Chapter 10
Portfolio living

If you've ever tried to change industries or careers, you'll know how difficult the process can be. This is true even for roles that require no formal qualifications. The old ‘experience' demon raises its head. They want someone with X years' industry experience, a person who has worked in clone conglomerate XYZ (probably their competitor), to fill the role that has just opened up. The recruiter — or increasingly these days the CV algorithmic short list generator — just wants to keep their customer happy, so they give them what they ask for. The hiring manager, well, they just want someone who can hit the ground running. Someone who knows the system, the rules, the game, the industry dynamics and business model. So they fill the office with clones and wonder why their industry and company is being disrupted!

It's not their fault, it's no one's fault, it's just the way companies and systems tend to evolve. What we need to do is be aware of it. It's why it's so hard to break into a new field. Everyone has been taught for so long that risk is bad and failure is bad that they don't want to bring in anyone who hasn't been vetted by the system. Sure, there are ways to hack your way into a new field, but the traditional method of doing it is ridiculously difficult. They say they want entrepreneurs and to act like startups, yet most won't even take the micro risk of employing someone who hasn't worked in that realm before.

Even companies that send you on training programs aren't doing it for you, they are doing it for them. It's a kind of software upgrade for their employees — a software patch for the human OS. You'll learn more stuff and become better, but they are investing in themselves more than in you. Whenever I did a training course in my corporate days, I'd be thinking about how I could stealthily apply what I learned to my own life. I used their time to reinvent myself. We can all apply what we learn wherever we happen to be. Paying attention to the world around us is more valuable than ever, because change is happening so fast that we can see it on the street long before it's ratified by research findings, appears in social commentary or populates corporate financial results.

IF WE WANT CHANGE WE HAVE TO INITIATE IT OURSELVES — NOT WAIT, NOT ASK FOR PERMISSION, JUST GO.

The good news about reinventing ourselves is that all the gatekeepers have left the building. We can learn anything we want, on any topic, drawing on the world's best thinkers, mostly for free. This has never happened before. On the one hand, people are worried their jobs and industries are disappearing; on the other, we all have the gift of choice on what we do about it. We can whinge while we watch another reality unfold, or we can draw on the potential we all have to reinvent ourselves. We can go out there and learn new things, create new value and start anything with next to nothing, other than time. Yes, the changes are mind blowing, but so are the choices on what we can do about them.

How to become … anything

I used to be so skinny I got teased at school. My friends would say, don't open the door, it's windy out there, Steve will blow away. For a teenager any type of teasing hurts, so I was kinda scarred by it. I got a bit obsessed with losing my nickname, Pencil Neck, and I hit the gym big time. I knew absolutely nothing about weight training, except that people said lifting weights, over time, builds muscle mass and beefs up even a skinny guy. I went at least five times a week for many years. Within three months I knew I'd achieve my goal; after a year I was physically a different person. All I did was work hard in the gym for 45 minutes a day and eat healthily.

No tricks, no special food, no enhancements. All I did was change places. I changed where I invested my time after work, and it transformed me physically. But I noticed some interesting things in the process. If we continually show up at a place where a certain thing happens, the place itself teaches us what we need to learn to be successful at that thing. I got talking with other weight trainers. We shared ideas and tips. We watched each other and learned lifting techniques from each other. We discussed food and books to read. We also motivated each other to do our best. It was a really cool experience, because weight training is both personal and collaborative. No two bodies are the same shape or have the same potential. So you run your own race, and it's up to you to develop your body's potential. You get immediate feedback on how strong you are becoming, but you don't see physical progress for some time. But gym junkies also collaborate with each other. We ‘spot' for each other, ensuring we push ourselves to our maximum potential. We watch our collective progress, and we all hate missing a session. Through this process, you learn what works best for you; you take some advice and ignore other bits. You try out different things — some work, some don't. You even invent your own techniques. You use what you learn to develop your own regime.

