Digging Deep with Happiness Through Subtraction

Columbia Gorge Munra Point View Hike

Ten million self-help books exist, all promising to improve our lives. Many focus on a strict schedule and the addition of various tasks or practices: Meditating, exercising, time scheduling, eating well, always smiling, never complaining, being a perfect person…

Just turn into a robot and BOOM, life becomes easy.

Except it doesn’t work for most of us, including me. Changing multiple variables usually creates overload and a short circuit back to old habits.

A Different Approach

I prefer happiness through subtraction. Cut out the activities and habits that create misery, then add back things that make you grin each day when you open your eyes.

I was introduced to this concept by Nassim Taleb’s book AntifragileHe writes:

Happiness is best dealt with as a negative concept…the pursuit of happiness is not equivalent to the avoidance of unhappiness. Each of us certainly knows not only what makes us unhappy, but what to do about it.

Unfortunately, humans are terrible at guessing what will make us happy. We are great at figuring out what makes us miserable though! As Francis Jourdain said, “One can furnish a room very luxuriously by taking out furniture rather than putting it in.”

A magical spot at the base of Elowah Falls in Oregon.

A magical spot at the base of Elowah Falls in Oregon.

Subtract the Unhappy

Start with basic activities that make you unhappy. Perhaps it’s feeling guilty about a caffeine addiction, loathing daily mind-numbing conference calls, or the overwhelm of emails stacking up like Tetris blocks. What are the root causes of those things, and would eliminating them add considerably to your happiness?

Maybe we need caffeine because we’re exhausted each morning. But why are we tired? (New parents, you know why…sorry, but I can’t help you there!)

Was it from staying up late flipping through social media, or not sleeping well because computer screens churn out mind-stimulating blue waves? (Try Flux to address the latter; Apple’s new OS incorporates this idea.) Cutting social media or computer time after dinner might result in better sleep, decrease the need for caffeine, and create a cascading positive effect.

Spring flowers in the Columbia Gorge looking west toward Portland.

Spring flowers in the Columbia Gorge looking west toward Portland.

Hitting inbox-zero feels great, but it’s a Pyrrhic victory since doing so in a hurry often creates more work. There’s no faster way to build giant email chains than a quick email. (Try Cal Newport’s technique to fix this.)

Still, developing an efficient system to deal with email doesn’t address the core question: why are we getting so many emails?

We can be efficient, but at some point there’s too much to handle, or the work itself is mind-numbing. I faced this in 2013 when I received 5,000 emails per month (and sent 2,500). I was efficient, but even using canned (saved) responses and other templates only worked to a degree.

Drilling deep, I saw the source of my unhappiness wasn’t email. Instead, I was completely burned out from working daily with clients who asked for (and deserved) immediate responses. My solution was to hire staff to take over those duties. This lowered my income, but allowed me a more flexible schedule to focus on other things.

I still work daily, but incoming email has dropped to a fraction of the volume. It also isn’t as time-sensitive, so I can deal with it when convenient.

My solution is only one approach. For my industry, I didn’t see another way since automation wasn’t an option. Your situation is probably different, but figuring out the root causes of what makes you unhappy is a powerful place to start.

Tenuous ground on the way to Munra Point.

A day hike in Oregon.

Work unhappiness is only the beginning. We can apply happiness through  subtraction to all aspect of our lives, including friendships, food, and physical workouts that we dread. I hate indoor cycling, but will mountain bike until my legs fall off.

As Leo Babauta of Zen Habits wrote recently, “we fear only one thing really: not having control, certainty, security, comfort.” Cutting away activities that make us unhappy leaves us with fewer stress points. We can’t erase the fear of losing control or security, but blowing away negative chaff in our life gives us more energy to powerfully deal with the headaches that do come up.

The next time you’re feeling overwhelmed or down, don’t add habits to your life. Take to heart the old Swedish proverb: “Fear less, hope more; eat less, chew more; whine less, breathe more; talk less, say more; love more, and all good things will be yours.” What else could we possibly need?

Straddling a narrow ridge near Munra Point in Oregon.

Straddling a narrow ridge near Munra Point in Oregon.

