Since the pandemic, the working landscape has completely changed. For the first time, people were forced to look differently at how they earned their living and how work impacted on their lives. For many who had never thought about self-employment, becoming their own boss became the new dream. But nothing is perfect and even the excitement and freedom of self-employment can have a downside. So, if you’ve got the urge to tell your manager you’re done and you’re off to farm alpacas, wait a minute! Let’s consider the important pros and cons before jumping into self-employment.

When thinking about the pros and cons of self-employment, the crucial thing to understand is that EVERYTHING becomes YOUR responsibility! So the pros and cons can look a little different than those of a normal job. Does the responsibility excite you? Or scare you? Either way, let’s dive deeper into the pros and cons of self-employment so you know what you’re getting yourself into.

A Bit of Background….

I was employed all my life until a couple of years back. Not only employed but working in some of the largest, most bureaucratic institutions you can think of. There were varying degrees of dependency – mine not theirs. They were never dependent on me! When I left the RAF for instance, I was like a little baby. I didn’t really know how to do anything for myself. My housing was provided. My meals were cooked for me. Dental and medical services were provided free of charge. Someone sorted out my pay and my tax. I didn’t even have to think about what I wore every day.

So, transitioning into civilian life meant taking on more daily responsibilities. Working for civilian companies meant my pay still turned up every month, but now I had to decide what to wear every day and organise my own living situation. Since I transitioned into the self-employment life, sorting out everything for myself – both personal and professional – has now become second-nature. It has been a steep learning curve though. Becoming your own boss needs to be properly thought about.

So, in the spirit of starting off with the positives, before we get to the cons, let’s talk about the pros of self-employment. These will be the things that have made you look into this in the first place. But indulge me – let’s talk about them anyway.

Pros and Cons of Self-Employment – PRO No.1

Flexibility and Autonomy

This is the big one and the the one we all started to think about differently during the pandemic. People realised that there was no real need in many industries to insist that work was done between 9am-5pm. Why couldn’t you do the same work between 11am – 7pm or for 3 hours in the morning and 4 in the afternoon? People got a real taste for feeling a bit freer when earning their daily bread and some wanted more of that feeling.

The joy of working for yourself is that you alone decide when, where and for how long. Some of your commitments will be driven by the business you choose to be in but, as we’ll discover, there’s a lot more to self-employment that just the work itself. So, when it comes to all the other stuff, why not start work at 5am and be done by midday? Or take the kids to school, have a lazy morning and start at midday?

You decide. Some arbitrary clock does not dictate your working hours. The business will decide how many hours a day you need to work. Some days it will be 12 hours, but on others you may be able to give yourself the day off and take the kids to the park or go to the coast. There is real freedom and joy in this approach to working and there can be real benefits to the wellbeing of you and your family.

You also make all the decisions in relation to your work. This allows you to align your career with your values and ethics, something that is not always easy to do in paid employment. It also affords creative freedom and expression, leading to greater personal fulfilment. As we move through life it is natural to want to build a legacy, to leave your mark on the world rather than feeling like a corporate drudge or drone. Building your own business hits the sweet spot.

Then there’s being the boss, rather than having a boss. We have all experienced poor management in our time. Working for a bully or an incompetent can cause real stress and can make work an unhappy place to be. Though there are numerous workplace protections, nothing can protect you against working for a boss who subtly undermines you, under-values you or micro-manages. Self-employment frees you from these concerns. You are the boss, you determine what kind of work environment you exist in and how you meet your goals.

Pros and Cons of Self-Employment – PRO No.2

Unlimited Earning Potential

This can be a key driver for some. And lets’ be honest, can you think of anyone who ever got rich working for someone else? It just doesn’t happen. The income you earn is a  direct benefit of the effort you put in. So, if you work hard and keep developing your skills and abilities, there is no reason why you can’t reach – or even exceed – all of your financial goals. There is nobody else deciding how much you can have, what you are worth, what your time is worth.

When you work for yourself, there are numerous ways for you to take your cut and you decide how much of a cut to take, If you want to take a salary, then you decide the size of that. Another key decision is how much you can and should invest back into your own business or into other opportunities. This provides greater freedom than living pay-check to pay-check.

Every penny feels infinitely more precious when generated directly by you. You are much less prone to waste them. You become so aware of every penny in and every penny out, especially in the early days. All my money these days has to earn its keep. Self-employment income can be inconsistent month to month and vigilance is vital. But when it works – what a great feeling!

Pros and Cons of Self-Employment – PRO No.3

Professional Development

Running your own business requires a diverse and broad range of skills. As I said in the introduction, you are now responsible for everything. Marketing, sales, finances, stocking the printer paper, branding, social media, tax, strategy. Everything. Even if you decide to employ others to undertake certain tasks, you still need knowledge of that task to oversee it. Ultimately, you are responsible for everything that happens in your business.

It is important to make time to improve these skills as you go along and that time should be factored into any strategy you come up with. We are lucky that the internet has brought up so many options for increasing your knowledge and many are free or low-cost. YouTube has videos teaching you how to do absolutely everything. I have used it to learn how to write blogs, how to edit them, what alt text is, what plug-ins to use, how to maintain the site – the list is endless. I have also used online course providers like Hubspot for SEO courses at £25.00 a pop – invaluable.

Your personal development needs will depend on the type of business you are in. Even if you know everything about the actual work, there is always something to learn about running a business. A key thing that gave me a boost last year was finding a YouTube video about writing a strategy for my business. I had never thought about it. But once I did, I realised that not having one had been responsible for the lack of forward progression. Finally coming up with my strategy was like lighting an afterburner – I actually felt the forward acceleration!

