Know Where You Are Going

Going deep. Learning. Having intention. Sounds great but what are we supposed to go deep and have intention about? That is the pivotal question. For what I would speculate is a significant amount of the population (and certainly readers of this blog), the challenge is not having any directions to pursue. The more significant problem is having too many choices and options.

When asked what is important to you, the mind readily goes off in a variety of directions. There are personal hobbies. Family pursuits. Old passions and interests that have waned. New passions and potential interests that are yet unexplored. There is our job, and our career. But there are also job possibilities and career choices never undertaken. Dreams and ambitions that are not yet realized. Perhaps a book that you have always wanted to write.

There are consequences to having too many choices. Often, it results in absolute paralysis on what to actually do. Faced with a plethora of options and opportunities, we do none of them. Alternatively, we stay stuck in the routines that we have always followed, continuing inexorably down the same path we have been on. Stepping off the path, following a different one or pursuing a side quest doesn’t normally happen without a significant prompt—even when we theoretically have a burning desire to try alternatives or realize other goals.

I‘m frequently reminded of this when I’m mired in other work. When committed to client deliverables or getting a presentation prepared, I have often looked up at a shelf to think, “I wish I had time to read that book.” And yet, when time does present itself and a day (or longer) is in front of me, I can have an overwhelming sense of indecision about how to fill the time. Hundreds of unread books, and yet somehow there is nothing to read. Dozens of possible activities, and there is nothing compelling to do.

There is a reason that this occurs, and it is—unsurprisingly—rooted in psychology. Research has shown repeatedly that when faced with an overwhelming number of choices, our capacity to decide is diminished. The more options we have available to us, the less we are likely to avail ourselves of them. Any of them. A research study on investment choices demonstrated that the more retirement options made available, the less likely potential investors were to make an investment, period (no matter how ill-served by that decision in the long term that they actually were).

Of course, dreams and goals are often bigger than just reading a book. The challenges of choice extrapolate and scale up, though. Very often, the things we have identified as potential future projects and plans wind up as undifferentiated options that don’t move forward. Because there is not clarity of choice and no prioritization behind them, they sit as fuzzy future possibilities waiting until the time is right.

One of the significant challenges in viewing our future options is the perspective from which we are looking. If you imagine yourself looking out at the horizon of the future, there will be some point beyond which you don’t feel like contemplating. That might be a year out, or even two. For most, it isn’t much longer than that.

The time horizon that we are most comfortable with is often measured in months or at most a very few years. Everything beyond that is fuzzy and grey, as is every aspiration we have moved out beyond that horizon. Our future choices sit awaiting us, accumulated in fuzzy future buckets of possibility, for the time when we rediscover them. As we slide through time, that horizon slides further away towards infinity, as do the buckets of possibility and their contents.

If that sounds philosophical or metaphysical, it’s neither. It’s a direct product of a few different factors: our inability to contemplate far-away future events and possibilities, our aversion to contemplating our mortality and how much time we have left—which is much of the fodder for midlife crises in general—and a belief that there will always be time to get around to doing everything that we want. We believe we will have more time than we will to do more than things than we have capacity for.

It’s a lovely problem to have, except for one minor and pesky detail. If the buckets containing your future wants, hopes and dreams are continually sliding off beyond the horizon, it means you’re not making them happen. They continue to fall into the category of, “one day, I will…” Until you grab a bucket by the handle and drag it firmly into the present, unpack it and start playing with the contents, nothing is going to change.

It’s easy to let things slide, of course. Busy schedules. Demands on our attention. Lots of urgent items jumping up and down in front of us, wanting us to deal with them. There is also inertia, procrastination and—particularly in the midst of a raging pandemic—a perfectly understandable and human desire to pull the shades, pour a glass or three of wine and chill.

