You’re going to fail!

The words still sting. It was five years ago. I was having an argument with someone who was significant at the time (long story, another day… maybe), which the curve of her eyebrows told me.

No cups were hurt during the making of that argument. But my ego took the full force of the verbal battering ram as it crashed into me over and over again. I was bruised and shaken.

What had I done to arouse this anger?

Simple: I’d made a decision to switch from a comfortable permanent job – the comfy, ‘never get fired unless you’re a complete idiot’ career path – to running a consultancy. Oh, and pouring my spare hours into learning the art of SEO and writing.

But not all at once.

My consultancy would be a side hustle. As would my other online activities (gotta love what you can do with the power words).

So, I started my own side hustle school (not THE side hustle school, that one is pretty awesome, and someone already owns the name). Hours were given to learning how to use words to influence and sell. Yeah, I’m still working on that part, but I am a pretty good public speaker – just ask Microsoft and the other companies I’ve had the privilege of standing in front of.

At this point we need to pop my ego and bring me back down to Earth. Falling, falling, falling…

I’m back.

My first task was to create a business that could replace my current salary. Fast. I work in technology and have skills that can be transferred (lesson number 1 to learn, unless you want to fall flat on your face). Building an IT consultancy seemed a more realistic option than becoming a farmer, or stuntman (my two original career choices).

SEO and copy would be tackled in stage 2 of the plan.

I think I’ve got a handle on SEO. It’s not complicated but needs a fair amount of explanation in order for the jigsaw pieces to fall into place. We’ll do that another day.

Writing was, and is, an easy skill to learn. In fact, you don’t need to learn anything – if you can put pen to paper you can write. But you might need to tweak your message and learn the art of entertainment.

At first, developing new skills can seem scary. Like lion taming. Without a whip, or chair!

Trust me – nothing could be further from the truth. Everything I’ve talked about so far is a skill that can be learned. Even lion taming.

You just need to break it down. Step by step. Until you become a hero in your chosen niche.

And I mean, ‘Hero’. Your fans will mob you, waiting to receive your words of wisdom (or pay for your courses, which is a much more appealing thought than simple fandom).

I can hear you already: James, why the long intro? When you are going to tell us how to start a successful side hustle?

There’s a reason why – it’s about the story. Every successful business, every method of making money online, or offline, comes with a story attached.

Recess is over – let’s get this side hustle school moving.

Lesson 1. What do you really want from your side hustle?

A vital question. If you choose a side hustle for the wrong reasons you’re going to be disheartened fast. Really fast. Like, a couple months after you’ve set up shop.

And that’s bad. For you. And your family.

Take your time and really think hard about what it is you want and why.

Most common reasons for starting a business, online or offline line include:

  • More money
  • Boredom in your current job
  • Worries about job security (because of the rise of automation and the recent COVID pandemic)

These are the top three concerns right now.

Whatever your reason, there is a real concern niggling in the back of your mind and you need to scratch that itch.

No matter what, you feel the need for change.

I’m with you on that one. The thought of freedom is powerful and dizzying and one you need to nurture like a small child.

Once you’ve found your ‘why’ – the reason for starting a side hustle – your next step is to consider what skills you have and any you’ll need to develop.

Lesson 1 Takeaway (TL:DR)

Find your why. This is the reactor that will fuel your side hustle into something amazing.

Chasing money may work for some people, but you need to be honest and ask yourself if it’s simply the cash you’re after.

There are many ways to side hustle. Find one that you can fit in with you lifestyle and family demands.

Lesson 2. The skills gap

I like to work in ‘the gain’. It’s a simple and powerful idea.

Every evening, when my tasks are complete, I spend 20 minutes journaling. During that time, I think back over the day and remind myself of what I have achieved. Nothing is overlooked.

What I’m doing is to remind myself of the progress made during the last 12, or 14 hours. This gives me a massive sense of agency, the belief I have in my ability to do what needs to be done in order to make progress with my plans.

Any ‘failures’ are noted. But instead of beating myself up about them I add the ‘failures’ to a backlog on a to do list.

Before we move on, I must add that there is no such thing as a failure. Each one is a learning point to be analysed and used to boost me to the next level. Let me explain.

Let’s say I have a schedule of three important tasks for the day. Over the course of the 11 hours, between 0730 (the start of my working day) and 1830 when I unplug, I work three these tasks. At 1830 the alarm on my laptop rings, I save my work and close the lid.

But I notice that one of the tasks wasn’t finished.

Do I beat myself up about it, curse my lack of efficiency?

