How to Win the Lottery of Life without Winning the Lottery

Cocktail with twizzle stick

Imagine you win the lottery. You’re lying in the sun on a warm beach. You think about walking down to take a dip in the sea. No, no, on balance, you prefer to cool off in the swimming pool. Then you flop back onto the sunbed and a lovely drink appears in a cocktail glass at your elbow.

Maybe it has one of those little swizzle stick things that you loved when you were small. They make you smile even now that you’re “old”.

Is that what you’d spend your money on if you won the lottery? Is that your dream of what retirement would be like? Is that the life you want?

A journey to a 1000 beaches starts with the first beach – and you need your bucket and spade

The people who get to live their dreams are imaginative, curious and problem solving.

Dreams don't work unless you do


They get up and do things. They plan to make things happen.

They overcome the obstacles in their way.

They WORK at it.

Is that what you’re doing? Or are you just dreaming about winning the lottery?

Turning your dreams into your life

I can hear some of you: no point in dreaming — dreams are all airy fairy and surrounded by fluffy white clouds. They haven’t got anything to do with real life. They’re just like winning the lottery — it ain’t going happen.

But what if it could? What if you could take a small step towards making your life more like your dream life? What if you could take control of those dreams and work out how to make them come true? Would you not end up with the life of your dreams?

Make your dreams out of concrete

If we believe that airy fairy doesn’t get us anywhere, then we have to find the steps to take that will get us moving towards our goals. Let’s take an example.

Lots of people say they want to travel when they get a gap year/retire/have a sabbatical/win the lottery.

But what does it mean when you say, “I want to travel”? How do we turn the airy fairy into the concrete?

The best dreams are in full glorious technicolour with all the details crisp and clear. And underneath them, there are solid concrete foundations.

So instead of the wishy washy, try writing down everything about your dream. Write the screenplay. Imagine it as it will happen, the things you will see and do.

A blockbuster has really detailed practical stage directions. ‘I want to travel’ turns into “I want to go on the coach to Blackpool in June”.

Or, if you’re more ambitious, “I want to go overland on a camel to visit the Gobi Desert next summer”.

Or, if you’ve a strong sense of community: “I want to work as a cook in a refugee hostel this Christmas”.

Now you’ve got something for your brain to get working on. If you plant an idea, your brain will start coming up with ways to make it happen.

Let’s start busting the blocks to our blockbuster

It’s easy to be overwhelmed with all the problems you have to solve to make your dreams come true. That’s where the work comes in. Ask yourself these questions.

Travel lifestyle without age limitation
Waiting for the flight


HOW? How are you going to get there: by car, by bus, by plane — how are you going to get to the airport?

WHERE? You’ve already decided where in broad terms, but you need to focus down on where you’re going to stay. Will you sleep on that beach, in an AirBNB, couchsurfing, a hostel, a swanky hotel?

WHEN EXACTLY AND FOR HOW LONG? Check out what’s available. Check how long you can stay away — if you want to stay there 3 months, you’ll be looking for different solutions than if you’re staying for the weekend.

WHAT DOES IT COST? This is the tough one, which often sinks our dreams. But there are ways to get on top of the costs.

Focusing on what you want to do and how you’re going to do it, means you’re taking the steps to make it happen.

It starts to bust the blocks you have in your head and identifies the concrete blocks that you still have to move out of the way. Let’s look at a few solutions.

Not enough money? Here’s how to find it.

Generally, money is the biggest hurdle to get over when you’re thinking about making your dream a reality.

Think of it this way: what is your dream worth? Is it worth giving up things to make it happen? Is it worth the effort to make your dream life?

If not, then give away your bucket and spade and cross it off your bucket list! Try the next item on the list.

If it is worth it, then you need to get to work. Here are some ideas:

· You start saving hard, doing without all those little comforts that you’ve suddenly realised that you’ve been indulging in (no more eating out, no more satellite TV, no more new shoes).

· You scour the internet for travel bargains.

