The Great Self-employment Trap – part 2

How do you get the most out of your voluntary slavery? By graciously saying yes, and tactfully saying no. Sounds simple doesn’t it?

The skills you need to perform, and the confidence that you require to pull it off, are not topics this article will focus on. This article will assume you’ve established that prior to becoming self-employed, which itself usually stems from a previous career, or work experience. The people who start from scratch, especially in a new field, will have challenges unique to them; training courses may have helped with the work skills, but never addressed the social skills to make contacts quickly.

Once you’ve leapt into the role of being a one-man-army, it’s time to set ground rules. Every profession has rules of conduct, and every business has regulations to follow, being self-employed makes you both employee, and employer. Double-whammy, or double the fun, depending on your point of view. This can mean more work than you anticipated, which can mean working less, or paying for some of the housekeeping that others handled before. There may not be enough man hours in a day when there’s only 1 person working, it can make a lot of sense to offload less critical tasks.

You’ll have to start re-programming your habits too. There’s many things you could get away with as a wage-slave, those wasted moments after meetings, extra long lunch breaks, leaving early because the boss is on vacation, etc, but that time is over. Remember you’re the boss now, you have to make sure the employee is working, you can’t trust that they will just work, we all know how demotivated they can get. You really need to prioritize between things you’d like to do, as well as things others would like you to do, versus things you need to do.

Then there’s your relationships. All your friends, all your blood relatives, all those people that encouraged you to drink alcohol with them, eat poorly, and watch sweaty men hurt each other on their big screen TV, are now your landmines. You have to start evaluating the dangers each and everyone of them poses, to your business process, to acquiring jobs, to finishing the overdue projects before your client screams at you. The people that hurt you most, won’t be the people that dislike you.

Perhaps most important of all, your goals must be very clear. If you have no idea what the outcome of a task is, how can you reasonably focus on it? Likewise, if you haven’t got a destination (or at the least milestone) in mind, how will you ever know whether you are making overall progress? When you have to get to get to a trade show, telling a cabbie to "just drive" likely won’t get you there. There’s a reason that personal trainers ask you what you want to achieve, first, it lays the groundwork, they can build a roadmap for you to follow, connecting where you are, with where you intend to be.

Remember, the pain of change doesn’t just apply to you, it affects everyone in your circles. Gird your loins.


Time is that eternal constant, robbing us all of our youth, our vitality, and our enjoyment of life. Probably one of the simplest aspects to understand, but not necessarily how easily it can run away from you. Time management is a silent skill, it doesn’t make money, and won’t make people around you happy, but without it always in the back of your mind, you could end up less productive than the average employee.

Get a day planner that covers all 7 days of the week

If you plan to get a lot done, it is crucial to divide your activities into time slices. Do you have enough space to take notes on the saturday and sunday columns? Yes, you need it, make every day count. And you might have to give up on the silly notion that there are are "weekends" or "holidays"…

Divide your day into 15 minute blocks

Your laundry doesn’t take anywhere from 2 to 4 hours, no matter how much you’ve convinced yourself it does. Your laundry actually takes several 10 to 20 minute segments, with as much as 45 minutes between, if you’re even vigilant enough to stay on top of it. Most likely, the 3 hours you spent doing laundry consisted of 2 hours wasted in the kitchen, on the couch, or talking to someone else even less productive than you are, with the remainder spent doing laundry. Every idle 15min block, is a chance to schedule a task, even if that task is hydrating, or dehydrating.

Categorize tasks into Priority and Filler

Using the 15min block rule, schedule Priority tasks in such as way as to leave small gaps, don’t lump them back to back. Those pockets of time will handle Filler tasks when possible, with the option of rescheduling Fillers, if the Priority task just needs a little more time. By doing this, you can roll with the punches. When things are set to throw off your schedule, like an airport cascading flight cancellations across the board, you will only need to shift the Filler tasks out.

