Backpacker’s Guide To Planning Anything

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Photo by Jack Anstey on Unsplash

The future is uncertain and the present is endless. Planning gives us a way of coping with that intimidating uncertainty; it’s a way for us to impose our will into the lives we live and to have some measure of preparedness for the uncertainty of the future.

Maybe you prefer to “feel” your way through whatever it is, rather than plan — but often that instinct needs to be honed through conscious structuring until you have the expertise to do away with structure once structure becomes engrained.

Planning is not a way of creating such rigid structure that we do away with the joys of serendipity and exciting spontaneity that colour our lives, but rather to create a frame in which practical concerns need not distract us from enjoying life’s creativity.

The practical world is worried about costs — monetary costs, time, effort, emotional costs of anxiety and confusion. Planning reduces these costs and gives us the freedom to focus on what it is we’re actually trying to accomplish by offering the sense of direction needed for coherence and the sense of progression needed for motivation.

This is a long read so here’s the tl;dr straight up:

1. Brainstorm

2. Mark your roadmap

3. Connect the dots

4. Control your plan

The detail of a plan ought to be inversely proportional to the length of plan.

Shorter trip = a more detailed itinerary vs. Longer trip = a less detailed itinerary

Daily to-do = very specific details vs. Five year plan = a few broad goals

You get the idea. The more external dependencies, the more details you’ll need. Prepare plans at multiple levels.

That’s it. Start with the big picture, a vague sense of where you want to go. Then plot down a few milestone markers, start to fill in the outline, eventually connecting the dots and filling in the details. These planning principles are familiar to you, I’m sure of it. Your high school English teacher probably drilled it into you with basic essay writing. You know this stuff. The challenging part is to actually commit to planning and doing.

The rest of this is largely a specific explanation of how to apply these principles, with an extensive example on planning a trip, plus additional examples on how to apply this to other tasks, such as company quarterly planning, writing, designing, etc.

Planning a Trip

1. Brainstorming (Planning to Plan)

The world is huge! How do you know where you want to go? Maybe you have a Pinterest board of all the places you dream of visiting one day — these could be vague like “Visit Spain”, or more specific like “walk the entire Camino de Santiago by the Original Way”. Maybe you have nothing more than a vague sense of adventure. You could backpack through Europe, Southeast Asia, South America, etc. Maybe you have travel books with dog-earned pages. Or a bucket list somewhere in Notes or a physical notebook with little cut outs from magazines.

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your dreams are a fugly slut

Without any restrictions, where are all the places you’d want to visit? Pull out a map and circle all the places you want to go. Get a feel for where they are. Don’t worry about realistic concerns like budgets or vacation time right now. “Maybe one day” dreams are allowed. Everything is purely potential at this point.

Once you have these vague goals, begin to organize them. Start with organizing by geographical proximity and personal priority: this shows at a very high level what might be realistic in a single trip and where you really want to go. Maybe you don’t have a great sense of where all those pins on your Pinterest board even are in the world and what your dreams really are — that’s okay too. Start doing the basic research to find out that Mount Everest borders Nepal and China so it would make more sense to see Everest on an Asia trip rather than a South America trip.

This is all preamble to actually making a decision on when and what to plan.

2. Mark Your Roadmap

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the beacons are lit (gondor calls for aid)!

By now, you should have a sense of where you could potentially go. The next step is to bridge the gap between potentiality and actuality.

Decide when and where to go and for how long. Pick one of those vague potential trips. Look into when is a good time to visit which places, considering climate, tourist seasons, and historical flight costs. For example, let’s decide to fulfill our dream of backpacking through Europe during summer vacation, giving us 12 weeks.

Maybe you’ll see a great one way flight deal to London and jump on it (seek elsewhere for tips on finding flight deals and the costs/benefits of open jaw flights). This is the first day and place of your trip; this is the first marker on your roadmap. So you have a flight to Europe — there are so many places, where do you go from there?

Pull out a map. There’s a reason the analogy is “roadmap”. Pull out a literal map, be it a paper map or maps.google.com, and the figurative map, some sort of calendar.

