As an entrepreneur, it is inevitable. One of these days, your best laid plans will be derailed by an unwelcome surprise. Whether it’s your hard drive crashing, the IRS knocking on your door or a flood destroying your office, we, as entrepreneurs, will all be faced with our own disaster some day. When that disaster hits, it is easy to recover if you have a solid Hit-The-Fan-Plan (HTFP) standing by.

Good HTFPs require a large dose of creativity and imagination. Without it, every setback and obstacle will seem insurmountable. The biggest key to a solid HTFP is to think long-term. Particularly, you may want to ask yourself these questions:

• What are the potential disasters my business could face down the road?
• How, specifically, would those disasters affect my business operations?
• What can I do to prevent or reduce those disruptions?

Rest assured, no HTFP is written in stone. You will constantly adjust the plan as your business grows and new opportunities and threats present themselves. The key is to just get something started now.

Here are a few areas I recommend evaluating to help you get started:

Business entity – Form one; keep it healthy. Here is a chart to get you started.

Accounting system - Use some sort of accounting software and scan all of your receipts. Small business accounting software these days is inexpensive, reliable and easier than ever to use. As for receipts, indexed electronic copies of all your business receipts WILL save you one day (I promise). Neat Receipts or Shoeboxed provide excellent receipt archival systems.

Intellectual property protection – If you are in the business of creating anything (tangible or intangible), it pays to protect those valuable assets. Jill will help guide you through the sometimes dizzying array of intellectual property protections.

Personal estate plan – Form one, even if it consists only of a simple will and medical power of attorney.

Emergency fund – Create one. If you live paycheck to paycheck, you’re in trouble. The simple act of setting aside a few bucks automatically each month will give you the cushion you will need in the future. ING has a great savings account that is easy to set up and automate.

Income diversification – A key ingredient in any good HTFP is being able to weather fluctuations in income. It almost always helps to integrate related products and services into your offerings to moderate fluctuations in demand. See Pam’s posts in her “Side Hustle and Flow Series”.

Royal guard – Marshall your helpers, defenders, allies, friends and cultivate those relationships. None of us can do it on our own. See Rachael’s post.

Data security and redundancy – Sooner or later, a hard drive will fail, your web host’s server will go down, or someone will hack into your computer. An ounce of prevention now will pay huge dividends when one of these happens to you. Willie has some excellent online security tips here.

Most importantly, cultivate a flexible mindset while developing your plan and talk with other entrepreneurs about the challenges they’ve faced.

With a solid Hit-The-Fan-Plan in place, you will weather those anticipated disasters and emerge relatively unscathed. As for unanticipated disasters, do what every good entrepreneur does: chalk it up to a “lesson learned” then add it to your Hit-The-Fan-Plan.

Trip data

• Days: 21
• Flights: 14
• Miles traveled: 23,013
• Current location: Oranjestad, Aruba
• Next Stop: Castries, St. Lucia

Recap

Following a rough trip to and from Bogota, I finally made it to Boston via Orlando. Arriving in Boston haggard after 14 hours of traveling and detention by Colombian and US Customs officials, I made the decision to kill the 13 hours until my flight to Aruba in the airport. I staked out a quiet and power-accessible spot near the gate and went to work. Around 11pm, I was ousted by a security guard and told to move into the main concourse. Luckily, I had staked out available camping spots on SleepinginAirports.com and decided on setting up shop in a rocking chair in a hallway connecting two concourses. Unable to get any shut-eye in an upright position in the bright, cold and noisy hallway, I resorted to watching movies on my iPad until 2am.

On the hunt for a restroom at 2:30am, I ran across a food court that was not barricaded off like every other eating establishment. Dark, quiet and filled with long benches, I had hit the airport camping jackpot. I laid down with my travel pillow and was unconscious within seconds. That didn’t last long, though, since the morning crew showed up at 4:30, flipped on the million-watt lights and started blasting Def Leppard over the sound system. I tried to sleep through the commotion but was given the boot by a foot court employee along with three other blurry-eyed travelers.