If you need help with strategy, THIS IS THE ACTUAL VIDEO video I watched last year. CEO Entrepreneur has lots of good advice about running a small business so check out his channel.

As Albert Einstein said, “Education is a lifelong journey; the moment we stop learning, we cease to truly live.” And I would add to that, if you stop learning, your business will cease to live. Businesses thrive by constantly moving and evolving. So, professional development becomes the lifeblood of your business rather than something you do to tick a box for HR.

So, as we’re doing the pros and cons of self-employment, let’s move right along to the CONS……..

Pros and Cons of Self-Employment – CON No. 1

Financial Uncertainty

When talking about the pros and cons of self-employment, this is a big one and, let’s be honest, it requires nerves of steel. Last year I found myself in a situation where I unexpectedly went from 3 streams of income to zero streams of income almost overnight. This was totally down to my own planning errors and lack of foresight and it taught me a valuable lesson (see above about writing a strategy). Luckily I had things to fall back on but it caused a more than a few sleepless nights.

If the thought of that situation scares you, that’s normal. But you need to know that markets will fluctuate, unexpected things will happen, income may go down as well as up. You have to hold your nerve.

As I said in the ‘Unlimited Earning Potential’ section, when you are self-employed, every penny becomes important. Even when you have a bumper month, the following month could be lean so you need to take care of those pennies and always have a complete understanding of your financial situation.

Financial Reserves

I can’t stress enough the importance of having a buffer and a robust financial plan. If you are on the cusp of resigning your employment to go and work for yourself, I would urge you not to until you have AT LEAST 4 – 6 months of money squirrelled away somewhere. That means 4 – 6 months of living and bill money. It just make sense and, believe me, it will help you to sleep when things in your business are moving slower than you’d hoped, especially in the first few months.

Financial Records

Some banks or financial institutions make it harder for the self-employed to obtain certain products. Its all calculated on risk and when your income is inconsistent, those risks can be harder to assess and so the banks get nervous. Accurate financial records should be kept to minimise rejections and delays. Hire an accountant. Or at least a book-keeper. If you can’t afford either, there are so many pieces of accounting software available to you that are pretty easy to use or, do as I do, and just make Excel spreadsheets. But account for EVERY penny!

Pros and Cons of Self-Employment – CON No.2

Lack of Benefits


The biggest aspect of this is sickness and inability to work. With the best will in the world, you can’t know what’s going to happen and illness can strike out of the blue. If you’re lucky, its minor illness and you can battle on with some paracetamol and a Lemsip. But is its more serious, it carries the risk that you may not be able to work at all.

Employers always have sickness policies and these usually afford you a certain amount of paid time off. Some companies even offer private health care. For the self-employed, sickness can mean there’s no work being done and no income. You will need to protect yourself against these eventualities. Many companies offer self-employed insurance schemes costing from £10 per month upwards.


The government requires employers to offer workplace pensions. As your own boss, that is missing so you need to factor in the provision for private pension, property purchase or another retirement plan. You also need to think about it if you are employing other people.

Pros and Cons of Self-Employment – CON No.3

Work / Life Balance


Be prepared that things could get worse before they get better. When starting a business, the learning curve is huge. Not only are you doing the work itself, but there is administration, financial management, invoices, strategy, marketing, sales, IT – so many things. And they are now YOUR responsibility. It’s entirely possible that you will be working harder and longer than ever before and burn-out is a real risk.

It is important to structure things so that you are taking some time away from the business and getting real rest. Try and set some start and finish times and stick to them. Make sure you have meal breaks even if you are just away from the work for 20 minutes. Learn the art of the ‘power nap’. Sit outside in the fresh air. Go for a walk. Commit to a sleep regime.

Your time management will also need to be top-notch. If its not your forte now, you’d better get working on it. Planning activities, prioritising tasks and finding ways to fit it all in are key to “making the juice worth the squeeze”.

If you need help in this area, try Bullet Journalling. It has provided me with an easy system to discard all the non-important stuff and focus on the things that are going to get me where I’m going. I can’t recommend it enough and made it one of my Top 3 Books for Personal Growth. Take a look – see if it can help you!


It can also be lonely. If you are transitioning from working in a busy office to working from home on your own, the peace and quiet are nice. But there is a lot to miss out on too. Social interaction with people in the same business, the sharing of ideas, collaboration, sharing of tips and tricks about how to do certain tasks.

You can also lack a support system. When you’re the boss, and especially as a sole trader, there is no-one to gripe to, no-one to vent to, no-one to say, “Don’t worry, I can do that for you”. The motivation all has to come from you, from inside, and the discipline too. It can be a lonely path. This can sometimes make it difficult to see what you have gained so it is vital to have a set of benchmarks to measure your progress against. This will help you stay motivated.

Working on your own can also make it difficult to keep up with changes in your chosen industry. Try to join business networks, forums or newsletters that help you maintain an up-to-date knowledge of what your competitors are up to and any new technological advances. Contact organisations like the Federation of Small Businesses and see what support or advice they can offer. All of these contacts can keep you in the loop and provide networking and support opportunities.


I’m sure that you there are many, many more pros and cons of self-employment we could come up with. But these are the big ones. The benefits and disadvantages that could really impact your life. It is so important to weigh these things up against your personal preferences and circumstances before taking the leap. If self-employment was easy, then everyone would do it. It can be a hard road and its not for everyone. But if the fire is in your belly, and you can find a way to make it work, then why not jump?


Let me know in the comments below what pros and cons of self-employment you can see.

I love hearing from you so don’t be shy – get in touch!

Also, let me know if there are any subjects you would like me to write about, especially if you have already taken the leap to self-employment. Your experiences could be the catalyst for someone else to make that jump.


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