pulling down great money. None of them will lose their jobs in the teeth of the incoming recession. (“How’s the new biz, Dakota?”) Remind me why my dumbass Millennial, want-the-world-on-a-silver-platter self left a solid, respectable job with upward mobility?

I scattershot my approach in mid-2009: selling search engine optimization, hawking website design for a company, learning web design myself and building niche websites, joining a couple teams pitching grants in the sustainability marketing realm, and teaching a class on sustainability at a local college. (Funny enough, I’d forgotten ALL of these until going through Gmail for this blog!)

My shifting intentions force me to refocus and buckle down on my real estate finance business. I brainstorm ideas about green building and sustainability, reach out to build relationships, and finagle presentations to Realtors who are listing efficient, green homes. The federal government offers a first-time homebuyer tax credit to rekindle the swooning economy and people start buying homes again…but I still have zero clients.

I’m freaking out. My savings are dwindling and my meager stock investments are cratering. I’m a saver by nature and hate living without a safety net. That cubicle and monthly paycheck sound miiiiighty fine. Free lunches and a Christmas bonus? Sign me up. (I’m in The Dip, as Seth Godin calls it.)

I’m somewhere in the trough of sorrow/crash of ineptitude…

Changing Tides!

Momentum! Chelsea refers me some clients and I build relationships with Realtors. Two of them are a progressive team that sense opportunity with a review platform, Yelp. I’m intrigued (and desperate).

Referrals trickle in. I finally start making some money. Not a lot, and it feels unstable, shaky. Still, we’re frugal and it’s enough to cover my expenses. (Mostly because I’m not into the expensive sport of mountain biking yet.)

Ohhhh but I WILL be into this sport… (Photo: the talented Scott Rokis.)

So much trial and error. Does this marketing work? Can I offer classes about technology and a paper-free office and get referrals? (Yes.) Some business relationships blossom, others dead end, time wasted for no pay.

I’m learning the hard way that efficiency and effectiveness are different beasts. I can spend all day working efficiently on things that don’t deliver revenue! (“Maybe I’ll sort my contacts into groups and delete old archived emails.”)

I’m working hard, harder than I EVER did as an engineer, and the payoff is uncertain at best. Still, Yelp reviews are coming in and I’m seeing a glimmer of hope. (Essentialism is a great book that helped me focus on what mattered.)

Curveballs, Always Curveballs

I receive a job offer that is too good to refuse and become the Sustainable Finance Director for a local nonprofit. I’m tasked with developing relationships with organizations to push forward the green building market. Do I land my fledgling mortgage business? Hell. No. I double down and work harder.

Adding fuel to the fire, I commit to a budget of $200 per month to invite engaging, curious business professionals out to lunch or coffee. I build my network and meet dozens of driven people who are creating and contributing to what makes Portland a fantastic city. (The book Never Eat Alone is a significant influence on my approach.)

For 1.5 years (early 2010 to fall 2011), I’m pinning it, full throttle. Flights all over the country presenting on sustainable finance, meetings, work work work. My mind never rests, stress cascading off me in waves. I’m thinking about work from eyes open to head on the pillow. I lie awake at night thinking over difficult conversations, tactics, possibilities, risks. I’m so much fun to hang out with…

Kauai vacation (to elope!) in 2011. Not shown: me working half of my freeeeaking wedding trip.

It’s an exciting, exhausting, unsustainable pace. Only my morning bike commute, lunch runs and the climbing gym keep me sane. Chelsea is also working nutso hours on her business, so our time together is limited. Trail mix dinners over the kitchen counter, yum.

Breaking point. I have to choose. (Choose Yourself James Altucher says!) I leave the nonprofit and invest in my own business in fall of 2011.

Own or Be Owned by A Business

Positive reviews of my work on Yelp continue to drive new clients my way. My work is gaining steam and 2011/2012 are insanity. I’m pulled in 700 different directions. In no way do I own my business; it owns me.

Chelsea and I get married. Even though we don’t have kids and her business is booming, she leaves paid work, opting to support my fledgling business and focus on creating an awesome life for us . (Check out Radical Homemakers.)

We joke that she’s our Ambassador of Fun, but more accurate is that she’s consciously making our lives well-rounded and deep through community building, travel planning, and (eventually) a focus on veganism. To this day, it’s the best decision we’ve made to improve our quality of life, forge new paths and ways of thinking.

Chelsea brings the fun while I rethink cycling and ride two rental bikes in Arizona.

