self employed

5 Reasons Why You Might NOT Want to Work For Yourself

Have you ever thought about quitting your job and working for yourself? Maybe it’s an idle whim that you have from time to time – or perhaps a much more serious intention. Whether it’s your two-hour commute, your gossiping colleagues, the office politics, the boss, the boring work or the inflexible hours, your job just isn’t much fun. It’s definitely not your true passion.

If “quit the day job” is one of your resolutions for 2010, you’ll find lots of encouragement around the internet. I’m a fan of plenty of freelancing and self-development blogs, and many writers can’t wait to extol the virtues and pleasures of being your own boss and working for yourself.

Don’t get me wrong, I really enjoy working for myself; I get to work in the comfort of my home, doing what I love. But I’m going to be brutally honest in this post and offer you six reasons to reconsider working for yourself – before you end up making a move that you might regret.

Plus, I’ll give you some tips on negating all six less-than-stellar aspects of the self-employed lifestyle…

1.    It Isn’t Stress-Free

First off, a lot of people think that working from home is going to be amazing. Surely freelancers get to sit around in their pajamas watching daytime TV?

The reality is that you’ll probably be ditching one lot of stresses for a different set. Sure, you won’t have the boss with the anger management problem any more … but you might be having a panic attack at the sight of your bank balance. You may also find yourself taking on more work, or more complex work, than you can comfortably handle.

Fix it: If you’re taking the leap into self-employment, be prepared for it to be stressful at times. Get honest with yourself: how much risk and uncertainty will you be comfortable with? How much down time do you need? You can determine exactly what you do and don’t do, so make sure you’re putting yourself in the best possible position right from the start.

2.    No-One Tells You When to Start Work

Yes, I know this doesn’t sound like much of a drawback! If you work from yourself, you can keep whatever hours you like. You don’t have to be at your desk at eight am. You don’t even have to get out of bed before noon. However…

It’s easy to end up wasting valuable time (and when you’re working for yourself, you’ll become all too aware of how time = money). If you work with clients who’ll expect to contact you by phone, or who want swift replies to emails during office hours, you might find that you’re losing out on potential gigs.

Fix it: Choose your working hours based on when you’re at your best. I’m a morning person, so I’m often at my desk at 7.30am; other freelancers work late in the evening. Be clear about which days are working days (it doesn’t necessarily have to be Monday to Friday). Try having a routine that gets you out of bed and into the day – like a brisk walk, a shower, and an energizing breakfast. If you regularly have a problem getting going, learn how to overcome procrastination.

3.    …Or When to Stop

The flip side to having no start time is that you don’t have a stop time, either. I wrote a piece about Why You’ll Never Be Finished in response to a question from a reader who said “Now I am working for myself I do find it hard to stop because who is telling me when enough is enough?”

This is a real problem for a lot of self-employed folks – and it can lead to substandard work, high stress levels and eventual burn-out. However much you love what you do for a living, you need time to rest and recharge.

Fix it: Recognise that when you work for yourself, your job and your hours of work can expand beyond all recognition. Give yourself a firm “stop” time each day (perhaps tied to your family or household’s schedule) and make sure you at least have a couple of hours of non-work time before bed. You’ll sleep more soundly for it.

4.    There’s No Guaranteed Paycheck

In a traditional job, you know exactly what you’re being paid and when. As a freelancer, you’ll find that cash flow is sporadic. This can be a particular problem if your self-employment involves a large outlay on equipment or materials of some sort.

Many freelancers either work on a succession of small jobs (with a few hundred dollars coming in from each – often not on time!) or have one huge project on the go (which could mean getting paid in large sums every few months). If you’re used to getting a paycheck every two weeks, you may end up running into serious financial problems – especially if you have a non or late paying client.

Fix it: Have an emergency fund or a buffer that covers you for late and irregular payments. When you get large sums, resist the temptation to splash out. Put unexpected bonuses, such as gifts, into a savings account. For big projects, bill in installments during the work. Get new clients to pay 50% upfront.

5.    No-One Has Your Back

In most office jobs, there’s a limit to how much you can screw up. Even if you do something so awful that you get fired, you’ll be entitled to some period of leave. And generally, it’s hard to make huge mistakes: someone will be double-checking anything vital.

When you’re self-employed, everything is your responsibility. If you forget to bill a client, it’s your problem. If you’re so poorly organized that your clients start leaving you, or if you can’t get yourself motivated to complete your work, or if you take on so much that you rush it all and do a poor job … you could ruin your reputation in the industry. You might even get sued by an angry client.