No. Rather than make myself feel bad I look back at the work done and ask why that last piece of work was not finished. In most cases I find the expectations have been unrealistic. For example, expecting to write 10,000 words and balance other daily needs such as family and consulting work doesn’t add up.

Rather than feel down, I make a note in my journal, celebrate my achievements and relax for the day.

This process makes identifying my existing skills easy. It also simplifies the jobs of finding the gaps in my knowledge.

Once I know both my strengths and weaknesses, I can create a development plan.

So where do your strengths lie? What skills do you have and which, if any, do you need to learn in order to give your side hustle the best chance of success?

At this point, you need to sit down with an old. Fashioned pen and paper and start writing. Note down any skill you have. Don’t leave any off the list.

Go to a friend or family member and ask them to list your strengths. You’ll be amazed at the insights others have into you.

Here’s a list of marketable skills I wrote down before starting my side hustle:

  • Project management
  • Public speaking (it’s easier than you think!)
  • Disaster planning
  • Technologist
  • Cloud skills
  • Writing
  • Teaching
  • Mentoring
  • Leadership

That’s just a small set of the ideas I wrote down.

The next step is to work out where you strengths lie. Now, there is one key question: do your strengths lie in your current job – the one you want to leave behind – and do you want to continue to follow that path?

Let’s say your aim is to leave the world of permanent employment. You want to set up a consultancy. If your plans involve using your current skills and that you want continue in your chosen industry, then stop here.

If you’ve decided to ditch your current career path and map a new direction, then it’s time to dig deeper.

Your next steps will require you to look over your list of skills and choose one to form the basis of your side hustle. This will be an easy task for some, others might find it scary. Then you need to factor in any additional training required to build your hustle.

The key here is not to give up. You’re have already learned a trade so picking up new skills is easy, no matter how old or inexperienced you are. And you need to be prepared to put in the hours to grow your business and make money.

At this point, some of you will be screaming at your computer monitor. “Courses cost money!”

Yeah, sometimes.


The world has changed. Paid courses are all over the web. And the higher the earning potential the higher cost of the course.

Actually, that’s not true.

You can pay big ticket prices for online courses. As an alternative, you could leverage the power of free courses. MOOC (Massive Open Online Courses) give you the depth of knowledge that comes with a degree course, without the huge price tag (or a degree).

And you don’t have to complete the courses. Just learn the modules you need and move on. Then pick another course, and another, until you have the skills you need to take the leap into your own business.

MOOCs aren’t the only places you can learn for free. Free learning courses are dotted all over the web.

Here’s a list of useful places that offer free learning:

Lesson 2 Takeaway (TL:DR)

What skills do you have now that you can use as the basis for your side hustle?

How much time do you have to invest in learning new skills needed to build your business?

Use free learning resources to test your interest levels in a particular topic. If you don’t enjoy learning about the topic, take a moment to ask if your side hustle idea is right for you.

Lesson 3. Assessing the competition

“Enter a market with no competitors to win big!”


Maybe that will work for you, but it does require a huge leap of faith. When you build a side hustle in a market with no competitors you have no way of validating your chances of success. The only metrics available will be the ones you gather.

Having access to data about your market is important. How else will you plan and grow your business?

Sure, further down the line you’ll have figures, keywords and demographics available but having that information available at the start of your journey will make progressing easier. As will a hungry sea of customers from the start.

Even some of the biggest companies in the world were not first to market with their ideas. Google is a prime example.

Way back in time, when the many search engines existed, Larry Page and Sergei Brinn decided they had a business model that could compete, and win. The Google algorithm was, and still is, reliant on links. But the founders of the company added in a not-so-secret ingredient: quality (more on that later).

Within a few short years they had propelled their search engine to the most used in the world. Not bad for a side hustle. A few billion in the bank simply by putting in a few extra hours!

I’m joking. Google was a act of passion for the two men. And continues to be.

Page and Brinn dedicated thousands of hours to building a search engine that would go on to become a huge success.

And they did this by assessing the market.

Remember how many search engines were available in the 90s and 00s? Can you also remember the problem with most of them?

Quality of the SERPs.

Like Google, most search engines used the number of inbound links to rank a web page. Brinn and Paige understood this was a signal that could be manipulated, so they built in a quality check. At the heart of this check are a number of trusted domains and the closer your links are to the domains the higher the value of the link.

High value links carry more weight with Google and result in higher placement in the Google SERPs.

A quick example:

  • The US White House website is a trusted site. Get a link from here to your company selling Viagra and you’ve going to rank high in the SERPs.
  • If you get a link from a site like QuickPayDay hosted on Tripod, it’s not going to give you a boost.

