Have you have spent time imagining how great it would be to be your own boss? You would have the freedom of choosing your own working hours and decide who you want to work with. You can finally bring your creative ideas to life. But as great as it sounds, what would it really be like to say goodbye to the day job, and is going self-employed a good idea?
This article explores the underbelly of self-employment. I am referring the type of self-employment where you put a piece of your soul out in the world because what you are offering is your own creation in some form, and where you need to develop an audience for your offering.
You will always be on a blind bend
What this means is that the perceived predictability of what is ahead of you will be gone. Slipping into autopilot mode and turning up for work each day will no longer be possible. Employees are afforded a sense of safety because someone else is ultimately responsible for making sure that there is enough business available to pay the wages. Arguably, this sense of safety is an illusion to some extent, but either way, self-employment brings you into much closer contact with uncertainty, and it is something that you will have to learn to work with.
Business owners have to look at the bigger picture and think about how they will sustain the flow of income. Without the benefit of a crystal ball the best they can do is to construct the most resilient business structure possible, whilst accepting that unexpected events in the future could change everything.
The pandemic was a perfect example of this. Contracts can be lost, orders can be cancelled, and all manner of other events can occur that were not anticipated. Similarly, new ideas and opportunities can also appear.
Although this blindness might feel very unsafe, the self-employed have the capacity to adjust their work in the face of changing market conditions, so if you can accept the discomfort of this heightened awareness and you are prepared to think on your feet when conditions change, you actually have more control to steer your way through tough times. Employees, on the other hand, may have a sense of predictability and security, but they are also at the mercy of the decisions of others when the chips are down, and that may include termination of contracts or redundancy.
The early days are hard
We are often led to believe that people became successful overnight, and while this might be the case for a select few, mostly it comes from the use of artistic licence in storytelling. Beyond those who were blessed with the serendipity of being in the right place at the right time, most people will need to spend time and effort in developing an offering, making it visible and building a reputation, regardless of how talented they are.
Being an overnight success sounds desirable when you are struggling to attract clients and customers, but there are often benefits to starting slow. There will likely be important lessons to learn, you will need to hone your skills and build your stamina for your new occupation.
It is useful to treat the early days as a process in which you are adjusting and refining your work and getting used to wrestling with the challenges that present themselves. Some months you will wonder how you managed to muddle through.
Your willingness to accept that failure of some sort is inevitable, to modify your offering accordingly and to keep going is essential. That modification might include taking on some part-time employment, or even returning to full-time employment in the short term, if needed.
You will take on many different roles
Unless you have significant financial backing, you will most likely need to wear several hats: marketer, accountant, office manager, debt collector, operations manager, and general dog’s body. This means that there is a never-ending pile of things to do, some of which you will enjoy and others which will get in the way of what you love doing.
It can be helpful to break these tasks down into categories: firstly, figure out what you are good at and like doing. Next, establish what needs outsourcing now because it is critical to the success of your business but beyond your skill-set. Finally, earmark anything that you would prefer to outsource as your business increases in the future.
The more competent you are, the more tempting it will be to try to do everything yourself. This can lead to burn-out or stagnation, depending on whether you tend to burn the candle at both ends, or whether you get overwhelmed and end up procrastinating.
Your efforts do not necessarily guarantee results in the way you expect
A key difference between employment and the early days of self-employment is that you will spend time putting together your offering without knowing if anyone is interested. A friend recently said to me, “I am so much better at responding to incoming orders. When it comes to doing promotional work that has no deadline other than the one I put on it, I really struggle.”
Unless you are comfortable generating new business, this is likely one of the biggest hurdles to cross when you leave a salaried role to begin your own endeavour. Creating a course, putting together a new range, writing books, blogs and press releases: such tasks may not have an audience waiting to receive them.
If you are producing something on spec, rather than for a defined audience who has agreed to publish or pay for it, you will need to dig deep and find the discipline to push it over the line. You may meet all sorts of inner resistance from the parts of you that are frightened of criticism or rejection.
Your ultimate success is dependent upon thousands of actions, big and small, some of which might have an obvious impact and some of which may seem so small as to be insignificant, like tagging a blog article that helps your future audience to find you, for example.