Stumbling through the terminal, I felt as though I had been dragged behind a truck from Columbia and was in dire need of some personal maintenance to freshen up. I ducked into a restroom to brush my teeth, change my clothes and wash my face, all the while feeling like a hobo. “Screw it,” I thought. My goal had been to embrace this whole vagabond entrepreneur thing, and freshening up in an airport bathroom after spending the night in a foot court seemed to be part of the drill. Fresh as a daisy, I darted off to the gate to meet my wife Cynthia, and we jetted off to Aruba together.

The Tip: Connecting to your data while on the move

As we discussed in a prior post, a vagabond digital entrepreneur needs to maintain access to his or her data while on the road. We talked about powering your device, but two other elements are still required: data storage and access to that data. In this post, let’s tackle connecting to cloud-based data.

Before that, though, I feel compelled to throw in a disclaimer: Although I run an IT company, I am not a skilled network technician. I have just found what works for me through trial and lots of error.

How to find a connection

The first step to connecting to the internet and to your data is obviously finding an available network. There are several ways that you can scan for and connect to wireless hotspots while on the move:

1. Use your laptop, cellphone, iPad or other wireless device to scan for available, non-password protected WiFi networks. Networks that are locked with WEP or other pre-shared keys are marked with a padlock and will be unaccessible without the key.
2. Use a WiFi finder device to detect hotspots. There are a number of devices available that you can use to detect WiFi hotspots, obviating the need to turn on your laptop or other wireless device. Most WiFi finders come in a key chain or credit-card shaped form and notify you of WiFi signals using a series of LED lights to show you the signal strength. Some of these devices will also notify you if the detected network is password protected.
3. Use web services like JWire to find available hotspots before traveling. Simply enter your destination into the application, and it will spit out a list of free and paid WiFi hotspots.
4. Find the nearest Starbucks or McDonalds. Most, if not all, Starbucks and McDonalds branches across the US and around the world have free WiFi available for their customers.

Making a connection

When it comes to accessing the Internet when you’re away from home, you never really know what you’re going to get in the way of speed, reliability or security. You would be shocked to learn how easy it is to capture unsecured wireless data or to access someone’s computer on a public WiFi connection. It does not take a lot to protect your data from exploitation, so take the time to plan out how you will stay secure and protect yourself and your valuable confidential data while traveling.

Three easy steps to securing your connection

1. When connecting to public WiFi, don’t automatically accept the first available hotspot. Look for one that comes from a legitimate source.
2. Run firewall software when using a public network. All new computers running Windows or Mac OS X come with some sort of firewall software. Make sure you have yours enabled.
3. Install and use a Virtual Private Network. This is probably the single most important step you can take.

The Virtual Private Network (VPN)

A VPN protects your data by creating an encrypted tunnel between your computer and a wireless internet access point and sending all your data down that tunnel. This prevents others in the vicinity from intercepting your data before it hits the access point and makes data traveling through the network to the internet useless to hackers. Without a VPN, everything you broadcast can be captured by other computers in the vicinity, and you leave your computer open to being accessed directly by users on the same network. With a VPN, all of your transmitted data is encrypted and immune to exploitation.

VPNs come in free and paid services and self-hosted devices. Here are a few you may want to check out, if you are interested in using a VPN.

Free VPN Services:

• Hamachi: Windows only. Hamachi claims to be a zero-configuration VPN and is free for personal use. I found the software to be fairly easy to install and set up, but, since I travel with a Mac, it is useless for me.
• Hotspot Shield: Compatible with Mac or Windows machines. The installed program creates a VPN for your browsing sessions but is ad-supported. It is an excellent free option, if you can stand the ads.
• OpenVPN: An open source VPN solution that is cross-platform compatible. If you are technically oriented and want to set up your own VPN using your home computers, this might be the ticket for you.

Paid VPN Services:

• StrongVPN: Cross-platform compatible (Mac, Windows, Linux) and robust VPN service. This is my VPN of choice, and I’ve tried a bunch of them. I have never had a signal drop off with StrongVPN, although I have experienced problems connecting to the PPTP (standard VPN protocol) in some countries where the ISP blocked the VPN. Luckily, StrongVPN has a remedy in the form of a pre-packaged OpenVPN configuration. I found the instructions for set-up easy to follow, but changing from a PPTP to OpenVPN must be done over an unsecured connection.
• PublicVPN: Another cross-platform compatible service. I used it for one of my international trips and found the service to be pretty good. I never had problems connecting but found the VPN speeds to be a bit lacking compared to StrongVPN.