The Secret Weapon for Organizing Your Life and Achieving Bucket List Goals

Santa Cruz pier

Staying on top of life’s tasks can be overwhelming. Post-It notes disappear beneath the fridge; long-term goals get punted downfield, bouncing into the weeds. That’s no surprise, given all the activities of a busy life, plus the huge amounts of information we all consume daily. Tracking tasks for work, fun, travel, and hobbies is enough to short out C3PO. Some aspirations drift away into the mist like an unmoored boat.

As my friend Sean says, there are only seven days in the week, and Someday isn’t one of them. It’s easy to put off mailing that passport renewal app, delay signing up for Spanish or guitar lessons, or procrastinate starting your dream side business.

Organize Your Life!

To help people avoid looking back at a giant pile of Somedays, I always recommend one powerful tool.

It’s called The Secret Weapon (TSW). TSW is a free technique that helps me organize my life, stops things from slipping through the cracks, and empowers me to execute on both annoying to-dos as well as bigger projects.

Like most good things in my life, my wonderful wife brought it to my attention. The Secret Weapon is now the cornerstone for organizing all the information and tasks that cross my path.

I use it both professionally and personally and hope (/know!) you will benefit too.

Mendocino coast line

What Is The Secret Weapon?

Simply put, TSW is a combination of Evernote and the Getting Things Done (GTD) method.

Evernote is a web, phone and computer app that allows you to easily clip, save, record or otherwise archive information of any type.

GTD is a popular technique introduced by productivity consultant David Allen that moves planned tasks and projects out of the mind by recording them externally and breaking them into actionable work items.

TSW merges technology and work-flow techniques. In the words of its creators, the Secret Weapon is:

A free organizational methodology for both professional and personal aspects of life that re-organizes emails, ideas, and every to-do big and small into one system that stays synchronized across a person’s computers as well as their smart phones.

Deploying TSW allows me to keep track of personal and business tasks for both near-term and distant timelines without taxing my brain with stuff that clutters the corners and makes my eyes glaze over.

How the Secret Weapon Works

TSW organizes my life into discrete chunks to manage tasks. That ranges from copying a house key to negotiating business contracts to organizing a future bucket list trip like bikepacking the Colorado Trail. I also track quotes and book passages while I’m reading, clipping all my ebook highlights and importing them into Evernote for easy reference. You can use TSW for anything!

What does this look like? Here’s a sample section of my list prior to departing for Utah in late March, sorted for most pressing actions (1-Now, in TSW lingo). This is just part of the list – I’d wager most of you have similar things bumping around in your head that wake you up at night slapping your forehead.  (“AH, I forgot to drop the bike off for a tune up!”) By referencing this list every morning as our trip approached, we whittled down tasks until we were ready to launch.

Secret weapon

It’s Easier Than It Looks!

Not gonna lie: it took me awhile to start using TSW. I used Gmail’s task feature for years and thought it worked great. I’d type in tasks, handle pressing or easy items, and delete the ones that slipped to the bottom of the list. This worked well in some respects, but wasn’t ideal. It was task management fire fighting: spraying the biggest flames and praying small, untended fires would go out.

The power of TSW became apparent in 2013 when we were prepping our house so we could travel, building out the van, handling business changes, and generally burying ourselves with a stack of tasks taller than Paul Bunyan on growth hormones. With an endless pile of to-dos, my simple Gmail-based task system blew up into a hairy snarl of too much to do and no way to prioritize anything. We needed to crank out a serious volume of work. Our tenants’ arrival grew closer…

Enter TSW. I watched the free video tutorials that walked me through setting up GTD with Evernote , and dialed in the system. It continues to deliver value to this day!

Chelsea herded me along, focusing my efforts with skill a pyramid-building Egyptian foreman would envy. Maybe we were sweeping the front porch as our new tenants rolled up to the house, but we got it done! I’ve used TSW ever since. (I’ll say it again: this may sound complicated, but the video tutorials are short, easy to understand, and walk you through everything step-by-step. You don’t even have to be Type A. TSW can help anyone!)

The key to realizing TSW’s full potential is creating a habit for each morning. After my morning reading, meditation, and writing routine, I cue up Evernote, brain dump tasks on my mind, and then scan for things to accomplish that day.

