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How I quit the rat race to work on my terms – without quitting my job.
I've worked with the same company for almost 22 years. When I first started in '97, it looked like most offices – people in suits, rows of desks and bad coffee. We had meetings, watched PowerPoints and set sales targets. We clocked on at nine and off at five.
I soon realised, though, this wasn't a typical company.
Our quaint Victorian terrace in Melbourne's Italian district had a real warmth to it. It's period carpet, sunken boardroom and salmon furniture lent an air of calm. The whole environment was cosy and welcoming – more like a family of monastic nerds than a traditional corporate setting.
The people were wonderful, too. Our likeable development boss, Frank, gave instructions through coffee-stained smiles, and each of us gave him our loyalty and respect in return. He remains one of the loveliest and most intelligent people I've ever worked with. Our MD, Ken, soon became a mentor to me, informing many of my business and personal decisions over the decades that followed. You might recall his story in the Midlife Mentors series.
Back then, the Internet was still quite new, and I got to work on our very first website. The millennium bug had taken over the tech world, too, and Frank's team spent many months prefixing dates in our software with 1 and 9.
What does it mean to ‘go to work'?
After the world didn't end and no planes fell from the skies, our company merged with another.
In the years leading up to the merger, I'd begun questioning the traditional corporate setting and the stories we told ourselves about what it meant to be ‘at work'. Why did we wear suits every day; who were we trying to impress? Why did we speak differently when we entered an office? And why did we have to sit in the same building together every day?
I discussed this with Ken on various occasions, and slowly, things began to change. I started wearing black t-shirts to work, and the sales materials I produced took on a more relaxed, conversational style. Sometimes I worked away from the office with a notepad and pen; hashing out ideas in a park somewhere. I once spent a whole week by a lake 200 km from home, designing the bones of a software solution. It was exciting – one of my most enjoyable and productive weeks since I'd joined the company.
Ken valued deep work and he recognised the importance of thinking time. He once told me that if I needed to spend a whole day staring at a wall thinking through a problem, that was fine by him.
Two Roads Diverge…
After the merger, and as the company grew, things didn't feel the same. I felt less like a trailblazer and more like an employee. Just another body with a cubicle and a set of KPI's.
My saviour came in the form of a new job opportunity. It had everything I thought I lacked: more money, more status, and best of all, a chance to shape the future of an exciting tech startup. But within a few weeks, I knew I'd made a bad decision. Far from feeling energised, I felt more trapped than ever. The money was huge, but the sacrifice was even greater. Within two months, I asked Ken if I could return. Luckily, he said yes.
Upon my return, he asked what I wanted to do (he'd already filled my previous role). He then asked me something that triggered a massive pivot in my life. He asked whether I'd like to go back on the payroll and work in the office, or bill the company each month and work from home.
At that point, I felt I'd already pushed my luck with the last decision, so going for the security of a desk and an office would have seemed logical.
I chose the second option.
For all intents and purposes, I remained like the rest of the team – with projects, goals and deliverables. The big difference was, though, I now had agency over where, how and when I worked. And that, I soon discovered, was everything.
That was 15 years ago, and it remains my single best career/life decision.
Does it mean I spend my days watching Netflix and stalking the fridge? No. I'm often so busy I forget to eat. I still have to deliver results – perhaps more so than others who show their faces in the office every day.
What it does mean is I can walk my son to school every morning and pick him up in the afternoon. It means I can dress like a bum, shower at midday and play my music as loud as I want. I can fart when I like, and if the weather's nice, I can pull my convertible out of the garage and go for a drive.
It's the perfect life for someone who still needs or wants to work, but hates fluoro lighting, peak-hour traffic and pointless meetings.
It satisfies my need to be productive – to do great work – but in an environment that truly supports it.
Fifteen years ago, this arrangement was unusual, and some in the company saw me as a black sheep. Today, though, things are very different. My t-shirt rebellion is no longer considered an affront to corporate protocol. Many of my colleagues now work from home, and plenty of large businesses owe their success to t-shirt-wearing entrepreneurs.
Thanks to the Internet and a suite of inexpensive tools, working remotely is becoming the new norm. That's because it benefits both parties.
