Liberating yourself from the chains of full-time employment, saying “Sayonara!” to your boss and setting out to create a business on your own terms—that’s the dream. Working for yourself can be everything you’ve ever wanted. And then sometimes it’s not. Solo-work definitely has its challenges.

Let’s look at the five biggest hurdles that independent workers face every day.

But don’t worry! We’ll also give you some strategies that will have you leaping over those hurdles with grace and determination. Well, at least with determination.

Challenge #1: Getting any work done at all

In a ‘proper’ job and an office environment, there is a system and a routine.

You have a desk. You have certain set hours that you’re expected to work. You have meetings to go to (yes they often suck but at least they give you a purpose). And you have a boss and other team members on your back to make sure that you deliver your projects on time. You may have a stressful commute and a know-it-all colleague who drives you crazy, but there is a whole organization in place that gives you a framework to easily slot into.

Woman lying in bed during daylight
Late mornings are nice. But at some point, you’re going to have to get up and do some work. Via Nomao Saeki.

Starting out on your own—not so much! Working for yourself means that you can stay in your PJs and start working as late as you want. And you’ll probably be working from home at first, with all the distractions that this brings with it. Laundry. Coffee. Deliveries. Or maybe you’ll go to a café—but which one? Will it be full of moms with screaming babies, or hipsters and loud music? Does the Wi-Fi work and is there a socket? Will the owner shoot you disapproving looks as you nurse a small cappuccino for four hours?

The solution: Bring back just a teeny bit of structure.

Once you’ve had that first rebellious period of throwing off the shackles of your job and staying out late on a Tuesday night because you can… Once you’ve frolicked in the freedom of having a complete lack of schedule and caught up with 10 years’ worth of sleep deprivation… Then it’s time to knuckle down and get to work.

You need to put in place a structure that works for you:

  • Decide on a regular starting time. Yes, you do have to get up at some point! Determine when you will take your breaks and when you will finish your working day.
  • Think about when you do your best work, and use this time for your toughest projects.
  • Find a space that provides the environment you need where you can work without being disturbed.

You’ll soon realize that a little bit of structure is what will make all that freedom you want possible.

Need some help? We’ve got a great blog post that will teach you how to set up a structure that will help you get your work done and get the freedom you need.

Challenge #2: Choosing what you’re going to work on

In a regular job, you’ll have a defined scope with an individual work plan that says which projects you need to complete. Your boss will tell you what your priorities are (or at least you’ll agree on them together). On top of that, you’ll get urgent requests, be invited to last-minute meetings or have random things thrown at you. Even as a senior manager, there will always be other people giving you things to do.

Open laptop sitting on a tidy desk.
Okay, so you’re finally sitting at your computer. Now what?! Via Kari Shea.

The advantage of working for yourself is precisely that there is no one telling you what to do. But the challenge is that there is no one telling you what to do! You need to figure out what your top priorities are and what you should work on today. You need to choose which projects to say “yes” to and which ones to decline. And if a new urgency arises, you’ll need to decide what to de-prioritize.

It can be hard to choose what to focus on each day and how to effectively juggle all your different priorities. And, no, getting the perfect Instagram shot of that cappuccino with your MacBook positioned artistically next to it is not a priority.

The solution: Put on your big boy/girl pants and start making some calls.

You wanted to be your own boss. Well, now’s the time to step up to the plate. You need to have a clear vision for your business and what you want to achieve. Then, put a plan in place to achieve it.

It used to all be about multi-tasking, but the latest research and advice on time management is all about focus:

  • Decide on your biggest priorities and the specific actions that you need to take to get the results you’re after.
  • Each day, choose the one thing that will make the biggest difference and start your day with the thing that you most want to avoid.
  • Make sure that you include both personal and professional priorities in your planning. This means going to the gym, taking proper breaks and blocking quality time with your friends and family.

This focus and intentionality will make your business successful. And never forget that the delicate balancing act between work and play is a big part of the reason why you wanted to go it alone in the first place.

Take a look at this blog post for some help in getting your priorities right.

Challenge #3: Knowing when to stop

Stop sign in the woods.
You need to learn when to say ‘stop’—or your body will do it for you. Via Michael Mroczek.

The corporate 9-to-5 is a well-oiled machine. Set your alarm, travel to work, put in the hours, travel home, take that suit off—and relaaaaax! You’ll take coffee breaks during the day, you’ll go for lunches with your colleagues and you’ll probably have commitments like gym classes or after-work drinks at the end of the day. You may work late sometimes but, at some point, security will throw you out and you will go home.

Working from home, the lines between work and play, house and office, can easily get blurred. When you’re super motivated and excited about your work, you can easily end up working all the time. And since your income is directly tied to the effort you put in, you feel guilty when you stop.

