Self-Employment Pros and Cons

Given, I’ve not been full-time self-employed for long, but here are the ups and downs I’ve discovered thus far.



No insurance.  Health, Dental, Rubber Ducky, etc.  While I’ve not been deathly ill, I do take a few twice-daily prescriptions, one of which is a bit expensive.  As such, my doctor and I will be discussing alternatives.  I’m fairly sickly, but usually with illnesses that don’t overly hinder my ability to work.  A cold here, strep throat there, whatever.  Point being, I hope to do OK without the insurance.


I’m not constantly paying out of my check for coverage I may not use.

Retirement Planning


One thing I liked about having a full-time job was the retirement benefits package.  Given, over the last couple of years my employer sorta butchered it, it was still nice to have part of my paycheck be automagically taken before I saw it and put in to a tax-free account.  Now, I’ll pay tax on it, toss it in bonds, or a mutual fund, or the stock market, and hope to make a high enough percentage to actually retire when the time comes.


This gives me more control, and education.  Not only do I now have to decide exactly what to do with that money, I am also educating myself on the possibilities (OK, my wife is much more focused on this than I am, but cut me some slack).



This one might sound silly, but I don’t drive nearly as often as I used to.  Working from home has not only spoiled me, I now must put more effort in to driving.  Funny how that works out.


I needed new tires a while back…still do.  Go me.



I used to look forward to quitting time on Friday just like any other working stiff, now it just doesn’t mean much.  I’ll work until the early morning hours of Saturday…get a few hours of sleep, then work in to the early morning hours of Sunday.  Never underestimate the goodness that is weekend relaxation.


Well…now I’m doing it all for my own company.  It means quite a bit more to have the effort so well rewarded.



I used to get 30 minutes per day for lunch, and two ten-minute breaks — one in the morning, one in the afternoon.  Now, if I’m pushing a deadline, I might not get any.  Sure, I try to squeeze in some downtime when I can.  Grab some lunch, watch part of an episode of The X-Files, but I don’t always have the time.


At the end of the day when I look back on what I’ve accomplished, I don’t worry about those skipped breaks.  Looking at the bigger picture makes it worthwhile.

So, what are your pros and cons for self-employment?

2 thoughts on “Self-Employment Pros and Cons

  1. Cash flow: sometimes it’s awesome and sometimes it’s non-existent. This is the nature of consulting and hopefully you’re disciplined enough to make it through the lean times.

    Time Off: There are times I envy people with ‘regular’ jobs. There is no time ‘off’ and when you do you’re still thinking about something about work.

    On the plus side, the flexibility is awesome. I’ve been able to devote significant amount of time with my son and his robotics team. If I want to sleep in for another hour or go have lunch across town I can do that. If I want to work out during the day it’s a great time to do it as the gyms aren’t very crowded.

    Working from home is good for the reasons you stated. My wardrobe is incredibly cheap these days as is gas and lunch expenses. But, the fact that I answer emails at midnight and think about work all the time can be tough to get used to. Working from home isn’t for everyone as there are a LOT of distractions: yard work, laundry, kids, dog, spouse, etc.

    I’m sure I could write a small mini-novel on this topic since I’ve been doing it for 10 years. 🙂

  2. I’ve experienced much of what you’ve mentioned, as well. I’m trying to plan my projects, currently, where I’ll have a couple of weeks of downtime in between. I’m still going to school, after all, and getting ready to transfer my credits to ETSU.

    As far as wardrobe, my pajamas get quite a workout now. Occasionally I’ll get up early, take a shower, shave, get dressed, and go to work, but more often than not I’ll roll out of bed, brush my teeth and hit the office with a Nutri-Grain bar.

    The flexibility is great. Normally I’m lucky to mow my yard once every 2-3 weeks, but I’m proud to say I’ve already mowed the first time, trimmed all the trees, and planned my assault on the bushes in the front yard that I despise.

    Thanks for the excellent response, Bob. Your input is greatly appreciated.

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