Being your own boss is pretty great, but it comes with plenty of downsides, too.
Whether you’ve started your own business or you simply prefer being part of the gig economy, being a freelancer is challenging at times, and really exciting at others. If you’re on this career path, chances are you’ll relate to these things.
1. Explaining what you actually do… again
Whether it’s family, friends, or a random person at a party, explaining freelancing is an ongoing struggle. People assume you either don’t work or that you’re constantly in your pyjamas. Getting them to understand what you really do can feel like a full-time job itself.
2. That weird excitement for Monday
Source: Unsplash While everyone else dreads Monday, for freelancers, it’s a fresh start with a bit of structure. You get to tackle new projects, set goals, and jump back into your rhythm. Mondays feel less like a drag and more like an opportunity—plus, you can still avoid rush-hour traffic.
3. The never-ending search for good Wi-Fi
Source: Unsplash Finding a café with strong Wi-Fi is like discovering a hidden gem. If it’s quiet, has comfortable seating, and the internet is reliable, it’s almost magical. Freelancers keep a mental list of “best spots for Wi-Fi” and are always on the lookout for more.
4. Forgetting what a “weekend” really means
Source: Unsplash When you’re freelancing, weekends don’t always exist in the traditional sense. Work can spill over into Saturday or Sunday without a second thought, and then you might take a random Tuesday off instead. Flexibility is great, but it makes the whole concept of a “weekend” a little blurry.
5. Having way too many browser tabs open
Source: Unsplash Project research, invoice tracking, client emails, and maybe a video tutorial or two—it all adds up. Freelancers often have more tabs open than they’d care to admit, juggling all their projects at once. Closing a few tabs feels like cleaning out a closet.
6. The freelance roller coaster of “feast or famine”
Source: Unsplash Some months you’re swamped with work, and others you’re refreshing your inbox just hoping for a project. This “feast or famine” cycle is a classic freelancing reality. It keeps you on your toes, and budgeting skills suddenly feel like a superpower.
7. The thrill (and dread) of new client emails
Source: Unsplash Every new client email is exciting… but it also means more work, more details, and potentially a steep learning curve. It’s a mix of “Yes, new work!” and “Oh boy, here we go again.” Freelancers know the feeling of wanting the work but also dreading the extra load.
8. Writing and re-writing that “perfect” pitch
Source: Unsplash Crafting a pitch that’s clear, confident, and catches attention isn’t easy. You might spend ages refining it only to get no response. It’s part of the game, though, and freelancers learn to get creative with their pitches to stand out.
9. The elusive work-life balance
Source: Unsplash Working from home can make it tough to “switch off” at the end of the day. There’s always something that could be done, so work-life balance sometimes feels like a myth. Freelancers know the struggle of drawing the line between work and downtime.
10. Loving and hating “flexible hours”
Source: Unsplash Flexible hours are a blessing… until you find yourself working late into the night. While it’s great to work whenever you want, it’s easy to lose track of time and end up with unusual working hours. Freelancers know the joy and curse of that flexibility.
11. The excitement of landing a “dream client”
Scoring a client you’ve always wanted to work with is a huge high. It’s validation that all those hours of pitching and hustling paid off. Freelancers understand the thrill of finally getting to work with someone they admire.
12. Overthinking every word in an email
Crafting the right tone in an email is an art form for freelancers. Should you sound friendly or formal? Did you use too many exclamation points? Freelancers can spend far too much time perfecting emails, knowing that first impressions matter.
13. Random mid-week “weekends”
Sometimes Tuesday is the new Saturday, and freelancers embrace it. Being able to take a day off mid-week feels like a mini-vacation. You can hit the grocery store without a crowd or have a long lunch and still be back at your desk by evening.
14. The guilt of a “lazy day”
Taking a day off as a freelancer can come with a side of guilt. Even when you need the break, there’s that nagging feeling you should be doing more. But everyone needs downtime, and freelancers slowly learn to embrace the “lazy day” without regret.
15. Celebrating even the small wins
Source: Unsplash Freelancers know how to celebrate every little victory, whether it’s finishing a big project or finally getting paid on time. Each win, no matter how small, feels like a big step forward. It’s those little moments that keep freelancers motivated and remind them why they’re doing it all in the first place.
