Some Thoughts on Planning


As a Project Management professional and consultant for over two decades, I know firsthand that success is often determined before the first action is taken. I’ve developed project plans for critical systems that include over 1200 distinct activities that need to be managed in order to assure success, and success is not just the ability to complete all the tasks and activities, but to do so within time and budget constraints. George R.R. Martin may be the consummate author of the A Song of Ice and Fire (Game of Thrones) series of novels, however he has difficulty managing time constraints. Is he successful? Incredibly so, however if he managed his writing like a Project, with true deadlines and tombstones, HBO wouldn’t have to worry about getting ahead of his Muse. And he would be even more successful than he is today. Yet Mr. Martin seems happy with his life and means, so he doesn’t require the discipline of a project plan. As an avid fan of the A Song of Ice and Fire series (they are the only fiction works I’ve read in over a decade) my greatest fear for the series is that the next character to be killed off will be George himself – before finishing the epic saga.

Planning 01

The key to any plan is to document all the activities that need to take place in order to complete the project. Some of these activities can be done in parallel (during the same time-frame) while others can only be done after one or more other activities have been completed. For example, when brewing beer you need to heat the malts, hops, sugars, grains and water, allow them to cool, then add the yeast and place the entirety into the fermentation vessel and allow it to perform its magic until fermentation is complete. Only then can you bottle your brew, but you still shouldn’t drink it because it needs to complete the fermentation process in the bottle and age. Waiting for your home-brew to age is actually the most difficult part of brewing your own beer. Few of the cases I brewed ever survived proper aging. The key elements of the brewing process are the ingredients and following the proper steps in order. If you add the yeast prior to heating, or while the ingredients are still hot, you’ll kill the yeast and wind up without beer. If you bottle your mix before fermentation has approached completion, your bottles will explode from the pressure of fermentation. Therefore, understanding the activities and tasks in a plan, and their relationship to the other activities and tasks is crucial to success.

So how does one begin? I usually start with what I call a Brain-Dump. I jot down all the things I plan to accomplish (Deliverables in Project Management jargon), then jot down all the activities and tasks that need to be completed to successfully reach each accomplishment. Then I place these tasks and activities in chronological order. Yes, there are activities that can be worked in parallel, while others need to follow a logical sequence. In the case of The Boot-Strap Expat the high-level plan looks like this:

  1. Define the adventure – What does success look like? Safe arrival in Chile.
  2. Planning (Yes, you have to plan the plan)
    1. Define the deliverables – In this case what needs to be accomplished along the way.

i.      Equipment required

ii.      Budgeting

iii.      Funding and Sponsors

iv.      Route to take, including work-arounds for possible detours, inclement weather, mechanical problems, miles per day, where and when to stop and camp, layovers, etc.

  1. Define the tasks and activities to successfully reach all these goals.

i.      For each of the high-level items in the plan, break them down into their individual elements such as:

  1. Specific equipment  – Vehicle, Video and Photo, Camping, Tools, etc.
  2. Estimate the cost to acquire equipment that needs to be acquired – not what you already have on hand.
  3.  Estimate the travel costs including fuel, food, camp/lodging fees, tolls, etc.
  4. Identify possible Sponsors and funding sources for the adventure.
  5. Create a detailed route for the adventure including planned stops, and layovers along the way
  6. Specify the relationship between all activities – can they be performed in parallel? or are they sequential?

i.      I can’t get to Louisiana until I have passed through the states between the Great Lakes and Louisiana, but I can video the trip while traveling, record draft narration, blog while cooking dinner over an open fire, etc.

  1. Estimate the time required to complete each activity.

i.      This is critical because it will directly impact your costs. My initial plan leads me to believe that it will take me approximately 40 days to reach Santiago, Chile. Each day beyond 40 days increases my costs. According to my preliminary estimates, if it takes 45 days, instead of 40, my costs will increase by over $1000.00 US.

  1. Identify any Resources that are needed to complete each activity – Resources can be materials, equipment, people, skills and currency (It’s hard to think of the US Dollar as money).

Executing the Plan

Having created an initial plan it’s time to take action.

Liquidation and Sponsors

As this adventure will culminate in beginning a New Life in another land, and as currency resources need to be made available I will be liquidating almost all of my material belonging in the States. Being a serial entrepreneur, and wandering soul I have literally started from scratch no less than nine times over the last few decades. Most material possessions aren’t assets at such times, they are anchors that will drag you to your death in the depths if you attempt to hold onto them. If you can’t fit them into a vehicle they are anchors and should be cast off, preferably for cash. If you can’t sell or barter them give them to someone who will appreciate them, thereby blessing you both.

