How to improve your life with a few simple decisions.

In June 2005, Steve Jobs gave his famous Stanford University commencement speech. In it, he said:

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something – your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”

This simple statement isn’t just profound, it’s reassuring.

We can’t know everything in advance. We don’t know how things will turn out. We can plan for possibilities, but as John Lennon said, “Life is what happens when you’re making other plans.”

My life is very different to what it was 15 years ago. I haven’t switched employers, I’m still married with kids, and I serve pretty much the same people. What’s made it different (and better) are a few very deliberate decisions. Plus a few accidental ones…

Some of them almost killed me, some saved me, and others altered the course of my life forever. Some made life worth living even when the evidence suggested otherwise.

What doesn’t kill you might still crush you.

We like to believe what doesn’t kill us makes us stronger. But that’s not always true.

In my 30s and early 40s, I endured a long period of deep frustration, anxiety and unhappiness. And if anything, it made me weaker – not stronger. The causes of some were my own creation, while others were beyond my control – at least for a while.

Expanding our property investment portfolio too fast was a bad decision. I should have been more patient, but money was flowing from the banks and I wanted to ride the curve while I could.

We could have made it through the GFC (and the 50% drop in income) had we not made our last buy. It was the straw that broke the camel’s back, and everything tumbled from there.

I’d toiled so hard to build what we had – working a job by day, then painting walls and tiling floors at night. For the longest time, I survived on 4-5 hrs sleep.

And then it was gone. By the time the divorced settled, I’d lost all three houses and both apartments – all gone.

And then the divorce almost killed me.

Were it not for the support of just two people, I wouldn’t have made it to the other side.

I maintain that ending a toxic relationship was the right move. But leaving my children (if only five miles away), was a wounding experience. It was so painful I wanted to bleed out and die.

I became so fatigued by it that today, I can’t stomach conflict. Even a raised voice sees my eyeing the nearest exit. And it’s the same with investing and debt. I’m super conservative, now, and I sense the disquiet in the pit of my stomach as soon as I deviate from that position.

But none of this would have happened if one of my clients had succeeded in killing me, which he very nearly did.

It was about 3 am when it started – the tightness in the chest, the pain down the left arm, and the sudden shortness of breath. Sitting in the lounge room with my bare feet on the cold tile floor, I thought, “This it – I’ll never see my kids again.”

I dropped him the next day. I told him I couldn’t answer emails at two in the morning, and I wouldn’t tolerate the verbal abuse for failing to march to his dictatorial standards.

I said, “I’m not going to die for you.”

Firing a client, as it turns out, can save your life – I know it did mine. And that applies to friends and family, too.

I haven’t needed to, but I’ve ceased all efforts to stay in touch with people who are no good for me, no matter how long I’ve known them.

The Decisions that Saved Me

I was good at my first job and rose quickly to a responsible position. But were it not for a phone call 33 years ago, I’d be a fat (okay, fatter) upper-management banker today. I’d have a nice salary, a company car, and an expensive suit. And I’d be miserable.

The call came from an art director. I’d submitted an article to my favourite motorcycle magazine, and he was redesigning it.

Joe lived in a luxury home with a big swimming pool, a massive fireplace and a Ferrari in a pink marble garage. It’s funny what you remember.

He called me up and spent an hour trying to convince me that I didn’t belong in banking. He told me I was a photographer and a writer, and that’s what I needed to be doing with my life.

And so after a few weeks of anguish and second-guessing, I agreed with him and entered the world of fast cars, celebrities, race tracks and adventure.

That one decision – encouraged and supported by my parents (I was only 18) – opened the door to a whole different life. It proved that work didn’t need to be boring or structured. Work could be exciting!

In my banking job, I struggled to drag myself to work at 8:30 am. As soon as I joined Syme Media, I was at the office at seven. I couldn’t wait to start ‘work’ every day. My work and my life bled together, and I loved every minute of it.

Until I didn’t.

We humans are a restless lot. No matter how good we have it, we want more; or better. So, unsatisfied with driving other peoples’ fancy cars (by then I was working on two motoring magazines), I decided I wanted to get one of my own. That meant I’d have to leave so I could make more money.

If only I knew then what I know now. I’d have invested my money, run a few side hustles, and stayed in publishing. I could have had my cake and eaten it too.

I went on to sell cars, advertising and software, and I did rather well at most of them. But the whole corporate lifestyle left me numb.

So my next breakthrough decision came when I decided to work from home. It remains one of the single best decisions I’ve ever made.

I realise now that my work environment is a major contributor to my levels of productivity, happiness and contentment. I could never go back to my old life of suiting up, battling traffic and sitting in an office all day. I feel a bit sick even thinking about it.