Start by marking down non-negotiable commitments and deadlines. Some deadlines are softer than others, but treat them as if they are firm for now.

Are there certain places you have to be at a certain time? If you’d like to see Coldplay in London on June 15th and Radiohead in Switzerland on July 2nd, and then be in Krakow by July 18th before meeting up with a friend in Prague on August 1st — those are firm deadlines. Mark those down in your map & calendar. Those are now actualities.

Where are the places you have your heart set on visiting? Mark those down in the roadmap. These are confirmed actualities not yet tied to a time. You know you’ll schedule those stops somewhere, but not when yet.

Looking at the map, in the spaces between all the current actualities, are there places you’d like to visit, have a whim about — “it’d be nice”? Mark those down in the separate list for possibilities.

With several markers now on your roadmap, they become a frame. What’s left is all the potentiality in the space and time between those markers.

3. Connect the Dots

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My favourite type of activity book activity. Too bad real life doesn’t come with number sequences.

This is where it gets hazy and you’ll have to use heuristics and your best judgment. Some guidelines:

  • Go in one direction on your route; no doubling back. This saves both time and money.
  • Figure out your budget. What’s your overall budget? Divide that by the number of days for a rough daily budget.
  • Be realistic about how much time you have and how much time you need

For all of the actualities and possibilities in your plan, do the research:

Getting there:

  • What are all the routes you can take to get there? What are the most common paths? Planes, trains, buses, cars, horse-drawn carriage, walking. Multiple options and routes within each mode of transportation.

Cost:

  • What’s the average cost for a day there, including lodging, food, attractions?
  • Maybe in one city you can afford a 5 star hotel, while in another city, you’ll have to settle for a bunk in a hostel.

Time:

  • How long does it to take to do the typical tourist attractions?
  • How many more days would it take to really enjoy the city and explore some of its neighbourhoods?
  • Up to how many day can you afford to spend in more expensive cities?
  • Are there any interesting day trips nearby?

Trace the outline of those actualities and possibilities on your map. If you have two weeks to get from London to Zurich, as outlined by your markers, the possibilities are either going south through France, or north through Belgium/Netherlands/Luxembourg/Germany.

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Choose your own adventure

In the limited time of 2 weeks, how many stops along the way can realistically be made? Do enough research such that you can make a rough estimation. You can spend almost all 2 weeks in Paris, or spend several days in Paris, a few days in Amsterdam, two days in Bruges. Do the research into those places and make the tradeoffs.

One of the most common travel planning mistakes is rushing. You’ll want to see as much as you can in the limited amount of time, so you try to pack everything in, but this leaves everyone exhausted and burnt out at the end. While that might be okay for a shorter 2 week trip, you can’t sustain that pace for a 12 week trip.

Rookie mistake: “oh, it’s only a three hour train ride from London to Paris — let’s plan to take a morning train from London and we’ll get to Paris in the afternoon and count that as 1 day in Paris.”

No. You have to take into consideration the time it takes to pack up your things in London, check out, make your way to the train station, arrive at the train station early, then once you arrive in Paris, find directions and make your way to where you’re staying, check in, and unpack. All of that is exhausting and it takes time.

I don’t count travel days as part of the number of days in a city. The time in a city right before departure and right after arrival are a few bonus hours which you can use to catch your breath or squeeze in one last trip to your favourite crepe place.

Yes, that’s a lot of research. That’s how you start to connect the dots. It’s up to you whether to do a depth-first or breadth-first approach on connecting these dots (finalizing each segment between markers before moving onto the next vs. doing research for all segments and then finalizing all segments). Once you have a rough idea, you can begin to tune your parameters.

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Personal planning notes (I didn’t end up doing any of those things in Hamburg). Confirmed bookings go separately into a spreadsheet organized by expense type.

You should start to have an idea of what it is you want to see in each of those places. You know you’ll want to see Big Ben and London Bridge, Platform 9 3/4, etc. You don’t need to have detailed day by day itineraries, but at least have a few spots in each city you know you want to hit up. Check to see if any of them have restricted hours, whether you need to purchase tickets months in advance. Maybe the city offers travel passes that includes those attractions.