I generally purchase most material items of value at auction. My homes have been furnished primarily with artwork, antiques and vintage furniture acquired at auction. I buy all my vehicles at auction. For the Boot-Strap Expat adventure liquidating assets quickly is more important than holding out for top dollar. So I’ll rent a space at Gibraltar Trade Center in Taylor, Michigan, move all my belongings into the space and attempt to liquidate them all in less than three weekends. I have an original oil painting by Jack Jordan that was worth about $3000.00 when it was painted decades ago, and it would be worth a lot more if Jack had not decided to live forever, so if I can sell it to a gallery for $3000-4000, I’ll be happy.

While these funds will contribute to underwriting the Boot-Strap adventure, sponsorship is key to the overall funding of the project until the documentary film and book are completed after the trip. I’ve identified over two dozen potential sponsors for this project, all of whom I respect and admire and with just a few exceptions I have supported with my own earnings over the years including:

  • The Dollar Vigilante and Galt’s Gulch
  • Lew Rockwell
  • Laissez Faire Today
  • Stansberry and Associates
  • Peter Schiff
  • Ford Motor
  • The Detroit News
  • Investors Business Daily
  • The Wall Street Journal
  • Go Pro
  • Cabela’s

Other Keys to Success

MacGyver Instincts

Having lived in the wilds of the Great Lakes for five months in 2002, and in the Kissatchie National forest for ten months in 2010, I know firsthand that we are capable of abilities we never knew we possessed. When the nearest town is 20 – 40 miles away, and you have limited resources, you will be amazed at the creative problem solving abilities you can muster when needs arise. Some examples:

  • In the absence of ice to keep food and beverages fresh and cool, creating evaporative coolers from clay pots and wet fabric wrapped around bottles.
  • Taking apart, cleaning and repairing your camp stove when it suddenly stops working with nothing more than a couple wrenches and a bit of sandpaper.
  • Carving a pipe from a Hickory branch with a Buck knife, pair of pliers and a screw (to hand drill the channel from the bowl to the mouthpiece) when a key part of your cigarette machine breaks.
  • Finding a safe place for a Wild Turkey to bleed out over night with predators and carnivores all around.
  • Digging a pit to keep your keg of beer cool and refreshing during the summer heat of the bayou.
  • Building an enclosure to keep you and your gear safe from storms, falling limbs and cold with five tarps and plenty of paracord.
  • Making Turkey Jerky since there is no way to consume a Wild Tom in one sitting, and you have no way to refrigerate the leftovers.
  • Using an awl to repair your boots,  tent and take in your pants when your waistline shrinks four inches or more while not dieting or working out.

These are some of the amazing skills hiding within you just waiting to be let out.

DSCF0096 DSCF0097


If you ever live as an integral part of Nature rather than just a tourist you will develop a love of life in all its forms, especially after sacrificing living creatures in order to sustain yourself. In the Kissatchie National Forest it was common for Copperheads and Ground Rattlers to venture into camp after dark. Most idiots would immediately decapitate them, but they are there for your benefit, keeping rodents and other pests out of your food. Whenever they visited, I would take a few photos of their beauty, then gently escort them out of camp with a small plastic rake.

Catfish was on my menu at least three nights a week, but any fish beyond what I could eat that given day was immediately released. As were the giant turtles that sometimes grabbed my bait. The locals thought I missed an incredible feast when they learned about the turtles, but I was just fine with fish, wild turkey and squirrel.


One of the great benefits of camping and living close to nature is the physical fitness that naturally comes with living. During my stay in Kissatchie National Forest I went from a 34 inch waist to a 30 inch waist (Like I had in college!) simply by hiking a few miles with Max and New Moon each day, gathering and chopping wood, and taking care of the forest around me. Take all activities at a comfortable pace and only strain when survival depends on it. You’ll be healthier than you can recall in no time.

