I’m not going to tell you setting up a side hustle is easy

A woman working at her laptop at midnight

It’s not easy at all, in fact it’s bloody hard, it’s nerve-wracking, it’s doubt inducing, it’s downright terrifying. For most of us, it is so far outside our comfort zones that most people will slam on the brakes and return to their “comfort zone” instead. I used inverted commas on ‘comfort zone’ there because it’s not comfortable at all, it’s just easy. Easy to go to work at someone else’s company and draw the salary each month to pay for all the things you’ve grown comfortable with having, but you still bitch about the boss and the way the company does things and you still fantasise about how you would do things differently if it were your company, but it isn’t and it never will be unless you step out of your fake comfort and realise your dreams.


Personal Experience

I became permanently self-employed in 2008, before that I had a permanent job and several temporary fixed term roles. I’ve always liked the variety of being self-employed, because I get to manage my trajectory within the industry and therefore my salary too. I was contracted into various financial services organisations and worked with many, many wonderful people but I came to realise that while my contract work may be underpinning the cultural and regulatory changes needed in the industry, it wasn’t exactly changing the world and many people within the industry felt the same way and were looking for more. So, I started my side hustle, Coaching, back in 2015 while I was contracted full-time. I was working on my Coaching business (Ahead Together) in the early morning, evenings, weekends, during my lunch breaks and holidays.

Below are some of my key personal learnings from setting up my side hustle, hopefully they will help you to set yourself up for success from the start by knowing some of what to expect.

It is tiring and impacts on your home life

Adding a side hustle was not easy, I was often exhausted from work and still needed to review my website copy, write blogs and creates designs in the evenings or talk to clients on the weekends or very early mornings. But it also energised me, because I knew I was making a difference to other people’s lives and helping them to be happier and find a more fulfilling path.

If you have a family or a partner, it can also place a strain on the relationship because suddenly you’re all in it together, even if only you are working on the business. You need to involve the people in your life, you will all need to make compromises and you cannot expect your loved ones (or your clients) to read your mind. Sometimes your closest loved ones can seem hyper critical about your business and your dreams, but this can be a fear of them not seeing you enough and a concern that more work for you in your business, means more work for them in the home. Set goals together and work out your compromises early.

Remember your business needs to fit in with your life, so you need to communicate well with those around you and you need to set boundaries for yourself, your business, and your clients.

Don’t break promises to your family, if you say you’re not going to work on Saturday afternoons so that you can have family time together, keep the promise otherwise their resentment towards your business will grow.

Be wary of time theft

Completing work for your own endeavours, while being paid by a company to be working 

A golden carriage clock about to strike midnight

 on theirs is time theft and you can be sued and fired. While you sometimes may need to make calls relating to your side hustle during company working hours, you must wait until your breaks. You can take phone calls, send emails, or respond to texts during your scheduled breaks from your job. Just as you would check on your kids, or go grab lunch, these things should be done on your time, not your employer’s. Respect the division and remember that your main job is fundamentally enabling your side hustle.

Set your working time

It is 100% ok to determine your own working time. In fact, that’s one of the major draws of working for yourself, if you want to take Wednesdays off to go trampolining with your dog, that’s your business – literally. You don’t have to explain to anyone what schedule you set or why. Your working time is yours to explore, it’s yours to fit into your life in whatever way you need it to. Communicate your working hours to your clients and your family.

It can be lonely – get support

Working for yourself can be lonely, especially if no-one else in your home understands what you are working on, or you live alone. Aside from being lonely, I found if I didn’t have my network and my fellow entrepreneurs to lean on and be held accountable by, I would work until 1am most nights. I would be isolating myself more and more, becoming increasingly lonely. It’s a catch 22 to be honest, so getting the right support for you and your business is essential.


A support network of 7 surrounding one person in the middle

I have a Mastermind that I attend every Thursday and we are in constant WhatsApp contact, to discuss all things business, ideas, and frustrations. Often it is easier to come up with ideas for others than for ourselves, so this group is massively helpful. I also have an accountability partner, an accountant, a web designer, a backup web guru, a coach and a virtual assistant to make things to easier for me and my business. And I use ClickUp to keep me on target in my projects and annual sprints, even better is that it’s free.

The right support is paramount to the success of your business, because in the moments of doubt or when you lack clarity, they can turn everything around for you, especially when your inner critic is being a monstrous bitch.

It does not happen overnight

In spite of what you may have heard, “THEY” will not come just because you’ve built it, that really is just a field of dreams. You need to build your brand and your visibility and get yourself known for what you do. It takes time, do not quit your job just yet.  

Remember that this is your
business, not a hobby, treat it as a business by completing revenue generating tasks first (i.e. speaking to clients over social media posts) and you will find your business starting to grow.

Don’t allow scope creep

A woman working at her laptop late at nightThis one is huge for most entrepreneurs, especially early on in the journey because we are trying to please customers and develop ‘raving fans’, but constantly allowing scope creep not only steals time from your other projects, but also diminishes your pay rate, your boundaries and ultimately your confidence in yourself. If the terms of the project have changed, the terms of engagement must change too.

Don’t let perfection disrupt you

Every entrepreneur I know has fallen into the perfection trap in one way or another over time, whether that is by not starting because they don’t have the perfect name or logo or website. Some also don’t post anything on social media because it doesn’t look perfect. Once you come to understand that perfectionism is just a form of procrastination, the sooner you will be ready to acknowledge that done is better than perfect. Besides, you can always make tweaks and reissue at another time.


Self-employment and side hustles are not easy, but if you are prepared to put in the work, build a support system and lean into it, you will find that it can be fun. It is a huge learning curve that forces you to learn about yourself and all the aspects of business you never thought you would need to learn and that you certainly weren’t taught in school. It is rewarding, exhilarating and completely freeing. Why not add a coach to your support system by signing up for a discovery call and we can talk through your business ideas? Next week I will be talking about the Money side of side hustles – it’s a biggy, don’t miss it.



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