How to start a Side Hustle while working 9-5

June 11, 2019 / Comments Off on How to start a Side Hustle while working 9-5

What is a side hustle?

A side hustle is a way of earning some money outside of your 9 – 5 job and it can be something you want to do to just to increase your income or something you want to use to build or test a business idea that will let you ditch your job and fire your boss!

Many jobs today simply don’t pay the bills and with the nature of the economy, people are living in fear of their jobs, and pretty much everyone today knows that there is no longer the idea of a job for life.

In fact, I would argue that we are moving more and more to a gig economy giving more power to freelance workers as more and more companies will be outsourcing job roles simply because it makes more commercial sense and creates more efficiencies.

Here are 50 side hustle ideas from entrepreneur.com.

tips-to-start-a-side-hustleI am not going into specifics regarding the side hustles you could start, I am just going to talk generically about starting one as I believe each type of hustle really needs its own in-depth article and I will look to add these in the future.

I’ve seen many people jump in and start to do something online, for example, only to abandon it later for one reason or another and simply waste time – on the other side I have seen some blatantly break their terms and conditions of employment and who have ended up with a lawsuit filed against them from their former employer, so things to need careful consideration and I am going to cover the big picture here.

How To Start Your SIDE HUSTLE! ft. @chrisguillebeau

Tips to start a Side Hustle while working 9-5

Before you fire your boss, let’s look at a few important issues and we will cover:

  1. Doing A Personal Audit
  2. Check The Legal Implications
  3. Financial Goals
  4. Making A Plan
  5. Getting Started
  6. Websites, Technology, And Random Things

So let’s begin:

1. Doing A Personal Audit

It is extremely important to conduct a quick review of your real passions, skills and what options you have to turn those passions and skills into income.  You may not like your job and desperately want to leave, but what are the real compelling reasons?

For example, I have spoken to thousands of people in my career as a recruiter and while so many are really unhappy with their jobs, they actually love what they do – are you in that category for example?  Also for most, it wasn’t about the money and more about other things such as flexibility of hours, working location and being given the freedom to get on with their jobs and not having to deal with an overpowering or interfering boss.

I know you want to get on and start your side hustle, but it is important to understand why, as running a side hustle requires drive and commitment to get started and both of those qualities require passion to fuel them.

So a great place to start is to sit down and work out what your passion(s) is or are – it is not always possible or easy to earn an income out of your passion, but it is a great place to start and many people do.

Take stock of your C.V./Resume and update it – treat this as a new job application albeit for yourself and look carefully back through your life and work to find out what really motivated you and ask yourself the following question:

If I were to start my career over, would I choose the same career path again?” 

It’s a question I ask everyone regardless of what they want to do in life and so many people answer with an immediate “No” to the question and very quickly come out with an alternative and this could be one way to start a side hustle for example.

The important thing here is to think things through and start to work out what is really driving you and also think about issues that are burning deep inside you as you may want to start to voice these and build up a following, which is very possible in the Internet economy we are firmly in today.

Other things to consider here are how effective a communicator you are and what method of communication do you prefer.  I love writing and I would have loved to have been an author if I had my life over again, so now I love blogging and my passion is all things business, hence this blog, but I also have other passions such as cooking, wine, golf, sport, reading and Martial Arts to name sone, so I could easily see myself writing about those in the future.

But I don’t mind doing videos as well – it is important you dig deep within yourself to make sure you know where to start in communicating your message, which will be essential if you want to start a side hustle and build a long term business for example.

This aspect is far less important if you want to start FOREX trading for example.

2. Check The Legal Implications

It is a much better idea to fire your boss than having your boss fire you and in certain circumstances being able to pursue you legally, if you have broken anything in your employment contract here in the UK and if you are in the US, then look here.

In any event, there will probably be some rules of employment and you need to look carefully at them to make sure you don’t breach anything.

In the recruitment/staffing industry, it is commonplace to have a non-compete clause and I have seen many people fall foul of this by blatantly trying to set up companies while they are still employed.  All that happens here is a stroll down ‘legal lane’ and that is good for neither party.

Make sure that you will do nothing to conflict with your current job and it may pay you to take legal advice.

I employed many people around the globe and I had no problem in people doing what they wanted outside of work as long as it:

  1. Didn’t affect the job they had when they were working for me
  2. Didn’t create a conflict of interests by doing something that would compete with what they did for me

But that is my view and I am not your boss!

