Employee or entrepreneur? The pros and cons of self-employment

In my recent review of Pam Slim’s Escape from Cubicle Nation, Chett left the following comment:

I was talking with a good friend last week who is self-employed. I told him I envied his entrepreneurial spirit and the ability to “go it alone.” He told me he envied my work as a teacher and the set hours and guaranteed pay check and insurance. (I told him there was nothing “set” about the hours, so I guess we both misunderstood each others work.)

So many people dream of working for themselves and only find out the true benefits and heartaches after they make the leap. Take you for instance, what do you miss the most from the box factory in terms of security, or interaction? What bothered, (or motivated) you the most to drive you to self-employment and what have you learned about your decision over the past year and a half?

In the same thread, Caitlin wrote:

Every time I real an article like this I wonder if I’m really that unusual because I love my job. I’m a molecular biologist, and it’s just not something I could do on my own…I’ve had a small side business for over 5 years. In that time, interesting and educational though it was, I’ve learned that I don’t particularly want to run a business.

I am not one who believes that everyone should be an entrepreneur. I think there’s a sort of continuum: Some folks should absolutely work for somebody else, others should definitely work for themselves, and many should do a little of both.

Although I tend toward entrepreneurial endeavors, I don’t consider myself a die-hard entrepreneur. The best job I ever had was actually flipping burgers at McDonald’s when I was in high school. I’m not kidding. I loved that job. My fellow employees were smart and fun. Together, we made serving burgers and fries a game; we tried to do the best job we could. Our manager was great, and she fostered this attitude instead of stifling it with bureaucracy.

Since then, I’ve had jobs I loved and jobs I hated, and many that just paid the bills. I’ve also tried self-employment twice: once as a computer consultant, and now as a professional blogger.

Here are my responses to Chett’s specific questions:

What Do I Miss From the Box Factory?

I miss daily interaction with my family. My father began the business almost 25 years ago, and since then there have always been several family members involved with the daily operations. I also miss talking with my customers. As much as I disliked the actual sales portion of my job, I genuinely liked many of the customers I dealt with. I find myself wondering how Robert is doing, and whether Lance finished building his house.

There is almost no social aspect to the life of a professional blogger; I sit here alone in my office typing all day. While this is intellectually challenging, I miss seeing people and being a small part of their lives. This is one reason I’ve struggled with my restaurant spending over the past year. I often go out to lunch simply to be near other people. It’s also one reason I rented office space.

Note: Trent and I both discussed this loneliness on last Monday’s episode of The Personal Finance Hour. How bad does this loneliness get? Very bad. It’s Thursday afternoon as I write this. A couple of hours ago, I had a near panic attack from the loneliness. No joke. To cope, I came down to the coffee shop for a couple of hours.

What Motivated Me to Self-Employment?

There were a couple of things. First, I did not like my work at the box factory. I did not like sales. I wasn’t good at it, it didn’t interest me, and I found it frustrating.

Meanwhile, I wanted to write. I’ve always wanted to be a writer; I just never knew how to make money from this desire. When I stumbled into personal finance blogging, I was startled to learn I could make an income from it. It seemed natural to make the leap to professional blogger once that income sustained at a level that could support me.

What Have I Learned About My Decision Over the Last Year-and-a-Half?

There’s a difference between blogging as a hobby and blogging as a job. When you’re blogging as a hobby and the income is “extra” income, the process is fun. It’s a lark. But when you throw the switch and it becomes your sole means of making a living, some of that fun vanishes.

I still love what I do — no question — but sometimes I feel as if I’ve lost the spontaneity I used to have. That’s one reason I’m hoping to reduce my workload around here a little. I’d like to pursue other projects: write a book, dabble with other blogs, possibly promote financial literacy education.

There’s a lot of pressure when you are required to generate your own income. Sure, there’s pressure when you work for somebody else, too, but there’s also a sense of freedom. You’re not responsible for the daily decisions. And if you don’t like the job, you can leave. Plus, the actual source of income is not your responsibility.

I often think that working for somebody else is like renting an apartment; working for yourself is like owning your home. Both have their rewards, but they each have drawbacks, too.


As Caitlin mentions, not everyone is cut out to run a business. It just doesn’t interest them. My wife is a perfect example. Kris loves her job. It’s challenging and fulfilling, and she enjoys the interaction with her co-workers. She has no desire to strike out on her own.

As always, I think it’s important to do what works for you.

Trivia: According to the U.S. Small Business Administration, on average, self-employed people make more than those who work for others [PDF]. But there’s a wider variance in incomes among the self-employed. Also, earnings for the self-employed are lower at first, but tend to grow more quickly until they surpass that of traditional workers.

Now I’d love to hear from you. Have you ever been self-employed? Did you love it, or did you hate it? What prompted you to pursue entrepreneurship? What do you envy about those who work for somebody else? Or, if you work for somebody else, are you content with where you are, or do you envy about the self-employed? What is it that keeps you doing what you’re doing?

More about...Career, Side Hustles

Become A Money Boss And Join 15,000 Others

Subscribe to the GRS Insider (FREE) and we’ll give you a copy of the Money Boss Manifesto (also FREE)

Yes! Sign up and get your free gift
Become A Money Boss And Join 15,000 Others

Leave a reply

Your email address will not be published. Required fields are marked*