Technology makes all this possible, but you can end up being a slave to your laptop and your smartphone. “Ooo there’s a new email!” “Someone just messaged me on LinkedIn…” It never ends. You risk your work spilling over into your personal time and eventually crashing down around you.

The solution: Put. The. Phone. Down. Move awaaaaay from the computer.

You may love your work, but you know what they say about “all work and no play.” You’ll neglect your most important relationships, you’ll burnout and your work will suffer, making it all for nothing.

The best way to tackle this is to start putting in place some boundaries:

  • Create physical boundaries by setting up a designated work space in your house—ideally a study, but at least a little work corner.
  • Create virtual boundaries as well, putting your phone on silent when you’re having dinner with your partner, shutting down your laptop at the weekend and setting an out-of-office message when you’re on vacation.
  • Make sure that you communicate these boundaries clearly to your friends and family so they understand that your working from home doesn’t mean they can always call or visit.

Your ideal week may not be a traditional Monday-to-Friday, 9-to-5 set-up, but let work be work and then take some time to enjoy your life!

Challenge #4: Working in a vacuum

In a corporate environment, you’ll be working under a manager, you’ll be part of a team and you’ll be interacting with different departments. Your experienced colleagues can answer your questions, and training programs will help you develop skills so you’re equipped to deliver on your projects. You’ll even get rewards like salary increases or promotions as you progress in your career.

Empty table and chairs with a blank whiteboard.
Right, let’s get going with this brainstorming session, shall we? Who wants to start? Via Breather.

Working for yourself means that you have the final say on everything you do. The other side of this, though, is that you have no one (except maybe your dog, Gizmo) to brainstorm with, no feedback, no second opinion. Working solo means you will be making a lot of creative and professional decisions alone. Plus, there’s no training, no one to tell you how to improve and no one to reward you when you do well.

The solution: Phone a friend! And get a support system in place.

Working for yourself, you are the CEO, the manager and the employee. You can fulfill a lot of these roles yourself, but get other people to help you out from time to time.

Here are some of the things you can do to make things a bit easier for yourself:

  • It’s absolutely vital to your success—and your sanity!—that you find some kind of mentor or coach. (Gizmo doesn’t count.) Find someone that you can connect with regularly and use as a sounding board. They can help you when you get stuck, tell you if what you’re thinking makes sense and provide a different perspective.
  • You may be a solopreneur, but consider getting a small team. Hire a virtual assistant, social media manager or accountant to provide a support structure and take some of the operational work off your plate.
  • Celebrate your wins, and give yourself regular rewards. Open some bubbles when you get a big client, book a massage when you’ve had a tough week and make sure you plan some little celebrations to recognize the incredible progress that you’re making.

It’s not a sign of weakness to ask for help. It’s the only way that you’ll be able to keep things up in the long run without reaching burnout or feeling completed isolated.

Challenge #5: Managing feelings of loneliness

Man sitting alone with his phone, laptop and an iced coffee.
Ah, yes, that classic “stare-intently-at-my-phone-so-you-see-that-I’m-super-busy-and-don’t-mind-being-here-all-by-myself” trick. Via Muhammad Raufan Yusup.

Possibly the nicest thing about working in an office is the people you work with. It’s great to have a team, grab coffee with a colleague or have a drink after work to complain about your annoying boss. You’ll work hard together on a tough deadline and then celebrate when it’s over. There will be Christmas parties, team events and even birthday cupcakes. You may not get along with every one of your colleagues, but having people around you can be both comforting and stimulating.

Working for yourself? You guessed it: no dream team, no one to complain to when something doesn’t work or to celebrate with when it does. Nobody brings in cake to the office, nobody chats at the coffee machine and nobody asks to grab a beer after work. When you’re working for yourself, you can go for days without meeting anyone face-to-face.

The solution: Pull yourself together and put some pants on!

Missing the social side of office life might be the hardest thing to deal with when you’re working by yourself. But don’t suffer in silence!

Depending on exactly what you’re missing, here are some ways to deal with your loneliness:

  • Find a co-working space to simulate an office environment. You may also be able to take on bigger projects and spend time in your client’s office for a longer period of time.
  • Conferences and industry events can be good for meeting like-minded people, or you can join a professional club or organization.
  • Make sure you’re getting in those after-work drinks, dates and calling/meeting regularly with your family.

Just make sure that you get out of those PJs and you actually leave the house now and then!

Working for yourself: challenge accepted.

Working for yourself really does have all those awesome benefits that attracted you to it in the first place. You have a huge amount of freedom, much greater flexibility in your day-to-day life and so many more opportunities for creative decision making. Just be realistic, recognize that there are also some challenges and then set yourself up for success in a way that is sustainable for both you and your business.

And don’t forget to put some pants on.

Which of these do you find to be the biggest challenge as you navigate the stormy seas of working for yourself? Share your biggest struggles (and solutions) in the comments below.

Featured image features an illustration by Pinch Studio.