In many ways, we have it so, SO good. However, like a dam overloaded while cranking out electricity, the cracks are starting to show. I’m stressed and edgy. Is this effort worth it? We start dreaming about living smaller and dig into the tiny living movement. What if we live in a mother-in-law unit and rent out the main house? I could dial back my work and stop thinking about money all the time. Wait, wasn’t that the plan four years ago?

We take a roadtrip in fall of 2012 to “decompress.” I spend the entire time working and more stressed. (Where’s a wifi signal?! We’re losing reception!) It. Is. Miserable. We spy a Vanagon on that trip and almost buy it on a whim. Instead, we start researching camper vans. Four months later, we spring for a new Sprinter van. A new chapter opens.

Two contract employees I rely on are yanked out from under me. I’m terrified, but make the leap and hire my first full-time employees. (My guiding principles stem from the book Let My People Go Surfing by the founder of Patagonia.)

We’re in contract on a new house. WAIT. I realize I want to break free, to roam, to feel that footloose feeling of travel from my days in New Zealand, Russia, Laos…

An all-time travel moment: we switch boats on Inle Lake (Myanmar) and learn how to paddle like the locals.

Hanging off the back of a tuktuk in Laos in 2006 with my buddy Eric!

The Life Pivot

We turn on our heels and hatch a new plan: a 4-month van trip from Portland to San Diego. I focus on finishing our van buildout, of planning and execution with freeeeedom as the goal. At the end of 2013, we drop our kitty Oliver off at the in-laws and head south.

The van doesn’t have any running water and there aren’t any interior lights. We are ecstatic. Nature and creative time fill our days. Chelsea and I spend more quality time together than we have in years. We decide four months is wayyyy too short a trip…

I’m working remotely. It’s flexible, but not enough. We crunch some numbers and make another leap: I’ll refer all my clients to my staff. The goal: trade time for money. It’s time to own my business, not be owned.

I’m terrified it will fail, that my hard-fought efforts to build a business will crumble. The risk feels worth the potential reward – what’s the best that could happen? I make the leap.

Sometimes you’ve just gotta do it!

It works. Somehow. There are new headaches and surprises with the people I hire to cover my client load, but also mental space. Less money, more time. As a business owner, at some point hiring and delegation are key if you want to pursue other passions. The timing is never right. Scary. And also life-changing.

We celebrate the new flexibility with a bike tour 4,100 miles across the U.S. I only work a few hours per week on the tour. The decision to leave my engineering job is finally vindicated. This is the reason I started a business, not just to make money!

Two more years of travel follows, followed by the ability to choose where we want to live (Bend!) and sculpt our lives along lines true to our values and priorities. It’s never perfect – I’m still a Millennial, dammit – but the effort feels worth it.

A strong community AND outdoor fun: the perfect mix. 

The Journey Continues

Almost five years from our initial launch in the van and a decade out of the cubicle, I’d forgotten many of these trials. Writing this was a stark reminder of the truth: creating a business is HARD work, often filled with drudgery, dead ends and stress.

What seemed like terrible timing at the outset was actually luck, since I started in the murk of a recession and shot out on the upswing with a lean, nimble business. Even now, there’s no certainty of success. With the housing and stock market overheated again, who knows what will happen! Whatever. I’m confident in our ability to adapt, learn, live frugally, and create income if needed.

One thing’s for sure: I’m glad I didn’t buy a Camaro. I’d rather own a camper van.


Tips for Working Remotely Overseas (Even While Bike Touring)

Hanging in Bruge

As a digital nomad, my freedom to work from anywhere hinges on internet access. Our European cycle tour this summer would be impossible without bits of data buzzing toward me across the Atlantic. I would love to shut my laptop and vanish into the Alps, but disconnecting for so long isn’t an option (yet). A link to the nets and tech to stay plugged in remain necessary.

I have tools and programs for working remotely figured out and it’s easy to stay connected in the United States. I simply use a Verizon wifi hotspot or my iPhone’s data plan. For this trip to Europe, I needed similar solutions with a few tweaks.

Switching on an expensive international plan and paying overseas roaming charges with Verizon or AT&T didn’t make sense. Handing over a gold coin to surf the net for a minute sucks; I’d rather spend that money on delicious dark chocolate in Belgium. There are much better ways to have a data connection.

Taking Your Tech With You

If you’re seeking to escape and disappear off the radar, by all means stick your computer and phone under a mattress and head to the airport. Nothing in the below list is tricky, but most is necessary given the long-term nature of our travel+work arrangement.

