One of the biggest perks of being self-employed is having the freedom to set your own hours. No boss to ask for time off, no rigid schedule dictating your day. But with that freedom comes a trade-off, one that I was reminded of recently when I had to go to the dentist.

The Perks: Flexibility on Your Terms

When you are your own boss, scheduling appointments is easy. Instead of squeezing in a dentist visit during a rushed lunch break (and hoping they are on time) or trying to get the last available spot after work, I could simply book it at a time that suited me best. No stress, no negotiating time off, no guilt about leaving a workplace short-staffed.
And after the appointment? I could take the time I needed to recover without worrying about someone questioning my productivity. If I needed to rest, I could. If I wanted to ease back into work with a few admin tasks, I could do that too. That kind of flexibility is priceless.

The Downsides: No Work, No Pay

But then there’s the flip side. While I wasn’t at my desk, I wasn’t making money. There’s no “sick leave” when you work for yourself. If you’re not working, the income stops, but the overheads don’t. My business expenses still needed to be covered, my to-do list didn’t magically shrink, and client deadlines still had to be met.
Plus, there’s that lingering feeling of falling behind. A few hours away might not seem like much, but in a business where consistency matters, every break from routine can feel like playing catch-up later.

The Reality of Self-Employment

This is the reality of self-employment. The freedom comes with responsibility. It’s a constant balancing act between flexibility and financial stability. But knowing this, we can plan ahead. One way to create more breathing room is by automating parts of the business. Things like scheduling tools, email marketing sequences, and templates can help keep things running even when you need time off.

Another key strategy is incorporating digital products into your business. Unlike client work, which requires you to be present and actively working, digital products like templates, courses, or e-books can generate income in the background. Having something that sells passively means that even when life gets in the way, your business isn’t at a complete standstill.

Would I trade my self-employed life for a traditional 9-to-5 just for the security of sick leave? Not a chance. But moments like these are a good reminder that while working for yourself offers incredible freedom, it also requires discipline, planning, and a willingness to embrace the unpredictable.

Have you ever had a moment where the perks and challenges of self-employment became crystal clear? Send me an email or leave a comment below.