How To Make The Mental Leap From a Job to a Business


Today I sat down to install one of my most-used programs: Dragon Naturally Speaking.

I use Dragon a lot in the membership site, on our courses and also for e-mail. So when I got a notification that a newer version of Dragon was available, I paid my $99, downloaded the software and started to install it.

Except it wouldn’t install.

The software informed me I needed to upgrade from Yosemite to El Capitan —which is the Mac’s current operating system. And therein lay the problem. All my computers were humming nicely on Yosemite, and there seemed no need to rock the boat and install a new operating system.

At least if I were having some trouble with the existing system, it would be worth the trouble, but I was doing just fine. Then along came this new version of Dragon and it was forcing me to do something that involved a whole lot of risk.

When you’re in a job, it’s like living in Yosemite land

It’s not the best thing ever and you know there’s a world of entrepreneurship you’d rather explore. But it’s safe in Yosemite-land so why make the leap into the unknown? And how do you know things will work out anyway? You don’t.

That’s the whole point of being an entrepreneur. You have no clue if or when things will work out. The only thing you know for sure is that change is happening. That the Dragon wants to be let loose in your world and you’re holding back.

I understand there’s a huge difference between taking a leap from a job into the world of business. I know that the fear is a lot greater when you have a family, a mortgage, and bills to pay. Yet, there comes a time when your hand seems to be forced. You can stay where you are, or you can take the leap.

In this series we deal with three recurring questions
Managing the fear
Keeping the vision strong
Focus—And why you need a hatchet person

Part 1: Managing the Fear

I hated my job as a web designer.

I’d just immigrated to Auckland, New Zealand in Feb 2000 and my priority was to find a job. Compared with India, where I came from, Auckland was terribly expensive. And anyway, I couldn’t see myself starting up in business right away. To my utter amazement, I found a job that was going to pay me $50,000 a year to build websites.
By the second day, I was ready to quit.

My wife, Renuka, wasn’t so sure

To get a job that was reasonably well-paying was not an easy task. At the time she was still in India, and she asked me to hang on until she showed up in the following month and got a job of her own. “Then you can quit your job if you like, ” she told me.

However, things don’t exactly pan out the way we imagine

When Renuka got to New Zealand, she found it hard to find a job that fit her position. For the next few month, she bounced between temporary jobs and at least at the time, my job was the one that paid the bills—and the mortgage. Barely three months after we entered the country, we bought ourselves a house and had a mortgage of $200k.

The week after we bought the house, I was made redundant.
The fat, it seems, was in the proverbial fire.

What I experienced was a no-choice situation

It wasn’t entirely no-choice. I could have clambered back into the job market and got myself another job. After all, I was pretty good at Photoshop, illustration and had a decent track record in copywriting. Instead, I decided to say goodbye to the workplace once and for all.

Put yourself in my shoes for a second: new country, we had no family in New Zealand, Renuka had only temporary jobs (that she hated just as much). Plus there was that small matter of a $200,000 mortgage.

A no-choice situation doesn’t give you time to be fearful

All of the fear comes from waiting. While you’re waiting to quit your job, a thousand thoughts go through your head. You wonder if you’re making the right decision. You worry about your future and the future of your family. And you look for a bit of a safety net online.

This morning as I wrestled with the Yosemite vs. El Capitan operating system, I went through a similar tug of war. I looked for a safety net as I have for the past year or so. I read through the reviews. And there were over 5000 reviews, some new some old.

Some saying the upgrade was a breeze, others claiming it was an absolute nightmare. All of this build up fear and frustration. You’re put in a position where you don’t really know what to do or whom to trust.

And yet the outcome has already been decided well in advance

The reason you’re reading this article is because you too want to escape from that cubicle but you don’t know how. And no one can answer the question for you. No one can tell you the right time to quit. To find out if it’s going to work, you have to force a redundancy.