Weight training gave me the confidence to do anything in life. If you can reshape your body, then surely you can reshape your life. It's the only sport I know where you ‘wear' how good you are at it. This strange fact then evolves into an interesting social situation. Once people in the gym see how well you lift weight and the shape you're in, they start coming over and asking for advice. I'd been in the gym long enough to be able to offer the best advice possible for anyone wanting to reshape their body. I'd tell them, ‘You have to show up, every day'. They'd laugh and say, ‘Oh, I know that, Steve, but really, what are some of the best things I can do?' I'd reiterate that showing up is the only thing that matters. That just being in the gym regularly enough will mean you'll learn what you need to know. And you won't want to waste the sweat on a poor diet either. I'd tell them, ‘You'll only make friends with those who show up often enough, and guess what, they are the ones in the best shape. They'll respect that you show up and they'll share their ideas with you'. I'd assure them that they'll soon become hungry enough to learn the best methods and not waste their time.

Everything we need to know will be provided if we just show up — often. Frequency is more important than depth. Effort compounds in the same way investment returns do. Frequent deposits into doing something will have a greater impact than a single big block of time will. One hour a day at the gym is far more valuable than five hours on Saturday. For some reason we all try to find a way to clear up some future Saturday to do that project, when what we need to do is invest the first 10 minutes on it today.

I learned how to do it by doing it. I'm pretty certain that's the best way to learn anything. Sure, this book will help you with some ideas, but the ideas become your version of them once you start implementing them. You've already begun your journey to learning things that didn't make it into the classroom by reading this book. The fact that you're still reading at this point means you're the kind of person who shows up. You will have had your own weight training equivalent at some time in your life, that time you got obsessed with doing something really well. A sport, a hobby, a skill, a game, anything. It taught you because you put in a consistent effort over time. The best part of your future lies in repeating that process.

The 10-meeting method

There's another way just showing up can change your circumstances. People find it difficult to change industries for all the reasons I've already mentioned — the linear thinking, the risk the employer takes, just the simple inertia of doing what they've always done. But there is a way to hack the system, and it never fails for anyone who follows it through to the end. I call it the 10-meetings method. It goes like this.

If you want to get into a gig in a new industry, all you need to do is meet with 10 people in that industry. The hardest part is usually getting the first meeting, but you can hack that process. Most of us will have a friend or colleague who knows someone we can meet with. But if you don't know anyone in the industry, turn up at an industry event in your city and be a nice human being, and you can make a new connection. When you set up the first meeting, it is important they know you are not looking for a job, even though in the long run that is your goal. Instead, in the meeting setup phase, you will convey simply that you find industry X interesting, and that you'd like to catch up with them for 15 minutes to learn a bit more about it.

At this point you've done a few important things. You have connected through a warm introduction, not a cold call. You've removed the fear that you want something they can't promise — a job. You've established that you respect their time by asking for only a short meeting. It's often a smart play to offer to shout their morning coffee at their local café. Most people will give you more than 15 minutes anyway, because you've stroked their ego a little (we've all got one) by recognising their expertise.

The meeting should be about asking smart questions. If you can't think of any, outsource the process to your favourite search engine. Ask about their career trajectory, how they got there (everyone's favourite topic), the future of the industry as they see it, maybe a book recommendation, and some carefully considered questions in response to what they say when you are together. It's a good idea to take notes, which not only helps you move up the learning curve but is a great sign of respect. At the end of the meeting, ask politely if they have a colleague in the industry who wouldn't mind sharing 10 minutes with you as well. After a friendly, non-threatening discussion and some good questions indicating you valued their opinion, only a psycho would say no. Ask for contact details so you can connect with their colleague directly and not take up any more of their time. Ensure they are okay for you to mention their name and that they said you would meet with them quickly. This next connection hinges on their social credit with their industry colleague. If they didn't have this, they wouldn't give the other person's name.

At the second meeting you repeat much of the process of the first, but now you're a little further up the learning curve. You've got information from an industry insider. You've read your notes and have even more questions, tighter and better ones. You can start to discuss rather than just ask. At this meeting you begin to develop another perspective and widen your knowledge. You've already doubled the size of your industry network. At the end of this catch-up meeting you ask for an intro to another colleague, then you repeat the process. With every meeting you become more knowledgeable about the industry, learn more about what matters and ask better questions. Meeting by meeting, you are building a network of people who know each other. You're also building your reputation as someone who is courteous, enthusiastic and willing to learn. By the time you approach the tenth meeting, you're having valuable discussions about the industry; you have practically become an insider.

