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I was at the highest point of my IT career in 15 years. I could have gone even higher, but after almost 5 years with a leading software company, I quit my job in January to go off on my own. What was I thinking?!

I felt as if I had outgrown my position (I was getting a little bored) and kept asking myself, “So this is what I have to look forward to? Spending all my time in exchange for a paycheck and 3 weeks of vacation every year… there has to be more to it than this, right?”

I mean, it wasn’t that bad. All things considered, it was quite good for me and a lot of other people who work/worked there. I was pretty damn good at what I did, and I had been successful in my career achievements thus far.

After work, I’d spend leisure time riding my bike or go climbing with friends. I was in pretty good physical condition. I was living a comfortable life.

A lot of my friends were getting married, buying houses, having kids, and settling down. I thought that I should probably do that too.

I mean, there’s nothing wrong with settling down. It’s the path that society expects you to take. At a certain age, it becomes the normalizing social factor. It gives everyone something to talk about – they can all relate to one another, because they’re all in the same situation together.

And I thought that I was ready to go for it myself. I had stepped up my dating game and was having some relationships here & there. I had a stable job, a car, and most of the things that say, ‘I am ready for this next phase of my life.’ After all, I was 34, which is a good time to start considering a family, and also because most of my friends were already there.

But there was a problem – I wasn’t happy.

I wanted more freedom. I wanted to sign my own paycheck, not live paycheck to paycheck on a fixed income. I wanted to be able to go somewhere as I pleased, and not have to get a manager’s approval. I wanted to be 100% responsible for myself, and answer to no one (except my customers). Even if you like your job… to be the victim of some else’s decision to let you go? And your primary source of income dries up in an instant (which has happened more than once), then what?

After almost 5 years at my job, it became so incredibly clear – I couldn’t allow myself to waste any more time before I fixed this ‘happiness’ problem. I needed to be happy with myself and my life, and THEN everything would fall into place.

This ideal has been stuck in my head for a long time. I want to have my life together so that when the time comes to have a family, I’m good & ready.

Quitting my job was the first step to recovering my life. On January 10th, I made it so. I took the red pill.

Instantly in that moment, I was free soloing a really big wall without a parachute. I had untethered myself from the life line. Now it was time to find out what I was made of, to challenge & push myself in a way that most would never consider.

This was it. My big chance to start anew and live the life that I had dreamt of for a long time.

I know you think I must be crazy to leave a lucrative position like that, but your 30s are actually a really good time to do a career 180 if you’re thinking about it. You know yourself better, and you’re able to slow down and see the bigger picture, which isn’t possible in your 20s. You’re more experienced with life and work, so you’re able to look around and see other paths, where in your 20s, you just don’t have enough experience to be able to do that. You’re more clear about the things you want (and the things you don’t) and you’re less likely to make decisions with tunnel vision.

OK, so how was I going to pull off this career 180?

I had written enough code by this point that I was confident in my abilities to dive straight into a product and basically go all in until I got some customers (and some income). I was going to solve problems for people and build assets.

If I was going to bootstrap and make this work, I couldn’t stay in Boulder. I was burning through $2500/month without even trying. I needed to go somewhere else that didn’t cost as much, yet some place where I could still maintain a good standard of living. I had saved a bunch of runway cash, and I needed to make it last.

Chiang Mai was an easy choice for a number of reasons (which I won’t get into here), but good weather, delicious food, good coffee, minimal lifestyle overhead, good WiFi, good people, safe/little crime, beautiful women… the list goes on.

In the months after leaving VMware, I spent a lot of time tying up loose ends & getting prepared. I sold a few things, gave a lot of stuff away, donated shoes & clothes, moved stuff into storage, picked up a few last minute items, got my things together, got organized with a two week plan, and then boarded a plane to Thailand.

I landed in Chiang Mai near the end of April. Within 3 days, I was setup with an apartment, a SIM card, a motorbike, and I was writing code. It was a beautiful thing.

Jump ahead 8 months to now. How do things look a year after quitting my job?

This is my 2014 year in review.

Forward Progress

Built a WordPress Plugin (WP Motion)

WP Motion automates 100% of WordPress migrations between hosting providers, including DNS changes.

This has been a remarkable accomplishment for myself, as well as for the WordPress community. Unfortunately what I have started is far from complete. It’s a long term project which has not seen its true potential. I spent a lot of time working on it and I’m really proud of it, but I’ve not been able to monetize yet, and so it has fallen from the top of the priority list (at least until I can work on it without having to worry about my financial situation). Hopefully not too far in the distant future, I will come back to this project with renewed interest and continued efforts.

Built a software product (ReplyBoss)

ReplyBoss is a tool for sending mass personalized outbound email and automating followups, directly from your Gmail account.

It was created in order to cold email a market, setup conversations with people, and create relationships for conducting business. It’s based on strategies presented in Predictable Revenue by Aaron Ross. It exists entirely in a Google spreadsheet, so it drops right into your workflow and can even be handled by your virtual assistant.

