Tips for working for yourself

tips for working for yourself

Working for yourself is ever more popular, with all the shiny things that come with it: freedom, independence, creativity… It’s an incredibly attractive proposition, and in my experience it’s all true! But. That wonderful freedom that seems, and is, so appealing, can also potentially be a curse. There may be moments when you look back on those big Christmas parties with a twinge of sadness, or when you wish that all your taxes, insurance and other admin would still be dealt with by your employer. There may be moments when you feel lonely and lost in all the possibilities that are out there with no one to guide you.

Being aware of the negatives is important when you’re making the decision to leave behind your full-time job, so that you don’t launch yourself into something where you’re not prepared for the challenges to come – but I’m also happy to reassure you that there is usually a solution even to these challenges!

Here are 5 challenges when you’re working for yourself from my own experience:

1. Finding somewhere to work

It’s such a basic premise, and when you’re an employee you take it for granted that you’ll turn up at the office every morning and sit down at your desk. When you work for yourself, though, you can choose to work from home – bedroom? kitchen? living room? – or head out to a café – which one? – or maybe find a more formal co-working space. The fundamental requirements here are, first, WiFi – it’s embarrassing and frustrating when you’re in a call with a client and the connection is bad – and, second, a bit of peace and quiet. Personally I think there should be specific cafés allocated to parents and their screaming babies and others for hipster digital nomads who are trying to work (maybe there are and I’m just not hipster enough to know about them!).


Having a regular spot in a co-working space of course removes the uncertainty and ensures that you have access to a professional space with WiFi, alongside people like you who are trying to make a living (while drinking a nice big latte). I’d also recommend checking out a café, how busy it is at different times of day and how reliable the WiFi signal is, before you rely on it for an important call or meeting.

2. Deciding what to work on

This shouldn’t be so different to working in a full-time manager role, but the truth is that when you’re in an office you’re always going to have new instructions coming in from the board, an urgent request from your boss, a last-minute meeting, and various other disruptions throughout the day from people who need your help. Working for yourself, at home, you don’t have those disruptions (hurrah!) but you are then left with a whole day stretching out in front of you that you need to fill in a productive way. This can be especially difficult when you have a portfolio career and you’re juggling a lot of different projects and tasks – which one is most urgent or will create the most movement in the business?


Setting goals with deadlines and action steps for the next three months, one month, one week will help you to prioritise the most important tasks when you wake up in the morning and will ensure that you move ever forwards, even without someone on your back about when it’s due!

3. Knowing when to stop

Part of the attraction of working for yourself, when you’re looking at it from inside the walls of a full-time job, is the flexibility. You choose when to work, you can work from anywhere, you can take vacation whenever you want. What you don’t see, though, is that this same flexibility can be a curse, with lines becoming blurred between work and play, office and home. In a way, you never have any free time at all, as you can always do more, and it’s difficult to switch off. All this is compounded by the fact that you’re usually very passionate and self-motivated about what you’re doing, given that you’ve chosen and created this business yourself, which makes it even harder to let go at the end of the day.


Here too it’s important that you set specific goals and action steps, so that it’s clear when you’ve completed a particular part of your work and you can reward yourself with some time off. Regular breaks while you’re working are also crucial so that you can keep your energy and focus.

4. Having a social life

Yes, it’s very sad, but there are no Christmas parties when you’re a solo entrepreneur – at least, not like the ones we used to have at my old job! Nobody brings in cake to the office, there’s no one to chat with over the coffee machine, and no one asks you if you want to grab a drink after work. When you’re working for yourself, you can go for days without meeting anyone face-to-face and you really have to go out of your way to have some social interaction in your day-to-day life. You’ll also not as easily be making new friends as new people join the company or you have various off-site team-building events (there is no team!).


The co-working space can again help to simulate the office environment if that’s what you want, or you can take on contracts where you’re in a client’s office for a longer period; conferences can also be good for meeting like-minded people. Make sure as well that you book friend dates (and romantic dates if appropriate!) so that they’re in the calendar, and make time for your family – after all, that’s usually a big reason for why you’ve chosen to work for yourself in the first place.

5. Making all your decisions alone

Working for yourself means that you have no boss telling you what to do, no annoying colleagues who aren’t delivering on their projects, no office politics at all in fact… You have complete creative control and the final say on everything you do. The other side of this, though, is that you have no one to brainstorm with, no feedback, no second opinion. There’s plenty of free information to be found online but it’s easy to get lost and overwhelmed in all the different advice that’s out there and nothing beats having someone to talk things through with.


It’s absolutely vital to your success, and your sanity, that you find some kind of mentor, a coach, or a peer, who you can rely on when you need to. I have a partner and friend on one of my businesses who is always the first person I go to on my other projects as well, and I’ve also had several coaches over the past years; it’s just so valuable to have someone you trust to be there for you. It might be a friend, or a former boss who can serve as a mentor when you’re stuck on something, or else a professional coach or consultant.

What about you? Have you quit your job and discovered some different challenges that come with working for yourself? Share in the comments below!


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