Here's where it gets interesting. We know that most jobs never get advertised. Whenever a role pops up in our company, we first approach trusted colleagues to ask whether they know of any possible candidates, and these colleagues are often the same people you've been meeting with. In those discussions your name comes up. They say, ‘I met with this smart girl recently who seems like she really understands the industry challenges. You should give her a call. I'll connect you'. Which might even elicit the reply, ‘Oh, I've met her. Yeah, I'll call her'. Suddenly you have the inside running. Instead of being just a name on a screen or piece of paper, you're that person they know, and human nature takes over. You're invited in for a chat.

Prove it!

I've used this process often in my own life and have shared it with dozens of people and many students I taught at university, and I've never known it to fail for anyone who followed through on the 10 steps. Physical interaction always beats virtual. LinkedIn is for amateurs; this method is for players.

Often I'd be that first contact for people wanting to get to know stuff. While I was teaching marketing at uni, undergraduates would ask to meet with me. They'd say, ‘I'm really keen to get into marketing. I love it. I'm really into it'. I'd say, ‘Prove it!' They'd look confused for a bit and then explain to me it's their major. I'd laugh and say, ‘Your degree isn't worth as much as you think, especially given everyone else you are competing with for these jobs also has one'. It becomes a bit like an algebra equation, we remove the X from both sides and see what's left. It's the stuff you have outside of your basic qualification that really matters.

It's easy to see who the clear winner is. If you want to stand out, then increasingly it's about what you do that proves the passion — the informal, self-starting actions that put you ahead of others in the same space. Things that not only create a digital footprint (what people see when they google you) of your personal knowledge, but show you care more than the others who just say they do. It doesn't have to be over the top either. It's often something simple like having a well-curated YouTube channel with key videos from the industry, or writing a regular blog about the latest trends, or conducting an interview podcast series with people in the game. Through being more, you'll know more, and people will notice.

Of course you need to remember that these days your CV isn't a document you compile. It isn't even what LinkedIn says. It's what Google says. Because that's the first place anyone will look when checking you out. You need to think of Google as your ‘automatic CV generator'. And the good news is you can populate it however you want. Your goal should be to make the first page that pops up on your name search a page you can control, not some social feed. Your own dotcom address, your blog, something that makes you shine, while your competitors lead off with pictures of them at parties!

It's important to set this up before your 10-meeting strategy gets underway. Start the process of creating something in the industry, even if it's just thoughts. What you publish today can have an enormous impact on your fortunes, if you invest effort and thought in it. And don't worry that you're not an expert; it's the process and energy that matter, and as with all things, the more you do the more you'll know and be able to offer. It doesn't matter if hardly anyone looks at it; if just one person reads it after googling you, it could make all the difference. Having your own digital footprint while working through your 10-meeting method will boost its effectiveness. You can even quote and hero the clever people you meet.

Now some of these suggestions sound confronting. But we need to push past the doubt that will sometimes enter our mind.

WHEN WE ARE BLAZING OUR OWN PATH IN LIFE AND IN BUSINESS, DOUBT IS THE KEY ENEMY. IT'S EVEN BIGGER THAN FEAR, BECAUSE DOUBT ALWAYS HAPPENS BEFORE FEAR DOES. SO WHEN WE SENSE SELF-DOUBT, WE NEED TO FIGHT IT AND FORGE AHEAD.

We must ensure we don't stop what we are doing but keep writing, keep meeting people, keep calling, keep coding, keep building, keep creating, just keep doing whatever it is we ought to be doing. Even when we are not sure of the next steps, even when we can't see clearly where we are going, we must continue to move ahead. It's a bit like walking in the fog: the path reveals itself only if we keep walking. If we stand still, we'll learn nothing.