You don’t have to have your entire trip planned out, particularly the further out parts, but you should have an idea of how to get to each of your mandatory actualized markers and what you’ll do there.

Once you have this outline, you can start filling out the details. You need to know what you need to plan. For a trip, this is:

  • visas
  • transportation
  • lodging
  • attractions
  • foreign currencies
  • how & what to pack

When you know which days you want to be in which cities and how you’re going to get there and where you’re going to stay — commit to it. Whatever you need to book ahead of time, book it. Whatever can be postponed, such as train tickets that are usually available a few weeks or days before, postpone, but make sure it’s part of the plan.

From here, continue on to planning the details as your departure date looms closer.

4. Control The Plan

You’ve done the due diligence of connecting the dots and outlining your trip. Now it’s time to enjoy all your hard work of planning!

Do some planning as you go, especially on longer trips. I like to plan specific day to day itineraries for a segment on the first day of a new place, in those few hours during travel & settling in time. This is the time for fine-grained tuning:

  • Where are the best local eats?
  • Which attractions make sense to be grouped together in a day?
  • How many paintings can you reasonably be interested in seeing?

If you’re travelling with friends, they may want to do different things. Alice wants to spend an extra few hours in the museum while Bob wants to do some souvenir shopping and gelato eating? Sure. Scope in free time into your itineraries for everyone to explore particular sights.

Be open to spontaneity and the random shit that always happens. Maybe you’ll meet a new friend and decide to do something together the next day that wasn’t on your itinerary at all. Maybe you’ll catch a cold in Amsterdam and need to rest there for an extra day. Maybe you’ll lose your passport and need to pause and deal with that. Maybe you’ll fall in love with Budapest and decide to pass on Warsaw. Be flexible wherever you can — that’s why we postponed whatever could be postponed during outlining. It’s your trip and you control the plan; the plan does not control you.

Multiple Applicability

These planning principles are applicable to most endeavours, but you’ll need to do a bit of thinking to figure out what it really is you need to plan in order to facilitate getting shit done. For travelling, the goals were translated to concrete plans of where to go, transportation, lodging, visas, packing, etc. What you’ll need to translate your goals into will vary by activity.

Let’s look at a few more examples.

Applied to Quarterly Planning

For engineering teams, goals need to be translated to OKRs, projects, tickets.

1. Brainstorm: Your engineering team probably has a similar sort of long term roadmap in mind, not too unlike the Pinterest board of all the places you’re going to visit one day. These can be roadmaps guided by larger company and organization goals as well as team driven goals.

Brainstorm with your team about what the collective dream is. These could be far-off “maybe one day” ideals, or small 2 day projects. Start a shared document on which everyone can collaborate and share their hopes and dreams. Have a brainstorming meeting with sticky notes, T-charts, etc (see elsewhere for how-to-brainstorm advice).

2. Mark your Roadmap: Start understanding the importance and impact of some proposed projects, and group them together by shared goals and underlying themes. For instance, there could be several projects related to reducing code debt; group those together.

You know when your quarter starts — that’s your first marker. As for the rest of them — if your team’s to-do has hundreds of items, where do you start?

Does your team have prior external commitments? Is there something you need to coordinate with another team on? Are there company goals on which you need to deliver by a particular date? Is there a meeting with an investor on a particular day? By when do you need a minimum viable product? All other projects in the quarter will need to be planned around these priorities.

Are there projects unanimously understood as priority projects for the team? If there aren’t clear priorities, start a discussion with your tech leads to nominate projects and ask them to justify its importance. Perhaps they are passionately dedicated to particular projects — ask them to justify its priority. Tradeoffs have to be made. Make a judgment call on their proposed projects, then mark them down in a separate list as possibilities.

3. Connect the Dots:

Ask your tech leads to scope the projects — how long would it take to complete? A rough ballpark estimate. Is it on the scale of days or weeks or months? You should have a rough sense of how long of a commitment any particular project is, as well as its impact level. Priority is determined by necessity, impact, and time.

