You need an investing roadmap

When investing, aim for the best returns you can achieve, but no more. Once you start to ratchet up the risk, your odds of disaster increase.

piggy bank at end of winding road

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I caught up with a mate for a beer last night.

Oh, the beer was incidental. Promise! 

See, we got together to start planning our mid-year holiday.

For the past couple of years, my family has used the winter school holidays to head bush for a driving holiday.

Last year, COVID-restricted, we did the Darling River Run — visiting the Menindee Lakes, Broken Hill, White Cliffs, Bourke, Brewarrina and Dubbo.

The prior year — when state borders were more curiosity than checkpoint — we went to Birdsville (for the Big Red Bash) via Bourke, Thargomindah and Innamincka, heading home via the Birdsville Track and Adelaide.

We did the Bash trip by ourselves, but last year's holiday was with another family — good friends who also have similar-aged kids to our youngest.

We all had so much fun, we decided to travel together again this year.

Turns out there are two types of people: people like my mate and me who absolutely love the planning and anticipation, almost as much as the trip… and those like my wife, who, well, are just pleased that someone else is happy to take care of all that stuff.

Which is completely fine by me.

I've got maps, lists, more maps and more lists.

So last night, over a couple of beers, we sat down to think about what a trip might look like.

Places to visit.

Places to camp.

The best way to get there (usually, given our druthers, via the roads less travelled).

I'm already counting the days.

Don't get me wrong; I love the idea of just heading in a given direction and seeing where the mood takes us.

But when you've got families with kids to cater for, and limits on how long you can be away, time is precious.

As is balancing the desire to see as much as possible with the need to just stop for a few days every now and then to actually soak up what those destinations have to offer.

Yes, how's the serenity, indeed.

So, while I like the romantic notion of floating on the breeze, we'll plan, instead.

Not too strictly; we'll leave room for the possibility of wanting to stay somewhere a little longer — or shorter — as well as taking the advice of the locals for things to see and do.

But we'll have a rough idea of where we'll need to be, and by when, to make sure we hit the highlights and still make it home on time for work and school.

I seriously cannot wait.

Campfires, outback sunrises and sunsets. Nature at its best — and most raw, including a landscape carved by millions of years of natural forces.

But you're ahead of me already, aren't you?

Yes, planning a holiday is a lot like investing.

You've got the whole 'where do you want to go' thing.

And the map metaphor.

Good. Nice work.

I want to spend just a few lines on the 'planning' thing, though.

Because it's one thing to know where you want to go (financial independence, a comfortable retirement, money for the kids etc), but you really have to know whether it's possible.

I have a lot of destinations on my bucket list. More than I can reasonably get to, even in a decade of holidays.

Wanting to go to Uluru, Broome and Cape York is one thing. But expecting to visit them all in a few weeks is more than just a little optimistic.

Not only is trying guaranteed to be futile, because it's an impossible goal, but you also run the very real risk of vehicle damage and potentially injury or death — not to mention stress and dissatisfaction as you drive 16 hours a day for weeks trying to make it all happen.

A poor analogy? Obviously silly?

No, and yes.

There are a lot of investors throwing Hail Mary passes, in the hope that they might win the share market lotto.

There are many punting on big wins on cryptocurrencies or the latest hot stock.

Day trading.

Expensive 'trading courses' and software.

Even as I write this, I'm reminded again of Aesop's fable of the Tortoise and the Hare. 

I understand the impatience of the investor who can't or doesn't want to think in terms of two or three-decade returns.

I get it.

But there is no reasonable alternative.

As soon as you give in to the impulse that says "I can't do that so I'll…" you're on a very slippery slope.

I desperately wish I could see and do more when we head off in June.

I'd love to add more destinations. Tick more things off the bucket list.

But I know, to my own chagrin, that to try that risks 'seeing' things without really experiencing them, and, worse, ending up with a deeply unsatisfying, stressful and tiring 'holiday'.

Albert Einstein apparently (there are far more quotes attributed to him than he actually uttered) said that things should be made 'as simple as possible, but no simpler'.

The investing parallel (as well as the best advice for the traveller) is to aim for the best returns you can reasonably achieve, but no more.

Because once you start to ratchet up the risk, past a reasonable level, your building gets too tall, your foundations too shallow, and your odds of disaster increase, out of proportion to the potential return.

You never, ever, want to wreck a holiday by being overambitious.

The same goes for investing.

Fool on!

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Motley Fool contributor Scott Phillips has no position in any of the stocks mentioned. The Motley Fool Australia has no position in any of the stocks mentioned. The Motley Fool has a disclosure policy. This article contains general investment advice only (under AFSL 400691). Authorised by Bruce Jackson.

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