Should You Go Self-Employed? What I Tell People Before They Make the Leap
- Aug 16
- 6 min read
Three people asked me the same question in the space of two weeks. Each one worked in a different sector, at a different stage of their career, with a different reason for asking. But the question underneath was identical. If I set up on my own, what do I actually do?
That is not a small question, and it deserves more than a checklist. Going self-employed is not simply a change of job title. It changes how you earn, how you plan, how you are taxed, and how you think about your own time. Before any of the practical steps matter, there is a prior decision that most people skip past too quickly. Is this actually the right move for you, and are you making it for the right reason?
Why This Question Keeps Coming Up
Self-employment in the UK is not a niche path anymore. There were 4.53 million self-employed people across the UK between March and May 2026, according to the Office for National Statistics. That is a substantial slice of the working population, and it tells you something important. The people asking me about it are not outliers chasing a fashionable idea. They are responding to something real in how work currently feels.
In my experience advising professionals, the question rarely comes from nowhere. It tends to follow a specific moment. Someone reaches a ceiling in their current role and cannot see a version of progression that appeals to them. Someone else has been doing informal versions of the work they love, unpaid or unofficial, for years, and finally notices the gap between what energises them and what they are contracted to do. Sometimes it follows redundancy, or the threat of it, and self-employment becomes less of an ambition and more of an answer to a practical problem. Employment has not worked out, and something has to fill that space.
What all three versions share is this. Self-employment is rarely the starting point. It is usually a response to something that was already true about the person's working life, whether they had named it yet or not.
A Story Worth Telling Properly
Last year a man got in touch with me. He had spent years teaching, and alongside that role he had built up a genuine track record mentoring young people, both through the school and through a couple of youth organisations he was involved with outside it. He wanted to move away from teaching and work directly as a mentor and coach for young people. He was not sure how, or whether it was realistic, or what the first step should even look like.
We talked it through. Nothing formal, no programme, just a conversation grounded in what he had actually done rather than what he thought he needed to become. A month later he came back to tell me he had cut his hours at school. That change gave him room to test the mentoring work properly, on a smaller scale, without walking away from a stable income before he knew whether it would hold. I have not heard from him since, and I do not know how the story ends. But he made a considered move rather than an impulsive one, and that distinction matters more than people give it credit for.
The Misconception That Holds People Back
When considering self-employment, people assume they need one clean, singular area of expertise before they can start. They wait for the moment when their offer feels fully specialised, fully defined, and fully separate from everything else they know. For most people that moment never arrives, and the waiting becomes its own quiet form of avoidance.
What often surprises people is how much of their existing knowledge can apply in more than one direction at once, provided there is genuine depth behind it. Someone with strong language skills and a background running a small team, for example, is not limited to one obvious offer. They may be positioned to work in language tuition, in operational support for other small businesses, or in some combination of both, depending on where the demand and the energy actually sit. The teacher I mentioned did not need a polished, pre-packaged coaching business plan before he could move. He needed evidence of what he had already been doing well, and permission to take that seriously.
This is where a strengths-led view of the decision earns its place. The question is not "what is my niche," asked in isolation. It is "where has this shown up before, and who has already found it valuable," asked honestly.
What People Underestimate Before They Leap
Having run my own business for three years, I would not claim to be a business strategist, and anyone who tells you three years qualifies them to advise on tax structures or growth planning is overstating their own experience. But there are patterns I have seen closely enough, personally and through the people I have talked with, to say with confidence.
People underestimate the emotional cost of unpredictability before they underestimate the financial cost. Steady employment, whatever its frustrations, comes with a rhythm. Self-employment removes that rhythm and replaces it with a workload that depends entirely on what you generate yourself. That shift catches people off guard, even the ones who thought they were prepared for it.
People also underestimate how much of the early period is spent on work that has nothing to do with their actual craft. Invoicing, contracts, basic bookkeeping, and constant informal marketing take up real time, and none of it is the part the person originally wanted to do. Organisations frequently overlook how much this administrative weight affects morale in the first year, focusing instead on income projections and missing the toll of context-switching between the work itself and the running of it.
And people underestimate how useful it is to test the idea before committing fully to it. The teacher's decision to reduce his hours rather than resign outright was not caution for its own sake. It was a deliberate way to gather real evidence before making an irreversible change, and it is a move I would recommend to almost anyone weighing this decision, wherever they are starting from.
What Separates a Clean Transition From a Drift
The professionals who make the strongest progress toward self-employment tend to share one habit. They treat the decision as something to investigate, not something to declare. They talk to people who have already done it. They test a smaller version of the idea while the safety net of employment is still in place. They get honest, specific feedback on what they are offering, rather than general encouragement from people who want to be supportive.
The ones who struggle tend to skip that stage entirely. They leave employment on a wave of frustration, without having tested whether the thing they want to build actually has demand behind it, and they discover the gap too late. Self-employment does not fail because people lack ability. More often it fails because the decision itself was never properly examined before it was acted on.
There is a wee but important distinction worth sitting with here. A career does not always move in a straight, upward line, and self-employment is sometimes less about ambition and more about plugging a gap that employment has left open. Both are legitimate reasons to consider it. The mistake is not choosing self-employment for practical reasons. The mistake is choosing it, for any reason, without examining whether it fits how you actually work.
If you are asking yourself the same question those three people asked me, the answer will not come from a business plan template or a generic checklist. It will come from an honest look at what you already do well, who has already valued it, and whether you are ready to test that properly before you leap. That is a conversation worth having before any of the practical steps.
Frequently Asked Questions
Do I need a fully formed business idea before I consider going self-employed? No. Most people who move successfully into self-employment start with strong evidence of what they are good at, rather than a complete business plan. The plan tends to develop once the idea has been tested on a smaller scale.
Is it better to leave employment completely or test self-employment alongside my current job? Testing an idea while still employed, even in a reduced-hours arrangement, gives you real evidence before you take on the full risk of self-employment. It is not the only route, but it is often the more considered one.
How do I know if I am considering self-employment for the right reasons? There is no single right reason. Ambition, dissatisfaction, and practical necessity can all be valid starting points. What matters more is whether you have genuinely examined the decision, rather than reacting to a difficult moment without testing whether the alternative actually fits you.
By Paula Donnan
Strength at Work | Better judgement. Stronger leadership. Higher performance.
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