Struggling to Plan for an Untrustworthy Future

How do you develop future-ready ways of working?

When you review the many answers to this question, you'll find guidance for individuals and guidance for collectives.

On the topic of combatting overwhelm, the guidance skews towards individuals. People are encouraged to exercise their Just Say No muscle and perfect their focus using productivity tools.

Organizations, on the other hand, are taught to worship at the church of growth. Never-ending, metastatic, overwhelming growth at all costs. You rarely see companies call for doing less at work. So, in our series on overwhelm, that's where we focused. ICYMI: here's a guide your teams can use to collectively trim their workload together.

Planning for an uncertain future looks different. Organizations have loads of options. They can engage futurists and forecasters, explore scenarios, and develop contingency plans.

By contrast, individuals are told to embrace healthy habits, often with no regard at all for the context. (So, Mr. Performance Guru, you're saying we all should go for a 6 am walking meditation in the sun, put in an hour of quiet focus work, and then lift weights? That’s not going to fly for this working mother in the dark North. Thanks for the fat load of nothing!)

This month, we're changing the narrative by focusing on how individuals can prepare for changes in their professional landscape.

In the future, we can expect.... ??

Last week we kicked off by interviewing April Rinne, futurist and author of FLUX: 8 Superpowers for Thriving in Constant Change. She outlined several mindset shifts that reframe how you might respond to unwanted change.

Given the past few years and current future predictions, it seemed like the right place to start. Right now, 2024 looks like it will shape up to be... well, who knows?

If 2024 were to take animal form, would it be a butterfly – all grubby and nasty at the start, but lovely in the end? Could this be a raccoon-shaped year, causing a bit of trouble here and there but largely ignorable? Or will this be a shape-shifting year that morphs chaotically from kissable corgi puppy to eldritch anglerfish?

For some plans, context matters. What can you trust?

My extended family is happily burbling with future travel plans. This makes me uneasy.

In our interview with April, she shared how she "couldn't NOT write the book" – that her insights on dancing gracefully with change were what the world needed most from her, and that the disruptions that started with the pandemic made that clearer than ever.

Like my family's travel plans, this struck me because I had the opposite experience.

In 2019, I began work on my second book about designing meeting systems. It was 60% drafted when everything changed. 2020 totally threw me. I stopped cold. Who would focus on running better meetings when they weren't sure if their company could open? My book, my planned projects, and our exciting personal travel plans all dissolved.

I hadn't changed – but when the context changed, I lost the clarity I needed to thrive.

The 2020 shift destroyed my vision for myself both professionally and personally, and I've struggled to make any plans involving longer-term commitments since then. I was operating with too many assumptions: a stable economy, access to materials, future business demand, and a belief that the places I wanted to visit could be visited.

These do not seem like safe bets to me now, which makes me hesitant. Do you feel like this, too?

Now, I find myself embracing more stoic detachment and live-in-the-moment thinking than I should. This is great for inner peace, but as my friend Mark Russell once said:

So this month, as we talk to the researchers and thought leaders about how to prepare ourselves for an uncertain future, my interest is more than academic.

I want to know: How can we individually find the motivation to make plans for a future that might never be? How can we better recognize our assumptions and factor those into our primary plans, contingency plans, hopeful experiments, and hedging bets?

April Rinne has answers. So do André Martin and Hal Hershfield, who we'll feature in upcoming podcasts. Each one offers cool ways of thinking through future career decisions.

I realized, though, that I’m not ready to embrace their guidance because I've lost sight of where I am in my career right now. Will the work I was doing before come back? Do I want it to? What happens when the new rules for work aren’t so new anymore? I need to reconnect my career plans with the larger context in a way that restores some of my trust in the future.

As April pointed out, the issue isn’t that things change. It’s that things change in ways that catch us off guard. This means that if we can understand where we are and plan how we’ll respond to unpredictable changes, we can regain a sense of control over our careers.

For now, I'm borrowing questions from organizational techniques like retrospectives, premortems, and assumption mapping.

Using the simple Lotus Blossom visualization technique, I can start to place my career in context. This sets me up to consider new options and how I might respond if and when my assumptions go bust.

Want to try it yourself? Here's what I'm doing. Feel free to riff off this starting spot.