VPN Devices:

• IronKey: I have an IronKey and think it’s the best thing since sliced bread. It is an encrypted USB flash drive that protects any files stores on it and that comes with its own VPN software and a Firefox browser that runs automatically when you plug it into a Windows PC. This means that you can plug the IronKey into a shared computer, surf with the installed browser and not have to worry about keystroke loggers or other malicious software exploiting your data.
• VPN appliance: These devices are expensive and complicated to set up. My company has a VPN device installed on our network to protect our sensitive data and to provide remote workers access. Setting up a hosted VPN device is far beyond the needs of most independent professionals but may be something to consider as your business grows.

A VPN will not guarantee data protection when traveling and using public WiFi, but it significantly reduces the chances that your valuable data will be exploited. Combined with a modicum of care when selecting wireless networks and running firewall software, you will make your data significantly more difficult to capture or hack, especially when compared to your wireless brethren, many of whom take none of those protective steps.

Trip data

• Days: 16
• Flights: 12
• Miles traveled: 19,290
• Current location: San Juan, PR
• Next Stop: Boston, MA

Recap

I arrived into Bogota at 8:30pm after 22 hours of traveling and was immediately introduced to the mayhem that would be a pervasive theme of my 36 hours in the city. A bus crammed full of humanity transferred the flight’s passengers to a hallway where we and several hundred passengers from other flights stood in line for around 2 hours to clear immigration and customs. A few minutes after exiting the terminal, and by only a pure stroke of luck, I found my driver in the crushing mass of people. He escorted me to his car and treated me to my first harrowing experience on the mean streets of Columbia as he darted in and out of oncoming traffic and raced through along narrow, twisty and pothole-ridden roads. Thirty minutes later, I entered the Chorro de Quevedo bed and breakfast in the old colonial district of Bogota and soon passed out from 25 hours of traveling.

I woke up and headed out for my morning run, looking forward to getting the blood pumping at 8,600 feet. The Candelaria district was established in 1538 by a Spanish conquistador, and the roads are windy, narrow, made of cobblestones and not ideal for running. I truly enjoy a morning run in a new location, because it gives me a chance to explore when most people are still asleep and provides me with a sense of the geography. Zipping up and down the cobbled streets was a heart-pounding experience as I battled the altitude and did my best to avoid being run down by a car or eaten by one of the many dogs that chased me.  I can’t remember a run in which I was pursued by more dogs. None of them (I think) had vicious intentions; I think they were just as curious as the people who stared at me as I jogged by. After returning to the B&B, washing up and wolfing down the wonderful omelet and local coffee prepared by the staff, I prepared to explore the city on foot and later on bicycle.

The Bogota incident

When venturing out in foreign countries, I carry as little as possible to avoid looking too much like a tourist and to minimize my target value. I crammed $60 into my camera case and stuffed it and my passport into the pockets of my cargo pants. I picked my way through the old district, taking pictures of the several-hundred-year-old buildings on my way to the gold museum, El Museo de Oro.

I didn’t make it to the museum, though. After exploring a local craft market, I was approached by a police officer who showed me his badge and asked to see my credentials. He took my passport and told me to follow him for “identification verification”. I felt extremely uncomfortable being escorted off the main thoroughfares but was in no position to argue with an armed cop in Columbia, so I complied and followed him.

In a narrow street, the officer peppered me with questions about who I was with, why I was in Bogota, where I was staying, and why I was town for such a short time. The officer told me to empty my pockets and asked even more questions when they saw I was only carrying two items. He continually brought up the notion that the government was cracking down on drug trafficking and that I fit the profile.  In retrospect, I may have been better served by embellishing the truth and telling him I was with a large group, or was staying longer. But, given that I have a healthy respect for law enforcement, I answered all of his questions truthfully.