Bass guitarist, Paul Wolfe had a real problem back in 2008 or so

Paul was a bass player in a band that played at weddings and functions. While the going was good, the band was kept busy and profitable. Then along came the recession of the 2000s. Paul talks about a situation where the floor seemed to disappear under his feet.

Soon gig after gig began to dry up. Paul was in a state of limbo, unsure what to do next. Unlike my situation where I was in a job one day and out on the street the next, Paul’s situation dragged out for months. However, faced with no option and rising debt, he decided to teach what he knew.

And what did he know?

He knew how to play bass guitar. Paul then set about creating a simple site which talked about how to play bass guitar. Then he started buying some rudimentary equipment to record videos. Posting video after video online, he created a sort of catchment area.

Aspiring bass guitarists would see his videos, and Paul used a bit of his marketing knowledge to drive them to his website and list. Today, Paul Wolfe does just fine with his guitar site. He’s into writing fiction novels on the side, bikes to work and lives a life that’s different from the one he once knew.

(You can continue reading or listening online by clicking here)

Part 2: Having a no-choice situation is probably the only way to deal with fear

You have to take the plunge, and so you do.

The longer you wait, the more fear keeps you paralysed. When a Psychotactics subscriber, Kai Huang, asked me to write about “how to make the leap” this was one of the first questions: how do you deal with the fear? And the answer is, you can’t.

Once I was made redundant, I enjoyed the quiet for a few days and then I started knocking on doors. I went back to what I knew best and decided to sell my cartoons to advertising agencies, magazines, and newspapers. I was lucky that the Internet was still an unviable place back then.

I was lucky that e-books and fancy software were still to take off. If that were the case, I might have built a website and sat around and waited for a stream of clients to come through the door.

But I didn’t have that luxury

And so I decided to go out and do what freelancers do to this day: they go out and meet clients. They get freelance assignments. They spend time working on those assignments and get paid. If you sit around hoping that something magical will happen, there’s a pretty good chance you’ll be back in your cubicle faster than you think.

If that so-called guru is exploiting your fear and telling you that his program will certainly get you to sell thousands of books, then you’re buying into the wrong idea. And it’s the wrong idea because the failure rate is extremely high. You can’t just waltz into a business and expect everyone to pay attention.

I got work freelancing, I taught some people how to use Photoshop, and then slowly but surely I had my first presentation. That presentation was a disaster, and the fear came rushing back.

But with some practice that fear went away. I spoke at tiny events like at a Rotary club. And with every outing, I tried to sell the spindly version of The Brain Audit (back then it was just 20 pages). And the fear diminished.

In 2001, a year after we moved to Auckland, Renuka quit her job

She had a high paying job at the giant beauty and cosmetic giant, L’Oreal. She had a two-hour daily commute; a rancid workplace atmosphere and a boss that took credit for everything. If you’ve met Renuka you know she’s a happy, jumpy person with a mischievous smile on her face. Some days she’d come home with tears in her eyes.

Then one day, she had enough

She just quit. We were still saddled with our mortgage. With all the freelancing it wasn’t like I was earning a lot. But we decided we couldn’t deal with the jobs. We needed to cover our bills, and that’s what we’d do. We cut back on our spending (just $150 for entertainment per month), and we did what we needed to keep ourselves happy.

And yet, Renuka wasn’t quite done with her career.

Even back then we’d go for a walk every day. And every day it seemed like I asked her the same question: “What will you do if something happens to me?” I’d ask. And her response was the same every time. “I’ll just get a job.”

This is 2016.
That was 2001.

We were more scared when we had the jobs than when we had no safety net at all

I’m not saying your story will turn out like ours. I’m just saying that the fear is greatest where you are right now—in that job. That once you get out of that job you’ll have to do something. It won’t be easy, and it may take a year, and definitely more. But the fear, that will be gone.

Gone forever.

That brings us to the end of the first factor: Dealing with fear. But let’s say we make the leap. How do we then maintain a sense of vision and focus? Let’s get started with vision because that’s probably the one thing that will keep you going when things get tough.