The most valuable thing I've ever done

Of all the different things I've done in my working life, writing my blog has created the most value. It's right at the top of the list. I first started writing it 10 years ago, and it changed me and what I believed was possible for me. The reason it was so valuable is that it taught me how to slide across into new realms. The first iteration of my blog was about my personal journey, leaving the realm of the Fortune 500 and doing my first post-corporate startup. Once I started writing, the feedback I was getting from readers taught me how to write better and which posts were creating value for others. I also became curious about what best blogging practice was. The more I blogged, the better I got at it. So I began doing it daily. Knowing I had to write something every day forced me to look further afield for insights, and I started to see the world more clearly. I paid more attention to my own startup journey so I could share the lessons.

Because the blog was at the pointy end of the Web 2.0 revolution (remember, this was before the social media boom), it also taught me a lot about technology. I learned the art of the mash-up and how to hack blogging software and use the platform. I learned how to link seemingly disparate things and ideas and how to promote my work through digital forums. It taught me to think better, to propose an argument to my readers, because every blog post is a mini pitch. I made new connections with others in startup land through the blogging and startup community who were interested in the topic. Weirdly, the startup community thought my ideas were fresh, but all I was doing was weaving some classic marketing methodology through the emerging digital layer, which turned out to be something a lot of techies had never been exposed to before. It taught me just to do things and not wait to be picked, like okay Steve, you're now qualified enough to write about startups.

Remember, we are what we do, and I showed up every day. Through my blog, I invented a new career realm. It turned me from a corporate guy into a startup guy. The first post-corporate startup I did was a disaster. I lost my shorts, but the blog, sharing the failures, was a success. It gave me the confidence to keep going. My next startup did very well.

Blogging helped me understand that my life could become a series of transitions. I could take one skill and turn it into the next one. In big business they call it related diversification. I like to call it portfolio living.

The portfolio of you

Our chances of guessing how we'll be earning our income in 10 years' time are very low — close to zero, in fact. What we can assume is that it will change from today, that it will involve more than one revenue stream and that we'll need to learn a bunch of new skills to cope in that environment. We won't need to learn how to do something new, the x, y or z skill per se. We'll instead need a bunch of new methodologies and intelligences that will allow us to adapt on demand. Understanding the impact of a new technology will be significantly more important than knowing how that technology actually functions. It will pay to focus on the human impact of it. In future our incomes will depend on our ability to coordinate activities with other people, on our ability to work with various forms of artificial intelligence, on managing things collaboratively, on not being afraid of mistakes, and on running lots of little economic experiments to see what new things work. Learning in this way will allow us to build a micro-economy of revenue streams for ourselves.

The first thing anyone learns in investing is to diversify their risk, to make a range of investments so if one turns bad, they have the others; they average each other out, just as happens in an index fund. Which makes me wonder why people don't take this simple precaution in regard to their own revenue streams. It just makes sense. Having a single employer is like investing all your money in one stock on the share market and hoping it all turns out okay — not a very robust strategy.

Now let's add this thought: One boss is not a very good sample size.

I'd much rather have the market determine how good I am than a single person. Like it or not, your boss or manager has a big impact on your fortunes inside a company, so being liked is way more important than being good. They're just humans, and humans always have their favourites. There's a lot riding on your boss having your best interests at heart.

A BOSS CAN NEVER REPRESENT THE MARKET; ALL THEY'LL EVER BE IS AN OPINION. A SAMPLE SIZE OF ONE.

Robustness of sample size is something that researchers talk a lot about. In simple terms, it's the idea that we can really understand if something is true or is valued by the market only once we've tested it enough times or with enough people. I'd rather trust the market than a single person. The market is a weird and wonderfully varied place with a wide diversity of people and opinion. Some will align with us, some not. Placing our financial future in the hands of a single decision maker is less than robust, as a single disruptive event can cast us from 100 per cent to 0 per cent income.

So why restrict yourself to one boss when you can spread your risk? This is an incredible hack in the modern age, one that was nigh impossible even a decade ago. It reduces the risk of one revenue stream drying up. It gives us a better chance of finding good bosses and higher paying work. We learn to adapt more quickly and develop different skill sets. All of which make us more future proof.