After several minutes, the officer said he needed to run my “information” in the computer and took my camera, Timex watch and cash. Not wanting to let the items out of my site, I followed him but was quickly advised to stay put until he returned. As I stood in the street relieved of my stuff in a foreign country, I felt a wave of embarrassment wash over me. I felt violated and quickly made a beeline back to my lodging. I told the woman at the entrance about the incident, and she just shook her head and apologized, saying, “I am sorry to say this is not uncommon.”

The pity party

Back in my room, I threw a pity party for myself. “How could I let this happen? I thought I was a seasoned traveler. Why didn’t I put up more of a fight? Why didn’t I tell them…?” I was embarrassed and felt alone, so I called my wife, Cynthia, who is an absolute master at compassionately re-framing negative situations. In true Cynthia form, she expressed shock and dismay, told me how sorry she was that this happened and then turned our focus to the fact that the only damage done was financial. “Money is replaceable; you are not,” she told me.

After my call with Cynthia and a few conversations with friends via e-mail and Twitter, I concluded the pity party and turned my attention to work projects. I took them on with a vengeance, vowing that this leg of my trip would not be a complete loss. With a flurry of activity over the next few hours, I finished up and billed two client projects, banged out work for a few other on-going projects and was contacted by the manager of my IT business with news that we had closed a large contract that morning.

Take two

Satisfied with the amount of work completed and unwilling to let a corrupt cop ruin my entire Bogota experience, I prepared for another outing into the city. This time, though, I only brought $20 and my passport with me into the wild. With a great deal more vigilance, I picked my way down to the Museo de Oro and was treated to a tour of the largest collection of Spanish gold in the world and a good meal afterward.

The saga continues

The next morning, I rose early to catch a 6:30 ride to the airport. The same driver, contracted by the hotel, masterfully whisked me through Bogota traffic to the airport. I was again confronted with the inefficiency of the Bogota airport, standing in 10 different lines (many of which were redundant), only to almost make it to the gate before Columbian customs officials pulled me aside for questioning. In a separate room, the officers tore through every single item in my bag and subjected me to a litany of questions about my 36 hour trip visit to Bogota. At the time, I was virtually certain that there was a reservation in a Colombian cell with my name on it. Eventually, though, I was given the decimated remains of my careful packing job and sent on my way. Cramming all of my stuff back into my single carry-on as quickly as I could, I made it to the gate with only a few minutes to spare, and let out a giant sigh of relief as the plane left the ground.

Happy to be back on American soil in Orlando, I gleefully stood in line for the 11th time that morning to clear immigration and customs. But, as my luck (and apparently my drug mule profile) would have it, I popped up on the Department of Homeland Security’s radar. Again, I was pulled aside, my luggage was carefully searched by DHS officials and a drug dog, and I was asked a number of questions about my background and my reason for “flying all the way from Seattle for one day in Bogota.” To their credit, the DHS agents were very polite, but I understood the gravity of their questions. I regaled them with the story of how I decided to take my businesses on the road for a month and write about it, and even offered to show them my blog. Eventually, they released me, and I raced to clear security (the 12th line of the day) and board my next flight to San Juan, Puerto Rico.

A lesson in bouncing back

Traveling, like running a business is a roller coaster ride with the highest of highs and the lowest of lows. Despite having a carefully laid-out strategy, our plans WILL go awry at some point. The consequences vary and you could end up hiking through the rain forest, standing somewhere ripped off by a cop or in the custody of any number of government agencies. I suppose that the lesson is that resiliency is a key component to success in traveling, business or life in general.

On this trip I faced a broken-down vehicle in the jungle, wandering the streets of a foreign land after the motel lost my reservation, crooks, language barriers, loneliness and self-doubt.  There have been times where I just stood in place dumbfounded and almost shouted out, “Why is this happening?!?”  But, each of those moments was only temporary, and, in each case, I made an affirmative decision to bounce back and get on with living my life.

We all experience roadblocks, frustrations, and complete meltdowns when following our path.  No amount of planning will prevent the inevitable fact that we WILL fall down and get hurt at some point.  What matters, though, is that we get back up, clean our wounds and get back to living our life’s purpose.

