Where To: Planning Our Personal Next Steps

This is the second of what will likely turn into a series of articles about thinking about our personal and collective futures. As I write this in April 2020, the world is still in the middle of the Covid-19 epidemic. There aren’t yet any clear pathways forward or answers on how this will end. It doesn’t mean that we can’t forge some for ourselves.

A very large barrier to thinking about the future is contemplating how big, scary and uncertain things appear to be. This is true of the future in general. It is particularly true when you are in the middle of a global pandemic where infections and death tolls continue to rise daily, and there is no vaccine or cure on the immediate horizon. And as depressing as that might sound in black and white, that is essentially the order of things today.

It would be easy to take that information and want to turn into a turtle, or find a cozy blanket in a warm corner to hide in until this is all behind us. To those of you going “Yes, please! I’ll take the cozy blanket!” you have my sympathies and empathy. It’s a scare world out there, made scarier by many who don’t quite seem to get how serious things are.

When thinking about the present is discouraging, contemplating our future seems all the more difficult. And yet, it’s possible. It’s practical. And it might just have some value, as well. If nothing else, there is a sense of hope and optimism that can result from seeing a path forward. Even better, clarity about where to go next can help to define the steps we can take now to prepare for them.

Planning our personal futures is both simple and challenging. It is, quite frankly, one of the things that frustrates me about many time management and personal development programs. “Begin with the end in mind,” offers Stephen Covey in 7 Habits for Highly Effective People. Great notion. I totally by into the value of doing it, but what is the end, precisely? Where would we like to get to?

Getting Things Done is a book that I’ve sung the praises of many times. And it is a really great book for framing out the bones of what can become a workable time management system. As I’ve written as recently as January, much of my personal approach derives or relates to many of the principles that David Allen talks about. His definition of projects (bunch of things to do, with one clear “what’s next”) is contrarian but great. The inbox, mindsweep and review activities are all essential constructs. There’s a lot to like about his idea of “natural planning.”

One of the ideas in Getting Things Done that left me cold, however, was the notion of “runway” in thinking about long-term planning. Specifically the idea that there were goals that we had at the 50,000 ft. level, and then 40,000 and so on. This is an essential abstraction on figuring out time horizons; the idea that we should have goals that are three to five years out. From our long term goals, we can progressively scale back to say “what do I do this year?” “What do I do this quarter?” “This month?” “This week?”

All of the above is fine in theory, but it’s abstract. It ignores what for many of us is the most difficult question we know: “What do we want to be when we grow up?” Or at least, “Where do we want to be in five years?” More particularly, it lacks any constructive guidance in asking and answering either of those questions.

There is a fundamental problem with both the questions, and our attempts to answer them. It is a problem that we alluded in last week’s column. When we think about the future, we have an annoying tendency as human being’s to presume that there is a single, concrete answer. When we ask where we want to be several year’s hence, our brains default to wanting to answer the question specifically and precisely. There is a presumption that clarity is possible and necessary.

What happens next is that we trip ourselves up in possibility and opportunity. Our ironic quest for specificity collides headlong with an amorphous blob of possibilities that our future might hold for us. We struggle with figuring out what the best option is, and whether we have even considered all of the options that are possible. In essence, our future-thinking brain has a giant complex that can best be labelled “fear of missing out” even as it wants a single, clear answer as to what the future might hold. We are nothing if not complex.

There is a path forward to thinking about the future, though, and it lies in an exploration of uncertainty. In particular, it centres an idea that I introduced last week: the notion that there are multiple possible futures. A specific illustration of what I mean by this can be framed by thinking differently about the “where do you want to be in five years?” question. What if instead of one answer, you had four? Or five? Or six?

Exploring multiple futures still means we need to narrow down our options. But we don’t need to be quite so drastic or exclusionary when we do so. And in fact, we don’t start with trying to define the answer. What we first need to do is go back and explore the problem. We need to identify what our biggest uncertainties about the future are, and how those might play out in shaping different potential possibilities.

In our current reality, all of us are facing more uncertainties than we can contemplate. When will the crisis end? Will family members contract the virus? Will I? How long will we be practising quarantining and social distancing? Will there be a vaccine? When will it be released? How effective will it be? There’s a lot in flux here, and a lot of variables in play. We have control over very few of them, and acknowledging that truth is a significant source of stress for many of us.

How we think about possible futures, though, is by sifting through the uncertainties we face and identifying the big, meaty ones. The ones that make the most difference. The uncertainties and choices that would nudge the needle in a substantively different direction. We need to pay close attention to our environment. We need to get critical insight on what’s going on around us.

In particular, it’s helpful to get objective feedback or perspective on what we’re doing, where we are and how we are being perceived by those whose perspective we value. And intuitively, we should pay attention to the things that make us most anxious and our gut most knotted; those are probably the critical uncertainties we need to be paying attention to.

