How to Plan When Planning Feels Impossible

By Erin Ewart

If you’re anything like me, these last few months have passed in a weird time warp, seeming to both take forever and fly by at the same time. And it’s no wonder we’re feeling this way: we’re experiencing something called “temporal disintegration”, which means we lose track of time when the future is in question. 

And the future is definitely a great big question mark right now – but we still have to think about what’s next.

It’s such a paradox: how can we plan our lives, careers, or anything else, when things are changing all the time and we have no idea what will happen next month, or even next week?

It’s a question I’m really grappling with right now, both personally and professionally. We have some big decisions to make on the home front in the coming weeks: do we stay in our apartment for another year? How can we sustain this working + childcare routine for months longer if we need to?  

Professionally, it’s thinking about how to adjust our strategy and offerings to respond to the very real needs of our clients, while getting better at prioritizing and saying no to  things (never my strong suit!), and being thoughtful about how our team is best positioned to provide support. 

I know many of you are also navigating major life and career decisions in the midst of this uncertainty. Do I stay where I am or relocate to be closer to family? Do I stick it out in my current organization even though I was planning on looking for something else? Do I hold out for a job I really want in this climate, or take whatever I can get? 

It’s so challenging right now to think beyond today, or this week, but at the same time we have to make plans and we can’t stay in this limbo forever.  

So, how can we balance this need to plan for the future with the very real knowledge that we have no idea what the future holds? 

I’ve been thinking and talking about this a lot recently, and there are a few key themes that keep coming up that I wanted to share. These are all good practices to engage in even during “normal” times, and I think they are even more important right now: 

1. Track your thoughts

It’s so important to stay in touch with yourself and what you’re thinking and feeling right now, and the best way to do this is to regularly reflect and document your thoughts.

Yet now is also NOT the time to saddle yourself with a big new project that feels hard to take on. 

So if this isn’t yet part of your routine, try setting aside 5-10 minutes at the end of the day to answer a few quick prompts: (1) What was energizing for me today and why? (2) What was draining for me today and why? (3) How was today overall on a scale of 1-5, and what bigger picture reflections/implications can I take away? 

This type of rapid, continuous reflection can help you identify trends and themes for your future planning, as well as concrete actions you can take in the short-term to improve your day to day.

Recently one of our clients started this practice and after just a week she had already identified some of her key energizers and drainers and devised some simple, specific experiments she can try in the coming weeks to shift toward what works for her – like blocking out specific work time on her calendar when she knows she has more energy.

2. Plan in smaller chunks

Let’s face it: none of us know what’s going to happen in the coming months, and most of the predictions that are being made now will probably turn out to be wrong. But that doesn’t mean we shouldn’t think about the future on a smaller, more immediate scale.

So try to focus your planning around the next three months, which seems like about as far out as any of us can reasonably imagine right now.

Think about where you’d like to be three months from now, and what decisions you’ll need to make between now and then. Then break down the steps you need to take to move forward, whether that’s doing research or gathering information, talking to others, or getting external support. 

This may not feel like the best time for you to make major life decisions, and if that’s the case, consider if there are ways to create an interim solution or delay the bigger decision. For us, that might look like going month to month on our apartment lease instead of signing for another year. 

Then again, this situation may be helping you get some real clarity about what’s important to you, and in that case it may feel like the time to rip off the band aid and make some big changes.

We’re all experiencing these times in different ways, so as you start doing more journaling and tuning into what this all means for you, you’ll start to get clearer on how much change makes sense for you right now. 

3. Take action & focus on what you can control

Building from the above, when the future is uncertain or you’re feeling stuck or paralyzed – which I think is the case for so many of us right now – it’s critical to regain a feeling of control and agency over your life. 

The best way to do that is to take action and focus on the things that are within your control. You may not know the right action to take (and spoiler alert: there is no “right” one!), but taking some small steps will help you start to feel more in control and will help you build valuable momentum.

If you’re job searching, this might look like taking just 30 minutes to create a target list of organizations or start updating your resume or LinkedIn profile. Remember: one step at a time.  

On this topic, I recently listened to this video series from the authors of Designing Your Life about how to plan during these times – I recommend checking it out! I had two key takeaways, which were things I already knew but were really helpful to be reminded of:

    • Set the bar low and clear it often: create small, bite-sized tasks for yourself that build toward your bigger goals. Accomplishing these smaller tasks gives you momentum and motivation to keep going toward those bigger goals, which feel so overwhelming right now.
    • Designers build their way forward: we learn through taking action, and we have to get out of our heads and try things. If you’re feeling stuck or stumped about what to do next, DO something. Reach out to someone and ask for their advice, try a small experiment in the direction you’re considering, even get some exercise to clear your mind.

To wrap up, remember that this process of planning through uncertainty is kind of like doing a puzzle (I’m doing a lot of those with my daughter these days…). 

At first, when all the pieces are just in a mess on the floor, it feels impossible. 

But you just have to start somewhere and put those first few pieces together. Each piece you add gives you something to build from, and then that momentum grows and grows until those last few pieces feel easy. 

The key is to take it step by step, focusing on finding the one next piece you need to make progress. The rest will become clearer as you go.

If we can help you start putting the pieces of your career puzzle together, please get in touch. We’re here and ready to help!

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