This isn’t the easiest path, but I wouldn’t have it any other way. What about you?

Trip data

• Days: 13
• Flights: 9
• Miles traveled: 13,215
• Current location: Orlando, FL
• Next Stop: Bogota, Columbia

Recap

I made a quick trip to Seattle (Friday night to Sunday night) to touch base and to fulfill my Navy Reserve duty for the month. After a whirlwind of laundry, honey-do chores, military training and packing, I caught a red-eye to New York last night as the first leg of my 21-hour odyssey to Bogota.

Maintaining a Position of Power

One thing that struck me during this trip is how important it is to manage electric power consumption as a vagabond entrepreneur. Power availability is one of those keystone logistical issues that requires some planning, a few pieces of equipment and a bit of vigilance. Unless you’re planning on disappearing into the jungle for a week or some other remote location where there will be no power source, it usually doesn’t take much these days to ensure your critical equipment stays juiced. For most of my travel adventures, the following guidelines work well for me:

• Pick devices with long-lasting batteries and low power consumption. Most decent notebook computers these days come standard with lithium-ion batteries that will give you over 5 hours of power. My iPad will generally last well over 10 hours on a single charge, and my MacBook Pro will plug away for around 5 hours on most tasks.
• Reduce the drain. I keep the bluetooth on all of my devices turned off until it is needed. The same goes for the wireless transceiver when I am not connected to the internet. Turning down screen brightness helps extend the charge, and save the DVD drive for a time when you can plug in.
• Charge early and often. This is a no-brainer; when an outlet is available, max out the charge on EVERYTHING. I carry a mini-power strip for just this purpose and can charge three devices from one outlet.
• Carry a back-up power supply. Regardless of how well you choose your devices, minimize the drains and vigilantly charge, you will still find yourself in situations in which your devices will run out of power. That is why I always carry a back-up power source. My portable power source of choice right now is a Hypermac battery. If I need to power a dying device, the Hypermac acts as a charger via USB or a Magsafe adaptor. Hypermac maintains that the 60w-hr battery will extend my MacBook Pro’s battery to 14 hours, my iPad to 34 hours and my iPhone by 14 times. That gives me several days (MacBook/iPad/iPhone combined) to find a power source and is a segue to my last point.
• Sync data between devices. I am almost obsessed with ensuring I can access my data from a variety of devices and locations. With most of my systems, that means that the data from one device is synchronized with a central location which, in turn, acts as a hub to synchronize the data on my other devices. If one device is about to die from a lack of power, I simply switch to another and forge ahead. Among a variety of other cloud-synched applications, I use Dropbox and Box for data and Google Apps for mail on my MacBook Pro, iPad and iPhone to make sure I can switch to another device and keep working.

The Power Plan

We can spend a good deal of time, money and effort planning our business information systems to support us remotely. But, all of that is useless if we don’t combine it with a good power supply and management plan. So, before you take off on your next adventure, take a moment to consider how you will stay juiced and keep your business clicking along smoothly.

Trip data

• Days: 7
• Flights: 4
• Miles traveled: 5,390

Recap

• Work: Document review/drafting, e-mail and software interface design while bouncing along the Costa Rican countryside in a bus. Someone needs to invent a gyroscopic lap desk for those of using a laptop in these conditions. I don’t know how much money it would make, but I would buy one.
• Work-out: Ran several miles to a hill in the forest, where I ran repeats with push-ups and box jumps at the end of each repeat.

This is my final post from Costa Rica, as my destination today is Orlando. My Costa Rican experience has been quite an adventure, and I was able to take care of a ton of business while exploring the cities, forests and beaches. This is a glimpse into one of my days here:

If you enjoy outdoor adventures and wildlife, Costa Rica is a must-see!

Trip data (as of September 10th)

• Days: 4
• Flights: 4
• Miles traveled: 5,220

Recap

• Work: On the flights. I get so much done when left to my own devices.
• Work-out: Multi-mile mud march in torrential rain.

The first day in Costa Rica reminded me of how unpredictable traveling abroad can be and also of how small, random acts of kindness can make a significant difference in someone’s life.

