What kind of planner are you?

I naturally slip into reflection and review when I’m planning ahead. I like to look back at what’s happened, then think about what I want more (or less) of in the next chapter.

In my twenties I even had a dedicated hardback “goals notebook”. It starts in 1995 and runs through to 2004, full of lists, categories and careful reviews. When partner and kids came along, the notebook evolved into annual lists of individual, joint and family goals. At the end of each year we’d sit down, go through them and see what we’d “achieved”.

I recently revisited Marshall Goldsmith’s book Triggers. There’s a brilliant section where he suggests writing daily – even hourly – questions for yourself, and scoring them out of 10 to keep your goals on track. Even for a natural planner like me, that level of structure felt like a step too far.

Looking back, I can see that by 2004 I’d filled every page of that notebook and, instead of buying a new one, we just… stopped. If I’m honest, I’d been driving the whole planning operation for the family. It worked well for my motivation; it landed less well for everyone else. In hindsight, it was a bit much to try and plan their lives as well as my own! No wonder it got harder each year to corral everyone into doing their “review and goals” ritual.

The bigger point is this: we all have very different ways of planning and making change. Some of us love the formality of written goals and step‑by‑step plans. For others, that structure feels limiting, even suffocating. All that focus on targets can tip us into constant striving – subtly suggesting that what we have now isn’t enough – and can clash with being present and finding satisfaction in where we are today.

After my season of over‑planning, something interesting happened. Other ways of reflecting and planning started to emerge at home – and they weren’t led by me.

In 2008, after a particularly full year, my husband quietly created an A5 handwritten poster of our “family highlights”. We framed it and put it up in the downstairs loo. That one poster became a tradition. He began jotting key moments on our family calendar through the year and, at the end, he’d design a bespoke word‑art summary – not just the big events, but small things too: an in‑joke, a film we loved, a silly phrase that stuck. Over time, we’ve built up a wall of these yearly reviews. They’ve become both a record and a source of shared stories. (For the record, our rabbit Spot died in 2012 and was immortalised as “an ambassador for his breed”.)

A few years later we added another tradition: a “predictions jar”. Once a year we all sit around the table and write down predictions for each other, or hopes for ourselves, on small slips of paper. They go into a jar, sealed and forgotten until the same time the following year. Opening it is always fun and an opportunity for us to come together and take stock in some way. Some predictions are spot on, some are wildly off, some reveal things people hadn’t said out loud. When I wrote that I’d start my own business, I remember thinking, “Let’s see if future‑me actually does it…”

What I’ve learned from all of this is that planning isn’t one thing. It’s a spectrum.

• There are times when I’m on the cusp of a big change or transition and I need structure: clear goals, written steps, milestones. Getting it down on paper anchors me and keeps me moving.

• There are other times when I’m consolidating, recovering or learning, and what I need is more space: fewer lists, more conversations, more openness to what turns up.

  
  

Some people thrive on detailed plans and dashboards. Others work better with a simple theme for the year, a question to hold, a handful of intentions, or a light‑touch ritual like a highlights list or predictions jar. None of these are “right” or “wrong”; they’re just different ways of paying attention to our lives and choices.

A coaching reflection

If you’re reading this as a leader, coach or manager, it’s worth getting curious about your own planning style – and the styles of the people around you.

• Are you the detailed planner, the broad‑brush visionary, the “see what emerges” type?

• How does your default style support you – and where might it get in your way?

• Where might you be (even with the best intentions) trying to impose your preferred style on others?

  
  

You might ask yourself – or your team:

• “When you’re facing a change or challenge, what kind of planning or reflection actually helps you?”

• “Where do you need more structure right now – and where could you do with a little more space?”

Of course these questions can work equally well in relation to family dynamics too. :)