For years, I’ve called myself a planner, and others call me one too; it’s become a title of sorts, and it’s one I’m moving away from. I nearly always have a notebook in my hands and often say “I need to check my planner first”. When I was the IT Manager at a small midtown law firm, I had to plan both for what would happen if I wasn’t in the office (I wrote our IT Administration Manual) and for larger potential disruptions to work (I was part of a committee that drafted the Firm’s Disaster Response Plan). Add living my entire life in a hurricane zone, growing up on stories of the hurricane of 1938, living through Gloria in ’85, and being part of New York City in 2001, and there was a definite tone to my work. The closest description is that I was like a cat poised to pounce; I was nearly always ready to move and be the first to act when something happened.
So it’s no surprise that over the years, I’ve not only written about planning in general, but I’ve written (and rewritten) many words about creating and maintaining a disaster preparedness plan with an eye to smaller and solo businesses.
It’s important to have a plan and to think through some of the what-ifs, but a plan is only part of it.
When we talk about disaster planning, for example, we think of big alarms, bullhorns, crowds, and toilet paper hoarding; often the results of the events that make the front page. Those are important to think about, but I’ve realized my strength is a different piece of this. Yes, I love what is essentially war gaming to think through the what-ifs; however, I am better equipped to help with another part of the map.
Where’s my sweet spot? I care about what happens on the day after: when we need to pick ourselves up, brush off, and carry on. That’s resilience, and it needs strategies, not just plans; they last longer. Strategies also help us work through the small bumps, and that’s where, I strongly believe, we develop and strengthen our resilience and how we can then climb out of the abyss that threatens to swallow us.
From plans to strategies
This is not a big change in my work, but it is a change in my framing and my word choices. It’s going to take me time to get used to this terminology too. We all know the right word can convey clearly what another word will muddle.
In 2022, I reviewed Juliette Kayyem’s The Devil Never Sleeps, and I wrote then that constantly revising one’s preparations doesn’t mean living in an endless state of anxiety. Kayyem writes about crises on a large scale, but the idea holds for the smaller ones too: a serious diagnosis in the family, a key client walking away, a burst pipe over the office. Her proposal is spot on: rather than chasing a perfect response, we work toward a “less bad” one for the moment we’re in, and that buys us the time to build better responses for what comes next.
A plan responds to what and when; a strategy helps to focus on why and how. Strategic principles help guide you when the plan stops matching reality.
You may have a plan, for example, as to what happens if a hurricane hits your area. This might include updating websites, your voicemail message, and social media. You may also make sure to have toilet paper and food stocked for a while. Perhaps you have a go bag and a plan on where to stay for a few days if necessary. As I write this, there’s a nor’easter strengthening as it crawls up the coast, so this example feels a little less hypothetical than I intended. It’s also the start of Sukkot tonight, and rabbis are scrambling to explain how to (and not to) manage what happens to our perhaps even more temporary than expected sukkahs in this storm.
I really hope you have a basic plan and have at least drilled yourself once on talking through what you would do. In the midst of everything, it is important to have some idea. This is why we have the safety review before every commercial flight, and suffered fire drills throughout school1.
While you can’t plan for everything, I believe what would be more useful is a strategy that thinks through what happens if any one of those pieces falls through. What if it’s weeks instead of days? A strategy will help you weather this sort of surprise.
This can apply both for a day, and for a larger event as I’ve described above.
Small change strategies
I’m not saying don’t plan. I have guides written for my current businesses; the goal is for things to continue on as best they can without me. Over the next few posts, I’ll be exploring small change strategies working from a small discrete chunk of time and expanding wider: beginning by shaping a full, ordinary day around what I know about myself, letting plans shift, and building work so it can carry on without me.
It’s not magic, nor is my process a checklist I can hand off to anyone else. Yours will look different, for all the reasons. My anchors are mine, and you have your own. By sharing how I use mine, I’d like to guide you toward understanding yours and noticing the principles you already use. Those principles are your strategy. Write them down, and you’ll have something to reach for on the day after, when you realize the plan has fallen apart.
If you’re not sure what your strategies are yet, or how to write them down, I’d love to help you figure it out.

- Okay, modern students have drills for events that were not part of my 1980s grade school vocabulary. ↩︎

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