You have to be very careful here because if you go out and start a website and a company, for example, the information will become public and I know many employers who often check public registers if they become even slightly suspicious of any employee.

I know of people who also try to start something and put the website and company in their partner’s name and while this creates a ‘step-away’ from the person who is starting the business, it will arouse just as much suspicion as if they just went out and started a company themselves.

Remember, you have a duty to your employer to do the work you are paid to do and in a professional manner, so please be aware of that.

I will give you another example that on the face of it, should not have created any problems for anyone but it did – someone I know wanted to write short children’s stories and that person went to their boss, explained what they wanted to do and further explained that most of the writing would be done at weekends and a few evenings.  The boss said that the company would be concerned that it would consume too much of the persons’ leisure time and could affect their work – this was of course dismissed by the employee and the real reason for concern came out and that was the fear of losing a good employee if their venture was successful!

Please don’t think for a second that I am trying to discourage you – I am not, I am simply asking you to think through the steps and I must also add that I cannot offer you any specific advice because each situation and each employer is different.

3. Financial Goals of starting your side hustle

A side hustle will cost you some money and although it can be done on a shoestring budget, you will incur costs and those include setting up a website, getting hosting and it is something that I and Fernando Raymond bang on about all of the time and we take it a little further and recommend everyone to start a blog to get an online presence which of course is perfect for your side hustle.

Now let’s take a look at your financial goals – do you simply want to earn a few hundred extra pounds a month or are you looking to go all out and start a business?

When I talk to people about making a couple of hundred pounds a month extra, some scoff at the idea because they think it’s not serious money – but for many it’s a grocery bill, a car payment or a significant amount to their mortgage and it all adds up, so don’t feel that you have to go out there and make millions, just think about what your real financial goals are and then go after them.

If you want to start a real business then starting a side hustle is an excellent way to begin and here as I advise everyone, you mustn’t just start something for the money – I cover starting a business in the UK for example here, so take a look and use it to help you.

If you are passionate about what you do, then the rest follows including money, but passion does not always turn into income, so make sure there is a market for what you do, and that follows nicely into the next phase…

4. Making A Plan

Whatever you are going to do, you need to make a plan and it doesn’t have to be a full-blown business plan because this is a side hustle right?


If you are going to do some freelance writing, then you need to plan out things like:

  • Who are you going to write for and what frequency?
  • What software do you need and what is the format for your writing?
  • Who is going to check your work before submission?
  • How are you going to charge and be paid?
  • What happens if your work scales up or down
  • How much time is it going to consume
  • …and I am sure you can think of more

If you are looking to start a side hustle and turn it into a full-blown business, then for me, it is better to write a proper business plan from the start and I cover this in another article here, so take a look at the part about business planning.

You have heard the phrase – “If you fail to plan then you plan to fail,” they are wise words that many people simply know, but don’t hear and I should know from bitter experience – many a time in my youth I jumped in feet first into a business without giving it any real consideration, simply because I thought I knew it all.

Don’t make that mistake and here we are only talking about a side hustle!

Finally, let’s talk finance – whatever you do I would strongly advise you not to go into any type of side hustle and take on debt. I know you may think about the words ‘speculate’ and ‘accumulate,‘ but remember, even if this is going to be a full-time operation, you are still starting a side-hustle and while you may not mind failing, you will certainly not like debts.

Only start and side hustle with money you can afford to lose.

5. Getting Started the side hustle

I will give you a real-life example here and it is about someone who used to work for me heading up the marketing for my companies and he was also a business partner in another joint venture and his name is Jack Spirko who built up an extremely successful podcast called the survival podcast.

The podcast has been going since June 2008 and you can hear the first episode on the site and let me explain how he got started.

Jack was always passionate about survival and preparedness as he defines on his site and at the time, he was living in Arlington, Texas and our offices were in Frisco.

The commute was horrendous and something we both addressed when he came on board and I was prepared to be lenient in working hours to compensate for this although Jack never took advantage and routinely put in the hours.

We had always discussed how people in any company should be allowed and directly encouraged to start their own side hustle because we wanted people to break free of being tied to jobs and it may encourage employers to treat their employees with more respect.

To lessen the cost of the commute he purchases a second vehicle and a rarity in the Dallas Metroplex and that was a Volkswagen diesel Jetta, I think from memory and his commute took him on average one and a half hours each way, simply due to the traffic.