This quality benchmark allowed Google to eat up the search engine market and become dominant.

Can you see having an existing competition is good? Well, as long as you bring the quality your customers will expect.

Lesson 3 takeaway(TL:DR):

Competition is good. Always look for competitors in your market.

To stand a chance of competing for customers you need to focus on quality. Excellence doesn’t guarantee success, but it will give you a head start.

Making money online, or offline, can be hard work if you don’t deliver on the promises you make.

Competition in your chosen market is good. It shows there are customers waiting and money to be made.

To make your side hustle a reality you need to focus on being excellent at what you do (just like Google did). The dark arts of devious marketing and underdelivering will guarantee you business (online and offline) withers and dies in a short period of time.

Lesson 4. How much time does a side hustle need?

How long is a piece of string?

More important, what are you going to use that string for? If you’re making a spider ladder because you really don’t want that poor arachnid going down the drain (or you’ll pee your pants at the thought of touching a spider) you can have the escape route up and running in seconds.

Let’s flip this idea around. Instead of helping a spider climb out of a bath, you want to save the lives of mountaineers by building indestructible ropes. If you are – great idea, go for it. Save lives.

Notice that last sentence: “Save lives.” Both your spider ladder and climbing rope will save lives. On requires far more investment and time than the other (no, not the spider ladder).

And it’s this time investment you need to think about before launching your side hustle.

Let’s stay with the rope analogy for a while.

How long would it take you to design and create a way of rescuing spiders? Seconds, minutes at most. It’s not complex and, if the rescue mission failed, you could always start again… maybe even use your arm and the let the spider skitter over your flesh on its journey to freedom.

Now contrast this approach with designing indestructible climbing ropes. For one moment, let’s put aside whether you could achieve this aim and think about the reality of the situation.

Your rope needs to live up to the promise. What will happen if it fails whilst a climber is making and ascent. The mountaineer could be trapped or injured.

Extracting them from the clutches of death isn’t as simple as cutting a new ladder from a ball of string, or cotton.

Your climbing rope needs to be designed and tested to the limits of endurance. Not by you, but by an official body (the International and Mountaineering Federation in this case. Check it out). Any failures will need to be addressed and fixed.

Once approved, you need to find buyers. Establish demand. Create your production line and start shipping.

These tasks require planning and a lot of hours invested.

Making a spider ladder requires way less work.

How much time does a side hustle need? Depends on the complexity of your project.

If life and work commitments are heavy, take a step back – maybe even down – and ask yourself what you can achieve in the time you have.

Lesson 4 takeaway

Ask how much time you have to invest in your side hustle.

What will you have to give up in order to make a success of your mini-business?

Lesson 5. When to quit your day job

Congratulations! You’ve built a side hustle, crammed it full of your time and excellence. The business has soared, unlike your competitors rip-off products that crashed and burned like the first Zeppelins!

You are ready to quit your day job and go all in on your hustle.

You’ve planned this day for so long. The letter of resignation and your leaving speech has been stacked up and ready for unveiling for months now.

And you can’t wait to close the door to your old life, open one that leads into a future that you have shaped. And own. That’s really important you.

Why else would you build a side hustle? It’s about the freedom, right?

But hold up.

This story is appealing, but you need to ask if you’re jumping the gun. Is your side hustle able to stand up to the full force of competition and will you be secure if those violent winds bring your business to its knees?

I don’t want to sound like the voice of doom and gloom. It’s a reality check. If you believe your side hustle now has enough muscle to go head-to-head with your biggest competitors, for 12 rounds, then it’s time strike out and leap headfirst into the frothing seas of entrepreneurship.

Now, for a moment, let’s assume your business needs a little more work in readiness for the day you say, ‘au revoir’ (just adding in a little French to add to the ‘sophistication vibe’).

What questions do you need to ask before you quit your day job?

It’s about the money. If you don’t have enough profit every month and a good reserve to fall back during lulls in trading, then keep the day job.

Only when you’re sure your finances can told an otherwise knockout blow on the chin should you think about going all in on your side hustle.

And when that day comes, you’ll no longer be side hustling – you’ll have a business that can sustain you, or maybe even bring about huge change in your life.

Lesson 5 takeaways

Quitting your current employmnet is a big step. Before you leap ask yourself if your side hustle is ready to the place of your day job.

Can your new business compete in the marketplace?

Do you have financial reserves that will support you during times of lean business?

Wrapping it all up

On your journey to building a successful, profitable, side hustle, don’t leave the people you love feeling like they’re not wanted. If nothing else, taking them on your journey will save you a fortune in broken crockery!

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