As a rule, I immediately handle anything that takes less than two minutes, unless that item requires some research or coordination of some kind. In a few minutes, I’ve got my day’s road map.

Open road in Utah

An Example of The Secret Weapon

For a concrete example of how TSW works, let’s use the van buildout that I completed over the course of a few months in late summer 2013. This was an intimidating, time consuming, and complicated task. Put “build out the Sprinter van” on the task list and you’ll get to it later than “sort Tupperware lids.”

Instead, I broke everything down into smaller chunks and actions.  Every pending item for the van was tagged with “Sprinter,” and then given a When/Where/Who designation. Once everything was chunked up, it was a simple matter to add tasks based on priority, location (pick up at Home Depot) or who (me, Chelsea, or hiring someone, if needed).

Over the course of a few months, hundreds of tasks were researched, parts and components purchased, and the project was methodically completed in time for departure. (To be clear, “methodically” also involves me running about in a frenzy sometimes.)

Here’s a shot from the “Sprinter” tag that I pulled from Evernote, since we still have items we plan on updating or repairing.  A metal strip on our counter just ripped off and needs to repaired soon, hence the “1-Now” priority designation. If I decide something can be handled later, I can move it to 2-Next, or kick it way down the line to 5-Someday.

Sprinter TSW

This may seem complicated. It’s not. Once you get in a good workflow, maintaining this system from your computer or phone becomes a routine like brushing your teeth. The morning check-in prioritizes my day, and then I add or update items as needed, plus a late afternoon scan and update.

I’ve never felt more on top of things, even with my life pulled in many directions these days between managing investment properties, remotely handling my business and employees, writing this blog, and arranging our travel plans and friend meetups. (And sneaking off to mountain bike for hours at a time, of course.)

If you’re looking for a straight-forward technique for managing your life, look no further than The Secret Weapon. Not only is it totally free, I guarantee it will increase your productivity, get you to the fabled Inbox Zero, and help “free” time really be free time.

No more wasting minutes searching for lost info, or forgetting that small detail that hangs up a business deal at the last minute. You’re going to crank that stuff out and have time to focus on writing that book, starting a side business, or finally organizing all the photos from high school.

Head over to TheSecretWeapon.org now and get rolling! The tutorials are broken into bite-size snippets that are easy to fit in over the course of a week. Cheers to organizing your life!

Liberty Cap and Nevada Falls in Yosemite.

A Vision for 2014

Happy New Year! Onward we go into a fresh twelve months of new horizons and challenges, fun adventures and who knows what.

After a crush of activity for a few months, we took it easy over the holidays. No better time to disappear and kick back for awhile than the end of the year. We spent over a week with family in Santa Cruz, and then Chelsea and I rang in January 1 with a group of friends – cooking dinner together, watching the sunset turn into a starry sky, and laughing our heads off.

Biking on the Ohlone Bluffs with Chelsea and family.

Biking on the Ohlone Bluffs with Chelsea and family.

For the last three years, we’ve created Vision Boards with our rad friends Jamie and Evan to kick off the new year. The general idea: gather a pile of magazines (we got ours from a doctor’s office and a few salons – with permission of course!) and put them in a giant stack in the middle of the table. Flip through them, scissors in hand, and snip out words, pictures and symbols that speak to you for how you’d like the next year to unfold. Occasionally sneak a random funny one to a friend’s pile such as “hot sex” or a picture of a goofy animal or person. Then compile it all into a collage, a vision of the coming year. (I always end up reading articles and only finding a few images, but hey, it’s a team effort.)

Here’s our vision board for 2014. This was all Chelsea – other than the Mercedes symbol from yours truly – and I love it. Looking at it makes me even more excited for the rest of this trip and beyond!


With the holidays behind us, now it’s back to work. I am stoked to have hired two fantastic people who start next week – it’s amazing what can be done remotely – and we are also on the road again. Big Sur and SoCal, here we come! It has been a fantastic three weeks (my how time flies!) in the Santa Cruz area exploring the ocean beaches and cliffs, grassland trails, redwood groves and open meadows on foot and by bike. More pictures and stories to come from our time here as I fire up the ignored keyboard and get back to writing.