Related to this, I had an interesting conversation about the Eisenhower matrix recently (you know the one; it was popularized by Stephen Covey, and plots the relationship of urgency and importance of the various things we choose to pay attention to). As Covey noted, our tendency is to spend all of our time in the first quadrant, tackling everything that is urgent and important. Our recuperative end-of-day activities tend as a consequence to be firmly in the fourth quadrant, being neither urgent nor important (although frequently pleasant and distracting, if not outright indulgent). What that doesn’t leave much time for is the items in the second quadrant, that are important but not urgent. Like all those fuzzy future buckets of possibility.

What is important to recognize about the dimensions of the matrix is how we determine what constitutes urgent and what defines important. Very typically, important gets evaluated and set by ourselves. Urgent, however, is subject to the interpretation of other people: our boss, our boss’ boss, our partner, our children, our more distant family and our friends. As a consequence, every time we emphasize urgent over importance we are furthering the agendas of others at the expense of our own. We are spending our current days doing what others expect and demand of us, and we are leaving the things we say are important to us to future us to tackle.

Getting clear about where you are going, then, requires focussing on a few fundamental questions. First, there is a need to unpack what you’ve filed away for potential future consideration. What are the goals that you have for yourself that you have yet to realize? What have you told yourself is important to do, and yet you haven’t made time for it? What are the meaningful changes that you would like to attain, and what would they look like if you were to actually make them a reality?

Having defined the range of possible future options, second there is a need to take stock of which choice matters most. What are the one or two things you have filed away for the future that mean the most to you? What would you be disappointed not to achieve? What has greatest meaning for you in helping you to become the future self that you dream about? Certainly, those are easier questions to write than they are to answer. Realistically, you can focus on one or two big priorities at a time (and two might be a stretch, so let’s keep things attainable and focus on one for now).

Taking ownership of the thing you are going to tackle is an enormous action. You are acknowledging the choice for yourself. You are also owning a commitment to move forward on making it happen. You are moving your intention from the status of dream-for-another-day to something you are pledging to making happen now.

Related to this, it’s important to confront why you are making the step now (and what has kept you from moving it forward before). The reasons may be internal, and relate to your confidence, your commitment or how you perceive your skills or capabilities. Questions of being allowed to do it—and shades of imposter syndrome—may be relevant, as well. You may attribute delays to external focusses (up to and including the busy-ness of all the other stuff that you have on your plate).

Whatever the explanation, identify and acknowledge it. As well, define what you are going to do differently going forward in order to not fall quickly back into the same pattern and routine. If you’ve been resisting action for a while, it is going to be comparatively easy to slip back into that pattern of inertia going forward. Define the roadblocks, and build your strategy to overcome those obstacles.

Above all, define what success looks (and specifically what success looks like for you; this is your ambition we are focussing on, after all). What does attainment of a fully realized goal mean? Being clear and specific about this is critical to defining the work that needs to be done to realize it—and keeping you honest about the work going forward. As you move forward, distractions will emerge, opportunities will open up and different ways of proceeding will appear that you weren’t necessarily aware of at the outset. Without clearly defining the result you want, it is impossible to assess whether those opportunities are hindrances or enablers.

As a real world example (and cautionary tale) I offer up the example of my last book. Any writer will tell you that the hardest part of writing a book is getting published. As it happened, I had received an inquiry from a publisher the year prior, inquiring whether I was interested in working with them. A phone call and an email later (yes, it was that easy) I had a publishing agreement.

The only challenge was that the publisher was an academic one. For all the effort of writing a book and getting to the finish line of being published, the pricing—and intended audience—was such that it sold a few hundred copies, mostly to university libraries, for an astonishingly high price-per-copy. If I had been clear about my desire to have a broader impact (and a more affordable end product) I would have approached the exercise in a very different manner. It would have been a very different level of work to realize, but quite possibly a much more rewarding result.

Know what you are trying to accomplish. Pick the one thing that matters most to you. Be clear about what success looks like in realizing your goal. Figure out how you’ve been getting in your own way up until now, and what you need to do to stop hindering yourself. Above all, commit to moving forward and bringing your dreams to life. It’s your ambition, and you are the only one who can make it happen.