Avoidance and procrastination will appear like little devils on your shoulder, and you will be challenged to find a way to befriend and work with them.
The results of your efforts may be quite different from the ideas you had when you started, and a willingness to allow your work to evolve is essential.
There is no guaranteed income
There is great comfort in knowing that a pay-check will land each month, and how much it will be. Life can take on a rhythm, and the costs of daily life can be met with reasonable predictability. It is also easy to fall asleep at the wheel of your own life from this position, or to avoid taking worthwhile risks if you are not careful.
When you are self-employed you have to stay awake to how and where you invest your time and efforts to give you the best chances of success. Sometimes it is not obvious how you will pay all the bills, and you have to get used to taking action, renegotiating payment terms, and sometimes even holding out for a bit of good fortune to come your way.
You could look at it as part of a growing up process, whereby you leave safety and enter the unknown world of discovering what you might become.
You might also discover that your value is greater than the wages you receive from an employer, and that by working for yourself you gain much wider experience than you would in a salaried role. They say that necessity is the mother of invention, and there is nothing like the need to pay the bills each month to push yourself to develop your skills and your offerings in order to increase your monetary worth.
You will need to confront your money issues
Money often keeps people in toxic working environments that are damaging to them. It is true that employees often enjoy certain perks: private health care, paid holiday and sick leave, to name a few. All of these can seem extremely alluring, particularly when cash flow is poor, when a client doesn’t pay you, or whatever money monster arises to awaken your deepest fears.
One of my money biggest lessons came when I lost a week’s work due to sickness. It was my first experience of having no control over what was happening and no pay packet to fall back on. I resolved that I would have to work doubly hard to recover what I had lost, only to fall ill again the following month, and this time for even longer. My precarious situation was saved by an unexpected tax rebate.
The lesson was to accept my circumstances, to focus back on my business strategy, to start thinking about other streams of income that would help me to weather future storms, and to trust that I would find a way through.
The safest and most sane place to be during such times is in the present. This is where you have agency to make decisions, adapt what you are doing, and ask for help. The worry of future poverty – or whatever your greatest fear may be – has the power to be paralyzing.
You will end up walking this tightrope at some point. It is a rite of passage, an opportunity to face your fears, to learn your own value, and also to develop new knowledge, skills and attitudes to money management.
The strength of your boundaries will be tested
Even when you are your own boss, you will still meet characters who you find challenging to deal with. You will encounter the people who are disappointed by what you offer or had unrealistic expectations, the people who want you to be available at their convenience, the people who don’t show up when they said they would or don’t pay you.
These experiences can either defeat or discourage you, or you can see them as a series of strengthening exercises that are helping you to create new standards for yourself and your expectations of your customers. Refusing to work with people who do not respect your payment terms or who habitually turn up late for appointments would be a good standard to set, for example.
You will need to set your own limits
When you are the boss, you need to decide what working conditions you are going to set for yourself. For example, do you answer the text that your client sent you at 8pm on a Sunday evening? Or do you use the intrusion as a lesson in holding your boundary until Monday morning when you are at work again?
Each time you are confronted with the need to make a decision, you can derive a principle that you can work with. In this case, setting your working hours and deciding when you are available to others and when you are not will be paramount.
Over-workers need to focus consciously on allowing time for the other aspects of life, including rest and leisure time. It can be tempting to let this fall by the wayside in the early days when there is so much to do, but the risk is that this becomes a way of life, which is not good for you or your business.
If you have fears of not being good enough, you will need to set standards for yourself so that you do not spiral off into levels of perfectionism that push you beyond your limits, leaving you feeling depleted and despondent.
If you are considering self-employment because your boss is a tyrant, it’s best to make sure that you don’t simply replace them with your own tyrannical ways.
You may end up being successful
In taking conscious responsibility for your fate you might just discover that you are capable of so much more than you thought you were, and that new, previously unimaginable possibilities, open up to you.
You will need to build a strong faith in yourself, and success might arrive just as you feel you are being pushed to your limits and you are about to give up.
