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Decision Points: Prepare for Life’s Big Decisions

Andrew Sheves
5 min readJul 8, 2019


Right or left? The red pill or the blue pill? Speak up or stay quiet? Should I stay or should I go?

A decision point is a moment when a significant choice presents itself and the decision made will result in a significant change of course that cannot be undone easily. Moreover, that same choice or option is unlikely to reemerge in the future. The essential elements are that the decision is significant, non-repeatable, and non-reversible.

The problem is that decision points don’t always announce themselves as clearly as the examples above suggest. Sometimes, the decision point looks a lot like other, similar moments except the context or consequences are very different. At other times, the decision point might get overlooked, mixed in with other less critical choices amongst a flood of activity. So it can be easy to overlook or miss the decision point.

However, sometimes the decision point is allowed to pass by because no one wants to deal with the issue. It’s just too big and scary. Like the most significant issues that lie untouched in the corners, no-one wants to touch it.

The problem is that life moves on and the situation develops whether you make a decision or not: your inaction doesn’t mean that everything else is going to pause and wait for you to catch up. As the late Senator John McCain was fond of saying, ‘the enemy also gets a vote’.

Remember, the exact same circumstances are unlike to reemerge. So deferring a decision means forgoing it entirely which leaves you in a reactive position, susceptible to whatever else is taking place. However, you can spot decision points more quickly and be better prepared to exploit these if you spend a little time preparing in advance.


The first thing to do is to map out what the potential decision points might be. Sometimes this is relatively straightforward: anything with a due-by date or cut-off is easy to identify and make a note of. Similarly, things with a resource limitation — such as when your fuel is going to run out or, in the case of a business, when your cash will dry up — should be relatively easy to identify.

However, it can be more tricky when things become condition-based — the point when a business has sufficient traction to warrant significant investment or partnership has run its course can be hard to pinpoint. Nevertheless, you can spell out what success or failure might look like and write this down. You know that a decision point is probably approaching when you spot a similar set of circumstances.

Another thing you can do is play a game of ‘what if?’. S tart with your risk assessment and use the threat statements to identify the conditions that could interfere with your objectives.

Then start to ask ‘what if…?’. For example:

  • What if this situation developed? What signs might there be?
  • What if this were happening? What would it look like to us?
  • What if we had prior warning? What could we do then?
  • What if we had to choose a course of action? How long would we need to make a decision? What data would we need?
  • The exact questions don’t matter as much as going through the exercise to identify the likely decision points for various scenarios.

By the end of the mapping process, you will have developed a sense of what decision points might arise, what the lead up to a decision point might look like and what the associated timeframe might be.

Flags, triggers, and horizon scanning

Now that you have finished mapping and have a sense of what the decision points might be, you can move to the next stage: identifying flags and triggers and building an early warning system.

So flags let you know that something might be about to occur and triggers let you know that the event is happening. One tells you that a decision point is approaching while the other tells you it’s time to make that choice.

Now you have identified your flags and triggers, the final thing you need for an early warning system is some kind of horizon scanning. This is simply looking ahead as far as you can to see if you can spot any flags or triggers.

How far forward you can look is dependent upon a host of factors, but you don’t need to be able to see into the future. All you need to do is look ahead to see what’s coming your way in the next week, month or year, which is often more straightforward than it might seem.

We know when hurricane season is. We know when seasonal demand for a product will peak. We will have an implementation date for a new law or regulation. So while there can be real black swan events that leave us thinking ‘I didn’t see that coming’, many significant events are telegraphed in advance.

Horizon scanning isn’t foolproof, and it’s not always going to be possible to identify all the flags in advance and triggers can be missed. Nevertheless, horizon scanning can be highly effective and buy you valuable time.

The alternative is that you rush on ahead, blowing through the flags and triggers, ending up off the edge of the cliff, before you realize you blew through the decision point. By then, it’s often too late.

Prepare or you won’t notice the decision point until it’s behind you (Image © Warner Brothers)

Active decision making

Unfortunately, all of this only works if you have the appropriate mindset: one of active decision making.

If you approach things in a passive, reactive way, happy to let life’s currents take you where they will, this won’t work (nor will it probably appeal to you).

However, if your mindset is one of conscious, active decision making, then this approach will help you identify and prepare for decision points so that you are in a better position to take advantage of these when they occur.

Originally published at on July 8, 2019.



Andrew Sheves

I’m an analogue operator in a digital environment who thinks simplification = optimization. I build and share risk management tools at