“You’re so lucky, I wish I could do that…”

Being self-employed and freelancing is often described as either the ultimate dream or an ongoing nightmare, depending on who you ask. For me, the reality sits somewhere in the middle. Like every job, being self-employed comes with genuine advantages alongside some very real challenges, with both existing at the same time.

I have been self-employed since 2015, after walking away from an established and secure teaching career when it became so stressful that I ended up in hospital. In the decade since, I have created a whole new path as a self-employed social media manager and it still remains as one of the best decisions of my life. 

But it hasn’t been all flowers and rainbows and I have learned a lot from both the incredible and awful things I have experienced. Being self-employed and building something from nothing is hard, involving persistence, long hours, risk, uncertainty and plenty of effort behind the scenes to create something sustainable. So when others say that I’m “lucky,”  I will agree that luck may have played a part along the way, but it has been matched with consistency, hard work, plenty of tears and a willingness to keep going when things were really tough.

Are you thinking about becoming self-employed? Here are just some of the pros and cons of taking that step and building something of your own.

The pros of being self-employed

One of the biggest pros of self-employment is autonomy. Being able to decide how you structure your day, what work you take on, and how you prioritise your time is hugely valuable. There is a sense of ownership that comes from building something yourself, and I find that deeply motivating. 

Flexibility is another major benefit. Being self-employed often makes it easier to work around life rather than having to squeeze life around work, even if that flexibility sometimes looks different in practice than it does on paper. I can book a dentist appointment, or take myself out for lunch, or go and do a food shop during the day.

Working from home is one of my favourite things about being self-employed. Not having a commute immediately removes a huge amount of stress from the day, saves me a lot of money and it gives me back time and energy that would otherwise be lost. When it is cold, dark and raining and I watch The Bloke getting ready to go and battle his way through the traffic, I am grateful to be in the position where, on most days, I can put on some comfortable sweatpants and big jumpers and open my laptop from the comfort of my couch. When it is warm, bright and sunny, I like to go for a walk to get some morning fresh air. It’s a win / win. 

Similarly, in my job at least, I can also take more holidays than I would have done in a salaried job, because I am able to schedule content in advance. If I know that things are quieter and there isn’t a big project or a conference coming up and I feel like taking a few days off, I can tell my clients that I am on annual leave, plan ahead, get content approved and schedule it to go out on the days where I am not working. And that’s what I love about it – I don’t ask permission or need to get approval from anyone, and I have never had a client try and tell me that I’m not allowed to do so. 

There is also a creative freedom that comes with working for yourself. There is often the capacity to experiment, change direction and follow ideas without layers of approval or corporate processes (although this depends on your role – as a social media manager I still have to deal with the corporate process with my larger clients, which can be enormously frustrating at times). When things go well, the satisfaction feels personal, because the effort and the outcome are directly linked.

One of my favourite things about being self-employed is how much I have learned along the way. Working with different clients has meant being able to get first-hand knowledge of industries I barely knew existed before, and the incredible people who work within them. Every project brings something new, whether it is understanding a different audience, a new way of working, or a completely unfamiliar sector. It keeps things interesting and has stretched my knowledge far beyond what I would have picked up in a singular, more fixed role.

Another benefit of being self employed is the ability to walk away easily when something is no longer right. Whether it is a client or a way of working that does not align with my values or capacity, I have the option to step back and make changes. That level of autonomy is not always easy to exercise, but having the choice matters. Because of the fear I have about everything disappearing overnight (see the cons section), it admittedly takes an awful lot for me to terminate a contract with a client, but that doesn’t mean I haven’t done so in extreme cases, and I have ensured over the years that maintaining multiple clients and being diligent with my savings allows me the freedom to continue to do so should unexpected situations arise.

Being self-employed has offered opportunities that I could not have expected, both professionally and personally. It has opened doors to work that I would never have encountered in a more traditional role, allowed me to develop skills outside of a fixed job description and given me the chance to shape my career in ways that suit me and the way in which I work. Some of those opportunities came through people I would not otherwise have met (and I have made some lifelong friends because of it), and others have come through taking risks that I wouldn’t necessarily have taken before.

The cons of being self-employed

For me, the lack of stability is by far the biggest con of being self-employed, and I’m quite open about the fact that I live in constant fear that it could all go away overnight. Of course, stability is not guaranteed in salaried or hourly paid roles either and that security can disappear just as quickly, but the overwhelming responsibility I have felt since becoming self-employed simply does not switch off. Every decision, from finances to workload to long term planning, sits with me and me alone. There is no guaranteed income, no paid sick leave and no one else to pick things up when you are unwell. That uncertainty can be stressful, particularly during quieter periods or times of wider economic instability. I am now extremely diligent with my savings and spending, just in case.

