Stop planning. Start living. (Or maybe do both.)

I have enough pens to last me until I die.

I'm not proud of this. Actually, that's not true - I'm slightly proud of it. There's something deeply satisfying about a fresh pen. The weight of it, the click, the promise of a perfectly smooth line. I have pens for meetings, pens for notes, pens for the kind of important thinking that absolutely requires a different pen.

It's not just pens. I'll spend time thinking about what I might wear for a run, buy more running tops than I need (regular readers may recall this particular weakness) and then lose interest before I've laced up. I'll think hard about which new shirts to buy, order some trousers to go with them, and never wear them - or wait until I’ve had them for a couple of months at least.

Stephen Covey, in ‘The 7 Habits of Highly Effective People’, talks about "sharpening the saw" - the importance of preparation. I used to have an inspirational quote pinned up that said something like: “Don't spend all your time tuning the instrument; go out and sing your song”. And yet here I am, surrounded by very sharp saws, beautifully tuned instruments, and an awful lot of pens.

Does this sound familiar?

The comfort of ‘nearly ready’

There's something nice about putting an old hoody on. It's comfortable, familiar. You know exactly who you are in that hoody. New clothes are a different story - maybe that ‘best’ version of ourselves is actually a bit of a stranger. Someone we're slightly, unconsciously, intimidated by. A version we might not live up to.

It's easier and safer to always stay in the planning phase. The plan is perfect in your head - it's only when you actually dothe thing that reality gets involved. It’s then that what you’ve planned runs the risk of somehow feeling ‘less’.

Retirement can feel like this. It's comfortable to plan for it, to spend years dreaming about it. But when it arrives and you're asked to start spending the money you've carefully saved - money that suddenly feels like yours in a way your wages never did - it can be surprisingly hard to let go. You've spent decades being someone who saves - now you need to become someone who spends - and those are two quite different people.

Planning isn't infinite

My mum was diagnosed with dementia recently. Sitting with her in the memory clinic, it struck me that the luxury of planning - anticipating, experiencing, remembering - has a shelf life. Not everyone gets thirty years of retirement. This also reminded me of my friend Jenny, who had been planning a big trip for her sixtieth birthday. Six weeks in Australia became two months in a Spanish villa with a beautiful itinerary. Restaurants, day trips, the lot. It never quite happened, but the dreaming was part of the enjoyment, and that mattered. Sadly Jenny died in September. She didn't get another chance.

I don't say any of this to be morbid; I say it because it changes the maths. There are diamonds under your feet, as Rory Sutherland might put it. You don't need Machu Picchu - there's Lincoln Cathedral, a walk along the canal on a Tuesday, a wander through Regent's Park noticing what's actually in front of you.

You can have the best of both worlds though

If you love planning, don't stop. Retirement still needs planning out! Some of the happiest retired people I know are always planning something. A trip. A project. A new thing to learn.

I saw this first hand recently. The Friday after the tax year end, I did something I hadn't done for a while - I just picked up the phone and called a few retired clients. No agenda, no reason, just catching up. Like bumping into them in the street, but on the phone (it’ll never catch on!).

Every one of them was busy. One was on a train to France. Another was recovering from a cancelled trip to Thailand. They were all doing things - and every single one was happy I'd just rung for no particular reason. The planning never stops for these people - it just changes. It becomes something you do alongside living, not instead of it.

What financial planning is really for

You can only truly live in the moment if you've done the groundwork - otherwise it’s incredibly difficult to shake that feeling off of “Should I really be doing this? Perhaps it’s better to just keep waiting for the perfect moment. May be I should plan a bit more instead?”. Good financial planning isn't about building the perfect spreadsheet and filing it in a drawer. It's about giving you the confidence to spend the money and book the trip.

Harry Styles gets his audiences to lock their phones away so they enjoy his gigs and enjoy the moment.

That's what I want for you. Not a plan that sits on a shelf. A plan that gets you out of the door.

You might live off the memories for years to come. Or you might not. If you do, that's a bonus.

But either way - go and sing your song. You can still make different plans once the main one’s been made.