15 bad points about working for yourself

Having written earlier in the week on 20 great reasons you should be your own boss, it is only fair that I offer up some of the less pleasant experiences of working for yourself too.  It’s not all a bed of roses. In fact, in some ways, life can be much tougher than working for someone else.


1 – If you’re in charge then you’re also responsible for those tough times.  You can’t pass it on to your manager or in the case of my managers, dump it down on your staff.  One way or the other you as the sole proprietor of the business has to resolve every single issue that comes up.  This being whether it is something minor like fixing your own printer or giving an extra bit of effort to make a difficult customer happy or finding out fees or taxes have to be coughed up immediately.

2 – You have to learn to be tough.   So far, I haven’t really done this after 3 years as it just isn’t me.  However as my wife always tells me, I’m a business and not a charity.   What you might keep quiet about at a personal level is not the same when it comes to your business reputation, services offered or simply the bottom line when it effects your money.  At least when business is business, people don’t seem to mind as much if you play hard ball with them compared to if you take a tough stance at a personal level in which case you might simply just be thought to be a bar-steward.You’ll have your emo moments when you just want to put on a black hoodie, close all your curtains, and hide from the world. Because it can be overwhelming, and you’ll be talking to more people in one day than you used to talk to in a week. And even though you’re working alone, it will never feel like you have any alone time.

3 – Working for yourself is rather like having a split personality.  On the one hand, you never have any time to yourself.  You are always busy and you just want time on your own to either do what is important for your business or indeed for yourself.   On the other hand you can often feel entirely isolated from the world.

4 – Though once you have mastered new skills, they are obviously good things to learn for the future.  In every day life when you are busy it is difficult to be an expert at everything.  Whilst a big organisation has specialised teams dealing with every issue of the business and its customers plus its suppliers.  Working for yourself it is just you and there is no getting away from that.

5 – You might get stressed out.  It’s a different sort of stress from working in a team or having a bad boss. It’s the stress of having to do everything and being responsible for everything. If you’re having a bad day, you can’t go for a quick walk down the corridor with a friend.  You have no work-mates, no office friends, no one more experienced than you who can offer advice or even help you out with a task.  It is lonely at the top… but when you work for yourself you are simultaneously at the top and at the bottom.


6 – Because you are responsible for the entire business, you can’t have sick days.  It’s hard to have holidays too.  I didn’t have a day off in July but then in January and February I “worked” about 4 days in total though I was actually busy nearly all of those days.  Swings and roundabouts as they say.   You might also become more aware of your personal and business failings.  If you work for someone else, it is easy to put shortcomings down to circumstances or other peoples but if it is just you then it is harder to pass the buck.  Today is actually the first day of the entire year where I have had a day totally away from work and I went to see the cricket at Lords.

7 – You have to be excellent at time management.  This both goes for working too much and not doing enough.  My biggest problem is that I can work every waking hour God sends from 5am until 7 or 8pm.  It doesn’t feel bad as it is my work, my company…me and there is always something to do even if I am not touring.  Answering emails, making bookings, accounts and expenses, advertising.  Creating new products and new marketplaces.

8 – Other people might have the opposite problem working from home, the temptation to do absolutely nothing.  Unless you have a bit of backbone, it might be all too easy to lay in bed, watch television all day or have too many days out of the home-office.  Even if you are like me and are a workaholic, many of your family and friends will assume you are doing absolutely nothing, often because that is what they feel they would do but we entrepreneurs are made of tougher stuff.   Those millions won’t earn themselves.


9 – You have to be good or get good quickly with money and numbers.   Set yourself financial goals and stick to them.  I follow the same ideas as I do under my authors hat.  I’m in it to earn money not to give other people money.  If I provide a professional service, I have to earn a professional amount of money that must be X amount above your costs.  If like me, your business is variable then you have to earn and indeed charge money to cover those days when you aren’t earning money.   Sometimes I don’t just turn business away because the customer doesn’t seem a good match.  Sometimes the profit margin isn’t good enough.  Sometimes the money made just isn’t worth the time, energy and effort and I’m better off working from home on my business.  Sometimes you just have to have faith that a better offer will come in, it nearly always does.  In fact not once have my hunches been incorrect.  Every customer I thought might be difficult has proven to be the case.  ALmost every tour that I thought required a lot more effort, was not particularly appreciated by the  customer.  So why bother if money is not that tight?        On the plus side I have become amazing quick and accurate at just how profitable each one of my tours is no matter how many variables there are.  I can also tell you how many miles and how much time it takes to drive between almost any destination in England 🙂

