Taking your side hustle full time

So you’re seriously considering taking your side hustle full time. You’ve been working on your dream for a while now, and it seems like the time has come. It’s time to make a decision and you want to carefully consider your options. 

Before I talk about the things you should consider when taking your business full time, I wanted to say that I absolutely love working for myself. It took me a long time to build up the courage, and be in a financial position to take the leap, but I honestly think it was 100% the right decision for me. It can be the most rewarding thing watching your business grow. Having said that, I know that being an entrepreneur, self-employed, or a freelancer - whatever the term you like to use, isn’t for everyone.

There are so many things to consider when making such a big, potentially life changing, decision. It shouldn’t be taken lightly, but I have a feeling that if you’re reading this, you’ve already considered this in some detail. Let’s dive in!

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Working from home

Most of us are used to working in an office environment, and the jump from working with colleagues, to working by yourself, most likely from home, is a big one. You see, I was already working from home when I made the decision to take my side hustle full time. I had set hours I had to be at work for, but I was very much used to being by myself every day. Equally, I was used to working through my lunch break, too, which wasn’t all that healthy. But if you’re preparing to make the switch from an office full of people, to working from your spare bedroom - it’s going to take some getting used to. You may love the transition - I mean, rolling up to your desk in your pyjamas has its advantages, especially on dark winter mornings. But as you get settled into a routine, it can quickly become draining, with no humans to bounce ideas off of, no Karen from marketing to have a brief chat with whilst you wait for the kettle to boil.

Having said all of that, I LOVE working from home. The ability to adjust my daily routine as I see fit, and no morning commute, I think it’s a pretty sweet deal. If you find yourself getting a little low, or bored of your working day, I’d highly recommend looking into co-working spaces, or arranging co-working with a couple of your self-employed pals. Working with others, even when you’re working on entirely different things, can have huge benefits. You’re likely to swap your freelancer stories, the ups and downs of this life you’ve chosen, and you’ll feel so much better for it. A change of scenery is essential every now and then. If you can’t arrange a working date, you can always go to your favourite coffee shop and work from there for a little while. 

Working routine

If you’re used to having someone else telling you what to do all the time, the level of freedom that comes with the self-employed life can be a little problematic. It’s easy to get stuck in procrastination mode. After all, those Netflix shows do look rather tempting. Having a solid working routine, in my opinion, is key to getting the work done. Of course you want to be flexible, but I find a rough guideline of when I’m meant to be working really helpful. I’ve recently started using a time blocking spreadsheet, and it’s been the best thing I’ve done for my work schedule. I factor in breaks and lunch time yoga, because I have the tendency to just sit at the desk all day (which is bad, really, really bad). It helps with my productivity, too, because I’m less likely to skip out of the tasks I’m not too keen on. 

Ask yourself - will you have the self-discipline to meet deadlines and work on your business, even on days when you don’t feel like it? It’s much easier to opt for a day on the sofa if there’s no boss telling you to come in to work. How do you work best? Do you thrive when working on projects alone? Or do you really enjoy working with a team? If it’s the latter, then perhaps starting a solo business isn’t the right choice for you. And that’s okay - as much as entrepreneurship is having a big moment right now, there are downsides to it too, and it simply doesn’t suit everyone. I know people who love their full time jobs, and enjoy having a business on the side, with no intention of every quitting their job. There is no right or wrong here - it HAS to feel right for you.

Financial security

Of course - you would have considered this already. Self employment doesn’t guarantee the same level of financial security that a regular job would. As a rule, you don’t know how many clients you can expect to book in/buy from you in the next month. It’s up and down and there are periods of low activity, too. I spoke about this with Lucy Parker on the Fearless Hustle podcast not too long ago, but I think we all have a tendency to panic as soon as there’s a few quiet days with no enquiries or e-mails hitting your inbox. It’s natural, but I’ve come to learn that it’s just how things are. You need to make sure you’re visible both online, and wherever your audience might be, but it’s totally normal to have quieter days, weeks or seasons. 

It’s recommended that you have enough savings to cover any immediate living expenses when first taking your side hustle full time. I’ll be really honest - I didn’t really have any savings to speak of when I took the plunge. To some, that would be insanely irresponsible, and in some ways, maybe it was. But the wedding photography industry allows me to know how much work I have coming in, months in advance. This gave me the security I needed, knowing that I’d have enough money coming in to substitute my salary.

Track your income and expenses, work out how much you spend each month, and how much you have coming in. How much do you need to save each month? How much do you currently contribute to your pension? All of these things should be taken into consideration, so that you can enter into this world of self-employment knowing exactly where you stand. Map out how much you need to bring in each month to cover your basics - do you have any savings you can rely on if the first couple of months are more quiet than you expected? In an ideal situation, you’ll have a couple of jobs lined up, so that you’re not having to desperately search for clients when you first get going.

I wish I could say that enquiries started rolling in as soon as I announced my business to the world. They didn’t. It look some months to generate enough interest in my wedding photography services. Even then, when couples would book me in 2016, their wedding wasn't for another 8-10 months. This meant that I hardly had any money coming in, and leaving my full time job in 2016 would have been a mistake. Consider these things carefully, but equally, don’t let it put you off entirely. Stay aware of your financial situation, always.


This was a big one for me and it was one of the reasons I knew I had to take my business full time. Half way through 2017, I knew I had enough wedding bookings for the following year to sustain me and substitute my salary, and as the number of bookings continued to grow, I knew something had to give. I couldn’t work another full wedding season alongside my full time job. I would be sacrificing too much time with my family, and that was a non-negotiable. I knew that something had to change, and quitting the safety of my full time job to pursue the running of my own business was the only option.

Is your current workload of managing your job and side business, simply too much? If that’s the case, you know, deep down, that you can’t go on like this for long. Of course quitting your job isn’t the only option - you could consider going down to part time hours to allow you more time to spend working on your business. There are many scenarios here and it’s important that you follow what feels right to you. There is no point in following someone else’s advice if the alarm bells are going off and your gut tells you that something doesn’t feel right.

comparison and self-doubt

I didn’t expect this to be an issue when I first set up my business, but boy, was I wrong. There’s something about pouring your heart into your business, that makes you super vulnerable. Self-doubt and comparison are bound to make an appearance at some point, it’s inevitable. You begin to question everything that you do, and on low days, you’re seconds away from reaching for your phone, getting stuck down the comparison trap of Instagram. You see, as wonderful as this ultra connected world is, it also means that we get an insight into other people’s lives on a regular basis. We see their achievements, we hear about their big grand plans, and sometimes, that can be a little too much. I wrote a blog post all about comparison, and how to fight it. If you ever find yourself sliding into this pit of despair, remember, we all experience it, in one way or another. This too shall pass.

Be yourself - everyone else is already taken.

what do you want

If you can step away from it all to gain some perspective and clarity - what do you see? What do you want your life to look like?


Leaving the comfort of a full time job is tough - there is no certainty when you’re running your own business, but then again, there is no certainty when you’re working for somebody else. Companies fold, people get fired. So perhaps a better question to ask yourself is:

Will you regret not giving it a go?