Because of this, I often find that self-employed people end up working very long hours. Moving from teaching to social media management hasn’t really been a huge transition in terms of working unusual and unsociable hours as I often brought work home to do in the evenings and weekends in my previous life, and I have worked many jobs in hospitality that were predominantly evening shifts, but I can imagine it would be a shock to the system for anyone who isn’t used to it. 

Being self-employed requires a huge amount of discipline and motivation. Without set hours or external structure, it is entirely up to you to manage your time, workload, and energy. While this is certainly a pro in many ways, it also means constantly setting and resetting boundaries, knowing when to start, when to stop, and when to step away. It is easy for work to go into evenings and weekends if you aren’t careful, and maintaining those boundaries takes ongoing effort, and even then it is still often ignored. In my job, I receive emails and Whatsapps at any time – 6.00am, 11.30pm, and at weekends and when I’m on holiday. When I first started, I made the mistake of replying to them. Now, my phone is permanently on silent, my work emails can only be accessed via my laptop (to remove the urge to check them on my phone) and I don’t respond to anything before 8.30am or after 5.00pm. 

Another con is relying on clients to pay on time, or at all. When you are self-employed, there is a level of trust involved that doesn’t exist in salaried work. I consider myself lucky that in the decade I’ve been doing this, I have only ever had one client who did not pay me at all (for two months work) and then ghosted me, but that does not mean receiving payment is always straightforward. Chasing invoices, sending reminders and waiting for payments that should already have arrived can be frustrating, and it is an ongoing part of the job that never quite gets easier. The longest I have had to wait for payment? Six months. By two different clients, on two separate occasions. I’m lucky in that the majority of the people I work with pay on time, but even then it’s not uncommon that invoices are ignored for two months, or more, and yet they still expect the work to be done. Judging from the many social media posts I have seen from angry self-employed people about non-payment, I’ve had it easy – there are clearly many companies out there (which, thankfully, I haven’t had to deal with) who know that the time and money spent hiring legal representation sometimes isn’t worth it for some. I learned quickly to have a separate savings account as a back-up so that I don’t have any issues with being able to pay my bills on time. 

A con that is very job-specific is that being a self-employed social media manager means that because most people use social media in some form, they assume they understand what the job involves. Posting, scrolling and liking content looks simple from the outside, which can lead to what I do being very underestimated. What often goes unseen is the strategy, planning, analysis, problem solving and constant adaptation that sit behind it. Having to explain that it is more than just posting a picture or a video and why it is unlikely that their brand new account will organically gain 100,000 followers in the first month can be frustrating. I have an analogy about social media management:

If your roof needs fixing, you hire a roofing contractor because you don’t have the skills, equipment, materials and experience to fix it yourself. When someone hires a social media manager, they constantly watch them fixing the roof, while telling them how they have seen someone else fixing a roof that they think is better, while sending them articles and social media posts from 2014 about fixing roofs, all while expecting them to also fix their bathroom and provide advice on how to fix things in their kitchen for free. And they want the roof fixed yesterday. And they want thousands of people to be able to come and look at their roof by tomorrow.

Self-employment can also blur the boundaries between personal and professional time very quickly. When your work is tied closely to you, it can be hard to step away mentally. Even when you are not working, there is often a low level awareness of tasks waiting to be done or opportunities you should be following up. Without conscious effort, work can quietly expand into every available space.

Another downside for some is isolation. While freedom from an office can be appealing, it also means fewer casual conversations, less built in support and no immediate team to share the load with. Personally, I would put this into the pros section. Working on my own at home suits me perfectly – I like my own company and find long periods of conversations and socialising exhausting after more than a few hours. However, doing this every day could have a detrimental impact on some – the covid-19 lockdowns were a prime example of how affected many people are when they don’t have regular in-person interactions.

Two words: Tax Return. There is something uniquely stressful about being responsible for calculating, declaring and paying what you owe, all while checking and then triple checking that you have interpreted everything correctly. It isn’t difficult in a dramatic sense, but it is fiddly, time consuming and easy to put off. Unlike a salaried role where everything happens in the background, self-employment means facing it head on each year, which is never a fun experience. I have always done my own tax returns without issue, but now the system is becoming so complicated I know I will have to hire an accountant this year.

If you’re considering becoming self-employed, remember that it is not about escaping work. It is about choosing a different set of challenges and learning how to live with them. For me, being self-employed is neither perfect nor regrettable… it is a trade off. The freedom is real, but so is the responsibility. The flexibility exists, but it comes with a need for discipline and boundaries. And understanding both sides has been key to making it work in a way that feels sustainable rather than overwhelming.