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That’s me talking about ReplyBoss at the Leadgen Lunch DC meetup in Bangkok, Thailand, October 2014.

Started Recording a Podcast (finally!)

The Bootstrap Duel podcast will launch on January 6th, 2015. It’s a competition (between myself and Richard Patey) to see who can be the first to have a six figure month. Our audience (bootstrappers, freelancers, consultants, entrepreneurs) is invited to join alongside us and propel their own business based on the tactics and strategies we will be using & implementing ourselves.

Lift: Completed NOBNOM for two periods of 30 days

That’s an acronym for No Boose, No Masturbation. Sounds funny, but it actually turned out to be way more difficult than I thought. Not drinking alcohol was much easier than not wanking. NOBNOM was an experiment in self-control and willpower. It improved my quality of sleep – I was waking up well rested, ready to take on the day. I was more productive & focused. I had more time in my day to do stuff, which led to reading more books, and starting a regular meditation practice. Also, I was chatting up girls without even thinking about it.

Not So Good

Largely neglected my health

When your livelihood depends on building something, getting customers, and making them happy, that becomes your primary focus night & day. Unfortunately these initial stages of starting a business are primarily sedentary. I have my work ethic to blame for not being more active, though ultimately it’s just an excuse. I could have been more active, like I was for the 11 years that I lived in Colorado.

Here’s a comparison of the physical activities that were available to me (easily & without much expense) in Chiang Mai versus Boulder, in the order of most frequent participation:

[table id=1 /]

I didn’t have my road bike with me, and my mountain bike was stolen a few months before I left Colorado. In the early stages of business, buying or renting a bike (of either kind) was not an option. I could have had my road bike shipped, but that would have set me back at least $500. Also, it’s so damn hot during the summer in Thailand, that riding a bike was not even close to the first thing that came to mind as a sane thing to do. Even then, the few cyclists I noticed were mostly riding at night.

Swimming is a good way to get a full body workout in a short amount of time, and it’s low impact. (I stopped running because my knees hated me for it.) The swimming situation in Chiang Mai is pretty good. The 700 Year Stadium has a chlorinated 50 meter Olympic distance pool. Also worth mentioning, they have an exercise area which is great for doing free weights or tabata exercises before jumping in the pool. A membership only costs 500 baht per year, which is about $15. When I come back to Chiang Mai, this is going to be at the top of my list, because it’s also not far from where I lived. Just need to carve out the time to go do it and then I can finally start to feel better about sitting in front of the computer for 12 hours a day.

Chiang Mai also has a few climbing options. No Gravity is a small indoor gym off the northeast corner of the old city. It’s certainly no Earth Treks, Movement, or BRC, but it’s a gym nonetheless. It costs about 150 baht per visit (about $3) so you’re not forking over $20 per session, but it’s still kinda shitty. The walls are made of sheetrock, and I’m not sure how the holds are anchored exactly, but sometimes it feels like you’re going to rip them off the wall. To be fair, the holds themselves are decent.

About 45 minutes outside of town, to the east is an outdoor spot called Crazy Horse. There’s a decent amount of sport climbing and all of the bolts & anchors had a minimal “sketch” factor. Definitely worth checking out, but you’re probably going to make a day out of it if you go, so not the most convenient of activities. Plus after a full day of climbing, a backpack full of gear definitely starts to weigh you down on the ride home. It’s fun & good to do a few times, but too time consuming in my opinion.

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Leading a sport route inside a cave at Crazy Horse in Chiang Mai, Thailand.

Previous Goals

Quit my job

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Live in another country

So far this year, I have lived in Chiang Mai, Thailand for eight months, and now I’m located in Medellin, Colombia where I will be for at least three months.

Travel more

I had the opportunity to visit Portugal (Nazare, Peniche, and Lisbon), Burma (Mae Sai), and the Virgin Islands (US & British).

Go surfing

I’ve always had profound appreciation and deep respect for the ocean. It’s a force of nature that is still beyond our present comprehension.

I have always wanted to go surfing. I was visiting my parents in Portugal, so for a few days, I had the chance. What a good feeling it is to catch a wave and ride it all the way into shore, until your board bottoms out. I love it! I’m totally hooked. Plus nosediving is really fun.

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Catching some waves in Peniche, Portugal, July 2014.

Sailed Another Monohull

I love sailing. It’s always been something that I wanted to do on my own someday. Well, I’ve been building up my sailing resume for 3 years now (as crew). I’ve sailed a catamaran once, and a monohull twice. I’ve practiced all the maneuvers, and now I’m ready to charter on my own. Also, Captain Ben has been studying traditional navigation. I’m one of the few who can still navigate without GPS. Who wants to go sailing in the British Virgin Islands next December?

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Sailing from Anegada to Jost Van Dyk in the British Virgin Islands, December 2014.