Plan mandatory projects at the beginning of the quarter followed by other projects with descending priority. Only plan as many projects as will fit within your timeline.

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when you overcommit

You have 10 productive engineering weeks per engineer per quarter. [Additionally] budget 20% of time for generic sustaining engineering work across the board. — Camille Fournier, The Manager’s Path

Just as travel days aren’t real sightseeing days, be realistic with your budget of developer days. Team members will go on PTO, there are events, meetings, coffees, endless interruptions, all of which chisel away at those nicely blocked weeks of time.

4. Control The Plan:

Continue regular planning meetings to address progress throughout the quarter. Finer-grained planning will need to happen within the quarter — outlining projects, assigning tickets, meetings, daily stand-ups, etc. These are the vehicles by which any work is actually tracked & accomplished.

Sudden things may come up; it may be necessary to re-prioritize midway through the quarter. That’s fine. Remember — you as a team control the plan. As you’ll get to know your travel style with time, you’ll also get to know your team’s working styles with time.

Applied to Life & Career Goals

This is the clichéd five year plan. Or ten, twenty, fifty year plan. If it’s in your five-year plan to write a book, what do you have to do now to get to that five year plan? If it’s in your twenty year plan to retire, what do you have to do now to get to that twenty year plan?

If it’s a five year plan you’re working on, mark your roadmap for goalposts along the way. Connect the dots with action items that will get you to each map marker. Control your plan by keeping yourself on track and updating your goals as your aspirations change.

Applied to Essay Writing

Whether it be a blog, an essay, or a book: start with scattered ideas, a theme, and write down non-linear thoughts and points that may or may not even connect to one another — this is brainstorming. Do thorough research. Start marking out a roadmap by grouping ideas together and condensing them into coherent points. Do further research to support your points. Connect the dots by joining those points into a comprehensible piece.

Applied to Creative Pursuits

Designing something? Start with inspiration, mood boards, brainstorming. Then wireframes and low-fidelity mockups, proof of concepts, user studies, and eventually high-fidelity mockups.

Writing music? Start with themes and moods, pick a key signature, lay down a chord progression and a rhythm. Add harmonies. Build it up.

Learning jazz improvisation? Start with a single note and experiment with rhythms. Use only chord notes, then modes, then more complicated patterns. Eventually break all the rules you want.

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now you can pick up anything!

These planning principles are used all around you and you probably already naturally apply this pattern without thinking to activities you regularly do. If you ever find yourself overwhelmed with how to complete a project or by prospects of the future, it’s okay. Take it step by step. Start with brainstorming. Mark your roadmap. Connect the dots. Control your plan.

Now you can plan anything!

Thanks for reading! This is the first piece I’ve published on Medium. I’ve been hesitant to write anything like this — to write opinions in imperatives as “advice”. Like d’uh, everything here seemed obvious enough to me. Yet, a lot of articles and books are written about seemingly obvious things and folks eat that shit up; I eat that shit up. A few thoughts on this:

  1. Common sense ain’t so common.
  2. People love reading about what they already know, to reinforce and validate their knowledge.
  3. It’s never been easier to write and publish based on anecdotal experience, and qualification is hardly a prerequisite.

Whatever it is that has led to the banality of many articles and books of this type, I’m here to capitalize on it. Venmo me $10 @theresama to pre-order my book coming Fall 2039.

This is a self-conscious note simultaneously sincere & satirical. Am I disrespecting you, the reader, if I find it a little absurd to think that any of what I’ve written is useful or important? Am I disrespecting myself, the author, if I don’t believe that it is? To have put all this time & effort into it, I must believe on some level that this was worth writing, but I still feel like a phony on some other level for writing something so practical. If you’ve found this useful and have learned something about planning, this article was sincere and please pre-order my book. If you’ve found this to be banal, this article was satirical and please pre-order my book.

¯\_(ツ)_/¯

turning coffee into code @yelp by day / thinking about philosophy, religion, cognitive science, arts, intimacy, meaning at night. millennial techie scum.

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