  1. iPhone 5 plus Mophie Juice Pack Plus battery case – this adds 120% to the battery, enough to get me through an entire day of use with navigation, audiobooks, or podcasts.
  2. Ultrabook laptop – simple and light enough to not make me curse it on long climbs.
  3. XCom Global wifi hotspot – the heartbeat keeping me jacked in to The Matrix (more below).
  4. Goal Zero Venture 30 solar panel and battery pack – great for camping and long days on the bike to keep things charged.
  5. Lenmar USB 4-port charging pack – handy way to keep cords organized since I just leave them plugged in.

    Charging things in Europe is infinitely easier with a battery pack that has multiple USB ports. I keep four cables plugged in and ready to charge our tail lights, GPS and phones overnight. This is especially handy when electrical outlets are sparse, a common thing.

    Charging things in Europe is infinitely easier with a battery pack that has multiple USB ports. I keep four cables plugged in and ready to charge our tail lights, GPS and phones overnight. This is especially handy when electrical outlets are sparse, a common thing.

  6. DSLR camera (a beat up old Sony NEX-3 with an 18-200mm lens) and a GoPro – I’ll acknowledge that these items are not necessary for work…
  7. 1,736 USB charging cables, typically snarled into an epic Gordian knot
  8. Updated September 2015: I shot a lot of video on this trip and ran out of space on my laptop, which seriously cramped my style (or ability to develop any). Next trip, I’m bringing a portable external hard drive. They’re small (3 x 4 x 0.5 inches) and weigh 1/3 of a pound. I just ordered a WD Passport Ultra 2 terabyte drive.

Everything on that list is straight-forward except the wifi hotspot. For that, I researched like crazy and wound up settling on a XCom Global hotspot as the linchpin for keeping me connected. When I asked, the company generously sponsored us for our trip. There are other options out there (TEP Wireless is one), but I don’t have any experience with their services.

Ceiling in a church

XCom Global Wifi Hotspot

For my Verizon hotspot, I had to visit a physical location to activate it. What a pain. Planning a trip overseas comes with logistics – should I bring the giant cowboy hat, and which color Hawaiian shirt to pack? I didn’t need more to-dos. XCom proved to be e-a-s-y.

The process involved filling out a brief web form with my desired start date and selecting the countries I’d be visiting. I had the hotspot shipped directly to a hotel room in England and activated automatically on the arrival date. Simple and clean, the way things should be. Since this is a rental, there are no contracts or the need to buy anything. Renting works well for our fairly long trip, but I think it is especially handy for a shorter trip, especially if it’s business related. Here is more info on their hotspot, which is spendy at $15/day but perhaps worth it depending on your needs.

Connection Quality

During our travels through 13 countries in Europe, we had service most places. That’s a heck of a lot more than I can say about AT&T back home. Signal strength varies, but usually I can use my phone for Google Maps, log into email, surf the web and operate various work programs. I save downloading movies for wifi, and syncing large amounts of data for a daily backup isn’t recommended, but streaming quick videos online is totally possible. Score – I can still watch Gangnam Style every night.

One annoying thing: the hotspot will sometimes get disconnected when usage spikes over 200 MB/day. This isn’t XCom’s fault; the “Fair Usage Policies” of European telecom countries lets them cut a connection when some arbitrary, unstated amount of data is consumed in a certain (also unstated) time period. Update at end of trip: this has now happened a half dozen times or so (I lost count). Each requires an email (weekdays only) to XCom customer service. If I absolutely needed to be connected to the internet and was paying $15/day for this device, I would seriously question whether this was worth it.

One complaint I had for my Verizon hotspot was that it died after about 2 hours of use. So far, the XCom unit is getting about 4-5 hours. That’s enough for a solid day of cycling using it for navigation as necessary, and I can also plug it into a battery pack.

A brief stop at an office...

A brief stop at an office…

Communication While In Europe

Texting and Phone Calls

I keep my phone on airplane mode in Europe and only use wifi. We arrange most lodging via email with a host, using an app like ACSI to find a campground, or booking a place directly through a website. Texting could prove useful for a quick heads up regarding an arrival time, though I frankly haven’t needed it with email. Skype can send texts for $0.10 each, but you can’t get responses (annoying). Google Voice/Hangouts can be a good option, but doesn’t work in every country. There are tons of apps out there – WhatsApp is great – that send messages, but fewer people in Europe seem to have smartphones or popular apps that we use in the States. T-Mobile has an international plan with unlimited text and data, but the service only runs at slow speeds equivalent to Edge in the U.S., which is too slow for my needs.