Leaving the banking industry, and then leaving every other office, changed my life for the better. The thing is, most of us work in ways that don’t align with who we are or how we prefer to work. For most of us, being office-bound is less than ideal.

But having said all this, my real lifesaver was marrying my amazing wife. She is a force for calm and rationality; a beautiful person, and the perfect partner in every way I can imagine. She brought prudence, stability and unconditional love back into my life.

Just as the magazine job proved that work could be fun, Yingying showed me that marriage could be enjoyable. It shouldn’t be hard, and it needn’t be a struggle. It can be a place of mutual respect, support and friendship. And so it’s this decision that most positively changed my life. Before I met her, I was like a man dying of thirst in the desert. She appeared on the horizon like a cool, freshwater lake, and she has sustained me ever since.

The most important decision you’ll ever make is who you partner with. Get it wrong, and you’ll limit your life in all sorts of ways. But get it right, and together, you can do incredible things.

It took me three goes, but I got there in the end.

Decisions that Made my Life Amazing

Having kids is the most profound and meaningful thing you’ll ever do – but only if you want them. Millions shouldn’t.

I don’t care if you cure cancer, perfect fusion technology or make it all the way to the oval office, people will forget you. But through your kids, you are immortal. A part of you lives on; you are linked to the future of the human race.

According to my mum, I’ve wanted to be a dad since I was twelve. In hindsight, it’s easy to see why – I wanted to be just like my parents.

So for me, deciding to have kids was a no-brainer, and my two girls have at various times challenged, delighted, worried and surprised me. But more than anything, they’ve given me something to live for when I struggled to find any other.

It was never my intention to have a third child. I figured that another one wouldn’t make me any happier. And yet the arrival of my son, Tommy just before my 43rd birthday was a game changer.

All of a sudden my life had this new layer of richness, texture and promise. My thoughts drifted to what my little mate and I would do over the next 20 years. We’d go camping, hiking, motorbike riding. We’d make stuff, break stuff, and along the way, forge a friendship that would last until I died. Just like my dad and me.

We’re it not for my wife’s patience and singularity of focus, Tommy wouldn’t exist. Yingying’s like those lava flows you see in Hawaii – inching along too slowly to notice. But then you return a week later to find the lava has crossed the street and your house is gone. She waited and waited until the idea of having another child went from feeling unnecessary to inevitable, and then finally, exciting.

I killed my debts in the same way – through consistent progress and an unflinching desire to reach the end. Consumer debt chokes the life out of you. It makes you a slave; a puppet. It keeps you awake at night, it breeds anxiety, and it destroys relationships.

Buying stuff you don’t need with money you don’t have to impress people you don’t like is stupid. And almost everyone does it.

My divorce left me with no assets and $140k in useless consumer debt. So, killing that debt was a huge priority, and I’ve written about how I did that in various posts, and in this book.

Today, I sleep better. I don’t buy stuff unless I have the money to pay for it, and FOMO is no longer a thing for me. My life is just fine the way it is, without all that debt.

Finding Purpose

A few years ago, I emerged from a midlife crisis. I was burned out, depressed, lost. But as I Googled my way towards the mentors that would ultimately save me, I sensed something important was going to happen.

At that time, I didn’t know what it would be, but today I have joined the dots in reverse.

I’ve studied the human condition for 30 years. I’ve written (and been published) since I was 16. I have two failed marriages behind me and a litany of missteps and crushed dreams. But I’ve also had some spectacular wins and many glimpses at enlightenment. I’ve tasted success and gorged on failure. And my life today is the best it’s ever been.

In not rich in money – at least not by Italian supercar standards. But when I look around, I’m wealthy beyond measure.

A large part of my wealth has its roots in decades of triumph and struggle. It’s my intellect and my ignorance; my strength and vulnerability. And it’s my heartfelt desire to share what I’ve learned in these first 50 years so that others can avoid some of the pitfalls.

Through it all, I’ve learned that life can feel like it did for those graduates during to Jobs’ speech 13 years ago – full of promise, opportunity, and reinvention. It can be an exciting adventure if you choose it.

Over the next five years, you can shape and direct your life any way you see fit, and you should.

• If you have an idea, go and explore it.
• If you want to change your health, start today.
• If your marriage is killing you, get the help you need and do something about it.
• If money is a problem, sell your crap, pay off your debts and start a side hustle.
• If you have no spare time, start saying no to things.

The world won’t end. In fact, your world will re-begin – better than ever.

Because in the final analysis, it’s the decisions you make – the things you say ‘yes‘ to and ‘no‘ to that determine the quality of your time on this planet. It’s not complicated: yes, no, no, no, yes…

Or to quote one of my favourite thinkers, Timothy Ferriss, “What would this look like if it were easy?” 

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