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Lone wolf. Self-made. Free agent.

These phrases have always excited me. From a very young age, I wanted to blaze my own trail – machete in one hand and compass in the other. At the age of eight, I set about becoming an entrepreneur by making things in my dad’s shed and selling them to our neighbours. At the local golf course, I liberated balls from the rough along the 7th fairway and sold them to the pro shop, and I cleaned toilets at the local fitness club for three bucks an hour. I was tireless.

At school, I hammered my teachers with questions and excelled in every class. I was hungry to learn and to build my base for the future. I fully expected to be rich and free before I hit 30.

Unsurprisingly, though, life got in the way. Girlfriends, jobs, wives and kids. Bills, debts and consumption addiction. Each conspired to keep me imprisoned and working long hours. I flirted with business and I tried to invest. In my thirties, I even came close to having it all – five properties, two Benzes and a wardrobe full of fancy clothes.

Then, of course, I lost everything.

Through it all, I learned that rushing can be fatal. I learned that the slow path is actually the shortcut. Had I tempered my sense of urgency; had I not bet the farm at every turn, and had I only done what I could afford (instead of up to the limit of my borrowing capacity); had I left a buffer for the inevitable downturn, I’d have been fine. In fact, I’d be very wealthy now.

Most surprisingly, though, my most valuable lesson was that being a free agent wasn’t nearly as expensive as I’d thought. I didn’t need to be rich. I just had to make some adjustments in three areas:

  1. How I worked
  2. How I spent money
  3. How I invested money

Notice I didn’t include ‘how much money I have.’ That’s because it’s irrelevant. I’ll explain why.

If you’re moderately ambitious, you’ll already know that sitting on your arse and doing nothing for the rest of your life isn’t an option. Likewise, you’ll probably accept that indulging your whims and consuming without limits is a bit like chocolate or fine whisky – wonderful on occasion, but not something you want to do every day. More than likely, you’ll want to keep working in some capacity, either directly for an employer, or through a gig of your own.

So the question of how much money you have is largely irrelevant because you’ll always create it from somewhere, doing something.

How I Work

I like working. I enjoy being useful and I get a lot of satisfaction from solving problems and creating new ideas. That’s why I work for more than one company and I do more than one thing.

Years ago, I was a salaried employee like most people, but I knew this wasn’t ideal for me or my employer. So we agreed to a new arrangement. I would come off their payroll and work from home. In exchange for freedom and autonomy, I’d commit to a minimum number of hours a month and a fixed income, whether I exceeded those hours or not.

In essence, I made a conscious choice to join the gig economy before it was thrust upon me and in return, my employer freed up a cubicle, some insurance and red tape.

Sometimes I start work at 6:00 am, and other times at 2:00 pm – it’s largely up to me. When it’s required, I’ll work till midnight or on a weekend. And I’m fine with that. After all, I don’t have to commute, there’s no need to shave, and I can fart whenever I want.

Another huge benefit is that I’m free to pursue other interests. I can hone my skills (or explore new ones) with a few additional clients. I can write a book or learn the piano, and I can piss off for a few days in the country without seeking permission. Basically, I have enough freedom to feel free, but still some structure so I can feel relevant and useful, too.

So how I work, as opposed to how much I work, has had a big impact on how free I feel.

How I Spend Money

I’ve already chronicled my spending habits of the past over at midlifetribe.com, but suffice to say, I don’t waste money on stupid things anymore. Also, I don’t watch TV and I don’t read the junk mail that appears in our letterbox, so the common triggers for temptation are low.

Even when I want something, I think about it for weeks or months before I act. Often that’s long enough to realise the object of my desire won’t give me what I want and I drop it. For me to spend money these days, I have to be convinced it’ll remove a negative from my life or deliver sufficient value that, two years from now, I’ll still be happy I spent it.

How I Invest Money

For many years, this was a constant source of anxiety. I knew that to be wealthy I had to invest. But I was impatient and paid the price accordingly.

Buffett says the stock market exists to move money from the impatient to the patient. That principle applies to most things.

Today, I live in one of our investments (our home), a tenant lives in another, and I deposit a regular amount each fortnight into a Vanguard index fund. The result is, I can sleep at night. I know that no matter what else I do, those three things will continue to grow, and when the time is right, I can pull some equity from one of our properties and do whatever I like.

One day we might redevelop one of our properties and multiply its value, but for now, I’m happy doing my work, exploring other ideas and letting them grow on their own.

The Dream Realised

So, back to those beautiful phrases. Am I a lone wolf? Am I self-made? Without my hard-working, frugal wife, I wouldn’t be as comfortable as I am. Without the advice of experts and the daily inspiration of mentors, I wouldn’t be half as excited about life and what the future might bring. And without the love and support of my kids and my parents, I certainly wouldn’t appreciate the present quite as I do. So that’s a definite ‘no’.

But do I live on my terms? Absolutely, yes. I am a free agent whose security lies not in a promise given by an employer or benefactor, but one I give myself daily. It’s a promise is to work hard, but not too much, and to appreciate the fleeting nature of my time on this planet. The promise is to balance the relentless pursuit of more with gratitude for everything I already have.

Living on your terms is nothing like I dreamed when I was a kid. It turns out it’s so much better.


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Matthew Kimberley – How to Get a F*cking Grip

Matthew Kimberley – How to Get a F*cking Grip

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What it really means to live on your terms. | OfficeAnywhere
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