3 Unexpected Challenges When Working From Home

I dreamed of working on my own for many years. Finally I was able to start doing that this year. Ever since I started, people have been telling me “I wish I could do that!” and “Now that’s the life!”. Working on your own from home is not all it’s cracked up to be though. It really is work! During these few months I’ve been self-employed, I have come across many unexpected challenges. I thought I’d share 3 of the biggest ones for those who are looking to convert from the 9 to 5 job to working from home.


Sure a boss looking over your shoulder is irritating, but at least it made me get my butt in gear. With nobody motivating me to get stuff done, I have to rely on myself. This is extra difficult when the weather outside is nice and all I want to do is take my mountain bike for a ride. I have been forced to get strict and set aside a certain amount of hours per day to get stuff done. If I don’t discipline myself properly, nothing gets done and the business suffers.

Finding biorhythm

When I first started working from home, I treated it like a normal day job. I would wake up early, start work, then end it at around 5pm. This didn’t work for me. I found that my writing was much better late at night, around 11pm to 3am. Now I schedule my work accordingly. I try to devote a certain amount of hours into working each week, and get it done when I’m feeling it. Specific hours just don’t work for somebody who writes for a living.

Being social

This one’s a big one! I have nobody to talk to all day. Sometimes I go several days without seeing anybody except my girlfriend. The result is an extra clingy Mitch when she gets home from work. I’ve tried to use Twitter and chat to get me through the day, and that helps a bit, but nothing compares to talking to a warm being. Lately, I have made a better effort to go out with friends whenever I can.

With no proper, corporate-like structure in place, working from home is always a learning process. Hopefully I can stay out of the daily grind and learn to adjust to these challenges.

1 thought on “3 Unexpected Challenges When Working From Home”

  1. Basically what you are describing is the life of being your own boss. It doesn’t matter if you work at home, own your own business or are a CEO of a company, these are challenges most “bosses” experience.

    In regard to The Pickle Barrel, I have one advantage as far as motivation thanks to my employees. They are the only people that I have looking over my shoulder. Whatever they see me do, they feel that it is ok for them to do –this definitely keeps me in line and I appreciate this! As far as those bosses without this “luxury”, I would imagine that during these questionable times, money, along with being successful would be a definite motivator. Unless, that is not a worry, then practices in self-motivation are needed!

    As far as “biorhythm”, yes it is important to find the time when you are most productive which means that could be any time and you may not have control over what time this may be. As the “boss” of Pickle Barrel, I may be called upon at any moment to perform, so I must always be ready – whether I am sleeping, out with friends, on vacation, just got in my car after a 14 hr day about to drive home etc….any time has to be a good time and I never know when it will happen! You may call it inspiration, I refer to it as my “call to duty” – Both require you to be ready and to be productive.

    Lastly, I completely agree with you on the topic of “being social.” As the boss, it is not appropriate to pal around with the employees – there is a distinct line drawn between boss and employee that should not be crossed for sake of losing any respect you have gained with that employee. It has been said that CEO of companies are some of the loneliest people and I can understand. There are conversations that you are not included in, gatherings in which you are not invited to etc. Although, I may not be their “bff” I would rather be their boss.
    Again, for those that do not employ others, you may have to refer to the self-motivation exercises because it is important to get out, see what’s happening outside the confines of your make-shift office. You are not alone, I fall victim to the walls of Pickle Barrel, but there is life going on and, if not for a little reprieve, I need to see what is happening and what is changing in this city so that, from a business point of view, I can adjust. It could possibly put me at a disadvantage if I were to stay at the shop every waking hour.

    To sum it up, bosses have to create their own motivation that is why they are in the position they are in–some people need motivation, in which case maybe they should not be their own boss.
    Timing is everything – whether it’s when you feel exhilarated or whether your help is needed, you never know when this time may arrive, but as a boss you always have to be ready.
    Lastly, the lack of conversations on a daily basis vs. not being included in some, result in the same sort of alienation. I have realized that I would rather be my employee’s boss than their buddy. I feel I am more productive and can have more of an impact on the business, and more importantly my employees.


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