10 – There will always be people trying to rip-you off.  Like in the author’s business, there will always be people who have no real business but make their business to be exploiting you and making you think you need their services.  You really, really don’t in either case.  I’ve had foreign hotel concierges trying to extort bribes from me for tours.  Countless spammers and “business” specialists who are happy to make my business the next big thing if only I spend some money on them or attend their stupid conferences.  Sorry, I’m too busy making money to waste time or finances on you.  Find some other mug.  Also for future reference, business collaborators, I’m not your colleague and labeling your email as such or as friend just earns a deletion.  As a business owner, if people approach you, it is because they want something from you, usually money but if they want a genuine partnership or quid-quo-pro trade then it should be as equals…. I’ve been doing very well on my own and if you want a piece of me then it is you who should eat a little bit of humble pie.  It shouldn’t matter if you are Apple or Ye Olde England Tours, a business is a business and each is valid as any other, big or small.  Don’t pay anyone for favours but don’t expect any freebies either.

11 – You have to develop some tough skin.  Things will always go wrong.  In my case, it is never anything I do wrong.  It is 99% a customer and 1% London traffic.  If you have such a bad experience, mark it down as experience.  Never make the same mistake twice.  If it is a horrible experience then try just to think about the money, you need never deal with that bad experience again. It’s your business, your choice.

12 – You will never, ever have enough time in the day to do everything.  You will never ever be talented or lucky enough to be able to handle everything right first time.  Your business is like your life, a learning experience.  It’s ok to fail sometimes.  However, nothing is as difficult as it first seems.  I know little if anything about taxes but so far this year I have done my annual business tax returns in around 30 minutes.  Year one I was 13 pence out and Year two I was 34 pence out.  No need to pay an accountant, just use your can-do spirit.  If you have your own business, that is the only pre-requisite you need but also the only one you must have.

12 – Success rarely comes easy.  If you want to have a successful business, it takes more work than anyone can imagine.  It’s almost that your life is work… it’s ok as it is your work and your life but this is the level of commitment needed.  Don’t be lazy, don’t ignore things that need doing or put them off for another day.  Always do the best you can and exceed customer expectations.  I make a point of providing a better standard of service from initial inquiry to post-tour follow-ups than any big organisation I have dealings with myself.  Nothing is too much effort for my customers.  The result is that 3 years later I have a reputation that is second to none. People and business bigger than where I started and more experienced than I am now, let alone where I was when i started are now wanting my business when 3 years ago, nobody wanted to touch me.  It;s all down to old fashioned hard-work and there is no alternative to that.

13 – Always have a backup plan.  Not just a plan A but a B, C, D too.  I was constantly amazed when I worked for other organisations just how little common sense and planning the business had generally and my managers in particular.  In a larger business people can get by this.  For small businesses, there is much less wriggle room.  Take the simple thing of unexpected travel delays.  I’m in the tour business, being late is not an option.  Not at all even in London traffic.  I always leave plenty enough time for even the worst disasters, I always have multiple car parking options ready, different toilet points around the city.  I have never been late once and even though being late in London traffic is kind of understandable, I see it is unforgivable in my business.  Whatever your business is, you should have similar “impossible” standards to reach that your surpass on a daily basis.  Muddling through is for poor employees or over-promoted middle-managers, not for you and me.

14- You will never ever feel totally satisfied.  There will always be something you feel you could have done better with or that someone else would have done better.  The to-do list is never ending and you will often have missed opportunities or regrets.   It’s ok.  Every day is a learning experience.  If you were content with a normal career and lifestyle then you wouldn’t work for yourself.  If you are ambitious and want to do better for yourself in terms of income or quality of life then of course, you will always be striving for more.

15 – And remember if all else fails, it sure beats working for someone else!


About Stephen Liddell

I am a writer and traveller with a penchant for history and getting off the beaten track. With several books to my name including several #1 sellers. I also write environmental, travel and history articles for magazines as well as freelance work. I run my private tours company with one tour stated by the leading travel website as being with the #1 authentic London Experience. Recently I've appeared on BBC Radio and Bloomberg TV and am waiting on the filming of a ghost story on British TV. I run my own private UK tours company (Ye Olde England Tours) with small, private and totally customisable guided tours run by myself!
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