Workers want to reduce stress, recover wasted hours, and develop a greater sense of autonomy and purpose in their life. Working from home (or a cafe, a lakeside park, or wherever) gives them that.
Employers, on the other hand, want engaged staff members who love their work; who don't need to be pushed to perform. They want results and they care less these days about the geographical location of those who deliver. For each remote worker, there's one less office/cubicle/desk to provide, and meetings, when necessary, are a Skype, Zoom or Goto Meeting away.
Working from Home – Fears & Benefits
You might have the opportunity to do this. Maybe you want to do this. Chances are, you'll still have to overcome some resistance – much of it self-imposed. Like anything new, even if it's good for us, we fear the unfamiliar.
We worry about things like:
- Losing some of our identity and status
- Getting passed over for promotions
- Feeling isolated or lonely
- Being perceived as less valuable to the business
- Becoming a hot mess due to a lack of structure and routine
- Being accountable to our team up and down the chain
- The perception that we’re not committed to the job
- Work time bleeding into personal time
It's normal to feel these fears, but it doesn't mean they're justified or accurate. There's definitely a right way to do this, and there are a few traps for the unprepared. They can all be overcome, though, and they're well worth the price of admission to the work/life freedom club.
It's important, too, to you see it from your employer’s perspective and prepare your ‘pitch' in advance. You'll want to understand any likely objections and cover them off in your approach.
It might involve testing the waters with a trial. When you define expectations and establish simple metrics to measure outcomes, it's a whole lot easier for everyone. No one feels like they're on the hook if it all goes south and you become an icecream-eating daytime soap addict.
The Big Payoff
All these obstacles are worth tackling when you look at the benefits in more detail. Here's why I do it:
- I walk my son to and from school every day. We chat about motorbikes, trees, Minecraft and the universe, or whatever he’s into that week. Aside from a dozen stay-at-home mums and a smattering of grandparents, everyone I see in the morning looks rushed and anxious. Their day has just begun and already they're late for work. After giving my boy a hug, I go for a walk around the neighbourhood. I already worked a couple of hours before he woke, so I can afford (and deserve) some ‘me time'.
- If my kids are sick or need my help, I’m always available. Most of us believe that family is our main priority, but when did you last attend a school event in the middle of the day? When did you take your kid to a doctor without checking for permission?
- I shower at midday!! Okay, I’m weird, but I love knocking over five or six hours of work before I have a shower. It feels rebellious, which suits me to a T.
- I work where I'm most productive. I hate traditional office settings with bright lighting, background chatter and endless distractions. And most meetings are a complete waste of time.
- My office has floor to ceiling windows on two sides, with greenery all around and lots of natural light. My desk is height-adjustable, and a pair of quality speakers emit peaceful or motivating noises, depending on my mood. It’s all set out exactly the way I want it, decorated with family photos and visual cues that get me in the mood to work. It’s my office, and no one can take it away from me.
- No one cares if I fart, sing or eat at my desk. My son thinks farts are awesome.
- I can start and finish work pretty much when I choose. I know this isn’t possible for everyone, but the point is, I can get cracking on a project at 6:00 am if I want to or do a few extra hours at night – all without leaving home.
- I can access a lot more productive hours each day because I don’t have to suit up, drive to work, park the car or speak to anyone I don’t want to. My office is 35 steps away from my bedroom, so I can be up and working in two minutes flat. That’s efficiency!
- When the sun comes out and the mood strikes, I grab my laptop, jump in the car and head off to a park somewhere. This alone is worth the price of admission. Working outside feels kind of naughty, like skinny dipping. You have the breeze on your face and the sun on the back of your neck while enjoying the sounds and smells of the great outdoors. And most country parks are empty on weekdays.
The Gateway Drug to Happiness
The industrial revolution gave us many things: factory jobs (of which corporate life is only a cleaner version), cheaper goods and technical innovation. It also gave us pollution, consumerism and stress.
Despite the technology revolution, many of the old issues linger while new ones move to the fore.
We worry about income security, so we become married to our job. Our kids hardly see us. It feels like we live to work, and oftentimes, the work itself lacks purpose and meaning.
We long for change, but we can’t let go of the present.
I describe working from home as ‘the gateway drug to freedom and happiness’. Apart from the obvious benefits of working where you like, it opens the door to other opportunities with financial benefits. By quitting the daily rush hour and the stress and exhaustion it creates, you recover precious time and energy to try other things.
