Blog Post

What is a side hustle?

Janet Doran • Aug 26, 2018

Side hustle definition: A part-time job or occupation undertaken in addition to one's regular employment. E.g. ‘he started the blog in 2013 and has continued it as a side hustle’ (Oxford Dictionary)

So, I checked and yes the term 'side hustle' is in the Oxford dictionary but is it just me, the term still sounds somewhat underhand or not quite legal?

After all, if you look up the word ‘Hustle’ in the dictionary it’s derived from American slang with the definitions including pushing or forcing someone into doing something, selling aggressively and fraud (‘Hustler’ is even worse!)

This perception isn't helped by articles such as '10 greatest side hustle ideas to earn $1000 per month' whose suggestions include network marketing schemes or becoming an 'Instagram influencer'.

Maybe its a generation thing, as today the term is becoming more common, with people embracing the concept of having multiple sources of income from part time jobs to selling their handmade products, buying and selling on e-bay, even renting out your spare room could be termed your 'side hustle' as it supplements your main income.

So, whilst I dislike the terminology I thoroughly recommend the concept, particularly for anyone planning a career change into self-employment or freelancing.

Before you quit your job and take the leap into working full time on your own business, starting to generate income from your new venture is essential. This enables you to check your understanding of customer needs, and to test, then refine your offer - fundamentally to prove that what you plan to offer is actually something that people want to buy, that you know how to find those customers and how to convince them to buy it from you – to create your business strategy.

(Don’t be put off by the term strategy, although it is typically associated with big organisations basically your strategy is ‘How you will compete - where to play and how to win’.)

I also recommend that you consider how to retain your old day job, in some form of 'side hustle' to pay the bills in those early months whilst the new business gains momentum.See the conversion from employed to self employed as a transition, if possible, rather than a step change.

The temptation for a new business venture is to spend time and money making sure everything is 'perfect' and then launch, however there is a well known saying ' no strategy survives first contact with the enemy ' and whilst the origins are in warfare, it is also true that no business plan ever survives its first contact with a customer. Market research and gathering feedback will only take you so far - the real test of any business plan is getting people to actually commit and spend their money.

So, a ‘side hustle’ is a great concept; slowly building your business, getting the idea out of development and in front of potential customers, testing and refining your offer, after all

“Things may come to those who wait… but only the things left by those who hustle”*

(*This was falsely rumoured to be said by Abraham Lincoln, not sure of the true origins but it’s such a good quote I couldn’t help but include it.)

If you want help planning out your own side hustle to maximise the opportunity for building a sustainable business, please get in touch.


Janet Doran, is based in North Yorkshire, UK she works with freelancers, sole traders and small business owners helping them to answer questions such as ‘how can we stand out from our competitors, attract customers and win new business?’, developing business strategies to create sustainable Competitive Advantage.

Find out more at www.thepositivepen.co.uk or call 07505 120051

Follow me on twitter https://twitter.com/thepositivepen


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