Question: When does an apparently fun way to earn income become a "job"?

Answer: From the moment you start.

While I was in the middle of the Big September Gig, I found several times to post “tweets” to Twitter about my progress, using the text messaging feature of my Treo. Later, when I got a chance to read the tweets of the people I follow, I found this comment from a fellow Twitter member:

Wish I was out flying but after so much, does it become a “job”?

The question kind of floored me. After all, the flying I do for hire is a job. So I replied:

Any time you’re required to perform a task at someone else’s whim in exchange for money, you’re doing a job, aren’t you?

But that doesn’t mean it has to be a bad thing.

And that pretty much sums up the way I think about all the things I do for a living, whether it’s writing or flying.

Why People Might Think Otherwise

That got me thinking about why some people might think that my flying or writing was not like a job. What did they include in their definition of job that I wasn’t including?

And I came up with the following list of items:

  • Many people’s jobs require them to be in a certain place at a certain time every day, such as an office or a jobsite. There’s usually some regularity to this, for example, 9 to 5, five days a week.
  • Many people’s jobs have a limited amount of time off that has to be approved before it’s used. For example, a 2-week vacation or “personal days.”
  • Many people’s jobs include a manager or supervisor or some other kind of “boss” who keeps tabs on their work and has the final say over how their work is done. This same person will also evaluate performance and provide input into promotion and raise decisions. And this person can terminate employment at any time.

For many people, this is the true gist of what a job is. They go to work on a regular basis, they do something under the supervision of a boss, and they get paid. A few times a year, they take time off.

Freelancing and Business Ownership is Different

I’m a freelance writer and the owner of a business. These are my two “jobs.” And in both jobs, I’m subject to the same requirements of a regular job, but in different ways.

As a freelance writer:

  • Although I’m not required to be in a certain place at a certain time every day, I am required to complete my work on time. So that means I have to sit at my desk and work to get the book or article or whatever is due done. And if meeting a tough deadline means working 12- or 14-hour days — even on weekends — that’s just the way it is.
  • I get as much vacation time as I like and no one has to approve it. However, if I don’t work, I don’t get books or articles written. And I don’t get paid.
  • I have a boss: my editor. He or she decides whether I’m creating the content the publisher wants to see. He or she can also make changes to my work or require me to redo it a different way. And if I don’t do my job right, he or she is not likely to recommend me or hire me for future assignments.

As the owner and chief pilot of Flying M Air:

  • When I have a gig, I have to show up on time and stay until my client is satisfied that the job is done. That job can be any day of the week, any time of the day or night.
  • I get as much time off as I want — as long as there isn’t an upcoming gig on my calendar. But when I’m not working, I’m not making money.
  • My boss is my client. If he wants me to be on the ramp, ready to fly at 6 AM, I have to be there. (There are exceptions to this. For example, as pilot-in-command, I have final say over whether a flight is conducted. So if I feel a flight cannot be conducted safely due to weather or other conditions, I can cancel it.) If I don’t do my job satisfactorily, my client will probably not hire me again in the future.

But Wait, There’s More!

I can make a good argument that being a freelancer or business owner is a lot more work than being an employee with a desk job.

  • When I’m not working and have no work lined up, I have to work to find work. For example, I might need to write a book proposal or pitch an article idea. I have to maintain my Web sites to keep potential customers — editors, readers, passengers — interested in my services. Or meet with hotel concierges to convince them that they should be recommending my helicopter day trips to their guests.
  • I have to manage the finances of each of my businesses. That includes keeping track of all banking records, balancing bank accounts, paying bills, and filling out sales tax returns. (Thank heaven I don’t have employees anymore; dealing with that paperwork is a nightmare.)
  • I have to keep my competitive edge. That means learning about the new technology I might have to write about and purchasing the computer hardware and software I need to get my job done right. I have to take an annual Part 135 check ride with an FAA inspector and work with helicopter instructors to get advanced ratings (like the instrument rating I want to get this season) and practice emergency maneuvers. It also means preflighting and washing the helicopter and managing its maintenance.
  • I have to think about and plan for my businesses 24/7/365. So yes, I lose sleep when I have a seemingly impossible to meet deadline ahead of me for my biggest book. (I made it.) Or when I can’t figure out where that pesky oil leak is and wonder whether it’s serious enough to be squawked. (It wasn’t.) And I’m thinking in the shower or while driving or flying about things I can do to grow my businesses and my income.

Do you do all that in your job?

I’m Not Complaining!

I’m certainly not complaining. While it’s true that being a freelancer or business owner can be a headache sometimes, it’s never bad enough for me to face the alternative — that desk job. I’ve been there and I know.

