Skip To Content

    21 Everyday Struggles Self-Employed People Deal With

    Sure, being your own boss can be fun, but sometimes it's a drag.

    1. Having to check our emails during holidays or on our days off.

    Comedy Central

    If we actually take a holiday to try and relax, we often spend it worrying that we'll lose out on business so end up checking our emails anyway.

    2. Because some customers or clients expect us to be available 24/7.


    When it's not needy friends DMing us, some customers expect to be able to call at 7am or 11pm and have us answer their questions RIGHT NOW, thanks to the world of big business customer service.

    3. Not having sick pay.

    Karina Farek / BuzzFeed

    We long for the days of our 9-5 job of the past where we could call in sick with a hangover and get paid for it.

    4. The difficulty in knowing how much to charge for something.

    Paramount Pictures

    If I ask for a higher amount, do people think I'm arrogant? Am I undercharging and selling myself short? Awks.

    5. Sometimes getting distracted really easily.

    Becky Barnicoat / BuzzFeed

    Without a boss breathing over our shoulder and a whole world of fun things to look at online/outside the window/anywhere but your work, it's way too easy to lose an entire afternoon.

    6. And procrastinating from the boring but essential jobs.

    Loryn Brantz / BuzzFeed

    You know it's bad when you're considering tackling the ironing instead of that spreadsheet.

    7. Friends thinking we're free to talk all the time on social media and getting annoyed if we don't reply.

    BBC / HBO

    Just because we don't work in an office and can set our own hours doesn't mean we're sat twiddling our thumbs waiting for our bestie to message us.

    8. The isolation of working alone.

    Comedy Central

    Cue full blown conversations with the cat.

    9. Two words: Tax returns. / Scott Bryan / BuzzFeed

    It's either hellish calculations for yourself, or shelling out more money for an accountant to do it for you. Lose/lose.

    10. Having to persuade ourselves to change out of our pyjamas.


    Every good business guide tells you to dress as if you were leaving the house or going to an office, but we're just so comfy.

    11. Dealing with imposter syndrome.

    Hannah Hillam / BuzzFeed

    Even the most successful self employed people get it, that feeling that it's all been a fluke and someone will discover that you're actually just a worried child after all.

    12. Going from having no work at all to then suddenly having ALL OF THE WORK EVER.


    Feeling like a failure when things are quiet, then panicking when it's busy. Rinse and repeat.

    13. People trying to get freebies.

    Phase 4 Films

    You wouldn't walk into Topshop and take something off the shelf and walk out without paying, yet small business owners often get friends or acquaintances trying to blag something for nothing.

    14. So. Many. Invoices.

    15. Working multiple jobs.


    Especially when we're in the early days of our business, or working as a freelancer, sometimes we need to pick up other work to make ends meet.

    16. Trying to accept complaints and criticism. / DGC

    Constructive criticism is essential, but sometimes people just seem to enjoy bitching and when the business is our baby it can be hard not to take it personally.

    17. Trying not to let health and fitness fall by the wayside.

    Hannah Hillam / BuzzFeed

    Especially if we work from home, we often check our step monitor and find that we've walked less than 1,000 steps that day (and most of those were to the kitchen and back for more snacks.)

    18. Some family and friends asking when we're going to get a "real job".

    20th Television

    This is especially true if we make our living via the internet. The older generation sometimes seem to think that if it doesn't involve a bricks and mortar office then it doesn't equal work.

    19. Knowing when to say no.

    20th Television

    Sometimes the fear that no more work will come means we say yes to too many things and end up with way too much on our plate.

    20. Holidays and long weekends not always applying to us.

    William Varner / BuzzFeed

    See also "that Friday feeling" that your friends talk about.

    21. Never switching off.

    TLC / Via

    It can be hard, if not impossible, to get out of "work mode".

    Note: This post is based on one person's experience.

    BuzzFeed Daily

    Keep up with the latest daily buzz with the BuzzFeed Daily newsletter!

    Newsletter signup form