Developing your Mind

Camp living always seems to sharpen the mind and senses. Whether it is visualizing how best to set up camp and shelter, overcome an obstacle or gazing up at the night sky while seated next to your campfire, your mind will grow in perception, understanding and your critical thinking skills will be sharpened. I usually need to be in the embrace of Nature for a few weeks before I am able to practice deep, esoteric meditation. In my mundane life I find it virtually impossible to practice deep meditation which is one of the reasons I love living in the wilds. When time is no longer constrained by mundane considerations, it is easy for me to meditate one – two hours each morning after walking the dogs and enjoying my coffee and oatmeal breakfast. (Breakfast – another activity I find impossible in mundane existence.)

Bargaining and Social Skills

Bargaining is more than just the ability to haggle over prices, it begins with understanding and appreciating the value of things, especially when you are living close to the land. A Makita all-In-one power tool may be worth hundreds of dollars, but in the wilds, it isn’t worth anything. I prefer hand-tools for this very reason and always seek out vintage hand tools to improve my prospects away from so-called civilization. After drilling my Hickory pipe stem using a screw and pair of pliers, I made sure to buy the first antique hand drill I came upon in a flea market. That one item was worth four hours of effort and blisters – $500.00 US at my consulting rates.

But bargaining is also a social interaction. You need to determine what an item is worth to you, then suggest a price low enough that agreement will approximate your idea of value. Bargaining should not be an emotionally heated exchange, it is a means to exchange value, whether your are bartering with skills, labor, material goods or currency. Always be polite when bargaining and always be willing to walk away. If the seller wants or needs your business he or she will chase you as you walk away and you will have won the exchange.

Social skills will keep you alive or increase your pleasure. In my experience, the longer you camp in a particular location, the more likely locals will approach you to introduce themselves and find out what kind of crazy person lives in a tent for months at a time! Always offer them whatever you have available whether it be a beer (even if it’s your last), coffee, tea, cornbread or catfish. You will reap incredible rewards. The reason I have Cajun Family in Louisiana is because the locals who used to enjoy visiting Kissatchie National Forest introduced themselves after I had become a fixture for a month or more. Once we got to know and appreciate each other they would often bring me gifts – fresh vegetables from their gardens, a string of panfish they caught, blocks of ice they made in their freezer, a load of firewood, deer steak, sausage or burger, etc. One of my Cajun sisters, concerned for my safety all alone in the wilderness loaned me her .380 semi-auto so that I would be able to defend myself if accosted by Meth-heads or riff-raff that sometimes wandered through the area. I made a leather holster for the weapon and gave it to her in appreciation when I returned it to her.

There is only one type of instance when great social skills are worthless and that is when you are dealing with an Agent of the State. Although I lived in Kissatchie National Forest for ten months and was a US Forest Service volunteer (I cleaned up trash and refuse from the parks, campground, picnic areas, lakes and forest and cleaned the public outhouses), the first day of Duck Hunting Season I was accosted by a Federal Wildlife Thug (enforcement officer). Even though I was a recognized volunteer for the Forest Service and had even been visited by the local director of Kissatchie National Forest who was interested in the number and frequency of visitors to my area of the forest, I was cited with five violations totaling over $500.00 , three of which were for the same thing, just worded differently and ordered to leave the forest within 48 hours. Understand that you have limited Fourth Amendment Rights when camping – Your vehicle and tent require a warrant (if you can successfully assert your Rights), anything else is open to inspection.


If you don’t have Faith at the outset of your adventure, you will surely have it when your adventure draws to a close. Whether you are religious, spiritual, agnostic or atheist, you will develop faith in yourself, your abilities and in Nature to meet all of your needs if not your wants. This is not to imply that life will be easy. Ever eaten out of a trash barrel? I have, and there may come a time when you need to as well. This is a blessing not a curse, you are now more resilient and capable than 70% of the US population.


For more information regarding the Boot-Strap Expat see:

I will be documenting this adventure through regular updates on this Blog, through photos and videos of what I encounter along the way. To support my efforts, donations through PayPal can be made to:

Please be aware that all writing and images on this site are copyright protected. By all means, do share or reblog posts, but always credit them to Alexander Zayachkov and link back to this website. Thank you! © 2013


3 thoughts on “Some Thoughts on Planning

  1. Pingback: Boot-Strap Expat – What a Formal Project Plan Looks Like | Alexander, The Bootstrap Expat

  2. Pingback: The Boot-Strap Expat – Liquidating Assets – It’s just Stuff! | Alexander, The Bootstrap Expat

  3. Pingback: The Boot-Strap Expat – Dickering and Dealing | Alexander, The Bootstrap Expat

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