Wishing you an adventurous and fulfilling 2014. May new horizons open up in all the directions you envision!

Cheers to 2014!

Cheers to 2014!

Dakota and Chelsea

Digital Nomad Life – Tools to Work Remotely Instead of Sitting in a Cubicle

A day in Grand Teton National Park. Verizon signal throughout most of the park!

A day in Grand Teton National Park. Verizon signal throughout most of the park!

Ten years ago, there is no way I could travel so often. I’d be a stationary desk jockey, working from the same location every day.

LUCKILY, it’s the 21st century and technology is on my side. I’m an early adopter of new tech, and I’m frequently testing new systems, devices, and online services attempting to streamline my life. There is always a period of adjustment trying new tech, but a few years of tweaking and those lifestyle-design enablers are in place and working for me like enterprising Binary Gnomes.

(Side note: If you don’t already run a business you can operate remotely and are looking for ideas, check out my friend Sean’s awesome post. He’s not selling bullshit multi-level marketing gimmicks, and these projects will take actual work, but they can help you create a true digital nomad life if that’s your goal.)

The benefits of working remotely totally transformed my life. Instead of hanging around the office water cooler, the last 1.5 years included:

  • An eight-month road trip in our camper van to mountain bike the best trails in the western US
  • A 4,000 mile unsupported bicycle tour from Washington to Maine
  • Big city living in Manhattan for a month (we saw seven Broadway shows!)
  • An extended Spanish language immersion course in Tulum, Mexico
  • Exploring the islands and jungles of Belize (I updated this literally swinging in a hammock with a view of the Caribbean)

I always get questions on how I’m able to work remotely, so here’s how! I’m leaving out industry-specific items and focusing on tools that would work for any business.

The Tools

  1. First, and most importantly: a wifi hotspot – This handy-dandy device runs off a standard phone network and provides wireless internet wherever you might be. I’m using the tethering feature on my iPhone these days, which turns it into a hotspot. In the past, my hotspot was a Verizon MiFi Jetpack 4620L with 5gb of data per month.
  2. iPhone and Laptop – everyone has these!
  3. Power source – gotta have this! We have 200w of solar on the Sprinter, which then routes through an inverter (to switch from DC to AC current). Easily enough juice to power laptops, not to mention all the other accouterments of a working road trip like an espresso machine, foot massager, and indoor fountain. Ohhhh, if only life were that good! When we bike tour, I use the Goal Zero Venture 30 power pack, which keeps everything charged up.
  4. Google Apps – I power the back-end to my email, calendar, documents, and chat with Google Apps. It’s very affordable, ties most daily functions in seamlessly together, and I’d be a wandering hobo in the desert without it. (As compared to a hobo in a van with it?) My team and I email all day, update shared Google Docs, and chit-chat via Google Chat yet rarely speak on the phone. And it works great!
  5. Dropbox – this is my favorite file sharing service. I share a folder with every new client, and also have a main directory that I share with my team. It automatically keeps everything synced to both computers and to the web, plus backs it up. It also avoids having to email secure info or big attachments.
  6. Echosign (now Adobe Document Cloud) – many people assume legal documents need to be signed in person. Nope! Almost everything, thanks to President Clinton back in the late 90s, can actually be signed electronically. Echosign delivers clearly labeled electronic documents that are easily signed. I L-O-V-E electronic signatures for avoiding missed signatures, hungry fax machines eating client documents, and other technical difficulties.
  7. Efax – an old standby at this point. Instead of sending/receiving faxes, it’s just delivered to your email inbox. I use MyFax, which works great.
  8. Youmail – this is a great FREE visual voicemail service that allows custom voicemails (a fun, or annoying, way to let your friends and colleagues know you care) and also lets you receive voicemails as emailed MP3s, which is great for someone like me who filters, labels and saves all emails for reference later.
  9. Boomerang for Gmail – a helpful productivity tool that allows you to schedule when you send an emails, or set up reminders related to an individual email. This is now built into Google Inbox, which I started testing in November 2014. (Not endorsing it yet.)
  10. Toggl – time tracking software. I track all my time down to the minute as a way to maximize productivity. Since I started using this a couple years ago, my work hours have decreased by over 30% as I nixed the stuff that was wasting my time and not producing revenue or satisfaction for me. Classic Pareto simplification – someday, I’ll write a post on that.
  11. Skype – the old standby online phone and chat system. Great for hearing impaired clients (the chat feature), and then the voice/video feature for those times when you can’t get a cell phone signal or you or the client are overseas. I can run this on wifi while showing my cell phone number so I’m not calling from an unknown number. Working from Mexico or London much?
  12. Freescreensharing.com – a great tool to run tutorials remotely. I use this to train employees on the tools mentioned above.
  13. The Secret Weapon – I use this to keep track of everything in my life. Here’s the full write-up for how I use it. Can’t recommend it enough. In short, it’s Evernote paired with the Getting Things Done method. It’s the one thing I recommend to people who want to streamline their lives and knock off bucket list goals.
  14. Cozy.co – this free, handy rental management service helps us keep our passive income more passive. A simple, efficient way to screen tenants and arrange payment for rental properties. Check out my blog post about them.

