Whether you call yourself self-employed, an entrepreneur, part of the gig economy, or something else, when you’re freelancing, it means one thing. You work for yourself first and foremost. That life can look different from person to person but most people doing freelance work control much of their own working life, including where and when they work. It can offer a lot of freedom to work how you like, but it’s not all peaches and cream. There are some parts of the entrepreneurial lifestyle that do make you want to occasionally scream out the window, but also a few tricks to deal with them a little better.

Planning the day

How can planning your workday be a bad thing? It’s not, really, it’s the trying to get in the habit of it that can be truly painful. For instance, if you’re working at home, it’s oh-so-easy to end up being tempted by the TV, social media, or your cat for hours on end. For that reason, it’s important to maintain your own work environment, setting aside a space that’s primarily and solely for work, whether it’s a whole room, a corner of a room, or a single desk. For actually setting out the work ahead of you once you’ve got yourself in a distraction-free space, workflow planning apps can make it much easier to create a realistic, flexible schedule.

The constant hustle

Your ability to grow the business (and feed yourself) depends entirely on how well you’re able to win over clients. For that reason, you’re going to have to get used to reaching out. Or are you? When you first set up your own business, there will be a lot of outreach. As you keep growing, however, you can automate a lot of the client outreach efforts through branding and marketing tactics. From creating a high-quality site to writing fantastic content and making it all search engine friendly, you can do a lot to streamline the potential client’s journey to you, so you don’t have to work quite as hard on winning them over.

Cabin fever

Most self-starters start in their own home. If you haven’t yet moved to an office or you don’t plan to, then you should be aware of the main issues of working in that home. Primarily, it’s the breakdown of the work-life separation. Life can intrude on work by distracting you, as mentioned above. Work can intrude on life by making you a little less able to truly relax in the home since you may always feel like you’re in a work environment. Coworking spaces might be the perfect solution to cabin fever. You can also work in cafes, parks, libraries, and other public spaces, but coworking spaces have an air of professionalism about them, often with others in those spaces hard at their own work, making it easier to focus on yours.


Being surrounded by people can be important from time to time, too. While you will likely not miss the office politics, isolation and general feelings of loneliness are not uncommon when you’re working for yourself. However, you don’t have to resign to being forever alone. As you grow, it’s not unlikely that you will hire other members of the team. For now, however, there are plenty of entrepreneur networking events that offer not just company and the ability to make relationships with those that share your goals, but also practical advice and potential business partnerships.

Dealing with clients

Of course, not all clients are bad. Not even most clients are bad. You will be surprised by how good your average client can be, but that doesn’t mean you won’t have that troublesome relationship from time to time. It’s important to learn how to appease difficult clients to some degree. Tricks like reflective listening (voicing their concerns back to them to show you fully grasp and understand them) and the beginner’s mindset (not making assumptions about what your customer should and shouldn’t know) can help, as many difficult customers are simply misunderstood or in need of help. But for those who are truly difficult to the core, there’s another important rule you can remember. You can say no. If clients aren’t willing to let you work under your initiative (setting your own prices, your own schedule, your own methods), then not saying ‘no’ is essentially agreeing to let them be your boss. That’s likely not what you want.

Financial independence

The ability to support yourself financially is a big bonus, but a huge responsibility. You are entirely in charge of all your own expenses, as well as covering the business costs. If you get into the self-employed life, then you have to be able to manage your own finances, including building your own savings and putting together your own emergency fund. Do what it takes to become more financially literate to make sure you have plenty of economic security. There’s also the fact that you don’t get paid for sick leave or time off, so it’s wise to calculate how many days you’re likely to miss work in any given year and budget to cover yourself if it comes to pass.

Admin overload

Running your own business takes a lot more administrative work than simply working for someone else. Taking and replying to messages, sending emails, organizing your schedule, it can all pile on top of you. However, it’s much easier to get someone else to deal with that nowadays. You don’t need to open a permanent position. If you’re feeling like you’re snowed under, you can hire a virtual assistant as often or as seldom as you need to get a much more cost-effective helping hand.

While they may not seem like much, individually, each of the little issues mentioned above can easily build upon one another and become seriously stressful if you don’t take the time to work around them. Anticipate those pain points and solve them so you can enjoy the plenty of things to love about working for yourself.