You are an entrepreneur — right now

While the ideal earning scenario for any person is to have a portfolio of revenue and more than one boss, that is unlikely to happen until we become an entrepreneur. At this moment you may not see yourself as an entrepreneur, especially if you currently have a job. I've got good news for you: you'll be an entrepreneur by the end of this paragraph. It doesn't require you to do anything except change how you see the world, because you are already an entrepreneur. Yep, you're an entrepreneur right now. Even if you are reading this on public transport on the way home from cubicle land. You're an entrepreneur but you just haven't realised it yet.

We are all entrepreneurs, because we all work for ourselves. I work for Steve Sammartino Corporation. You work for [insert your name here] Corporation. Whether or not you have set up the formal structure, you're the CEO of your own personal corporation. We are 100 per cent in charge of our own revenue streams, brand positioning and distribution in the market. Instead of having an infrastructure and multiple customers, our mind and body is our infrastructure and our employer is (for many of us) our single customer. We are and will always be entrepreneurs. We just need to flip our thinking, and once we do everything changes. I know because when I learned this, the world changed for me.

Once we see ourselves as entrepreneurs, regardless of our circumstances, we can start to ask ourselves some interesting, potentially revealing questions:

• How are you currently treating your biggest customer?
• Would you pay yourself what you earn from your biggest customer?
• Are you creating more value than you extract from your current customer?
• Is your ‘brand' indispensable and unique to your customer?
• What value proposition does your brand hold in the market, and could you find new customers immediately if the existing one (your employer) went elsewhere?

These are the questions customers ask when they cast their dollar votes on a product or service. So we should ask ourselves the same questions, given that we are that product or service. This will quickly reveal the truth and put us on a path where our values and mindset are focused externally, rather than on ourselves. We shift from an extraction viewpoint to a value creation viewpoint. What this does is shift our mindset to creating value for others, rather than wondering what's in it for us. It becomes an important part of our mental preparation for the entrepreneurial journey.

Here's something to remember: We ought to work harder on ourselves than we do on our job. If we want to create value in perpetuity, then we have no choice but to become self-learning algorithms. We need to adapt to and benefit the ecosystem around us more than we benefit ourselves. On the face of it, this may seem to contradict what I have just been arguing, but when we do this with our new enlightened mindset, the major beneficiaries are the people around us — our customers and our employers. We've then become something bigger and more important than ourselves. This is what entrepreneurship is really about — creating value that didn't exist before we arrived. Inventing value is the process that creates the third type of money we discussed in chapter 6 — invented money. It's creating value that lives on once we leave the building, value that multiplies the benefits to you. The essence of being an entrepreneur is to realise that it's about a choice, right now, a choice we can make today by embracing a new approach and philosophy. It doesn't require us to launch a startup or even run a project; the first thing we must do involves a simple attitudinal mind shift. This new philosophy may lead us to a point where we begin to create systems and have multiple customers. But it must start with the single entity that is us.

Venn living

In future our working lives will be based on portfolios of various income sources. You may remember the Venn diagram from grade 8 maths class. It's a useful way of displaying the possible logical relationships between different sets of information or things. It's most often represented using overlapping circles to show where two different things intersect (see figure 10.1). This is how we should view our various income sources. We should do this for two reasons: it ensures our income isn't contained in one undiversified circle, but it also informs us as to where our opportunities lie.

Figure 10.1 shows how I have used each step in my career to evolve how I earn revenue. The overlapping areas show how I leverage previous work to gain a foothold on the next step in my career. Although each step was logical, much of what I do today is worlds apart from where I started. It's all about finding the links between what you do today, and how it relates to what you want to do next. It's not about formal qualifications, it's about doing it, selling why you belong and then learning as you go. To this day, I plot where I want to go next (see the dotted line on the diagram). Any skill and career can evolve — it just takes the effort to have a crack.

We invent new types of revenue for ourselves through identifying how what we know in one realm relates to the next. Draw up your own Venn diagram, and see how you've used this technique already. Think of the skills and opportunities in the circles you are already in. How do they relate to where you want to go? Once you see the relationship between what you already have and what you want next, you can focus on expanding or leveraging that particular skill in order to build the next circle. Over time you'll drop circles off the Venn and invent new ones.

