Ten Things That Are Different Now That I’m Self-Employed

My first day as an entrepreneur, I got sick. Seriously. It was Thanksgiving. And I got a virus, which grew steadily worse through that day and the next. Immediately, I got to experience two differences about working for yourself: No paid holidays, and no paid sick leave.

By Friday evening, I was completely incapacitated and coughing up big wads of… Well, suffice it to say I was feeling awful, and starting to worry a little. My cash-flow plan depended on me being able to bill enough hours for November in order not to starve the first couple weeks of January. So, I went to the emergency room. (And my first executive decision, to opt for COBRA coverage, turned out to be the right one.) And the doctor gave me some really nice drugs. And I slept straight through Saturday and most of Sunday.

Now that I’ve been doing it for a week, here are 10 more things I’ve noticed that are different since I started working for myself.

  1. The coffee tastes better. Seriously, it does. Because if it didn’t I would buy different coffee, or I would brew it differently. I get to drink just the coffee I like, brewed just the way I like, brewed with whatever equipment I want, in whatever cup I want to drink it out of. So it tastes much better than if I had to compromise with dozens of other people.

  2. Expense comes before income. As an employee, I got paid in rapid iterations on a rolling schedule. With this, it’s possible to live hand-to-mouth if you need to. Whatever money you make, you spend it after you put it in the bank. As a self-employed person, I need money in the bank before I do the work. Because how else can I finance my business equipment and expenses? And I bill on a longer schedule, monthly. All of this means the money isn’t in the bank until long after the work is done. So, I have a strict budget now, and a cash-flow plan, and I talk about “paying myself” a monthly and weekly allowance, and I worry that an unexpected expense will crop up and ruin my cash-flow projections. Still…

  3. I don’t freak out as much about money. The car started squealing at me that its brakes need tending. Our other car was still in the shop. And I really wasn’t planning on more car repairs right now. Normally, this situation would stress me out and plunge me into worry and denial. Because if the money ain’t there, the money ain’t there, and there’s not much I could do to fix it. But this time, the burning feeling in my stomach and the tightness in my neck just weren’t there. Because my life no longer depends on one company who owns me. I have several buns in the oven. I don’t even need that car, actually, since I do most of my work from home. And if worse came to worst, I have a client I could work extra hours for in order to earn extra quick cash. I have options. And that means I control the situation; it doesn’t control me.

  4. I don’t “get” Dilbert anymore. Reading it doesn’t feel the same as it did before. I mean, yeah, it’s still funny. But in a Scrubs sort of way. I find myself asking, “Do real offices really work that way?” Well, yeah, they do. I understand that, because I’ve seen enough of them first-hand. That used to be me. But that’s part of a different universe. I used to laugh at Dilbert, because I identified with him, because I myself lived in a cube. But now if I laugh at him, it’s ’cause he’s so silly. I think I need a new favorite comic strip.

  5. No more office noise, except for the noise I want. This is pretty obvious, but it’s still worth mentioning. The office noise always used to bother me. When I need to concentrate, I need quiet, and I never got it in an office. On the other hand, when I wanted background noise, I had to use headphones.

  6. It’s harder to say, “No.” When I was an employee, it was relatively easy not to obsess over what got done or how many billable hours I put in. Because ultimately, it was someone else’s problem to deal with real-world constraints and still make the company profitable. Now, it’s my problem. Now, I need to tell myself, “No. I won’t be able to complete all these things in this short a time-span. You’ll have to figure out which items are less important and put those off until later.”

  7. My upper-back hurts, but my head doesn’t. I never realized how bad my home-office setup was, because I just didn’t spend enough time here. My wife, who is a physical therapist, had to point out to me that I’ve been rolling the chair back and leaning forward to reach the computer keyboard. No wonder my upper back and arms hurt. I’ve adjusted my posture, though, and they’re starting to feel better. Still, that stress headache I’ve had on and off for the past 3 years is gone now. And I mean really, it’s gone. And I don’t think it’s because of the Tylenol with Codeine the doctor gave me to help me sleep. Because I only used a few of them, and I haven’t been touched them for over a week now. I’m really not sure why the headache is gone, whether it’s just the endorphins, or whether it’s really because I’m feeling less stress. Probably a combination of the two.

  8. My kids are behaving better. Again, I’m not sure why this is. But it could have something to do with the fact that I’m home when they get off the bus. I think they appreciate that I’m there for them, even if I do immediately have to sequester myself back in my office. I’ve also been able to set effective limits with them when I’m working, something I always had trouble with before. They’re more sympathetic to me when I’m working. When I was an employee, it was harder to get the rest of the family to accept that what I did in my home office was “work,” because I always went somewhere else to “work.”

  9. I don’t feel stressed out about sleeping in. I would if it damaged my performance. But it hasn’t yet. As an employee, if I had a bad night, or even a late night working, I got stressed out about sleeping in the following morning. Especially if I woke up at noon. Now, no problem. I’m still working enough billable hours. I’m still getting enough work done. This especially came in handy the last few days of November. I was in full crunch mode, cramming in as much work as I could before the end of the month. My sleep schedule got royally frelled up. But I got a lot of work done.

  10. If I get tired, I can take a nap on the couch. But I haven’t needed to lately. Working in an office, I frequently needed to take naps. There was a time in the afternoon when my head just felt like it was going to explode. And I needed to find a dark, quiet room to decompress in for a half-hour. At my last job, the only dark, quiet rooms I could find smelled like moldy carpet. And I found myself longing to lay down on my couch. Now I can lay down on my couch, anytime I want. I can cozy up and close my eyes for twenty or thirty minutes. Surprisingly, though, I haven’t wanted to. I haven’t reached that point where my head feels it’s going to explode.