Many people want to see their own success before they can trust themselves, but when it comes to creating a business the faith needs to come first. Building faith in yourself is an inside job. If you do not learn to find your value from the inside, no amount of good reviews or feedback from clients will fill that gap when your mind is used to churning out self-criticism.
You may also systematically sabotage the possibility of success in ever so subtle ways, particularly if you are accustomed to feeling disempowered. It might not be a nice feeling, but a part of you might be unconsciously invested in maintaining that position. It can take time and effort to get comfortable with the idea of taking a more empowered position in your own life.
So, is going self-employed a good idea?
Here are some reasons why it might be worth a try…
By creating a business that is aligned to your values and passions, this can sustain you in the times when you struggle to see your way to success.
A willingness to take your own authority by running your own business will bring personal as well as professional growth, and even if you find yourself returning to employment, you will have developed maturity and skills that will prove valuable in life.
The journey of self-employment is like an allegorical tale: you have to slay some dragons along the way, and that can be both terrifying and thrilling. Many of those dragons will be your own internal defense mechanisms and idiosyncratic habits. The reward is to gain a level of self-mastery that empowers you.
Until you try, you have no idea how successful you could be or who you could become, and your success might go far beyond your imagination if you let yourself take the adventure.
How Can Your Current Role Help You?
If you’ve read this far and you are wondering what steps you can take next or how to make the transition, here are a few suggestions.
Even though you may really dislike your job, you might need it for a while longer, and it’s amazing how the unbearable can become bearable when there is a bigger master plan at stake. So, if you are still part of the rat race for now, consider what might be good about this.
- Are there training courses you can do?
- Is there a qualification you need?
- Do you need to make the most of your holiday allocation so that you can still be being paid while you take time off to focus on the development of your new business? (Make sure that you are not in breech of your contract if what you will be offering relates in some way to what you do now)
- Can you use some of your salary to make investments in materials and equipment?
- Have you set up a “rainy day” fund?
- Are there projects you could get involved with that would give you experience that you need?
In my own case, I had almost three years of training to complete to become an Amanae Practitioner, which involved regular trips to Europe. My job was sufficiently flexible to allow me to take time off when I needed it, and my salary was just about enough to cover my living expenses and my training fees.
Work Part-Time
Another helpful step in the process of becoming self-employed is to allow a phased approach. Perhaps you can reduce the time you spend working for your employer so that you can gradually increase the time you spend working on your own projects. Make sure you check your employment contract before going down this route. If there are exclusions in your contract that make this impossible, you may need to look elsewhere.
Your current role may be too demanding. Perhaps you would prefer to do something that is more basic than you would normally choose to do so that you can keep your brain power for your own endeavours. You may also want to think about whether there is anything you can do that would put you in contact with people who could be your future clients/customers. There’s nothing like being paid to do your marketing!
Keeping a foot in employment not only helps to keep finances steady in the early days, it may also help you to maintain important social connections. It is all too easy to end up being isolated in your home office, and sometimes you may need social time with others to keep the ideas flowing.
Think Incrementally And Collaboratively
If you are going to leave your job in favour of working for yourself, think about whether there are ways you can test your business first. Consider how you might do this without having to make large investments.
If part-time work is not a possibility, can you dedicate part of your weekend to your new work in the short term? If, for example, you wanted to set up a restaurant, can you find a way of borrowing a commercial kitchen that is not being used, or can you create pop-ups using facilities out of hours? Perhaps you create a one-off event, followed by another one-off event, and you allow your ideas to develop over a much longer time frame.
The idea is to prove your concept, prove that there is a market for what you are trying to do, and to iron out some of the early-stage challenges before it becomes your only source of income.
Creativity is a process, and I would encourage you to look at your move into self-employment in this way too. You may have no choice but to pull together your new business at short notice, and sometimes necessity is the mother of invention. Where you have the choice, a gradual migration can be a more gentle and planful way of transforming out of one life and into another.
The Next Step
If you are still trying to understand what a meaningful occupation might look like for you, I offer Life Purpose Work, which uses a combination of techniques to help clients who are in a period of transition to gain clarity about what they are here to do and how they want to do it. You can read more about what I offer here.
If you would like to book a session but you have questions, please book a free 15 minute discovery call. Or, you can contact me to make a booking.
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