Part 3: Keeping the Vision

Let me give you the short version of my vision.

You probably know this, but back in 2000, my website had the embarrassing name of “million bucks.”
That, in short, was my vision.

And yet that wasn’t my vision at all

Back in India, when I got my first job at Chaitra Leo Burnett, I had a very kind and protective boss: Tannaz Kalyaniwalla. All around me, there were creative people whose company I enjoyed.

And yet, despite the generosity and warmth of the people around me, I yearned to be free to do what I liked, when I wanted to do it. Which meant that if it were a rainy day and I wanted to stay at home and do nothing, that’s exactly what I could do. If I asked for leave, my boss never said no, but I didn’t like the thought of asking.

My earliest vision was to simply be free to do whatever I pleased.

This vision clashes strongly with reality

In the first few years, I could do whatever I pleased, but I had to pay the price for goofing off. I had to make sure I met with potential ad agencies and editors (when I was a cartoonist). When I moved over to marketing, it was all about getting in touch with potential clients and some incredibly mindless meetings.

Meetings where you spent three hours debating whether the logo should go ?th of an inch to the left or right. Add early morning drives to make presentations and the endless needing to learn new skills and the vision seems to be nowhere in sight.

Vision starts off being a tiny spark of an idea

In 2004, we’d only been selling The Brain Audit online for little over a year. We’d done two workshops for companies, and one workshop of our own. The few people we had on our e-mail list weren’t always enough, and we reached out to networking groups and friends of friends.

Even so, there was no reason to be optimistic because we were still working quite a lot. We worked all week and then on weekends too. Getting a business off the ground seemed to quite rough, and it’s not like we had a lot of expenses.

We were operating from a spare bedroom

We didn’t even have a computer of our own. Renuka would sit at the computer for an hour; then it would be my turn. And then an hour later, it was her turn again. We didn’t go around buying fancy equipment; even the books we read were all from the library (and we read hundreds of them).

The vision was shrivelling. In that year alone we seemed to be moving away from the reason why we started the business. We started it to get more free time, not to double our income or get a squillion clients.

Which is why 2004 became our benchmark year

We were going to do something incredibly crazy: we were going to take three months off—just like that! Your vision may not be to take three months off. It may be to buy that mansion on the hill and take over half the countryside.

You may revel in the fact that you have 100,000 people on your list. We didn’t care much for all those trappings. For us, the vision of the three-month vacation embodied who were—and who we are.

When we take three months off, we have to make the other nine months really count
As a result, we got more efficient. It might seem like it’s easy to just scoot off on vacation, but like any project, it takes a lot of planning. And then when you get back, you need another plan, because you’re so relaxed that you don’t feel like working for quite a while.

I’d like to say it was all in place right at the start—this vision of the three-month vacation. But it wasn’t. And we still keep tweaking the way we work and we take our vacations.

Most businesses lose sight of their tuna sandwich

You’ve probably read or heard about this tuna sandwich episode because it was covered in articles and podcasts before. There’s this story in the comic strip, Calvin and Hobbes.

And how Calvin is drawing up his list for Santa Claus. At which point, Calvin turns to Hobbes and says: What would you like for Christmas?

And Hobbes says: I’d like a tuna sandwich. Calvin thinks Hobbes is crazy because Calvin has a list that seems to have rocket launchers, trains, boats, and a whole bunch of stuff he wants for Christmas. And all Hobbes wants is a tuna sandwich.

As is inevitable, Christmas morn arrives

And Calvin is now throwing a massive tantrum because Santa hasn’t brought him all he wanted. And Hobbes sits with a big smile on his face and says: “I got my tuna sandwich.”

The tuna sandwich of your life can be incredibly simple. Hold on to that vision. Never let it go.