And a bonus: My wife has been spending much more time building her business. We both have options. I can get the kids from the bus. She can schedule more patients on more different days. As a result, she’s busier than she’s ever been before.

So, some good things, some bad. It’s a trade-off. But even the bad things I’m happy about. When I wrote “Top Ten Reasons to Remain a Wage Slave,” I was being sarcastic. Not everyone seemed to get the sarcasm. I guess that makes sense, because sarcasm is based on irony, which contains a kernel of reality, or at least of plausibility. Reading it now, though, those reasons just sound silly. Why would anyone ever want to live for someone else, rather than living for himself? It just doesn’t seem real.


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Congratulations for doing this step. I did it myself a few years ago and it was three really great years – but honestly now I am a “slave” again working for an international company with more than 40.000 employees.

There were multiple reasons to return, but i think the most important was your point 6 – it’s harder to say, “No.” Be careful to not lose control of yourself or your clients. Because quicker than you might think self-employment can lead to a greater slavery than being a corporate drone ever could.

Anyway, I envy you for the time ahead. πŸ™‚

Glad to hear your liking your new gig. You didn’t mention the new commute to the office, but I’m sure your liking it.

Typo: “I’m don’t freak out”

Hi, mikx. Thanks for the kind words. I hear you. To quote Lorelai Gilmore, “I say if we go down after two years, it’ll be the most exciting two years of our lives.”

pdq, My old commute was less than a 10-minute drive. So it’s not a huge deal. But it is something, yes. What struck me as more significant for my situation is that the office environment is so much different. And thanks for the typo alert. Spell-checker didn’t catch that one. πŸ™‚


If Dilbert no longer fits, try this comic:


I was wondering about what you did for health insurance. COBRA is super expensive. But so is any other individual plan. What are you doing for longer term coverage, if you don’t mind sharing?

Tim, this is a great follow-up πŸ™‚ Glad to hear how things are progressing.

As a small business owner what are you using to keep track of your contracts/relationships? Drop me an e-mail if you want to try JibberJobber (its free, but I’ll tell you how I use it to manage my own marketing, etc.)

Mark, that WonderMark is hilarious! Coincidentally, on Dec. 4 was this Dilbert: http://www.dilbert.com/comics/dilbert/archive/dilbert-20061204.html

Michael, yeah, health care is super expensive. A group plan via COBRA is not as expensive as a similar direct plan. But here’s the thing: You can’t deduct COBRA premiums as a business expense. But you can deduct your business’s health premiums as a business expense. When you factor that taxes into it, the COBRA premiums seem to be about the same as those of a direct plan. What I’m doing is to go with COBRA to start with. That gives me time to shop around for the right plan for me. At some point in the near future, I plan to switch to a self-employed direct plan.

Jason, right now, I’m keeping track of contacts using an ad-hoc array of records that no one else could figure out. At some point, I’ll need to systematize these activities. But I’m not quite ready to spend the time looking at that yet. I’ll bookmark JibberJobber, however.


entrepreneur != contractor

entrepreneur = employees >= (self + 2) + big income + expensive car without squealing brakes


Hi, Jason. Hee hee.

Seriously, though, I agree that a contractor is not an entrepreneur. To me, contracting is just a stepping stone on the way to entrepreneurship. By my definition, an entrepreneur is someone who is doing something different, blazing a trail. It’s a myth that you need a million dollars to be an entrepreneur. But you do need to think outside the box.


Hi Tim,

Congratulations on going out on your own, it’s takes a lot of guts but it sounds like you are handling it very well. This past March I quit my family’s business after 16 years of working for my father and started my own company. (Started when I was 14 and I am 30 now)

Looking back 8 months or so, I can’t believe I actually did it. I too have a family and a mortgage but in hindsight, it wasn’t scary at the time and I am so happy I did it. I completely agree with the naps things too, I got a bit lazy at first but now I am kicking butt and focused on supporting my family and saving for their education.

Anyway, congratulations again and good luck to you.


Rich Cecere

[…] create challenges for yourself […]

Hey, I d’love to see this article on eioba.com. It’s really funny.

Hi, Rich. Thanks for the kind words. I’ve been working up to this for a long time. Now, I’m wrestling with how to keep the cash flowing while finding enough time for my own business-building projects. But that’s another blog post…

Rapid, I checked out eioba.com. It seems like it could be an interesting marketing opportunity. I’ll have to think about it.


[…] Tim King reflects on 10 things that are different now that he’s self-employed. First off, you’ll laugh (not at him, but with him) at the intro to his post. Just go read it and see. After that Tim’s got some great insights into someone that’s just switched from employee to entrepreneur. His insights are great – raw, humorous and important. […]

[…] J. Timothy King recently became a home based entrepreneur and began a blog.Β  He posted, at the Carnival of Entrepreneurs, his “Ten Things That Are Different Now That I Am An Entrepreneur, relating some of the situations he’s experienced about being self-employed. […]

[…] list and I agree with pretty much all of it. It’s the parts you don’t predict that are the […]

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I find your experience a common problem with home offices. The ergonomics is often poor. It is challenging to find great office chairs, ones that have adjustable arm rests, height, back rest, etc..

Since then, I’ve improved the ergonomics of my home office. Actually, I’ve found a way to work comfortably using the leather couch and my laptop. If I need to, I can move in the basement, where there’s a desk and a reasonably effective chair. My back rarely hurts anymore.

However, I do still have migraines sometimes. πŸ™‚


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