The Mindset

Technology doesn’t solve a damn thing if you don’t apply some mental juice to why you’re doing a task.

Put another way, being efficient gets you nowhere if you didn’t effectively choose the project. For instance, I could have figured out efficient ways to attend final document signings with my clients. Instead I tested not attending them at all, which worked fine. A magic gift to myself of 5-10 hours per week (!) freed up simply by asking the right question. That’s a day per week mountain biking instead of sitting in a conference room.

In the end, it’s about having a choice about how you spend your time. Whether it’s time off or space to focus on bigger, higher value-added efforts for your business, the below items put you in command and allow you to be in control, not just be a harried self-employed person. Ask yourself this: are you running your business or is your business running you?

Here are some of the things I’ve learned that made me more effective.

1) Be willing to let some clients go

It took awhile, and still is painful every time (progressively less though), but you can’t work with everyone. And you don’t want to.

For my work, some clients want to sit down and meet in person. I have all the online tools to make this unnecessary in a purely practical sense, yet completely understand when this is a request. It’s one of those trade-offs. Lose some revenue, gain some inspiration and happiness points working remotely. (GDP ain’t the only measure of one’s success in life.) For me, flexibility trumps gross revenue.

2) Don’t do it all yourself

Hire people, even when you don’t think you can afford it! Trust that your freed-up time will yield benefits. Hiring my first employee was one of the scariest things I’ve ever done, and one of the best. (HOW to hire amazing people is another subject entirely! I’ve been blessed with fantastic people joining my team.)

Don’t want to bring someone on payroll? No worries. I’ve outsourced via UpWork.com and Toptal.com; both are great for temporary workers to save you time or crank out a project you can’t do yourself. (Kevin Kelly, founder of Wired Magazine, says his advice to himself at 20 would be to hire out projects whenever possible.)

3) Challenge yourself to see how little you can be involved with your company

Initially, it was all me. Then I cranked hard on the 80/20 Pareto lever using #1 above.

Over the last year, my goal was Pareto squared: 4% of the hours while still making 64% of the revenue compared to doing all the work myself.

I challenge you to do the same.

At 30 hours a week, it’s hard to find the mind space to really create. At 2 hours a week, time in spades floods in and allows you to create, connect and envision your next challenge or contribution to the world.

And that’s not to say you can’t work more when you want to – it’s all about creating choices for yourself. Even hedge fund managers with billions in their funds use the Pareto principle. It’s all about being more effective with your time.

4) Have confidence that following your inner compass results in everything working out, even if it doesn’t seem that way at the time.

This is probably the most important. Ping mentors and close friends for their opinions, but trust your gut. Change leads to dislocation, which is always uncomfortable. And that’s where the good stuff is.

For me, the simple lens through which to view work is this: does it contribute to living the life I seek? There are periods where busy work and boring projects are required, but focus on a long-term goal, while appreciating what you’re building at the moment, and power forward.

In the end, ask yourself whether you’re building an intentional life that allows you to pursue goals that make your heart sing. If you’re doing that, life is good.

Anybody out there use anything not mentioned that I should know about? Shoot me an email or a telegram, or comment below. I’m always interested in learning new tricks.

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