Task switching, aka forced multi-tasking

If your work requires a steady focus on one task over several hours, or days, or even weeks, it might be worth breaking it up artificially. We aren’t meant to sit in one position for long periods, nor do our brains particularly benefit from monotony. Ironically, our boredom can make us more creative, but that creativity might be towards other ideas, and the last thing you want is your mind preoccupied the whole time.

Taking a 15 minute break every hour, can both slow your perception of the time, and give you a chance to feel productive by accomplishing a small task. It can give also you a chance to write down your ruminations, or elucidations, so that you can go back to your job with a clear mind.


Paying attention to how people, including family, interact with you during "business hours" can be very revealing. They will deliberately, or unconsciously decide, whether to support your freelancing, or not. The ones that will help you accomplish your work, or lend you tools, or even introduce you to new contacts, that group take priority. They must be nurtured like your new family, possibly at the cost of your bewildered, life-sucking friends.

Dividing those around you into Allies and Enemies

Once you know which people engender what risk to your business life, which ones distract you, which ones demotivate you, and which ones make life easier, they can each be categorized. How many categories everyone else gets divided into isn’t that important, as long as the critical two most extreme groups are defined.

Don’t let guilt get the better of you

Nothing great was ever accomplished by saying no, or feeling guilty. If your friends, family, neighbours, former lovers, or whomever are affected by your work, they will likely protest in their own ways. The common thread will be you feeling guilty about it, something they will encourage you to feel. But who’s life is it anyway?

This reaction some people in your life will have, is purely selfish. They gain nothing by doing it, they gain nothing by tearing you down. The only thing they are doing is expressing their feelings of annoyance, or even worry, they are barking like dogs at a passing stranger. You are changing their life without their consent. Naturally because you didn’t consult them.

Believe in your mission

As great as it sounds to you, your new life might seem unnerving to others. To them, your whole world view can seem to be suddenly unbalanced. It may seem like you are lost in your work, missing your favourite home-renovation show on TV, skipping your infusion of Douchebag radio, preventing you from having biased opinions on things that don’t matter, or not listening while someone is desperately trying to explain why Sherry at their office was such a bitch today.

Thing is, you haven’t got a need for these things anymore, if you’re serious about reaching your goals. Listening to people who work as little as possible, and complain as much as possible, isn’t going to help you. Nothing should deter you from reaching your goals, or else everything leading up to that point, all the hours you toiled, all the events with cake that you missed, was entirely pointless.


As odd as it may sound, setting goals might not come easily. Not goals like having 2.4 children, owning a house, and making your parents proud, but real goals, specific goals. And you have to make a list, preferably one you can stare at regularly as a reminder. Which means you have permission to make it pretty, with sparkles and everything.

Setting tangible, achievable goals is critical

Your list will be like a happier version of the bucket list. You can add line items at any time, whatever strikes your fancy, whatever you think would make a great entry in your Almanac. They can be personal, or family oriented, but they can’t be vague, whatever they are. A new car is not acceptable as an entry, but a new Nissan GT-R is, even if it’s silly financially. This list is motivation, it doesn’t have to be practical.

Giving each goal a timeline

Whether it’s a business goal, such as reaching $5,000 per month in sales, or landing exclusive rights to vandalizing city parks, there should be a deadline attached. Your efforts towards a goal will be much stronger, if you know when you have to achieve it. It’s just human nature, we procrastinate. If you can’t visualize the steps between you and the goal, you just won’t take it seriously.

Knowing when you ultimately wish to achieve your goal, allows you to think about how to hit milestones along the way, and what those milestones should look like. Buying an overpriced loft downtown might be the end result you hope for, but your first milestone could be fixing your credit, followed by accumulating a down-payment, and so on.

Don’t burn out

You may not even want to take vacations. As unfathomable as business is to sedentary people, it can be very addictive too. It isn’t selfish to schedule vacation time into your year, this is one of the opportunities you have to work around your family’s schedule as well, use your flexibility to your advantage. You don’t have to apply to HR for permission. If you’re single, pick off-season times to travel, late-january or early-november are awesome for that.