My introduction to Costa Rica

I rolled out of bed in Connecticut at 3am after three hours of sleep and shoved the final few items into my bag. My cousin Mark, the poor fool who offered to take me to the airport, and I then set out on the hour-long trip to JFK. The flight to Orlando and on to San Jose, Costa Rica was mercifully uneventful. My introduction to Costa Rica, on the other hand, was anything but uneventful.

The mob of people offering me a ride outside the terminal was surprising. Not wanting to become a missing tourist statistic, I looked for the government certified taxi counter. What would have been a $1 bus ride into San Jose was instantly transformed into a $30 taxi trip, but I made it safe and sound to the bus depot. My arrival at the bus station happened to coincide with the weather’s decision to begin dumping sheets of water on top of San Jose. I ran from building to building, dodging buses, people and animals, looking for the ticket counter for the bus going to my intended destination. I finally found it, but a sign on the door stated (after I deciphered it with my horrible Spanish skills) that there was a mechanical problem and it would be late.

Bus-ness as usual

When it did arrive 2 hours later, the bus pulled into the station sputtering black smoke and wheezing like an asthmatic. Un-phased, the other victims passengers ran from under the shelter we had all taken refuge and loaded into the bus. I followed after a brief moment of considering other options, and shortly thereafter the hulking smoke monster lurched out of town and made its way onto the dirt roads of rural Costa Rica.

Not for long, though. A few miles down the twisting, muddy roads, the engine noise simply stopped and all that could be heard was the rain pounding on the roof. The bus driver went out into the downpour, checked under the hood, and returned a few moments later with an announcement. I don’t know what he said, but as soon as he was done, everyone on the bus stood up, grabbed their gear and left.

A savior appears

I must have looked like a lost child just standing there in the rain, because a woman approached me and asked if I had anywhere to go. In broken Spanish, and with the help of my phrasebook, I told her that I had no idea where I was. She motioned with her hand and, in English, said, “then you come with me.” With no other plan, I complied and we hiked along the muddy, pothole-ridden road for close to an hour before reaching a paved highway and turning back towards San Jose. Along the way, I learned that the woman’s name was Elena, that she was a part-time travel guide and that this type of situation is uncommon (but not unheard of) in Costa Rica. We finally came upon a road house of some sort, where, unbeknownst to me, Elena had arranged for a cab to meet us.

On the ride back to town, Elena discussed lodging options for wayward travelers and suggested a specific hotel. I was not going to question the judgment of the woman who had saved my bacon and told her I was willing to go wherever she recommended. She called to the hotel and alerted them of my impending arrival. Standing soaking wet and covered in mud at the hotel, I thanked Elena profusely and tried to give her some money for the trouble and for helping me out. She adamantly refused and instead asked that I simply pay it forward by helping someone in their time of need. With that, Elena hopped back into the cab and was off, leaving me to contemplate how lucky I was to find someone so gracious in my time of extreme need.

The take-away

Sometimes, it doesn’t take much to change someone’s life for the better. Just because an action seems insignificant to you doesn’t mean it doesn’t have far-reaching implications for the person you help. I think we should remember Elena’s advice every day and help change someone’s life by taking a small step with no expectation of reward or compensation.

What about you? How can you pay it forward?

My one-bag mobile set-up

Trip data

• Days: 3
• Flights: 2
• Miles traveled: 2676

Recap

• Work: On the flights (of course), at Starbucks, and acted as a gaffer for a photo shoot at a location outside New York City.
• Work-out: Track intervals, jump-rope, bleachers

The trip started off with a whimper as I was hit with delays in Seattle and Boston making my way to New York City. When I finally hit the ground in New York after 12 hours of travel, I was whisked off to a photo shoot — but just to hold the lights.

Business Tip

If I could only give you one piece of advice for setting up a location-independent business, it would be to rigorously plan your communication systems – internal and external.

Communication is one of those prime movers of business, and a nomadic lifestyle will very quickly highlight the gaps in your communication systems. Clients and customers these days expect consistent and timely updates. Without regular updates, they will most certainly go elsewhere to satisfy their needs. Internal personnel – employees and contractors – require regular direction and feedback, or the train that is your business can quickly derail or stall.

