Dispatches From Self-Employment


In recent posts I’ve been reflecting on my decision to quit my job and become a full-time freelance writer and the challenges that have come with it. Today I want to look at the factor that runs second only to money in terms of how much it weighs on people who are considering this step: the lack of formal work structure.

A regular 9-to-5 job can be a grind and be repetitive, but it brings a comforting sense of security. You show up at a certain time, you leave at a certain time and you know there’s a negative consequence to be imposed if you decide to shirk. Most important, you know there’s a paycheck scheduled to be delivered at regular intervals.

Stepping out of that bubble is a genuinely frightening thing, even when you’ve properly prepared yourself for the move, and one of the many things you have to get used to is a change in routine. It may be possible for a freelancer to fit their work into the same 9-to-5 framework of a “regular” job, but for all its security most don’t consider it desirable and a lot of cases it’s not even practical.

I run a website devoted to sports commentary, TheSportsNotebook.com, and it’s necessary to have fresh material up early in the morning. My new routine has involved starting work around 5 am, working for a few hours and then going back to sleep. I’m often working in the evenings on other facets of the business not pertaining to content.

To say this can become a pain is understating it, and it’s imperative that anyone working independently have a clear sense of what needs to be done and a willingness to do it without being instructed. Failure to do so doesn’t bring the immediate negative consequences that not going to the office would, but it does gradually add up into missing out on income and networking opportunities.

When the alarm goes off early and I’ve been up late in the night tracking the end of the previous night’s games, it’s a challenge to avoid just turning it off. I find myself thinking of a line from the 1974 movie Godfather II, when Hyman Roth tells Michael Corleone, “This is the business we’ve chosen!”

Granted, Roth, a fictional Cuban mob boss based on the real-life Meyer Lansky, was reconciling himself to decisions considerably less benign than getting up early. But the line remains the same. The person that chooses freelancing has presumably made that decision freely. The person that chooses sports or some form of entertainment has also done so freely. If it’s the business you’ve chosen, then you have to carry it out.

There’s a flip side to a lack of a structured environment and that’s the invitation to be a workaholic. Without the structure of the clock hitting five o’clock, it’s easy to succumb to the temptation to work, work, and work — especially in the embryonic phase I’m in where you’re not only working but seeking to generate additional work.

I’d like to tell you how I work through this or find some movie quote that’s inspirational or goofy, but I don’t have answers right here. Perhaps that will be the subject of a future post.

Those who are single are in a unique position to work out these challenges. You have an ideal opportunity to live on the smaller income that invariably comes with starting something new and have more freedom to work through the questions of structure. By the time you’re settled into married life, a new structure, unique to your particular business will be in place. Take the opportunity now to make that happen.




Further reading

“Self-Employment Memo: Too Busy To Blog (Or Date)” by graphic designer Christina Mahady


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