Our hopes, dreams, and plans live in an unpredictable future. We need plans to channel our time, energy, and money, but we have no idea what will happen in the next few years or how well our ideas will work.
In my experience, there are a few things people do poorly when planning for the future:
Over-plan and under-strategise
Wait too long to review
Assume stability.
There’s no opting out of change. The further you extend your thinking into the future, the more uncertainty enters the picture. We can’t read tomorrow’s headlines, but we can position ourselves to achieve our goals no matter what.
For the next three weeks, I’m going to talk about how you can prepare for what you can’t predict. This week, we’re talking about how to avoid the first common problem - overplanning, and under-strategising.
Planning is the end result of deeper, messier, ongoing work rooted in goals, values, and principles. Detailed and directive plans serve the short term, but committing to meaningful goals that matter is what keeps you on track over the long term.
All the meandering talkfests and existential crises about what matters and where things are going – this is the stuff that creates the foundation for long-term commitment, though it will receive little to no space in your document.
When this work gets the time and space it needs, planning is a formality. This is particularly true in shared decision processes, where the biggest barriers are trust, purpose, and focus. When a group feels safe and heard, they can agree on a long-term vision for the future and medium-term priorities.
With the hard work done, the plan often comes together surprisingly quickly.
Plans are snapshots in time. We need them for focused execution and to measure progress against, but they will change often. When we’re clear on our vision, values and priorities – the things that drove the plan – we can change course.
If we move too quickly into detailed planning without this foundation, the plan gets chucked out as soon as something changes.
Advice: Don’t rush into detailed planning. Make time for talkfests and build a shared commitment to the big picture. You will slingshot forward at the planning end.
Use actionable, relative principles in your planning process to keep things fresh, flexible, and strategic.
“We will invest more in technology that boosts access for under-served communities and less in initiatives that don’t address equity.”
“We will prioritise sustainability—even if it means slower short-term returns.”
We will track how quickly we can respond to public emergencies, and if that metric falls below X threshold, we redirect resources.”
This works in your personal life, too.
“I’ll eat dinner with the kids five nights a week, even if it means I miss a meeting.”
“I’ll save as much as I can every week, and if that falls below 10% of my earnings, I will cancel luxuries like subscriptions and takeaways.”
“This year, I will invest more time in my friends, and less in my career.”
These principles aren’t fluff. They are clear about how you allocate resources, measure success, and decide between competing demands.
Stay tuned next week for how often to review your plan, and how to make the conversations useful.