Going it alone: the hardest psychological part of working for yourself

“At four on Friday I sent the client the final version. Then I sat in front of the screen for half an hour and waited. Not for the payment. For someone to tell me it was good.”

That is the kind of thing a graphic designer might say in her first month of working for herself, after ten years in an agency. She knows the work. She has clients. An accountant, too. What she does not have appears in no business plan: someone in the next office who would glance over her shoulder and say “yes, that’s it”. Someone who would say at six o’clock, “that’s enough for today”. Someone to roll her eyes with when a client changes the colour for the third time.

When you set out on your own path as a self-employed woman or man, you prepare for many things — taxes, finding clients, irregular income. You rarely prepare for the possibility that the hardest part may be psychological: that you will be left without the system that used to quietly carry half your load. That is what this post is about. Not start-up founders, and not how to survive months without income, but people who work alone, without a team, and what happens inside them as they do.

When the team goes, the roles go with it

In relational family therapy, in which I am training, we look at a workplace much as we look at a family. Every team is a system with roles, rules and relationships. Someone is the one who sets limits. Someone is the one who calms things down. Someone says when a piece of work is good enough. Someone complains on everyone’s behalf, so the others can stay pleasant. People share out these roles without ever discussing it — and that is exactly why we only notice them once they are gone.

When you go self-employed, you do not just lose colleagues. You lose the people who carried roles you may not even have known you needed. The manager who got on your nerves was also the one who set the deadline, so you did not have to. The colleague who always commented on everything gave you, in passing, the sense that someone saw your work. HR told you when you had holiday — and with it, that you were allowed to take it.

Now all those roles are yours. You are the director who sets the deadline and the worker who has to meet it. You are quality control and the assessor. You are the one who complains and the one who listens to the complaint. And all of it in the same head, often at the same kitchen table.

The loneliness of responsibility

When people talk about loneliness in self-employment, they usually mean the silence — having no one to grab a coffee with. I wrote about the quiet loneliness that sets in when the corridor disappears in Working from home and quiet loneliness: what is lost when the corridor disappears. But working for yourself brings another kind of loneliness that is harder to see: the loneliness of responsibility.

In a job, even a bad one, responsibility is shared. If a project goes wrong, several people share it. If a client leaves, it is not only your loss. When you work alone, every decision, every mistake and every success is yours alone. There is no one to say “we messed that up together”. The effects resemble loneliness at the top of a large company — the subject of Lonely at the top: why people in leadership have no one to talk to — except that a self-employed woman has no one beneath her with whom she could at least share the everyday.

Loneliness should not be taken as merely an unpleasant feeling. In 2015 Julianne Holt-Lunstad and colleagues showed, in a meta-analysis covering more than three million people, that feeling lonely is associated with a 26 per cent higher likelihood of early death, and objective social isolation with a 29 per cent higher one. These are associations, not proof of cause, but their size is comparable to well-known health risks. You will find a short explanation of the concept in the knowledge base under loneliness.

A self-employed person does not have to be alone in the ordinary sense. They may have a partner, friends, children. But if they share with no one what occupies them most during the day, then in one important part of life they are alone.

The mirror that is no longer there

In self-determination theory, the psychologists Richard Ryan and Edward Deci describe three basic psychological needs: for autonomy, for competence and for relatedness. Going it alone is often chosen for the first — for the freedom to decide when, how and with whom you work. A 2018 review by Ute Stephan shows that people who work for themselves often report greater job satisfaction precisely because of that autonomy. At the same time, working alone quietly takes away a good part of the other two.

A sense of competence is fed not only by work done, but also by someone seeing the work done. In a team there are many mirrors — praise in a meeting, a colleague asking for your opinion, even criticism that shows someone cares. Working alone, often only one mirror remains: the client. And a client usually says only two things — nothing, when they are happy, and something, when they are not.

That is why, for many self-employed people, their sense of worth slowly merges with the last invoice or the last client response. A good month means “I’m good”, a bad month “I’m not cut out for this”. I wrote about how a person’s worth merges with how much they get done in Worth only as much as you get done: self-image and productivity. For the self-employed this trap runs even deeper, because there is no one to say “it doesn’t all depend on you”. This is also where the feeling often appears that you have only succeeded by chance and that everyone will soon see through you — you will find it in the knowledge base under impostor syndrome.

The boss you carry inside

When there is no longer an outside boss, it often turns out that each of us has an inner one. And this one is not necessarily better. For some, it is stricter than any real manager: it knows no end to the working day, does not recognise sick leave, and declares every free afternoon laziness. Why people who work for themselves find it so hard to switch off is the subject of Always on: why entrepreneurs can’t rest. For others, the inner boss is powerless — it allows everything, and then panic sets in when the deadlines pile up.

From a relational point of view, this inner boss did not come from nowhere. It often sounds like someone we have known for a long time — like a father who said rest is for those who have earned it, or a mother who never sat down. While you were employed, this voice competed with an outside boss. Now it has the stage to itself.

A conversation might sound like this (composite, not a real person):

“Yesterday I shut the laptop at three and went for a walk. Then until the evening I felt as if I’d stolen something.”
“From whom?”
“I don’t know. From myself? From the business?”
“You are the business.”
“Yes. And still there’s someone watching me.”
“What would that someone say if you asked?”
“That other people can’t afford a walk at three. That’s what my father used to say when my mum stayed at home.”

Once you recognise whose voice it is, you can begin to negotiate with it. You do not have to silence it. But you can decide that it will not be the only one setting your working hours.

