On Friday, I had a breakfast meeting – which seems to be the constant preoccupation of the entrepreneurial and the freelanced. And because it combines business with pleasure food, I am a huge enormous massive fan.

We talked business. Then we talked shop. And finally, the conversation came round to how much we miss being employed by someone other than ourselves. What I mean is: nostalgic about that simpler time when your salary is something that you can expect to land in your account on the 25th.

Today, I may have more control over my own time. But my dentist tells me that I have about a year before I’ve completely worn through the enamel on my front teeth (night-grinding, apparently). He has an extremely uncomfortable mouth “plastic plate” for me to wear at night – but he says that he won’t prescribe it until that enamel situation makes sleeping impossible. To me, that sounds like I have a lifetime of (literal) sleepless nights ahead – filled with agonised tossing, turning, and brainwave gymnastics at 3 am. And, well, more liquid breakfast meetings.

All this? Completely foreign to me as an employed person in an 8 to 5. So here is a list of things that people should know about their bosses before they start whinging about no-salary-increases and where’s-my-bonus (yes – I have flipped):

  1. Responsibility: the transition from employee to employer is like putting on a fat suit. You graduate from worrying about your monthly finances to being worried about the entire company’s monthly finances. But properly though – it’s not just a niggle about a rumour that the company is struggling. Now you need to track down the source, identify the problem, and try to fix it. All the while conscious of the number of people that are depending on your fixing abilities because the company is their lifeblood. People forget that the majority of companies aren’t there to make profit for the owner: they exist to give a wide network of people (staff, customers, suppliers) a livelihood. Profits are secondary. Subsistence is everything.
  2. Panic about cash-flow: *shakes head* Cash flow is the cause of sleepless nights. Sherbet. After all – those loyal but disgruntled staff members have certain expectations around the 25th. As do your suppliers and the tax authorities and those damned trade unions. There’s also maintenance and the crashed computer that needs to be replaced. Meanwhile – your customers sit demanding longer terms and concessions; and they underpay because they’re fighting with you about the service/good after you provided it. And this is just the day-to-day – most of the concern stems from trying to see whether there’ll be enough money for next month, and that big order that you need to upfront in early August. *breathes deeply*
  3. The pain of finance: so you try not to borrow money unless you’re doing something meaningful (like expanding). That is, until you have to borrow to bridge some short-term bank shortfalls – which means that you’re stuck trying to work out if and when you’ll be able to pay it back. And what expenses to cut, and what suppliers you can push for more time (which makes you that annoying customer for someone else).
  4. Liability and exposure: in order to protect us all, our governments have kindly bestowed a bevy of laws and regulations to govern the behaviour of those in charge. Whether or not they’re reasonable: they are certainly numerous. Which makes nearly every decision an exercise in ass-covering. There is also liability (and some etiquette) attached to any form of communication – so words, phrasing and disclaimers are the constant counterpoint to the daily activities of actual work.
  5. Human Resource management, and Labour Law: so much time is devoted to arranging incentives and handling staff. We may all be adults, but we turn into preschoolers the minute we’re away from the real toddlers. Little games of authority and undermining it. Obstinate refusals to perform a task because it violates some preconcepted arrangement of turf, territory and personal dignity. Feminists that expect to be treated unequally (!) and demand recognition as the more awesome sex. Encouraging the lazy, and trying to balance their workload that’s being picked up by the good staff. Acknowledging complaints and the general humanity of staff that have personal lives and deaths and break-ups. Trying to gauge where the line needs to be drawn, and when it’s been crossed, and where it’s been crossed irrevocably. And always always weighing that up against labour law compliance, the power-mongering of trade unions (especially in Africa) and the political niceties of the impact on staff morale.
  6. The Hiring/Firing/Planning-for-it saga: and then staff up and leave. Or you’re forced to get rid of someone. Now that work needs to be done and you need to find someone suitable to do it and cover the gap while you’re undertaking the search. Which means constant pruning of the systems and procedures you’ve put in place in order make sure that there’s always someone who can take over in a bind without being overworked. Also, you need to rely on the ability of that system to take care of itself while your attention is focused elsewhere. Meanwhile, you have the usual procession of staff members who can’t understand why they have to do all these things, and they’re not doing it, and it would all be so much simpler if they were running the place.
  7. How do I see everything? Something somewhere is not being done. And it needs to be done. Jobs and livelihoods depend on it. But instead, there is a small disgruntled cog that is defiantly posting statuses on facebook instead. AAAHH.
  8. Holiday? What holiday? There are no holidays for business owners. When you’re away, you come back to crisis. Invariably. Also – where is your salary going to come from? No 25th of the month for you, buddy.
  9. Strategic leaps of faith. Because you can’t just manage the daily stuff. Otherwise, you end up like the fax machine makers: focusing on production and failing to realise that, like, “email”. So you have meetings where you watch what’s happening and you speak to your market and try to keep it all sustainable.
  10. Rolling The Dice: having tried to decide on direction, you then have to take the actual leap and risk things. And you just hope that you’ll be able to change course or make another decision if it turns out that you took a wrong turn. After all – livelihoods at stake!
  11. OMG tax: then while this is all going on, tax authorities arrive to do “checks”, always looking reasonably convinced that you’re doing something untoward. And typically, your accountant has learned all he knows about tax from the previous accountant, who learned all he knew about tax from the accountant before him, and so on. So you’re almost always violating some kind of tax rule. Of course – you’re also definitely not taking advantage of all that the tax code has to offer in terms of incentives and allowances – but no tax authority is going to point that part out to you.
  12. These damned banks: and finally, when you’re able to look back at your own personal finances – you discover that your bank doesn’t want to extend you credit or grant you a mortgage because you’re the business owner and not the salaried employee. But your employees can get credit. No fear.

Yes – maybe you think that this is the executive lament: “poor us at the top with our maseratis”. And I’m not saying that there’s no fun and that you don’t love being in charge and wearing jeans to work because you can.

But the point I’m making is: it’s not easy either. So the next time you’re complaining about a small pay increase or a bonus-being-less-than-you-wanted – you need to decide if you’re willing to deal with all the above.

And if you are, then go out and do it. No one is stopping you. Really.