I use Skype for calls back to the U.S. A wifi-enabled phone like one from Republic Wireless or one of its many competitors works well too. To avoid language mix-ups with hosts and businesses, I try to communicate by email versus phone whenever possible. There are many text translators online to interpret text from an email.

My cell phone is not unlocked (dang it AT&T), so I can’t plug in a Europe-based SIM card. This hasn’t been an issue, and I don’t want to find a new SIM card for every single country we visit anyway – six of them (so far) in three weeks of pedaling. Crazy as it sounds, even locals only have non-roaming coverage on their phones in their own country. This means that if a Belgian drives 10 miles north to Holland or 50 miles south to France, they are charged roaming rates the same way an American is charged while visiting Canada. Given that all 50 states in the U.S. fit under most cell phone plans with zero roaming, I find it hard to believe European telecom companies get away with this. Rise, RISE, and take to the streets, people.

Update September 2015: Google Fi just leapt into the arena with an incredibly tempting plan. $20/month unlimited texting/calling in 120 countries around the world, plus $10 per gigabyte. Mr. Money Mustache has a great write-up about it.

Making new friends in Holland.

Making new friends in Holland.


Wifi is everywhere so far. Most bars, cafes and lodging have it. Some connections are fast, but (like anywhere in the world) a place teeming with laptop-toting students will have dragging wifi speeds. Hotels can also be slow. Couple that with the recent proliferation of electronic crime and I prefer to use my wifi hotspot whenever possible rather than a public, unsecured connection. Call me paranoid, but the information I read or listen to leads me to believe we leave in an insecure online world where genius hackers can intercept a password faster than I can hoover down a piece of chocolate cake.

One tricky thing with wifi in Europe is that many of the “open” connections in restaurants or hotels are set up through the local communications company. They are free for local customers of that company who have a phone plan, but you can’t log in as a foreigner unless you have a local phone number. This means that many open wifi connections end up not working, which is annoying.

Tech tip: the app Wifi Map is a crowd sourced database of wifi locations and passwords. The paid version allows offline access to the data. For those of you traveling sans hotspot, this app is mandatory.

Getting some work done in a cafe in Belgium with live violin music from a street musician below the window.

Getting some work done in a cafe in Belgium with live violin music from a street musician below the window.


Some people love maps. I prefer the quick and easy method of using my phone, both with wifi on and off. I’ve tried many mapping apps, yet keep coming back to the old standard of Google Maps. I’ll get maps for big countries like France, but it never seems worth it for smaller countries where we won’t be around long. Luxembourg is only 40 miles across – we crossed it in a day. I will say that Google Maps occasionally calls a rutted, rocky goat track from the 15th century a road. Character builders, I call ’em.

I’m always plugged in while we travel. Blindly wandering a city to discover hidden gems is fun, and we do it all the time. But route finding at the end of the day while tired and hungry is worse than taking a calculus final with a hangover. Much handier to plug an address into Google Maps to help avoid marital strife arguing over directions. I’d rather hang out with new friends than wander lost through an industrial area while our hosts wonder if we took a wrong turn and disappeared toward Estonia.

Tech Gear: The Summary

A solar panel, charging pack, a laptop, and multiple cameras certainly aren’t necessary for everyone traveling in Europe. Simply having a smartphone can keep you sporadically connected. Initially, I was planning to explore Europe without a mobile wifi unit, but I’m relieved I didn’t. For a short-term business traveler or digital nomad trying to work remotely, a wifi hotspot like XCom Global’s may be necessary. Given the cost and how often we’ve been disconnected by carriers, I will likely look into other options for our next overseas trip. I’m not sure what else is out there, but consistency of connectivity is #1, especially if you’re paying for it. Google Fi could be a great option, as I mentioned earlier.

In general, with the above tech helping me out, I haven’t skipped a beat with my work during this trip. We cycle and explore during the day, hang with new friends or relax in the evening, and then I flip on the laptop to hammer out some work at night. I was concerned about balancing all these activities, but this adventure is proving fun (except maybe the last week with its 95 degree days) and low stress.

And there you have it! Am I missing any tech you always take on trips? Any other secrets for a data plan in Europe that I missed and should check out? Let me know in the comments or shoot me an email. If my opinion on any of this changes, I’ll update this post later in this overseas jaunt (see above!).

Belgium flowers and cycle touring