We too have our tuna sandwich

But there’s no telling when the winds change. In 2005, Renuka had an accident in the garden that required hospitalisation and three months off work. In 2009, we took on a personal project to help a family member. That made a big dent in the way we did things. And I think about the tuna sandwich every single day, even after all these years.

I’m super-generous with my time and advice (I know that), but I also need that down time to recuperate, to learn or just to enjoy a rainy day (and yes, we both love rainy days. Sunny days can be kind of boring).

Vision is hard to hold on to when you’re making the leap.
It sounds insane to do what you set out to do when there’s so much other stuff to be done.

But we kept the vision simple and worked around it.

You know the funny part about that million bucks?

Today we could stop working, and we could live the life of The Three Month Vacation for the next thirty years or more. We ditched the million bucks idea, and it came right after us.

Instead, we focused on what was important, our work, our clients and our break time. And in doing so, we continue to create the products we want, go to places we want, do the things we want. The vision, if you keep it strong, will breakthrough at some point in time. It had taken almost four-five years before we felt comfortable regarding revenue and clientele.

Even then there were some ups and downs. But the vision was always robust and straightforward. Keep it simple so that you can focus on it every single day. So that you know exactly what your tuna sandwich is all about.

Which takes us to our third question—our third point: why focus is going to need a hatchet person.

The Hatchet Person (And Why It Helps Focus)

When you’re making a leap into the unknown, fear is the biggest factor.
Fear of making enough.
Fear of justifying the decision you’ve just made.
Fear of not knowing enough—of wanting to learn more.

It makes you eager to press every “buy now” button online, just so that fear can go away.
But fear is only one part of the leap. The other is focus.
And focus to me, is less about persistence and more about “getting rid of the distractions”.

Which takes me to my first mentor Dough Hitchcock—also my first hatchet person

I didn’t know much about marketing, and at the time, Jay Abraham was easily one of the most well-respected marketers on the planet. There were other marketers, no doubt, but Jay seemed to be more eager to teach; to give.

Among those hundreds of books I borrowed from the library, there was one by Jay Abraham. That led to me getting on his list, and buying a book—a big, thick, blue book—that cost $300. We knew so little that the first thirty pages of that book took us months to implement.

But now we were well and truly on Jay Abraham’s list. I wanted everything he put out, so imagine the day I got this long sales letter (and yes, sales letters came in the mail back in 2003).

He was having a seminar and to get a seat I needed to pay $5000

I should have been horrified. I lived in New Zealand. I was paying off this huge mortgage. $5000 in US dollars was approximately $11,000 NZ dollars back then. Plus there would be airfares, accommodation, transport and food costs involved. Yet I was happy to go and I excitedly told Doug Hitchcock about it.

You know what happened next, right?
Doug brought down his hatchet. He forbade me (as kindly as he could) from embarking on such a silly adventure. “What are you going to learn that’s worth $10k-15k?” he said.

In effect he wasn’t stopping me from learning or buying into products, but he was certainly helping me focus. And being a hatchet person is not just restricted to money—which is the biggest struggle at the start—but also to other aspects.

Most entrepreneurs tend to be restless

They want to do it all. And I wanted to learn everything, do everything and promise everything. And that’s where my wife, Renuka, took over where Doug left off. To this day, I’m the one who conjures up dozens of possible products, workshops etc. and she gently cancels it off the list.

It doesn’t mean we don’t push ourselves. We take the weekends off, take our breaks and our vacations, but when we’re at work we still put in a decently long day. I am so happy for those who say they spend just 15 minutes in the office, but I know that to create great work you have to labour over it and make it better all the time. And yet, this restless nature you need to have a hatchet person.

Someone in your networking group could help

Maybe a friend who you could meet. It could be a coach, but it doesn’t need to be a coach. In 5000bc itself we have a taking action forum and people post their three goals (yes, only three) and they work through it bit by bit. You’ll find that if you ask for help, you’ll get it, but expecting to figure out everything yourself is the hardest task of all.