Speed, momentum and success

While we are on the topic of grade 8 maths, there's another, totally simple equation worth remembering. This one relates to momentum. We intuitively know what it means. We hear talk about people, businesses or trends as having momentum in a very positive sense. In mechanics, momentum is the product of the mass and the velocity of an object. The Sammartino definition is a bit simpler:

Momentum = how big something is × how quickly it moves

Hence the momentum of anything will increase if either its size or the speed it moves at increases. This means that to build momentum we only need to move faster. In life, in any of our projects or money-generation activities, we don't need to be ‘big' to gather momentum. A small thing moving fast uses its speed to generate momentum. At this stage, being small is an advantage. As the world is changing so rapidly, the small can change direction quickly and move more swiftly towards the future. Big things with a lot of momentum but very little speed often find it hard to change direction.

Big things, by definition, generally move slower, and big things are often facing in the wrong direction. Disruptive technology arrives at warp speed, which is why so many big companies are getting disrupted. It's not that they don't have momentum or power; it's that they move too slowly because of it. Long-time Fortune 500 companies have the laws of physics against them. As individual actors in the marketplace we ought to use this to our advantage.

So the lesson is straightforward. The most effective thing we can do to future-proof ourselves is to move quickly, because we are each small by definition (a single person). We know how slowly companies and most people move, so trying out more things more often puts us way ahead, at a time when knowing what's new matters more than ever, and it invents new money. By doing and learning things faster than others, we'll have the advantage of gaining momentum and progressing more quickly using the feedback loop.

The feedback loop

Mistakes are your friend. They are not the opposite of success, but the path towards it. They are part of the progressive realisation of success. The opposite of success is not failure but inertia, a lack of movement towards something we desire. In startups we often say it's good to fail fast and fail often, but this idea deserves some explanation beyond the rhetoric. Startups are trying to discover new business models, often using new technology. In this sense they differ from a small business, which I define as a business for which there is an existing, functional business model — like, say, a café or a local legal firm. People who start these businesses know what to do; they understand the business model and just need to execute it. A startup, on the other hand, is a discovery process. We are trying to invent something completely new, a system that can be converted into a bona fide business. So the more often we test ideas and they fail, the closer we get to finding out what works in the real marketplace. We can cross that misstep off the list and quickly move to the next idea, then the next one and the one after that. The shorter the feedback loop, the higher our likelihood of success. Every iteration moves it a step closer.

Everything we ever learn to do in life involves failure — think of important basic skills like learning to eat, walk and talk, and yet we had no fear of trying those things. It's ironic that we learned these skills before school indoctrinated us with the fear of failure. I was lucky enough to meet Australia's preeminent comedian, Wil Anderson, to record a podcast recently, and we got onto the subject of learning to be a standup comedian. If there ever was a calling that necessitated failure on the path to success, then being a standup comedian must be up there. Wil told me that once he had decided he wanted to be a comedian, he knew he had to go through a period of being bad at it. He did every gig he could, and would even drive an entire day to get a shot in front of an audience when the cost of the fuel for his car was more than he got paid. He knew it was just a matter of practice, in the real world, getting real feedback.

The cool thing is that when doing comedy you get feedback every few seconds on how well you're doing and if you are improving. So it's got the best feedback loop there is. This is what we should be aiming for with our work — the fastest feedback loop possible. This means not waiting for an annual review that might not turn out as well as we'd hoped. We need to invent feedback loops where they don't currently exist, and to ask for daily feedback on how well we are doing if it's not as obvious as it is for a comedian. The more frequent the feedback, the quicker we move up the learning curve. This is one of the reasons that digital firms can iterate so quickly and beat their industrial counterparts — all their user feedback is constantly tracked.

Whenever we connect with someone, publish to the web or do anything to enlarge our personal portfolio of skills we're sure to receive feedback. It's worth paying close attention to our own feedback loop not only to monitor how ‘the market' responds to our work, but to ensure we gravitate towards those who appreciate what we do so we enter a positive spiral of growth.