While you’re on vacation, it would be a great time to try to accomplish one of your dream goals. Spending a week in Hawaii is nice, but dammit there’s a volcano to climb too! Make a habit of reaching higher, doing more, accomplishing things no one else around you does; they’ll make great stories to tell to your 3 remaining friends.


Distill your working life down to it’s essence. You should be proud, to accept your skills, and knowledge, then accept that others aren’t even qualified to argue with you, as an expert. Being a specialist means you serve a function, that function isn’t personal, you are just the hammer, and the hand wielding the hammer.

Be flexible, with yourself and others

It may seem redundant, but flexibility can carry you through a lot of challenges. Thinking on your feet, and cleverly reorganizing your planner, will not only make you accessible to clients, but can prevent obstacles from settling into place. You just need to be careful, it’s very easy to lose control of your schedule, if you allow everything to change. It’s ok to push back gently, clients will generally understand. It is not a sign of strength to give in to their every whim, they won’t respect you if you do.

Try not to say NO to a client

Unbelievably, I’ve witnessed many contractors refuse work thrown at them, and I don’t mean work outside of their expertise, or work they would hate to do, just more of the same, for more money. Anyone serious about being self-employed, must be serious about making more money. Turning down jobs is antithetical to that.

If you’re in a trade, you will experience dry spells. There’s really no way to stop it, except by diversifying. Sometimes that means learning new tricks, or obtaining new licenses. Ideally, you want to place yourself before a client, where you can say YES, to any need that they have. If they promised you 10 jobs, and then offer you 2 more, you say YES.

Saying NO to a client is risky

If you are good at what you do, and you’ve trained your clients well, their first call should be your number. You want to be first in line, given first right of refusal. This is the key to maintaining long-term relationships with clients, this will help keep you fed during dry spells. However, they are also human, when you train them to call you, that means they expect you to do the work.

Also, you really don’t want to hear the same guilt trips that you heard from your friends, do you? So it’s probably best to avoid outright NOs. Too many refusals may also give the impression to the client that you just aren’t interested, which can quickly erase your preferred status in their contact list. If that happens, you should expect to fight against competing quotes next time.

Sometimes you have to negotiate your way out

So, if you plan to refuse any jobs thrown at you, you need to offer them alternatives first. Starting with alternate times. Frequently, clients will appear to demand a job be completed today, when it really isn’t even a priority to them, rather they happened to have the time to watch you work, or it’s just a lead-in to some other discussion they wish to have. Keep in mind, if they are a business owner, they like to get things done too, they don’t want lingering TODO list items anymore than you do.

If you can’t reschedule a job for any reason, for example repairing a broken camera system after a break-in at a jewelry store, dividing the job into two segments to tackle, could work for them. You know the priority is likely retrieving the video to hand to police, fixing the machine is secondary. Always discuss other approaches with them, they will appreciate that you are trying (not saying NO like those other assholes), and you can dictate what their choices are, giving scenarios that ultimately work for you.

In the end, you want to be in control, that’s what self-employment is all about. Whatever your job is, it all stems from controlling your activities, the people you spend time with, the jobs you do, the money you make. Control, not public relations. Being out of control leads to panic, panic leads to anger, and anger leads to unemployment. Your sanity could also come in handy at times.

Just as you need encouragement, so do others, offer it freely, and honestly. Everyone should pursue their goals and dreams, even the ones who forgot how to dream. Ignore those people who try to stop you, don’t listen while others throw dismissive comments at you, focus your attention on the few will step up to help. Negativity has no place in your head. Surrounding yourself with positive people, could make all the difference to staying determined.

Once you develop that thick skin, and really internalize your place in the world, it will feel like swimming in a kind of chunky soup. People aimlessly floating around in the currents, while you have a path. Your golden path, that’s leading you somewhere great. And, as tempting as it is, don’t allow passive-aggressive behaviour to influence your decisions, keep swimming.

You are the shark, not the fish, not anymore. And shark don’t sleep.

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