What goes in the suitcase?
Do I need a raincoat, or am I ok with a light jacket and an umbrella?
Do I need sandals, or will I be ok with my sneakers?
How much cold medicine should I bring?
Do I want fewer clothes and do laundry often, or bring a bit more so I can wash less?
I was packing for a 2 week trip to Italy. After spending a couple of nights in Sorrento to visit Pompeii and get over the worst of the jet lag, we’d be headed to Tuscany.
I try to pack light, just a small rolling bag and a backpack, so I needed to be intentional with my packing.
I kept running in circles trying to decide what would go and what I would leave behind. I laid out a few things, swapped things out, tried packing and repacking to make sure I had enough space.
It was hard to know how to prepare, when I didn’t know exactly what we’d be facing on the trip.
Have you ever felt this way?
We often try to prepare for the future, often running ourselves in circles.
What will they ask me during the interview?
Do I have answers for the questions that will come up in the Q&A?
What if my kid doesn’t get into their top choice school? What if they do, but without a scholarship?
Will all my furniture fit into my new house?
Will we hit our timeline without any more surprises?
What will this prospect be concerned about before we can close the sale?
While preparing to a degree is helpful, we rarely can prepare for all eventualities. And even if we could, it’s often not worth the effort.
In the case of my trip, I did a little research about the weather forecast and activities on our agenda, made sure most of what I brought would work in a few situations, and didn’t stress over things I knew I could find there if needed. The trip was a ton of fun, and nothing came our way that we weren’t able to handle.
But how does that translate to how we prepare for other things in our life? Here are a few things you can consider next time you find yourself stressing about how to prepare for your future:
Take stock of what you know
The first step is to consider what you already know about the future, or what you can find out with a little inquiry and research.
Perhaps you’re having your first serious conversation with an important prospective client. What objections have you faced in the past, and what common objections have your colleagues addressed with similar clients? Maybe your kid just started competitive taekwondo. Can you ask other parents or coaches what to expect before their first tournament?
Prepare for a few different scenarios
While we often don’t know for sure what will come our way, we can often anticipate a few different ways things could go. And what we find is that reality is often somewhere in between, where we can draw from things we expected in several possible scenarios.
Maybe you see several possible things that could derail your team’s success in hitting your deadline. Are there a couple of different contingencies you can put in place that could actually help in a few different variant scenarios? Perhaps you’re hosting a barbecue for the holiday weekend. Not knowing everyone’s food tastes, are there a few different dishes you could prepare to cover a wide variety of preferences?
Plan for what you can deal with when it comes
There are some things we don’t need to worry too much about in advance because we know we’ll have resources to handle them once they come. Identifying those things and making a plan to intentionally not plan for them now can help take a few worries off our plate.
Perhaps your in-laws are coming to town. Would it make sense to plan dinner out the first night and then do a grocery run the next day once you figure out how many meals you’ll have together and what dietary restrictions need to be considered? Maybe you’re planning a leadership offsite. Does it make sense to plan for 75% of the agenda, and leave the last 25% to address the topics that come up during the first two days?
Planning for the unknown is a tricky proposition. But when we consider what we do know, prepare for a few different possibilities, and plan to address some things later, we can often tackle that future with confidence.
Where do you find yourself spinning your wheels as you prepare for the future?
Should we talk?
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Let’s talk. Book time, and we’ll figure out how to get you unstuck and get going.
How will you iterate towards the person you’re becoming?
May 22, 2025
About the author:
Christina Von Stroh is a leadership coach who helps her clients become wildly successful by applying iterative software development practices to achieve their dreams. Want to work with Christina to help you iterate towards the person you’re becoming?
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