How To Start A Side Hustle?

The straightforward answer to this question is essentially the same as the Nike slogan. That is, whenever it comes to starting anything, you “just do it”! But, I know that obviously doesn’t fully answer the question. However, I do think the biggest takeaway thought, in the end, is that you just have to take action when you want to achieve something or work towards any goal you may have. Doing nothing automatically yields nothing.

My first proper job was working at McDonalds as a 15 year old. Still to this day, it’s my 2nd favourite job that I’ve ever had. By the time I turned 18 I was promoted to a management position at the local fast food store, and since then I’ve always been in positions of running businesses in some form or another. But never have I ever run a business or done anything where I’m working to earn money directly for myself. I’ve instead been in positions where the company I’m working for makes (often good amounts of) money and I, like most people, just get a comparatively small salary in return for my efforts. Starting a side hustle gives you at least one more option when it comes to earning money for yourself or in my case, for my family.

The old stomping ground – Lincoln Rd McDonalds.

But getting back to the question, how do you start a side hustle? Well, I can’t say that I have all answers, but over the last 3 to 6 months I’ve started the journey to answer this question myself. So, why don’t I give you a few of my findings as I’ve begun looking at my own gigs, whilst currently still working in my C-level management role (in IT). Let me try and answer a few subsequent questions along the way:

  1. Why even start a side hustle?
  2. What could you do?
  3. What am I currently looking at getting into?
  4. What’s the best advice I’ve heard on starting a side hustle?

What’s your WHY? Why even start a side hustle?

For me it’s fairly simple – I want to be in a better position to support my family. I read a article recently entitled “What Is Your Why?”, which was about how to find your purpose in life. You could easily find a dozen of these articles with a single google search. This one gave some useful tips to formulate your reasons to get up every morning and attack the day!

Now, I’m not really one of those guys that bounces off the walls when you meet them. I’m not really super ambitious. I’m not even much of a morning person. So, when it comes to answering: ‘Why even start a side hustle?’, I think it’s important to have a solid reason, or even better strong reasons, plural, that are compelling enough to take action; to at least get started. Constant progress towards your goals is what I think is key. For me, I just want to get to the first step, then look at what the next step is, and make sure I have compelling reasons that keep me continually stepping ahead.

Thankfully, to date, I’ve been able to live fairly comfortably whilst having only a single source of income. But it’s certainly time for me to make some changes. Because, as fast as my kids are growing up, I’ve quickly come to the realisation that:

1. I need to optimise the time I have to generate income for my family.

I’ve heard it said that time is our most precious but limited resource. So, we need to make sure we’re using it as best we can. I’m confident also, that the more time I’m able to devote to these personal endeavours, the more I’ll get out of them.

2. I need to (and want to) create some level of freedom & financial independence.

I know that saving is ‘a’, if not ‘the’ key to financial freedom. But I also know that once you have kids, saving can automatically become far more difficult. So, I see starting a side hustle as an obvious way to gain some additional income in order to be able to away more of it in savings and other investments.

3. I’d like to have more control around the things I do, and gaining this control includes influence over the enjoyment I get from doing it.

I mean, who doesn’t like the idea of being their own boss?

What could you do?

Running a Google search or two will give you an endless list of ideas. But even without Google, you may have ideas about doing certain things that you already know how to do, but doing them for yourself instead of working for others – that is, doing things you already know how to do as an income generating project for yourself.

Along with what may come up on your various Google searches, specific sites like (created & run by Chris Guillebeau) has tonnes of ideas and resources to inspire and assist you along the way.

The thing to remember is that in order for any venture to make you money you need to make an exchange of value. You will either have or you will need to create something of value that someone else will exchange for payment of cash. If you ask Chris Guillebeau, he’ll tell you that some of the ways you could do this is to sell a product, or provide a service or become a reseller or become an SME (subject matter expert) or create affiliate income or host events… these are some of the broad categories within which the list of possible options seems almost endless.

In relation to the time restrictions and other considerations from above, you should also think about creating assets that bring in passive income for you – that is, doing work up front to create something which in the end brings in income that isn’t directly linked to your time. If you’re able to do this, then you can literally make money while you sleep. A couple of examples of this may be writing a book or you might build some online courses. Once you’ve created those types of products, they are able to sell without you having to necessarily add much more (or maybe any more) time to the money making process.

One more approach I’ve come across in this space is acknowledging that a place like New Zealand is quite a small market. So, if you’re able to market yourself online in some way, it can and should immediately broaden your audience. A store in my street could ordinarily only sell to people that can physically make it to the store. But having an online store means that you could sell to essentially anyone with an internet connection & a browser. Having lived in New Zealand my whole life had made this concept a little hard for me to conceptualise initially (being quite accustomed to the environment in which I live – 1.5M people in Auckland or 5-6M people in the entire country vs billions of people across the globe). But certainly, this concept makes a lot of sense.

What am I going to try?

Having worked in IT for the past (roughly) 10 years it’s seems natural to first have a look at some online ideas of my own. I also have the benefit of a few close friends who, at the minute, are eager to partner together to start a small business.

Doing things on my own compared to working with some friends as partners requires taking some different approaches. But each of these slants creates a bit of variety; some different options for me. Although I have some confidence in the journey I’ve begun, I’m not naïve enough to believe everything I try will be a roaring success. One of the main challenges for me will be juggling my time across an already busy life, whilst looking to add some ‘money making hobbies’ with increasing pressures on my limited time resources as I move through to the new year (2023).

I’m also not naïve enough to think that I’ll be making money in these ventures right away. In fact, I’d be surprised if I’ve made any money before June of next year. But putting much of this together: for now, just getting started, and being able to keep chipping away at it is my priority. As Robert Kiyosaki, the author of ‘Rich Dad, Poor Dad’ says (and I’m paraphrasing), “If anything, fail quick, and learn from it”. It will take a little while to build up these ventures. So, 2023 will make for an interesting year for me.

What’s the best advice I’ve heard on starting a side hustle?

It would be nice if it were something along the lines of: “Find something of value that you like or even love doing, and figure out how to get paid for doing it.” But I’m not really sure if everything I love doing can actually be monetised.

So, instead, I think the best advice I’ve heard is around:

  1. How to overcome some of the natural fears you may have, particularly in getting started?
  2. How to get past the obstacle of not having enough time to start a side hustle?

I think for most people, if not everyone, when you start something new – particularly if it’s something you’ve never done before – it’s natural for fears to creep in. It’s natural to start asking yourself, what if this fails? What will my friends think of me if it fails? What will my family think of me I start this new venture? This new thing may seem like climbing Mt. Everest – how on earth do I climb Mt. Evervest?

The strategy to adopt when you have these thoughts is to think instead about all the things that you’ll gain if you succeed. Or even better, you ought to think of all the pain there would be from not doing this. How would you feel 5 years from now, or 10 years from now, or maybe 80 years from now if you didn’t even start? It’s often the case that the benefits outweigh the drawbacks. So, create bigger fears around not acting rather than taking action.

You can boil down the 2nd obstacle by simply realising that if it’s important to you, you’ll make time. So, if you don’t make time for it, then it’s obviously not important enough for you yet, and you probably need to revisit or properly figure out ‘your WHY?’ The things you make time for are (at least on some level) what’s most important to you.

I hope some of this has been a helpful read. Remember, even if you start small & build, just make sure you start. Be willing to make mistakes and learn from them. I don’t know if I believe in luck, so if you’re starting a side hustle of your own like me, then let me say to you, “all the best”! I’m wishing you all the success in the world.

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