Your hatchet person has to have a single role

To get you to cut the stuff that you don’t need, so you can focus on what you have to do. And trying to find a mentor like Doug, is a laudable task, but it’s often not necessary. Clients often mention that it would be wonderful to have a “Renuka” around, but when they say that, they’re missing the point.

The point is that you live in a world where you may not have Doug or Renuka

And that you still have to make the leap and keep the forward movement. You can’t hope and wish. You have to find someone who’s good at getting you to stick to the three things you need to do.

Once you get that momentum, you can add more, as long as you’re only ever working on three things at any given time. And should we forget, it’s the job of that hatchet person to bring us back on track. Focus is about elimination—that’s it.

Most people are too scared to make the leap and rightly so

I was afraid to go through putting El Capitan—the new operating software—on my computer. And guess what? There was this nervous wait and then it turned out to be almost fine. One of my programs wouldn’t work but it could be easily replaced. And that’s what you’re going to find as well.

Despite this leap into the crazy world of entrepreneurship, you’ll find that some “programs” may not work. But you’ll manage and then start to prosper. Most of all, you’ll never want to go back to a job ever again.

However, let’s see what we’ve learned because these three points are important.


1) The leap into the unknown is always scary
If it’s any consolation, I made it extremely hard for myself. I moved countries, changed into a career where I had almost no experience and then added the burden of a mortgage on top it all. You may find that you don’t want to do something so crazy. And so you give yourself a deadline and put away some money so you can last six months to a year.

Or fate may step in and throw you in the deep end like it did with Paul Wolfe—and with me when I was made redundant. However, one thing is clear. The fear is greater when you’re waiting than when you’re in the thick of things. When you’re in the thick of the action, you have to start executing and changing strategy to keep above water.

Start with consulting but then also do a bit of training and leverage. Please don’t buy into this idea that you can simply buy a program and you will have endless clients and income.

And if you make the mistake of buying into it, it’s a lesson well learned. Move on and go out there in the real world and meet clients. The internet is fine too, but it’s not the only source of work.

2) Your vision will be pretty clear at the start and then greed may set in
You can’t help it. You read how some guy is making millions and you want to do the same. Or you may start to work endlessly and the things you set out to do, like spend time with the family, or just have some downtime—all that will get lost in the pressure to get your work done.

This battle with work never stops and you have pull out your vision from the rubble and put it up on the wall yet again.

Keep the vision simple. My personal vision is The Three Month Vacation. My work vision is to care, guide and protect my clients. I may go off the road when life brings on its challenges, but the simplicity of the vision brings me right back to where I need to be.

3) Finally get a hatchet person
All this talk about focus seems more about keeping your head on the task. But how can you do that if you keep scampering off in every direction? This is where a hatchet person comes into play. You don’t need a fancy coach. You don’t have to find the perfect mentor.

All you need to do is find a friend in your networking group (someone you can meet once a week) or someone in an online group (like 5000bc). And that’s all you really need. You want to focus on three things and the job of the hatchet person is to ask awkward questions, and to cut down that scampering.

In India I grew up listening to a fable: called the Monkey’s Curse

To catch a monkey, a trapper would put lots of warm, fragrant rice in an earthen pot. The mouth of the pot was small enough for the monkey to slip an open palm, but the moment he clutched the rice, he couldn’t free himself. To be free he needed to let go. But the monkey was desperate for the rice and stayed long enough for the trapper to throw a net. And then the monkey was trapped for life.

We had to battle the Monkey’s Curse many times. We wanted to hold onto what was safe, what we knew. It was no fun stepping into the unknown. I can’t speak for you, but I know that if I could go back in time, I would still be afraid.

Then, I’d jump.

Sean d'Souza


15+ years ago, fresh out of college with a degree in accounting Sean de Souza joined an advertising agency where he *met* Leo Burnett, a man who had spent his lifetime in the hard trenches of communication and advertising.

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