Pros & Cons of Being Your Own Boss
Have you ever thought about working for yourself?

There are so many reasons why someone might want to work for themselves.
Just as we are each unique individuals, so are each of our career paths and goals in life.
Anyone may want to be an entrepreneur or freelancer and be their own boss.
Some people want the flexibility it gives, some hate working for others who tell them what to do, some want to travel the world while making money, and more.
Some people have had bad experiences with a jerk boss or a micromanaging one. Some may love the thrill and risk-taking of entrepreneurship.
For me, I actually didn’t care about being my own boss and always did well with the structure of working in an office environment, and my last couple of bosses were fantastic, though of course, I’d had “bad” bosses, too.
But I wanted to be a writer for as long as I could remember, and once I started taking on freelance clients and realized it was going to be a viable option for me full-time, I needed to quit my day job (sales) to focus on it and give it full-time hours.
I didn’t decide to work for myself as a reaction to corporate life — instead, working for myself was what gave me the ability to do my dream job.
In the end, being my own boss has been quite gratifying and satisfying, and it enables me to have a lot more flexibility than I had before, which is awesome!
Pros & Cons
But there are definitely both advantages and disadvantages of working for yourself!
If you have thought about or plan to go freelance or become an entrepreneur, it’s very important to look past the current issue (such as having a bad boss) and really make sure working for yourself is what you want. You need to understand the pros and cons and not look at entrepreneurship through rose-colored glasses.
That way, you’ll be making a considered, researched decision and have realistic expectations of what your new work life will be like.
Here are some specific pros and cons of working for yourself.
Pros of Entrepreneurship
- You get to set your own hours.
- Bring your passion to life; truly doing what you love.
- You gain a lot of flexibility with where you can work, meaning you can travel more often!
- You can set your own prices and potentially make a lot of money.
- No one is watching you (no boss), which means no micro-managing.
- You get to work in your pajamas!
- You get to choose the direction and goals of your business.
- It’s exciting.
- You can have a ton of variety in the work you do and get to choose your own clients and projects.
- You get to learn how to fail gracefully and keep moving forward.
- For service-based businesses, it’s free to start one.
Cons of Entrepreneurship
- Because it’s yours, you tend to work longer hours, including nights and weekends.
- You have to do all of the stuff you don’t like, too (bookkeeping, sales, make your website…). Especially at first, before you can afford to hire people or assistants to do some of the grunt work.
- There is no paid time off. You either take your work with you or you don’t work while on vacation and don’t earn any money.
- There is no 401(k) or taxes taken out of your pay — you have to set that up yourself, like an IRA for your retirement, and save a percentage of everything for taxes. I’m never getting a refund again!
- There is no set insurance — you have to either buy private insurance or get on your spouse’s work insurance (if possible).
- No one is watching you, so you have to make sure you track all your own projects and deadlines and stay super organized.
- It can be isolating and lonely.
- You MUST set your goals and path for your business and have a clear idea of what you want to do and where you’re going at least for the short-term future.
- It can be scary and unstable. You need to constantly be marketing yourself and looking for clients and having a pipeline.
- There can be too many ideas, avenues, paths, and variety sometimes, making it difficult to focus on your core business or clients. But a tighter focus is necessary for growth.
- It is too easy to procrastinate!
- You’ll definitely spend more on tools and supplies than you think.
For me, I am very confident in myself and my business, and I love what I do. It is not without bad or frustrating days, but it is worth it to me.
Conclusion
That cons list may seem longer than the pros, but for me, the positive aspects of working for myself outweigh the negatives. Part of that is because I have a lot of experience in sales and marketing, so I don’t necessarily think that having to do marketing is a con, and I was able to get on my husband’s insurance, which is a big weight off my shoulders.
What it comes down to for me is that I get to do what I love — and I am disciplined enough to do it every day without someone telling me what to do. It was a struggle at first and it took time to find my routine and what works best for me, but I figured it out over time.
Honestly, I am not opposed to going back to a regular job — as long as I get to do the writing and editing I love. My biggest motivation for going freelance was to get to be a writer and editor. If I could do that within the confines of an employer, I might seriously consider it.
But for now, I recognize the cons and revel in the pros of this entrepreneur life!
Are there pros and cons I have missed? What would you add to this list?
YouTube video which expands on this topic.
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