Now, I am certainly not advocating that you should ALWAYS be online or available by e-mail, phone or IM. That would counteract the independence inherent in a location independent business. One of the great joys of this type of business for me is the opportunity to travel, explore, meet new people and learn new things. If you were stuck monitoring e-mail, the phone or IM constantly, you would miss out on a major piece of the “independence” of a location-independent business.

My Communication Tools

I recommend that you set up internal business systems that do not require your constant attention and build communication structures around those systems that will meet the needs of your clients, customers and internal personnel. I will get into the internal business systems more in a later post, but here is a list of communication tools I use to run my businesses:

External – clients & customers

• Voice: I use a VOIP system that is forwarded to my cell phone when I am out of the office but that is also answered by employees when I am not available. I use Skype for voice calling when out of the country or when a client wants to conduct a Skype-to-Skype call.
• Email: I can check e-mail on my laptop, iPhone or iPad, but e-mail with certain criteria are automatically forwarded by filters to specific employees who deal with those issues.
• Communication management: Highrise: I maintain a history of all my client communication in Highrise by forwarding e-mail to my account’s secure dropbox or by typing in synopses of phone conversations. Also, Highrise allows me to set follow-up reminders to maintain the consistent feedback with my clients I believe is required in a professional service business.
• Project management: Basecamp. I am a huge fan of Basecamp for projects involving more than two people. Updates are sent to my e-mail, making constant checking unnecessary.

Internal – employees & contractors

• Voice: Skype is my preferred method of voice internal communication, especially when I am traveling overseas. I will also call my employees and contractors from my cell phone if absolutely necessary.
• Email: Same as external. My employees only send e-mail to me when sending dense content-laden communication.
• Communication management: SocialCast. I don’t know what I would do without SocialCast. It is a Facebook-like application for internal business communications. Employees post updates on what they are working on, issues they have run into, resolutions to those issues, and questions or issues for me to address. The threaded conversations make reviewing a chain of communication about a particular issue fast and easy.
• Project management: Basecamp. We use Basecamp for coordination with contractors, so everyone is on the same page.

These systems work for me. The bottom-line, though, is that I recommend testing different communication methods to find the collection that will keep your business running smoothly while you’re away.

Speaking of which — I am off to Costa Rica!

“We have a strategic plan; it’s called doing things.” - Southwest Airlines CEO Herb Kelleher

“The critical ingredient is getting off your butt and doing something. It’s as simple as that. A lot of people have ideas, but there are few who decide to do something about them now. Not tomorrow. Not next week. But today. The true entrepreneur is a doer, not a dreamer.” – Nolan Bushnell, founder of Atari

“A year from now you will wish you had started today.” – Karen Lamb

“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” — Mark Twain

Planning only takes us so far. Planning also has an insidious way of taking over. In every endeavor there comes a time to just start.

Just starting can be messy, but so can waiting around for the perfect plan to develop. If more people just started using what they know and figuring out the rest, we would all be a lot better off.

So, please, stop trying to be perfect and just start.

By the way, tonight is the start of The Art of Business Road Trip! I will be in Boston and New York City tomorrow and in the jungles of Costa Rica on Friday. I plan on meeting and talking with as many small business owners, entrepreneurs and other vagabonds as I can during my travels and will be posting interviews, pictures and other interesting business and travel tidbits along the way.

Please let me know if you are in the area, because I would love to talk with you about how you just started something.

Illustration by Hugh Macleod

Let others lead small lives, but not you. Let others argue over small things, but not you. Let others cry over small hurts, but not you. Let others leave their future in someone else’s hand, but not you.

- Jim Rohn

Lifestyle Entrepreneurship

I am a lifestyle entrepreneur. I punched out of the military and subsequently left corporate America so I could have the freedom to pursue those interests that were demoted in importance while working for “The Man”. I chose (and still choose) to work on remarkable projects and with remarkable and inspiring people instead of grinding away each day in an effort to amass a fortune that may someday allow me to do what I want. I don’t put off until “retirement” the adventure that life serves up in the present.