He actually launched his podcast from the car and during the journey, turning three hours of previously wasted time into potential profitability!

Smart move!

We all waste so much time in our lives and I know I have done and still do, so the first thing you can do is to work out where this time is wasted or not used efficiently.

Ditch the evening T.V. or the pint at the local pub and put that time into your side hustle and it’s amazing what you can actually achieve – you are going to have to make sacrifices and even if you are just buying and selling on eBay, it requires time if you are going to be successful.

Jack has turned his podcast into a successful business in its own right and one that gives him a significant income, but it has taken a huge amount of hard work, effort, and commitment and I am sure there were times where he wanted to quit, but it is not in his nature and success didn’t come overnight.

Along with the podcast itself, he has retreats at his farm, where people can learn how to become self-sufficient and I have been to one and seen the amount of effort he and his wife Dorothy put into it, so please don’t think it will be easy and I use Jack as an example because I have personally seen it start, witnessed the growth and the effort first hand, plus I always try to showcase real examples of everything.

So get to it and find some time you can put into what could end up changing your entire life.

6. Websites, Technology, And Random Things

I’ve said it so many times – everyone should have a website to at least get an online presence and build a personal brand.

It is an essential component of today’s life in my opinion and the reason why all of my children have their own domain names.

Talk to Fernando and let him explain to you how he can help you with all things web-based including design, hosting and marketing.

To technology – you are starting a side hustle so your time is precious so make sure you make full use of all of the technology available.  It is beyond the scope of this article to go into technology specifics, so look at this article to get an idea of what’s out there from a ‘big picture perspective’, and here’s another one looking more specifically at small businesses.

Remember, you are working for your audience or customer and keep things as lean and as efficient as possible.  Spend money only on what is necessary to improve your customer experience.

If it doesn’t ‘touch’ the customer then don’t touch it!

Start small and think big – just because it’s a side hustle, doesn’t mean you don’t want to think big and obviously, this doesn’t apply as much if you are simply looking and limiting yourself to earning some extra cash.

But side hustles can turn into huge businesses as you can see from the article.

To me, your mindset is the most important aspect in any business and you must have a ‘never quit attitude.’

Many successful entrepreneurs and I included have faced extremely challenging events and some that would have floored most people, but we have to simply keep going and you must have that same attitude. When things get tough, most entrepreneurs start to ‘wake up’ and some actually relish the challenge.

As much as you have to work, you also have to rest and it is important to rest in order to keep the creative juices flowing – for me, I love to watch comedy shows and laugh, or go out and smash a few golf balls at the range to get through a moment of frustration.  we all have our own ways of dealing with things and I do actually believe that stress in one of the most overlooked factors in everything – if it affects your mindset, your health, and your ability to function, so take time out to relax, but not too much!!

Involve your partner and your family – you may find out that they can provide some very valuable input and also it will make them feel part of what you are doing.  I’ve seen many entrepreneurs who shut out their partners and families and to me, this is a bad idea, especially when things go wrong as there is a tendency to ‘bottle things up inside’ and that just leads to stress.

Expect things to go wrong – they will for sure and it is better for things to go wrong in a side hustle than a full-blown business because you have a better chance of damage limitation and to put things right.  If you are involved in something like FOREX trading, like many people are being in my opinion wrongly lured into today, then you absolutely must manage your risk.  Even professionals get this art so wrong, but they have the security and backing of their Bank or company to support them, plus they earn an income and the worst they will suffer is being fired.

I know someone who uses FOREX trading to pay for his summer vacation and he trades very carefully, with small amounts and limits his losses – he has done extremely well to pay for his last three vacations.  Equally, I know of many who lose entire fortunes, so be careful.

Whatever side hustle ideas you decide on, make sure you choose it carefully and operate it for the purpose you decided to.  If things change and you want to scale it then fine, go ahead.

Most importantly, enjoy it and the journey!


How A Side Hustle Can Change Your LIFE


  1. How to start a business in the UK (Steps to starting your business)
  2. 7 Things to consider before starting your own business (can you do it)
  3. How to create a business that runs without making you a slave to it
  4. Starting a blog on WordPress: Why I decided to start a blog on WP (This blog)
  5. How to start a Digital Marketing Agency

Last modified: May 29, 2020