Are these Side Hustle obstacles holding you back?

Financial Autonomy - Blog
Are these Side Hustle obstacles holding you back?

A Side Hustle can be a hugely significant stepping stone in you gaining financial freedom and choice. They’re a fantastic way to develop new skills and broaden your network, both of which help enormously in your income generating resiliency. And of course, they can have a financial payoff as well.

But like most things in life, valuable and easy don’t sit comfortably side by side. Whether it’s the challenge of getting started, or keeping all the plates in the air once you’ve gotten the ball rolling, succeeding at Side Hustles is tough. In this post we’ll take a look at the various Side Hustle obstacles I’ve come across and offer some ideas as to how you might be able to overcome them.

Time Management & Life Balance

Most people who start a Side Hustle have a full-time job, whether a traditional paid role, or the often more demanding role of taking care of children at home. Figuring out time management and ensuring a balance exists that enables you to have a happy life whilst also pursuing your goals is an important consideration when mapping out your Side Hustle strategy.

When choosing your Side Hustle, consider whether you want to do something similar to your day job, or completely different. For instance, if you’re employed as an accountant, you could likely easily set up a Side Hustle venture doing individual tax returns of an evening and on the weekends. The benefit of this type of Side Hustle is that you already have the skills and experience and so can slip into it easily. But the significant pitfall is that it becomes just an extension of your normal workday.

A key attraction of doing a Side Hustle for a lot of people is the variety, the change from their normal 9 to 5 role. Pursuing a Side Hustle that is essentially a continuation of your day to day job is far more likely to lead to burnout.

If your primary goal with the Side Hustle is to earn extra money and earn it fast, then taking on an extension of your day job perhaps makes sense. But if, as is the case for most people, your Side Hustle is as much about enriching your life as it is about the financial outcome, a better approach is likely to be a Side Hustle that is completely different . So for instance the accountant who sells antiques on Etsy as a Side Hustle. I used to have a boss who worked in finance during the week and then on Saturday’s worked for a bookie at the horse races. When I asked him about it, it was clear that he did this side gig as much for fun as for the money. The fun and variety perhaps even outweighed the financial motivations.

When choosing the Side Hustle that you will pursue be really clear on the time you have available to commit to it and use this as a filter to help decide which ideas are worth pursuing and which should be discarded. Something like tutoring for instance is good in that you will likely have a regular booking and you can work your diary around that.

Some people however would prefer something more flexible, so for instance copywriting or freelance writing where you’re given a task and have a week to get it completed. The task can then be tackled whenever you have the time and energy.

Side Hustles have a wonderful variety of roles and methods of getting them done. Thinking through your time constraints and how you balance life is very important.

Another element of life balance is personal satisfaction. Research published in the Harvard Business Review found the attributes of work that give us the most satisfaction are:

  • Having the freedom to schedule work
  • Making decisions and choosing how to accomplish a given task
  • Seeing things through from beginning to end
  • Work done has significance for the other party
  • Receiving timely feedback
  • Variety of skills needed

Side Hustle gigs are often perfectly placed deliver on these attributes. Even something as simple as doing some Uber driving on the weekend could tick most if not all of the boxes.

Under Pricing & Imposter Syndrome

We all want to be liked by those that matter to us. Sometimes this desire, when folded into a Side Hustle can lead to under-pricing. Because you’re dealing directly with the end consumer typically, and you want to feel like you’re providing them with great value, it can be easy to feel that you need to provide your services at a price below what the broader market is charging.

Linked to this common desire is the phenomenon of the impostor syndrome. This is where you lack some confidence and therefore feel that you need to undercharge, either to win the business or to deliver sufficient value for your customer.

There are two dangers with under-pricing. The most obvious is that it costs you more to deliver the service than you charge. For example, you offered to paint someone’s house for $5,000 but by the time you pay for the paints, scaffolding etc, it costs you $6,000. Clearly a disastrous outcome.

More commonly though, you’re not losing money through the under-pricing, but you’re not sufficiently valuing your time. Initially you’re excited just to get the work and gain the experience, but pretty quickly you come to resent the time you’re having to give, and the pittance you’re receiving in return. You lose motivation and drive, and your performance or service delivery reflects this. You end up with an unhappy customer and an unhappy you. A complete lose lose.

To avoid this pitfall firstly have a clear understanding of your costs to deliver the product or services within your Side Hustle. Don’t forget things like bank and credit card merchant fees, equipment hire, insurance , stationary and the like. They all tend to be small expenses but they add up.

Next reflect on what your time is worth and what it is you’re trying to get out of this Side Hustle. If you believe you have 10 hours a week for instance that you can give to this endeavour, how much do you need to earn to feel this is a good use of your time? You can then potentially overlay that with the going rate for the service you’re planning to launch, and if there’s a big gap you might need to consider a change of tack. So for example if you were planning on starting a Side Hustle providing drum lessons for kids, and you determined your required hourly rate to make it worthwhile was $100 an hour, but found that everyone else advertising these services was only charging $40 an hour, then maybe you need to come up with another plan.

A side note on this one. Where the primary motivation of you starting a Side Hustle is to gain experience, it may be totally viable that you offer your services free of charge to a community group or other not for profit. This is totally valid and highlights the importance of being clear on your why.

Finding the Perfect Idea

If you look at any Side Hustle themed Facebook groups or Reddit threads a very common question goes something along the lines of “I want to earn $5,000 a year in a side hustle but can’t think of a good idea . What should I start?”

For a start I think this question has things ass about. The financial result of your Side Hustle will be determined by the success of your idea and probably the time you put into it. It’s certainly reasonable to have a financial goal but I believe that should be worked out as part of your Side Hustle planning process not an initial parameter to then work from.

Often the comments delivered on such a post are something like “just start anything and give it a go”. The pointlessness of the original question perhaps warrants such an equally pointless answer, but given this problem is so frequent let’s see if we can be a bit more constructive.

In Entrepreneur You – Side Hustle Edition I propose 3 questions that are worth considering in helping you find a Side Hustle idea to try:

  1. What do I like doing?
  2. Who do I like working with?
  3. What do other people ask me to help them with?

Perhaps most importantly, avoid fixating on the perfect idea. Side Hustles are about learning. Mistakes and pivots are all part of the experience. There was a great quote I heard some time back that I think is really relevant to people looking to start a Side Hustle. “Some opportunities aren’t evident until you are in motion”.

Need some Side Hustle idea inspiration? Download our 50 Side Hustle Opportunities for Australians


For me the number 1 benefit of starting a Side Hustle is the experience of operating a business. If you’ve read my Financial Autonomy book you’ll know that one the pathways we explore to gaining choice is running your own business or being self-employed. All three pathways – stocks, property, and self-employment, came from my observations after having worked with clients for over 20 years, and reverse engineering what it was that put them in a place of having gained choice in life. The self-employment pathway has been the one I’ve received the most feedback on. There are plenty of books espousing stock and property investments, but seemingly very few that highlight the wealth creation potential of operating your own business.

Now I recognise that when you start your Side Hustle, you likely have some other more immediate goals in mind, usually to do with money. Paying off the credit card or car loan, saving for a holiday, or building an investment portfolio. These are all great motivators, but recognise that Side Hustles don’t always work out exactly as planned. Even if the financial benefits you had hoped for don’t materialise, the time and effort you’ve put into building your Side Hustle won’t be wasted. The skills and experience learned is an asset you’ll have forever.


Useful Resources:

Entrepreneur You – Side Hustle Edition

50 Side Hustle Opportunities for Australians

18 ways to Build Passive Income that work in Australia


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