For the sake of example and exploration, let’s say we’re dealing with someone currently socially isolating, working from home for a mid-sized organization. Work has been steady, but there’s concern about the long-term viability of the company. Sales are down, costs are up, supply chains are being difficult and cash flow has been precarious. They’re still employed, but they’re concerned.

One key uncertainty here will very likely be, “Will I still have a job when all this is done?” Mostly, that’s a binary question; the answers are yes or now. It gets slightly more variable when you qualify it in a way that is possibly very important to the person it affects: “Will I still have a job that I enjoy and value when all this is done?”

To both questions, there is only so much control; in the second question, though, there is at least acknowledgement of some agency and ownership of the answer. This is not an uncertainty that is strictly done to you (although it may be). It is also one in which you get to ask the question, and also make the final judgement of whether things measure up. You get to decide if job is one you enjoy and value. The choice to continue in that job or not may be the organization; and it also may be made by you.

Let’s throw another uncertainty in there, one that might be closer to home. Let’s say that you’ve had an ambition for a while to shift gears and work for yourself. Your hobby has always been more than that to you, and you’re wondering if that could be something that you transition into, either part or full time. You’ve always worked for an organization and there is a lot you are not sure about in terms of running a business.

What we now have are several different questions, with a lot of potential variables in terms of answers. If we imagine how futures might play out given these uncertainties, there are several ways these might unfold in combination.
– In the most positive future, you emerge from the current Covid-19 crisis with a job intact; it’s one you continue enjoy, while at the same time having come to the realization that your side pursuit (I categorically and morally object to referring to it as a “hustle”) has also successfully gained some traction. Life is full and enjoyable, and you’re engaged and feeling more satisfied than you have in years.
– Another possible future is one where your organization has struggled through the crisis, and has ultimately decided on a round of layoffs, one that also includes you. While that’s disappointing after years of service, you’re still engaged and satisfied with the work that your side pursuit is bringing you, and you decide to make that your primary focus for the coming years.
– A third possible future is one in which you have spent time trying to figure out what a viable business model for your hobby, and have come to the realization that there isn’t one, or at least not one that works for you. Trying to make it a business has robbed it of the enjoyment you had, and you decide you’ll be much happier keeping it as something you do for its own sake. On the other hand, your job continues to be rewarding, the organization you work for is starting to expand again, and you have a job you still enjoy and a hobby you are rekindling your passion for.
– The fourth possibility is on one hand perhaps the most pessimistic. It’s one where you emerge from the Covid-19 lockdown with a fundamentally changed job that has radically different responsibilities, and one where the organization has also required you to take a cut in pay in order to continue working with them. Your side business has equally struggled, and despite investing significant time and energy, it is costing you far more in effort, emotion and money than it is bringing in satisfaction and revenue.

All of the above are possible futures. There will be ones you like more, ones you like yes, and at least one that you would probably like to avoid. That’s not to say that we get to pick the future that we want to pursue. If these are your current range of meaningful uncertainties, though, then it’s an honest representation of the options on the table.

The question is what to do with those options. But that is a very different conversation than the “what do you want to be in five years?” that we started with. We’re now having a significant conversation about where you are starting from, and where you might like to go from here. You are now able to consider answers that might sound like “I’d like to tend more towards here” or “I would like to veer away from here if at all possible.”

What that reveals is something that we do have within our power. While we don’t get to choose our future, that’s not to say that we can’t actively try to nudge towards the direction that we would most desire. We can also think about what we can do to mitigate and manage the consequences of less desirable futures.

If you want to optimally find ourselves post-crisis continuing to be engaged in meaningful and engaging work, then a fundamental question is how to bring that about. What can you do to lobby our organization towards shaping that role? What projects can you volunteer to take on now, working from home, that might help cement that for us? What learning or research could you take on that you haven’t had time for up until now?

A contrary take is what can be done to mitigate the loss of work that you find meaningful, engaging and rewarding. You might start focussing on reconnecting with your network (although ideally we keep that up). You may take time out feelers for new opportunities. You might clean up your resume and—cautiously—update your LinkedIn profile. You might still explore learning opportunities.

A third view becomes what might be required to make your side interest your main focus. You might spend time researching what it takes to run a business. You might connect with others who have successfully done so, and get their insights into how to make that work. You might spend time building up marketing materials or samples to show friends and potential clients. Learning about how to run a business could be an area of exploration. You might also look at finding volunteer opportunities to apply your skills as you build up, to get experience you can use as a reference.

All of the above represent choices about where to invest time or effort. They are all choices that you have within your control to focus on, or invest time and energy in pursuing. All of the choices are designed to move you towards the future you want, or to mitigate and reduce the impact of the future you don’t want. Most importantly, all of the choices are within your control; you decide the choices that you make and the actions that you take.

The future is inevitable. It will happen. We may not wholly get the future that we want, and it may not appear in the configurations and scenarios that we anticipate. But we get to make choices, navigate options and work towards shaping the one that we would like to see. You don’t have to wait to figure out the future you are going to experience. You can actively participate in shaping what it looks like.