To build an unconventional life, abandon conventional thinking

Throw out the rulebook and rewrite it as your own.

A few weeks ago I was sitting at my local café, casually observing people from the surrounding offices bustle in and order their takeaway coffee before scurrying back to what I can only assume was a day full of unnecessary meetings that they were desperate to cancel.

I was waiting to meet

Tim Duggan

, the author of Work Backwards; a book that turns conventional thinking on its head and argues that we’re approaching work and life wrong. Tim’s thesis is that we think about work first and lifestyle second, when really it should be the other way around:

1. Think about the lifestyle you want

2. Calculate how much cash you need to live that life

3. Design your work accordingly

Unsurprisingly, when Tim arrived we hit it off immediately. I was fascinated that he legitimately walks the backwards walk - he and his husband reside in sunny Majorca, working remotely 3 days a week and spending the rest of their time writing, traveling, gallivanting and generally making the most of this thing we get one shot at called life.

During our chat I started thinking about how few people truly live life on the edges. How many people say ‘screw the system’ and carve out a unique path even though it’s hard? How many have the courage to reorient their lives to work 3 days a week on a remote Spanish island?! (The answer is one. Two if you count Tim’s husband).

The reality is that most of us ascribe to a standard worldview. Most of us abide by a set of rules, norms and expectations that, if you think about it, are simply made up stories that we collectively agree to be true (this is pretty much the definition of delusion, lol). Here’s one of the classic tales: get a degree, get a job, climb the ladder, earn a ton of money, buy more stuff, need more money, work more, continue climbing, etc. etc. etc.

Some people enjoy being a character in this standard narrative arc and look, I get it. I’ve been there. In this story you have a fancy job title, a secure salary and the status that comes with working for a well-known brand. But also respectfully…no.

This is no longer something I aspire to and I think many others feel the same. Society is shifting. Consensus is changing. And while we can’t throw out the rulebook entirely, we must rip out the chapter titled Work and rewrite it from the top.

“Rules” to be rewritten

To create an unconventional life requires abandoning conventional thinking. It means debunking certain myths and challenging everything you believe to be true - including the following seven “rules”.

Rule #1: The only way to get ahead is by climbing the corporate ladder.

First of all, define ahead. Ahead in life? Ahead in cash? Ahead in joy? Second of all, I call BS. In the last 2+ years of portfolio-ing I’ve earned more than I ever have, while working remotely and maintaining ownership over my time. I feel more ahead now than ever, especially around my core values of freedom, creative fulfilment, meaning and money.

Side note: I’m not fully dissing the corporate ladder but I am saying that you shouldn’t blindly climb up it, rung after rung, without interrogating whether it serves you.

Rule #2: To be of value you must work 9-5, Monday-Friday.

I think we can all agree this one is redundant, null and void.

Rule #3: Financial security only comes from a salary.

False. It’s possible to engineer financial security into your life even if you earn variable income. I’ve paid myself the same amount every fortnight for the past 2+ years, even in the months I earned very little. To create financial security you need three things: an emergency fund, sales skills and a strategy to manage cash flow. Fortunately these can be learned.

I share sales strategies and my portfolio career cash flow method (ie. how I pay myself a consistent ‘wage’ even with variable income) in the Portfolio Career Operating System. If you want to engineer financial stability into your own portfolio career, check it out here.

Rule #4: Leaving a full time job is too risky.

Mostly false. Of course there’s an element of risk when you try anything new, but it can be mitigated by laying a foundation before going out on your own. Also, learning how to generate income from many places inherently decreases risk because you’re diversifying. And if the shit really does hit the fan you can always go back to a job. This is not a one way street. You have options.

Rule #5: To be taken seriously you need a singular career identity.

False. Business textbooks say that to stand out and succeed, you must pick one niche, one customer segment, one offer and one message, but in the personal brand era this no longer holds true. These days, you can be known as someone who speaks about multiple topics. As someone with a nuanced point of view. As someone worth listening to. Take me - I’ve been writing online for 18 months and am known to speak about portfolio careers, startups, being a generalist, writing on Substack, working in prestige beauty, my love affair with lego, the experimentation mindset, one person businesses, and many more things. Expressing a multifaceted identity has never held me back.

Rule #6: Specialisation is the only way you’ll make it in your career.

False. Society has historically been built around specialisation and therefore specialist workers have had utility because they served a specific need. But AI has entered the chat and is already the best resource to complete many, if not most, specific tasks. In 2025 being a generalist is not a weakness. It’s a hedge against obsolescence.

Rule #7: Work first, life second.

As Tim so eloquently stated in his book:

“The bad news is that the way we are currently working – and, by extension, living – is broken. The good news is that it doesn’t have to be this way. Instead of the default mode we have become accustomed to, where we think about work, money and life in that order, we need to reverse it and see it in a fresh light...this is a radical invitation to take your life back and wring every last drop out of it.”

It’s something to ponder, isn’t it? That instead of accepting things the way they are, you can ask ‘what if’? What if all of the things you believed to be true, were not? What if breaking free from convention was not only possible, but necessary? What if thinking backwards could move you forward to a place you never thought you’d be?

Here’s my take:

Accept nothing. Question everything. Challenge everyone. Willingly take the path of most resistance. Because if you want to be in a better storyline, you must write the (rule)book yourself.

---

It appears that summer is over, sigh.

Thoughts, feelings and emotions after reading Work Backwards (and why you should read it too!)

---

🫶🏼 When you’re ready, here are three ways I can help:

• Watch the Portfolio Career Operating System Info Session: if you’re curious about whether the Operating System can help you build your portfolio career, watch this free 60 minute deep dive into all areas of the OS, and see it in action before you decide.

• Portfolio Career Mentoring: 1-1 sessions to help you build a career that sits at the intersection of freedom, creative fulfilment, meaning and money.

• Generalist World x Portfolio Careers Live Event: I’ve teamed up with the legends at GW to host a free talk about why generalists are built for portfolio careers. Register now!

---

❤️‍🔥 Subscribe for more ideas and frameworks…

…to help you build a financially lucrative and creatively fulfilling portfolio career and life.