This is a question I’ve asked myself multiple times throughout my life—and one I still think about today.
I’ve been employed.
I’ve been self-employed.
I’ve gone back and forth more than once.
Right now, I’m in what I consider the best possible position for me: I’m employed as an SEO Specialist for an insurance tech company working nights, while also building and earning from my own personal projects during the day and in my spare time.
After years of experience on both sides, I can confidently say this: there is no “better” option—only what works best for your lifestyle.
The Pros and Cons of Being Employed
Being employed is often painted as “safe” or “boring,” but there are very real advantages—especially if you value stability. In my case, I need stability since I have a young son that I need to sustain and provide for.
Pros of Being Employed
1. Assurance of a Stable Salary
You know when your paycheck is coming. This makes budgeting, paying bills, and planning life much easier.
2. HMO and Benefits
- Health insurance
- Paid leaves
- Sick leave
- Government-mandated benefits
These things matter more as you get older or start a family.
3. Clear Structure and Schedule
You know:
- When work starts
- When it ends
- What’s expected of you
For many people, this structure reduces stress.
4. Workmates and Social Interaction
Having colleagues means:
- Shared workload
- Team support
- Someone to talk to during tough days
You’re not carrying everything alone.
5. Career Growth and Training
Many companies invest in:
- Skills training
- Certifications
- Leadership development
You’re paid while learning. And where I’m working right now, I’m paid really well financially and through skills-building.
Cons of Being Employed
1. Fixed Income Ceiling
No matter how hard you work, there’s usually a cap on how much you earn.
2. Fixed Schedule
You work when the company needs you—not always when you’re most productive. Night shifts (like mine) are manageable, but not for everyone.
3. Limited Control
You don’t always choose:
- Projects
- Clients
- Direction
You execute someone else’s vision.
4. Office Politics
Promotions aren’t always about skill. Sometimes, they’re about timing, relationships, or luck. Thank God, there’s none of that where I work right now. But this has happened to me so many times and I’ve both benefited from office politics and not. Mostly benefited…
5. Job Security Is Not Guaranteed
Layoffs happen. Companies restructure. Stability can disappear overnight. We recently had a few tenured employees laid off and boy did that scare everyone. I gotta say that the moment I heard that happened, I got my resume ready.
The Pros and Cons of Being Self-Employed
Let’s be honest: everyone dreams about being self-employed.
Freedom.
Flexibility.
Unlimited income.
But very few people talk about how hard it really is.
Pros of Being Self-Employed
1. Control Over Your Time (Eventually)
You decide:
- When you work
- What you work on
- Who you work with
That freedom is powerful. But it doesn’t happen overnight.
2. Unlimited Income Potential
Your earnings are tied to:
- Skill
- Effort
- Strategy
There is no salary cap. But you gotta work for it.
3. Creative and Personal Fulfillment
Building something that’s yours hits differently. It’s stressful—but deeply satisfying. And this is the main reason why being self-employed is so attractive to someone like me.
4. Skill Expansion
You don’t just write or work—you learn:
- Marketing
- Sales
- Systems
- Finance
You become more capable overall.
5. Ownership of Assets
Blogs, products, and brands can continue earning even when you’re not actively working.
Cons of Being Self-Employed
This is where reality hits.
Hard.
And many people aren’t ready for it.
1. No Assured Salary
Some months are great. Others are terrifying. Income is inconsistent—especially at the start. If you haven’t prepared yourself financially for it, you might just end up quitting and going back to being employed. So yeah… be prepared.
2. No Automatic HMO or Benefits
You pay for:
- Health insurance
- Leaves
- Sick days
If you don’t work, you don’t earn.
3. No Workmates
You’re often working alone. No teammates. No safety net. This is the one reason why I don’t really like being self-employed.
4. You Work More, Not Less
Early on, self-employment often means:
- Longer hours
- Weekends
- No real “off” switch
Freedom comes later—after discipline. Yeah so be prepared to be down in the trenches digging… hard to get your business up and running.
5. Emotional and Mental Load
You are:
- The boss
- The employee
- The accountant
- The marketer
Many people regret going self-employed because they underestimated this aspect.
A Quick Comparison
| Aspect | Employed | Self-Employed |
| Income | Stable | Unpredictable |
| HMO & Benefits | Provided | Self-funded |
| Schedule | Fixed | Flexible (but demanding) |
| Workmates | Yes | Often none |
| Stress Type | Job security | Survival & growth |
Why I Chose Both
Right now, I have the balance that works for me. I am both employed and self-employed.
- At night, I work as an SEO Specialist. That means I have a steady income, some structure, and benefits.
- During the day and spare time, I build my own projects and earn from them:
This setup gives me:
- Stability
- Creative freedom
- Long-term upside
- Reduced financial anxiety
It’s not easy—but it’s sustainable. And I worked long and hard for this. Even when I wasn’t working for Zywave, I was slaving hard getting my blogs up and running.
So Before You Choose,…
Being self-employed is harder than most people think. Being employed isn’t as limiting as some make it out to be.
Both paths have sacrifices. Both have rewards.
At the end of the day:
- There is no bad choice
- Only the choice that fits your goals, responsibilities, and tolerance for risk
Whether you choose to be employed, self-employed, or—like me—somewhere in between, what matters most is that you choose intentionally.
Because the worst position to be in isn’t choosing the “wrong” path—it’s choosing blindly.