Clients as a new family

Without a team, relational patterns do not disappear. They move elsewhere — most often onto clients. A client who emails at ten at night can become the demanding parent you can never please enough. The client who was first to trust you can become someone you cannot say “no” to, because it would feel like ingratitude. Two clients who dislike each other can place you in a real triangle, in which you carry messages and soften tension.

In self-employment, boundaries are one of the hardest tasks precisely because no one else sets them any more. In a company your working hours were written into your contract, and response times were more or less agreed. Now you have to set them yourself — and defend them yourself, often against the fear that the client will leave. You will find a short explanation of what boundaries are and why they are not walls in the knowledge base under boundaries. If you feel your worth lies in whether a client is satisfied, People-pleasing: when your worth is in other people’s hands may also resonate.

A price you have to defend on your own

In a job, someone else sets your salary. You may disagree with it, but you do not decide it afresh every week. When you work for yourself, every quote is a small conversation about what you are worth. And since there is no sales department to set the price for you, price and self-image stick together easily.

Among the self-employed the same pattern often repeats itself: they set their price too low because they fear rejection, then work too much for too little and feel exploited — even though no one has exploited them except their own fear. I wrote about why it is so hard to say the number out loud in Talking about pay: why it is so hard to say the number. For the self-employed the question is even more personal, because there is no one to hide behind.

Uncertainty without a safety net

All work brings uncertainty, but a job cushions it with structure — a regular payday, a notice period, sick pay. When you work for yourself there is less of that structure. How to live with irregular income is the subject of Irregular income and anxiety: living between projects. Here I would like to point to something else: uncertainty that is not financial.

Is this decision the right one? Would another professional do it better? Will I still be here in five years? Researchers such as Nicholas Carleton describe intolerance of uncertainty as a trait that varies between people: some experience uncertainty as unpleasant but manageable, while others find it almost unbearable and try to get rid of it through constant checking, planning or working. When you work alone, uncertainty cannot be removed. You can learn to live with it — and that is often more an emotional task than a business one.

What the family makes of it

Going it alone is not only a business decision but also a family event. Parents who valued a secure job all their lives may greet every uncertain stretch with the question “and when are you going to get a proper job?”. A partner who was enthusiastic about your decision may, after a few months, start to worry about what will happen. And sometimes the partner becomes the only person you tell about work every evening, which slowly overloads the relationship.

Murray Bowen called the capacity to stay in contact with those close to you while keeping your own position differentiation. You will find a short explanation in the knowledge base under differentiation. Working for yourself tests this capacity often: when your mother does not understand why you left “such a good job”, and you stay with your decision without falling out with her or setting out to prove yourself. When you are less differentiated, you hear every doubt from those close to you as a verdict. When you are more differentiated, you can hear it as their worry — and still make your own decisions.

Exercise: a map of empty chairs

This exercise helps you see which roles from your former team you now carry alone — and which one you could hand over. Take a sheet of paper and half an hour.

1. Draw a table with six chairs. On each chair write one role that someone else carried at work: who set the deadline, who said it was good, who said when it was time to stop, who listened when things were hard, who set the price, who spotted the mistake.
2. Next to each chair write who sits on it now. Perhaps a colleague, perhaps your partner, perhaps no one. On most, it will probably say “me”.
3. For the chairs that say “me”, add how well you are doing. As an inner boss, are you too strict, too lenient, absent? As quality control, are you ever satisfied at all?
4. Choose one chair to hand over this month. Not all of them. One. It might mean agreeing with a colleague on a monthly coffee where you show each other your work. It might mean writing down your working hours and sending them to clients.
5. After a month, check what has changed. Not in turnover, but in how you feel on Friday afternoons.

Most people notice in this exercise that the hard part is not the work itself, but the fact that every chair is occupied by the same person. Even one chair taken by someone else brings a surprising amount of relief.

If it turns out that no one but you sits on any of the chairs, that is not a sign you have done something wrong. It is a sign that you have been building a business rather than a support system — which is entirely understandable at the start of working for yourself. A support system can be built later too.

Where this is not a psychological question

This post looks at self-employment through relationships and emotions. That is an important part of the picture, but not all of it. A few things where the answer lies elsewhere:

When there are serious financial problems. If debts are piling up or you do not know how you will meet your obligations, you first need business and financial advice — an accountant, an adviser at an SPOT point (Slovenia’s business support points) or the Chamber of Craft and Small Business of Slovenia. Talking about feelings can help alongside that, but it cannot replace an expert in numbers.

When working for yourself simply is not for you. Some people find after a year or two that working in a team suited them better. That is not a defeat. It is information about what you need in order to be well. Going back into employment can be just as mature a decision as leaving it.

When it is more than loneliness. If for weeks you have not felt like doing anything, if you sleep badly, lose joy outside work too, or have thoughts that it would be better if you were not here, that is a reason to talk to a doctor, not to organise your work better. In a crisis you can call the mental health crisis line in Slovenia on 01 520 99 00 (every day from 19.00 to 7.00) or the Samaritans helpline in Slovenia on 116 123 (24 hours a day), and in an emergency 112.

In therapy we will not be working on your business plan. But we can look at which roles you carry alone, whose voice is driving you, and why it is so hard to say “no” to this particular client. Sometimes that is exactly what makes working for yourself sustainable. I also work with English-speaking clients, in person in Ljubljana.

What to remember

• When you go self-employed, you lose not just colleagues but the roles they carried — the deadline, the limit, the praise, the release valve.
• The loneliness of responsibility is different from the loneliness of silence: there is no one to share mistakes and successes with.
• When a client is your only mirror, your worth merges with the last invoice. Look for other mirrors too.
• The inner boss often sounds like a voice from your family of origin — you need not silence it, but it should not be the only one deciding.
• For financial problems, get business advice first; for lasting low mood, talk to a doctor.