Fix it: Get professional advice where applicable (perhaps when doing your taxes or accounts). Depending on where you live, you may need to set up as a limited company – so that you can’t be held personally liable for potential financial problems. Make sure that you have the time and energy to do your best work, and be careful about managing client expectations – don’t promise what you can’t deliver.

I know I’ve struck a pessimistic note in this piece – and I’d like to end by saying that I have never regretted leaving my own day job and striking out on my own! However, personal experience has taught me that self-employment – like any worthwhile endeavor – isn’t always easy. If you’ve got experience of working for yourself, or if you’d love to quit your job, why not share your thoughts in the comments?

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28 Responses to 5 Reasons Why You Might NOT Want to Work For Yourself

  1. Mike Harmon says:

    I discovered your homepage by coincidence.
    Very interesting posts and well written.
    I will put your site on my blogroll.

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  3. I like the approach of this article. I’m also a believer in working for yourself, but I also know it has some downsides which need to be understood and accepted, like the ones presented here. There is a right place and time for everything.


  4. Nacie Carson says:

    Number 2 and 3 were the hardest for me to handle when I first started working from home – well done for putting this out there! I love working from home, and wouldn’t change it for anything, but it definitely requires lots of discipline and attention (things I believe anyone can develop!).

  5. Personally im not that disciplined when it comes to working hours. I work 7 days a week on my startup and my work hours can be extremely odd due to having to fit things in with developers. I would hate it if it wasn’t for the fact I love what I do and can’t enough of it.

  6. Why not have the best of both worlds? Teleworking has many of the advantages of working from home while retaining some job security.

  7. Ramesh Raghuvanshi says:

    I donot understand why this writing appear on your blog.Have you know anything why some people are self employed and some are choosing working for others?My good friend, it is fix up what kind of experiences child get in his childhood.Childhood experiences are fix up which vocation you chose, so there is no use this kind of writing why you might not want to work for yourself.

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  9. If feel that it is also very important to seriously consider why you are quitting your job. If you do not solve your internal issues they will always be present no matter what job you have.

    I elaborate here: Love the Job you Hate Before you Leave it

  10. Excellent article Ali. I think most people miss these issues. In my experience, self-employment is often more stressful, at least early on, than a traditional job.

    A great way to reduce this stress is to start part-time while you continue to work at your job. Use this time to build up your income and learn the ropes. That way you face less stress when you go full time.

  11. don says:

    great honest advice. well received thank u.


  12. I personally thought this was an excellent article, Ali. Too many people have a romantic and unrealistic idea of what ‘working at home’ means. You have done everyone a great service by pointing out the realities. I thought it was great that you also provided solutions along with the realities.

  13. Ali Hale says:

    Thanks for the comments, all! I wondered if people would think this was a bit negative — but like Steve and Nacie, I think that working from home is a bit more challenging than some people admit.

  14. Ali Hale says:

    Ramesh, I’m sure childhood experiences can have a lot to do with the careers we choose — but the points in the article are ones which (almost) everyone is likely to have to consider, if they do think about working for themselves.

  15. These are all very true! Despite the negatives involved in being self-employed, I personally wouldn’t give it up for the negatives of being employed. To me, I have a greater chance of creating what I want in the long run than I do collecting a paycheck and having the “security” of a job. Great things to consider before going solo, but if you do something you are extremely passionate and excited about the good will outweigh the bad, no matter how ugly it gets.

  16. These are all really good points, and they are things I have been recently contemplating, as someone who wants to become self-employed. It certainly is no easy task getting there or staying there…

  17. What a great article! I am a stay at home mum and it is quite difficult for me to get any work done during the day with my 2 kids running around so I end up staying up late at night and being tired most of the next day – So I will be putting your advice into practice Ali – Thank You

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  19. Craig says:

    I wouldn’t see those as reasons NOT to work for yourself but as more of a reason why to work for yourself. Picking your start, finish and wage is the exciting bit. :)

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  25. Great post. Its refreshing to hear the other side of the issue. Some people really don’t know how well they have it at their 9-5. What is the saying “Be careful what you wish” it might come true.

  26. Rick says:

    I have been self employed for over 25 years. My wife and I payed for both ours sons college. We were able to purchase 2 rent homes as additional revenue. The main reason we were able to do this is my wife has worked full time at her job and has carried our health insurance also. It takes 2 incomes nowadays to get ahead.

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