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Decisions That Changed My Life

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 is as reassuring as it is profound.

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

My life today is completely different to what it was 15 years ago. Yet I still work for the same company, I'm still a married man with kids, and I serve pretty much the same people.

What makes my life different – and better – are some of the conscious decisions I made. Plus a few accidental ones.

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

If it Doesn't Kill 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 circumstances 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 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 itself almost killed me.

Were it not for the support of just two people, I wouldn't have made it.

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.

Life Changing Decisions - Divorce | Midlife Tribe

I became so fatigued by all of it that today, I cannot 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, as 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 that was it – I'll never see my kids again.

I ‘fired' 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 actually save your life. And that applies to friends and family, too.

I haven't needed to do that, 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. They soon get the message.

The Decisions that Saved Me


My first full-time job was in banking. I was good at my job and rose quickly to a responsible position. And 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 phone call came from an art director. I'd submitted an article to my favourite magazine (Trail & Track), and he was redesigning it. And this guy was seriously cool.

He lived in a luxury home with big swimming pool, a massive fireplace and a Ferrari in the garage (tiled in pink marble). 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 17) – opened the door to a whole different life. It proved that work didn't need to be boring. Or structured. In fact, 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, 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 was 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 just thinking about it.

Leaving the banking industry, and then leaving all offices for good, certainly changed my life for the better. Most of us work in ways that don't align with who we are or how we prefer to work. I'm no longer one of those people.

But having said all this, my biggest lifesaver was marrying my amazing wife, Yingying. She is a force for calm and rational living; a beautiful person, and the perfect life partner in every way I can imagine. She has 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 can 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 is 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.

I believe 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

Decisions That Changed My Life - My Kids | Midlife Tribe

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

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, and you become part of 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 ten 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 in Hawaii – inching along too slowly to notice any progress. But then you return a week later to find the lava has crossed the street and your house is gone.

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 dis-ease, 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 in Midlife

Decisions That Changed My Life - Finding Purpose | Midlife Tribe

About two and a half years ago, I emerged from my 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 have observed – no, studied – the human condition since I was very young. 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 western standards. But when I look around me, I'm wealthy beyond measure.

A large part of that wealth is rooted in my 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 just like you can avoid most of the pitfalls.

Because if you really want it, midlife can feel just like it did for those graduates during to Jobs' speech 13 years ago – full of promise, opportunity, and reinvention. It can be exciting.

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

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

Because in the final analysis, it'll be 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, yes, no, yes, no…

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



PS. If you want a nice simple guide to mastering your midlife, get my free guide here. I created it just for you.

What makes life different - and better - are the decisions you make, one at a time. Yes, no, yes, no... Click To Tweet

Recommended Books

Tribe of Mentors – by Tim Ferriss
The Art of Non-Conformity – by Chris Guillebeau
Choose Yourself – by James Altucher
Tribes – Seth Godin
Side Hustle – by Chris Guillebeau

Related Articles

Midlife Crisis or Chance to Reinvent Yourself?
Why Working From Home has Made all the Difference
The 5 Things You Need to Work From Home
It’s time you decided what you REALLY want.
How it Feels to Live on Your Own Terms

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