Most interesting directions

We move from our most interesting directions. These are the ones that, compared to others, interest us the most. We create these in stacked timeframes, like 2 decades, 2 years, 2 quarters.

We move from iterations of questions, causing the shape of our chosen directions to shift and change, combine and give way to unpredictable directions.

It's all about questions

When we're thinking about the future with a sense of agency, we move forward in any direction with questions. A sense of agency is clarity that we can shape the future we want to see. The opposite is a sense of anxiety, feeling like we're at the mercy of forces and conditions beyond our choice.

The quality and velocity of our progress in any direction is equal to the quality and velocity of our questions.

The idea of working from questions is new to many. It makes more sense when we realize that much of what good we have done in our life to date were energized and organized by implicit and explicit questions. These are the questions of what would it look like if, how could we and what if.

Mindful roadmapping

Mindfulness is noticing differences in time, from this moment to the next, from this day and week to the next. It allows us to see possibilities and opportunities we miss when we're mindless. Mindlessness is noticing sameness in time. It misses new possibilities and opportunities. Roadmapping is most efficient and effective when we practice mindfulness.

Where do we get the time?

When it comes to exploring a future different from the past, a natural question is where do we get the time for it?

Reality is, each of us has time flexibility. This comes in the categories of:

  • Found time, even small moments

  • Things we do that have very low value yields

  • Spending less time trying to make things perfect

People who create a future different from the past do not typically have more or less time than people who leave the future up to habits and circumstances.

The future, simplified

Creating the future we want to see should not be complicated. It should not make us feel anxious, worried or overwhelmed. It should be simple.

There are four simple rules to roadmapping:

  • Choose one or more directions to work from

  • Name any questions relative to each direction

  • Explore your directions through your questions

  • Adjust your directions and questions as you explore them

That's it.

Transforming obstacles

When we turn them into questions, we transform path obstacles into assets. As questions, the can lead to any manner of learning, experimenting and progress. If we treat them as inactioneable constraints, we lose the opportunity for them to be teachers rather than tormented.

Why questions work over statements

Questions have more power to energize, align and organize us than statements because they don't require the assumptions that statements of will do.

They don't evoke doubt and concern the way statements do. They open our minds to exploring, learning, creating, experimenting. Best of all, they help us thrive in uncertainty because no matter what direction we move from, life will always give us more unknowns than knowns.

Single focus

There is nothing wrong with a singular focus in any aspect of our life and world. One can be quite fulfilled moving in one exclusive, dedicated direction.

Alternatively, moving in multiple, even quite varied, directions can also work. Especially when our directions or direction is larger than us.

The reality of achievement

Reality is, every time we achieve anything at any scale and significance, we do so with a future that is largely unpredictable. We have as many unknowns when we attempt nothing and when we attempt even the impossible. We don't have more capabilities or possibilities in a more certain future. We make good things happen either way.

Side hussle passions

We don't have to quit our life to pursue the direction of a passion. We can give it a few hours a week or an hour a day. We can always be working on what interests us at margins of our daily and weekly routines. We can carve out an amount of time on a regular basis to manifest in any direction of choice.

The 3 R's of RoadMapping

RoadMapping is about being continuously realistic, responsive and resonant.

In contrast to assumptions that make us unrealistic, questions keep us realistic. Assumptions aren't intrinsically bad, except when we act from them. They are ideal sources of new and useful questions. The temptation to act on assumptions is stronger when we have a lot of experience, expertise or a deep need to be right.

In contrast to following a plan regardless of what we're discovering, we keep our actions responsive to the constant of change. We can shift our approach in any given direction. We can discover new directions that would be even more useful than the ones we have been engaged in.

In contrast to directions that evoke a sense of doubt or irrelevance to our values, we resonate with our directions of choice in RoadMapping because we are part of shaping them and they engage our strengths. We naturally support what we help create. We are naturally committed to what we resonate with.

Who has good questions?

It's unpredictable. What does factor in is how welcome and comfortable people feel voicing whatever questions they might have. Good questions can come from the most or least knowledgeable relative to the focus. It's a more level playing field than that involved in who can come up with the “best ideas.”

Three types of directions

There are three relationships between and among directions. They can be confluent, complementary and contrasting. In confluent directions, some feed into others. In complimentary, they are stronger together. In contrasting, they differ in approach or operating values. All three can have value as lenses revealing better, new questions.

Getting realistic about constraints

An interesting logic flaw is working from assumptions about the intractable nature of constraints. One is that they cannot change. The other is that removing them is a requirement for moving forward in directions of choice.

One way to frame the challenge to these is reflecting back on any of our achievements and survival and identifying what constraints were still at play when we accomplished what we did. We can also reflect on how we diminished or depleted constraints.

The improvement trap

There was a point where the design of candles was optimized. Solving for many of the problems plaguing candles, light bulbs were not better candles. Light bulbs were not answers to old questions about wax or oil.

They were answers to new questions. What could be a completely different approach? How could we get to better outcomes using none of the required materials or designs? It's always the new questions that lead to new options.

The delusion of stasis

One of the most unrealistic assumptions people make in planning is that the right goals and plans can finally achieve a desired state of stasis. In a world of constant uncertainty, no such state is possible, in fact the more we try to achieve it, the more reactive chaos we create. We typically have as many problems in the future as we did in the past. The choice is not how many we have but whether we have the ones we get or the ones we create.

RoadMapping fail

One of the classic ways to make RoadMapping fail is to return to the planning mistake of working from assumptions. This is the failure of not turning even the most logical and reasonable assumptions into questions.

These are assumptions about the realities related to our directions, the scope of our resources and capabilities, how long things actually take, what people want, need, expect and prefer.

Why goals don't work

One reason why the vast majority of goals on any level go unfulfilled is that they typically provoke more doubts and resistance than enthusiasm. Directions do the opposite. They intrinsically express interest, desire and commitment.

RoadMapping as exploration

Exploration is an interesting metaphorical alternative to what we usually think about as planning. Rather than provoking the doubt and resistance of planning, it provokes curiosity and engagement.

Exploration is engaging because it involves going somewhere, as in exploring new places. It involves creating new things, as in exploring new kinds of cooking or art. It involves new ways of connecting, as in exploring new people and conversations.

At its core, RoadMapping is sheer exploration, fueled by continuous curiosity and engagement in our directions and questions.