Maybe you’re brilliant at what you do and you'd like to offer the same expertise to other people. Or perhaps you want to explore other aspects of your industry and create products or services around those. Maybe you have a passion for something unrelated.
Once you gain control over how, where and when you work, you can explore other tantalising options. This is where the practice of working remotely gets exciting.
Money buys nice things, but autonomy and freedom buy happiness.
Lock me in a corporate cage on a $300k salary or let me work on my terms for $100k and I'll take the second option every time. There are lots of reasons, but a big one is this. In corporate life, others determine the rules of the game and the limits of my creative and financial reward. And they can revoke them on a whim.
When I work on my terms, I know it's all up to me. There's no arbitrary limit, only blue skies and oceans.
I don't want a billion-dollar business, but having multiple revenue streams has changed my life.
Over the years, I've taken the skills I'm good at, combined them with opportunities I enjoy and built extra sources of income. If one thing goes south, I can always ramp up another. To me, that's the ultimate form of income security because I control it.
“Normal is getting dressed in clothes that you buy for work, driving through traffic in a car that you are still paying for, in order to get to a job that you need so you can pay for the clothes, car and the house that you leave empty all day in order to afford to live in it.” Ellen Goodman
When the GFC hit, my employer almost went bust and overnight, my income halved. Because I had a couple of side projects on the go (at that time, property development), I simply devoted more time and energy to those. It was still tough, but I made it through.
Then I got divorced and lost everything, anyway. Life is funny like that.
I've written about ‘midlife mastery' for a few years, now, but the one thing that's made the most difference to this season of my life is this ability to work from anywhere. To work on my terms.
Today, there are lots of opportunities to build a side business. But it's tough to create anything after ten hours away from home each day. You're exhausted. Your kids need you. Your partner needs you. You have to tidy up, empty the dishwasher, put away clothes, eat and sleep. When do you find the time?
The truth is, doing your ‘normal' job at home gives you a lot of the benefits you're seeking anyway – without starting a business.
I'm so convinced of the power in this, I began working months ago on a new project called OfficeAnywhere. It launches in September.
When I reclaimed my wasted hours in transit, in meetings and aimless distractions, great things happened. I started to get my life back; I recovered more of life's most precious resource – time. By reclaiming just two hours, five days a week, I gained 520 hours a year, or thirteen working weeks. Thirteen weeks!
From there, it was easy to get two of life's other coveted assets – autonomy and purpose.
If I had to return to the daily commute and sit in an office every day, I'd have to start drinking at noon. Or I'd hang myself. I just couldn't do it.
I've seen the other side and there's no way I'm going back.
Over the next decade, I want to help people get their lives back by learning to work from anywhere. I know it isn't possible for everyone; you can't drive a metro bus from your den or do orthopaedic surgery from your kitchen table. But for millions it is. Maybe you're one of them.
I care very much about midlife reinvention, so I'll keep writing about it. But I'm also going to write about working on your own terms because I know it's a life changer. That was part of the reason behind the podcast name change.
The simple fact is, I have a wonderful life these days. There are many reasons for it: a great wife, wonderful kids, good health, etc. But two of the biggest reasons are:
- I work when, where and how I want.
- Because I work on my terms, I'm free to pursue other things.
That's it in a nutshell.
If this idea sounds appealing; if the thought of working on your terms gives you goosebumps, go and download the free Escape Plan at OfficeAnywhere.co.
It's actually the first of six guides in my Work Anywhere video course (coming soon), so you'll notice some references to course videos. I'll fill you in a bit closer to launch, but don't worry, I won't start badgering you to join the course.
The free guide includes the intro to the course (feel free to ignore that bit), plus a sample draft letter – with instructions – to pitch your boss on letting you work from home. I hope you find it useful.
So until next week, thanks for reading all the way to the end of this very long post. If you have any questions, email me anytime at email@example.com.
Here's to living and working on your terms. 🙂
Why Working from Home has Made all the Difference
What Freedom Really Looks Like
Decisions That Changed My Life
It’s time you decided what you REALLY want.
Midlife Crisis or a Chance to Reinvent Yourself?
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