Notable Books & Texts

Overall Thoughts About 2014

I’m still feeling good about quitting my job. However, what they don’t tell you before walking out of the building for the last time, is that you also leave behind the structure and routine provided by the job. When you quit, you’re no longer required to work 9-5, or 11-7, or at all. Nobody is going to ask you if such-and-such project is done yet, or if you can take care of something for them. You’re on your own. Everything is entirely up to you, which can be liberating to think about before you quit, but is a different story once you do. I ended up consistently putting in 10-12 hour days, 7 days a week, so I didn’t have to work 40 hours for someone else.

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Insane amounts of work are crucial at this early stage, but it’s not sustainable, nor is it healthy to do for long periods of time. Work smart, not hard, right? I’m going to be leveraging virtual assistants over the course of the coming year to alleviate some of the workload. I need to be working on the $1000/hr tasks, not the $10/hour or even $100/hr ones.

This wild roller coaster of sensational ups and wickedly brutal vicissitudes has been kicking my ass. Due to resistance, many people throw in the towel just before reaching a good level of success. Books about stoicism have allowed me to see valuable lessons from every situation, good or bad. It’s natural to be controlled by emotions when something doesn’t go as you would have expected. Right now, more than ever, is the time when I need to get over the rough patches and persist through endless battles of resistance that I’ve encountered throughout my entrepreneurial endeavors, with the tenacity of a stoic.

“[Marcus Aurelius] truly saw each and every one of these obstacles as an opportunity to practice some virtue: patience, courage, humility, resourcefulness, reason, justice, and creativity.”

Ryan Holiday, The Obstacle Is the Way

I’m feeling a great deal of uncertainty. I’m trying really, really hard, but haven’t achieved the level of success, or gotten to the place where I thought I might be at this point. From the inception of a software product, it takes no fewer than 12 months to grow into something substantial. I’ve aware of this. I’m starting to see revenue only 4 months into my second product. The small wins mean everything to me right now. I realize there’s no place for second guessing myself, but sometimes I still do.

Notes to self:

  • From little acorns grow the mighty oak; everything worthwhile takes time.
  • Everyone has their own path. Some are ahead of you, some behind. Doesn’t matter. Believe in the decisions that got you there, remain true to yourself, and stay the path. You will arrive at good results. They are worth the effort and will be massively satisfying.

“The professional tackles the project that will make him stretch. He takes on the assignment that will bear him into uncharted waters, compel him to explore unconscious parts of himself. Is he scared? Hell, yes. He’s petrified.”

Stephen Pressfield, The War of Art

Location-independence can be really fucking lonely. When you adopt this lifestyle, you will quickly make friends with others doing the same. Then you discover that all the friends you made are just as transient as yourself. So you’re never really able to be with your friends for more than a month or two before they (or you) go somewhere else. I’m constantly thinking about my friends back in the States, too. All this work stuff can be really taxing. As an introvert, (the majority of the time) I’m pretty good at hiding behind the computer screen with my headphones on, plowing through a bunch of work. But sometimes I’m severely lacking social interaction and being around other people, which isn’t always possible. I dated a few Thai girls (including the one who took this photo), but sadly, no significant relationships had developed before I left the country.

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Yet another coding session at Camp in Chiang Mai, August 2014.

 

I screwed up. Spending the better part of 5 months to build a WordPress plugin was a costly mistake. This was a mind expanding project for myself, and something good for the world. Unfortunately, I need money to feed myself, and I discovered that my efforts were focused on a revenue source that did not exist where I thought it might.

I have learned a lot. Now that I reflect on everything I’ve done this year, it’s kinda nuts to think about. I’ve gotten better at writing code, my problem solving abilities have advanced, and I have a different perspective on how my multidimensional array of skills (geekiness) can be applied in so many areas. This has opened doors for me. Now I just need to go through them.

I’m optimistic about 2015. I have zero doubts that 2015 is going to be a really big year! Things are happening. Not only for myself, but also for so many great people that I’ve met this year. I’m super excited!

2014 in music

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2014 summarized in a photo

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Photo from APOD.

Goals for 2015

  • Achieve my first $50K month
  • Invest more heavily in the market
  • Become conversational in Spanish
  • Charter a monohull with my own crew in December

Predictions for 2015

  • Simplexity (as it applies to software development and SaaS) will dominate existing apps which fail to solve complex problems via a simple interface with good UX.
  • More companies will strive to become data driven and embrace tools that make it easier to interpret data, which leads to actionable steps, ROI, and a better understanding of their business.
  • The flow of money through payment systems via smart cards and mobile/NFC will spread rapidly.
  • Security vulnerabilities in mobile payment systems will introduce an entirely new market of products that prevent the proximity-based hacking of your financial accounts.
  • Increased adoption of bitcoin will make the currency more readily available in places where it currently is not (ATMs, and as a more commonly accepted payment method online/offline).
  • VMware has been lacking technical innovation (at least by a factor of 10 over what’s presently available in the market). Cloud services have become a commodity with fierce competition, so the stock will find resistance and fall to around $50.

Wherever you are in the world, I hope you have a beautiful holiday, that you’re in the company of friends and loved ones, and have plenty of delicious food & libations, laughter, and good times.

Happy New Year!