· You think of alternative ways of getting there — how about trying car sharing like BlaBla Cars — that could cut the cost considerably.

· You go and work in a bar every Saturday night, (or something similar), to top up the travel fund. Or try some other part time job. The gig economy means that there are opportunities for flexible part time working where your age doesn’t count against you (whether you’re young or old).

· How about being quite radical and looking for a job at your destination? How about trying to get a house-sitting job there?

· Could you rent out your place and then use the rent to get somewhere to stay in your dream destination. For 6 months? For a year?

Oh yes, you could buy a lottery ticket too, just to be on the safe side.

Adjusting the dream

Another way of doing it, is to adjust the dream a bit — after all, you’re the screenplay writer in this dream. It includes an island, a beach, sun and a nice drink by your side. Or maybe the desert. Or snow shoeing up a mountain.

If you’re in Europe, maybe Spain is a substitute for tropical. Maybe you could try for the Isle of Wight on a sunny day. (We’ve had some great holidays there with some perfect weather.) If you’re in the Americas, maybe there is a beach not too far away, or a river, or a lake that gives you your dream experience.

Persistence and imagination will help you find a way to do it on the cheap. It might be hard. It might take a long time to achieve: but altering your own attitudes to what you’re doing is the way to make your real life closer to the life of your dreams.

Procrastination is another big block

Guilty as charged! Staying overnight in a mountain refuge is on my bucket list. I’ve looked up ones that are not too far away from where I’ve been staying in the Alps at least 20 times, but I still haven’t got there. I’ve been indecisive. I’ve made excuses.

Other people might say, they haven’t got around to it. Some people say they don’t have time. There’s loads of reasons why you can’t do something.

It’s another way of saying that you’re procrastinating, dithering, and generally being indecisive.


Here’s how you stop procrastination in its tracks.

1 Book an appointment on your calendar as to when you’ll have time to do the work to make your dream concrete.

2 On schedule, sit down and work out the actions so that you can book.

3 BOOK when you’re going.

4 If it doesn’t work, change your dream for one you can achieve.

Make a commitment and you’ll be much more likely to go and do it.

You say it’s too difficult to organise

This one can be an all-encompassing excuse or be covering up valid reasons for not being able to follow your dream.

For example, a friend of mine said they couldn’t go away because somebody has to look after the cat.


1 Take the cat with you.

Cat in a bicycle basket
Take the cat with you. © Max Ogden

2 Book a cat sitter — (I did a stint of cat sitting for a week at the end of October).

3 Offer a week’s stay in your place in return for cat sitting.

4 Ask a local teenager who’d like a bit of money to feed the cat.

5 Put the cat in a cattery for the time you’re away.

Okay, your problem is different. Maybe you’ve got an elderly relative who needs looking after.

Yes, it’s more difficult. But don’t forget that you’ll do your job with your elderly relative all the better if you have a break. It’s worth working on your dream — and no, it isn’t selfish. You’ve a right to the life you choose. When you come back you can choose to devote yourself to your relative and help them to make the most of their life.

It’s never too late for you to win the lottery of life

So, you’ve made it! Here you are on that beach, up that mountain, volunteering in the refugee camp or in that desert. The drink is at your elbow, you’re twirling the little twizzle stick and smiling. Or you’re serving out soup or admiring the view or glugging back water out of your water bottle as you tramp around searching for fossils.

It’s the experience of a lifetime. You’ve got some great stories to tell when you get home.

You didn’t need to win the lottery to follow your dream. And it’s a richer experience for all the work you had to put into it to achieve it.

Now you know how to make your dreams come true, how to have adventures, how to have fun. You know how to make the life you always dreamed of — without winning the lottery.

It’s never too late to win the lottery of life.


Rosemary Bointon
Rosemary Bointon


Having sailed the Atlantic in her own boat, Rosemary’s passion is thinking up new adventures and challenges for older people to do NOW, to help them have loads of fun in longer, more fulfilled and active lives.

This article first appeared on Medium

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