When I set out on my own several years ago, my goal was to establish a business that complemented my desires to travel and explore, to participate in endurance sports and to help others pursue their dreams. I needed a business infrastructure that provided the flexibility to live, play and work anywhere and at any time I chose. I spent months researching and testing business systems and business models until I found a combination that met my goals of flexibility and profitability.

The Summer Adventure

I put my business systems to the test by traveling a lot and make it a point to set out on some sort of extended adventure every summer. One of my missions during these summer adventures is to take a mental step back from the day-to-day rigors of life and entrepreneurship, to take stock of and be thankful for the abundance in my life, and to re-focus my priorities for the coming months. I also use these trips as opportunities to push past my perceived limitations and demolish any imaginary ceilings that may be holding me back.

The Road Show Starts on September 7th

This summer will be no different. On Tuesday, September 7th, I will be leaving my home base in Seattle for a month and heading to the East Coast, Central America, the Caribbean and South America. To make it more interesting, I will not be checking any luggage and will be traveling with only a carry-on bag. My office will be my laptop and wherever I am sitting at the time; my running routes will be in the jungles of Costa Rica, the mountains of Columbia, and the beaches of Aruba, among others; and my commute will be via boat, plane, bus and horseback.

So why am I mentioning all of this? I would like for you to join me on this adventure. There will be challenges, business and travel lessons learned and funny stories, and I would like to share and discuss them with you. My goal is to demonstrate that you can travel the world, pursue your interests and earn money at the same time. You don’t need to sit in cubicle for the next 30+ years to earn the right to follow your dreams. Those dreams are there for the taking right now.

In the end, a meaningful life is the only life that is worth living.

A key component of the Art of Business is recognizing and evaluating big ideas as good opportunities. Notice that big idea ≠ good opportunity. There are many factors influencing the big idea-good opportunity diagnosis, including market readiness, growth potential, gross margins and many others. Ideas interact with real-world conditions and entrepreneurial creativity to determine opportunity potential.

A good idea is just a tool in the hands of a creative entrepreneur. Finding a good idea is the first step. Turning that idea into an opportunity is part of your challenge as an entrepreneur. Opportunities do not step up to you and present themselves with a clear price tag and a value. Rather, it is up to you to use your creativity, do the proper research and figure out if an opportunity can be built on the big idea. And, you need to do it quickly.

The paradox

Entrepreneurship requires a significant amount of careful preparation and planning but is, at its core, fundamentally something for which you can’t plan. The highly dynamic character of markets and technology make it virtually impossible to model and envision the future. You can spend a ton of time examining the competition, conducting customer research, and building financial models to produce a comprehensive and carefully prepared business plan that is obsolete by the time it hits the streets.

Should I just wing it?

No way. You need to invest in thorough research and evaluation to shape an idea into an opportunity. All of the hard preparative work in researching the market, figuring out how much it will cost to implement the big idea and adding up the potential payoff will shape the opportunity. Very, very few ideas make it through this process and turn into opportunities without being modified by the process. Research and evaluation is all part of the creative process. Like an artist shaping a lump of clay into a piece of ceramic art, you will constantly shape the big idea and reevaluate your options in light of the information you gather.

The importance of decisive action

Timing and decisive action are just as important as the opportunity analysis process. Decisiveness in recognizing and seizing an opportunity can make the difference in the successful implementation of an opportunity. Because the big idea-good opportunity analysis is not a straightforward calculation, you will never have an iron-clad promise of success. Don’t wait for the perfect time, because there will never be a perfect time to take action. Opportunity is a moving target, so when you have enough information to tip the odds in your favor, take decisive action before the opportunity passes you by.

Predicting the unpredictable

Evaluating and executing on a big idea is not neat, tidy, linear, or consistent, regardless of how much time or effort you put into the process. To be successful as an entrepreneur, you need a bias towards action founded on considerable thought and planning. So, to turn a big idea into a good opportunity, do your homework, prepare to execute and hold on for the ride of your life.

“If everything’s under control, you’re going too slow.” – Mario Andretti