There’s something enticing about collecting a regular paycheck (with benefits, if you’re lucky) and moving your way up the corporate ladder — or even just skating at a ho-hum job. There’s something sweet about not having ultimate responsibility for profitability of a business. It’s certainly great to leave your job at the office door when you leave at the end of an 8- or 9-hour day.

I made the move to a freelance career in 1990, after eight years of a “9 to 5” job. And after 18 years of working for myself, building a writing career and flying business, I simply could not go back to the 9 to 5 grind. I’d rather work my ass off on my own schedule, taking the ups and downs that come with the freelance/business owner lifestyle, and be completely responsible for my livelihood than to tie myself to an office job again.

But that’s me.

What do you think? Use the Comments link or form for this post to share your thoughts.

And please, no get-rich-quick links. They will be deleted.

5 thoughts on “Question: When does an apparently fun way to earn income become a "job"?

  1. I think people who have jobs often think that the grass is always greener on the other side. Speaking as someone who has a job, I often think that wouldn’t it be cool if I were a writer or had my own business. Then I realize just how much work that would be and I become overwhelmed. I think if I did write or have my own business it would have to be at something that I felt so passionate about that the chance of me regretting the decision would be almost nil. I also think that our ideas of “work” and jobs in our culture is shifting. I like to think of what I do to pay my mortgage as “work”. I also think of my creative pursuits of writing, photography and radio production as my work also. What I’d really like to see is some income come from those creative pursuits and that’s where I become hung-up.

  2. I always wanted to be a writer, from the time I was a kid. But my parents pressured me into a more “practical” career. I got a BBA in Accounting and became and auditor and financial analyst for 8 years. I didn’t like it. In fact, sometimes I hated it.

    The move to a writing career came with lots of preparation. I began by writing a lot of freebie articles about the things I knew about from work. My first published piece was about auditing construction project budgets. (Still can’t believe I did THAT for a living.) I became a part-time trainer with the Institute of Internal Auditors through a special arrangement with my employer. I knew how to use computers. My big break was a $10K contract to write a 4-1/2 day course about using computers for auditing. That was in 1990. In those days, laptops weighed 20 lbs (if you were lucky) and everyone used Lotus 1-2-3. I left my full-time job to work on that project and filled in the income gaps as a freelance computer applications instructor teaching Lotus macros (I really was a Lotus whiz in those days), and various Macintosh topics.

    My first book proposal, which was about Macintosh telecommunications, was turned down because the topic didn’t have a big enough market. (Truth is, I was ahead of my time by about 2 years.) But I eventually got a ghostwriting assignment that led to a co-authorship assignment that led to my own book. That was 68 books ago. (You can read more about this at

    The point is, if you want something bad enough — for example, to earn your living by doing the things you love — you need to work hard to set yourself up as someone who can do that thing for pay. That means getting your work out there for people to see and coming up with ways to market yourself. It’s a long, hard road sometimes — especially with creative endeavors like writing or photography or art. But if you’re good and you’re patient and you work your butt off to find buyers for your work, you CAN succeed.


  3. I really liked this post! My thought when I read the title was exactly the same as the first sentence, “Immediately!” I absolutely agree with Mark as well, that for many people the grass is greener somewhere else, wherever that may be. I have another theory too though.

    I think that people want to believe that there is some perfect job out there, one that pays all the money they think they want, and that does not feel like work. It is this desire to escape the feeling of work that causes people to ignore the reality of any job, that it is still work at the end of the day.

    My personal solution to this was to find a way to live where I did not have to work very much. I figured the best job was the one that earned me the freedom to spend serious time unemployed and living on my own terms. That lifestyle also comes with a price. Not everyone wants to live in a vehicle, have all their stuff in a storage unit, travel far from “home” for work, or live with the uncertainty of where the next chunk of money will come from.

    Interestingly enough the reactions to my lifestyle choices and the idea of work-free work were very much in line. My friends would glorify the aspects of my life that appealed to them while completely ignoring the hardships and sacrifices I made.

    • You definitely have the right idea. I’m in a similar situation — once my home is built and the expenses are covered, I can settle down in to an existence where I work hard about 4 months out of the year and can basically do what I like for the rest of the year. It took a long time and a lot of work to get into this position. If it weren’t for the expenses of my divorce, I’d already have my home done and be living that dream.

      Life’s short and it’s what you make it. People look at us with envy, not willing to admit that they could live a similar lifestyle if they work hard to make it happen. Too many people are afraid to think out of the box and prefer the dull 9 to 5 existence with a steady paycheck to the freedom self-employed people often have. To them, its about accumulating wealth; they don’t see the value of time. But at the end of the day, who will have lived a more full life?

What do you think?