Ten Surprising Things I Learned While Running My Own Business

For eight years, I co-owned a successful Toronto PR agency.  At its peak, we had 13 employees and a nice portfolio of global brands and local start-ups.  I’m a freelancer now but I often draw upon the lessons I learned at the helm of a “real” enterprise.  Some of them might be interesting for you if you’re running a small business or thinking about it:

1. The business is always with you - A small business is like a child.  It’s just as demanding and it needs you 24-7.  It makes you work on your days off and puts a damper on your vacations.  It wakes you up early and whispers to you when you’re sleeping.  It's unpredictable and just when you think you've got it figured out, it hits you with the office equivalent of teething pain. 

2. Rules are not a bad thing - When you start, it's tempting to eschew boring, restrictive things like time sheets, office hours and signed contracts but eventually you will need them and they are a lot harder to introduce later on.  Take the time to develop processes for your office, your employees and your clients.  You won't alwyas look at them when things are good but you'll rely on them when relationships sour.

3. When you are responsible for someone's livelihood, you make decisions you wouldn't make as an independent - We all know when a client isn't a good fit or when it's time to turn down another low-paying account.  And when it's just you, you can do that.  But when people are relying on you to pay the bills, you will sometimes compromise to keep the cash flowing.

4. Management theorists are not always right - There is no shortage of business gurus peddling their books, preaching about swimming with sharks and getting out of your comfort zone.  The thing is, most of them aren't actually running a small business and some have never even worked in a corporate setting.  Read the books, stay abreast of the trends but remember, the concepts are theoretical.

5. You can't lead without a map - When finding clients is your main focus, it's easy to forget about business goals that aren't related to sales.  While you don't need a sophisticated vision/mission statement, you do need a plan for the kind of company you want to create.  If you don't have a roadmap for growing your business, someone else will grow it for you, and not necessarily in the way you envision.

6. You can't do everything - This is one of the toughest lessons for business owners to learn, especially in a consulting business where human capital is the equity.  The only way to expand is to hire other people, train them, trust them and let them sink or swim.  Yes, mistakes will be made but if you micromanage, you will never get out of the office. Note: I'm not sure I ever perfected this.

7. You won't believe the paperwork - Until you are big enough to pay someone to take care of your non-core business, you will be a CEO, HR director, accountant, procurement officer and sales director and you'll be up to your ears in tax forms, leasing agreements, photocopier rentals, paycheques,  invoices, IT upgrades, and, sadly, termination papers. 

8. Never count your chickens before they hatch - Nothing is confirmed until everyone signs on the dotted line.  People will accept job offers and then change their minds.  Potential clients will ask you to spend hours on a proposal only to decide they're going to handle things in-house.  And people will tell you the cheque is in the mail when it's still on their desk.  Be conservative in your projections.

9. Things move much slower than you anticipate - Occasionally you'll get a new client who needs you to start immediately, but more often, the sales cycle is glacially slow and there can be a few months from a first meeting to winning the business to working on the account to seeing that first cheque.

And most importantly...

10. If it doesn't feel right, it probably isn't right - You will know within a couple of months if something isn't working whether it's a project, a new employee or a new office process.  But no one wants to admit they made a mistake so you hold on and hope that things will change.  They rarely do and you end up having a tough conversation two years later than you should have.  Follow your instincts.  They're what got you where you are. 

Whatever happened to good old-fashioned shame?

I'm so embarrassed...

About fifteen years ago I had a job that was very important in terms of my career development.  I wasn't 100 per cent qualified according to the job description but my boss saw some hidden potential in me and took a chance on my future success.  He turned out to be a great leader and I have a tremendous amount of respect for this person and for his commitment to the role, which he still holds today.  I desperately wanted to impress him and to prove that hiring me was the right decision. But I wasn't perfect, and like everyone else, I screwed up from time to time.  When this happened, and especially if it was due to negligence, laziness or carelessness on my part, I was mortified, apologized for my role in the mix-up and asked what I could do to fix things.  Later, in the privacy of my own home, I would watch TV in bed, eat most of a medium pizza, down a bottle of wine and go to sleep feeling miserable. This was how I coped with the shame of letting down not only my boss but also myself. The next day I would clean myself up, dust myself off and start all over again, vowing never again to make the same mistake and keeping a somewhat low profile until I had "proven" myself again.  In this case, shame was a case of short-term pain, long-term gain.  It was a powerful motivator to be more aware, try harder and do better.

This kind of shame is not something I consciously set out to experience.  Thanks to a combination of innate personality and strict upbringing, I'm somewhat hardwired to feel shame when I screw up and even now, when I forget to bring the dessert to a family potluck or my kids tell their dentist that they don't floss regularly, I feel the heat of shame and embarrassment rise from my neck to my forehead.

Imagine my surprise then in my first management role when I learned that some people are not ashamed when they screw up and worse still, most are not even embarrassed.  One of the toughest things for a manager is the realization that what motivated you to succeed is not necessarily the same thing that will motivate one of your employees and in fact, you need to learn what motivates each person in order to properly lead them.  For some it's public recognition, for others its money or a new title and there are some people who will only work hard in exchange for something tangible like the privilege of working from home.  I can accept this but up until then, I had been labouring under the misconception that the concept of shame was universal and could always be relied upon to help people improve.

Not so. But the concept of screwing up is universal and no one is immune to it.  It's human and in the fast-paced environment of a PR agency, it's probably inevitable.  So, the first time I called someone on the carpet for a screw-up caused by their failure to properly proofread, double-check details or use sound judgement, I expected that they would be appropriately shamed, would deal with it in whatever way worked for them (not everyone has to eat an entire pizza after all) and come back the next day with a renewed passion for excellence.  But the person just smiled, shrugged her shoulders and said, "These things happen".  I was so ill-equipped for this response that I reacted with stunned silence followed by yelling, which was not my intention at all.  While some of the people I've worked with have shared my proclivity for actually being embarrassed by their gaffes, it seems that nowadays, most don't, or if they do, they don't show it in any discernible way.

Shame has fallen out of fashion in the past few decades.  A major tool in the disciplinary arsenal of my parents' generation, it has been cast aside for more modern, humane methods like talking it out, boosting self-esteem and putting the blame elsewhere. There was some method to this madness.  A couple of decades of psychoanalysis revealed that carrying around shameful reminders of childhood transgressions was having a serious impact on many adults' ability to live a fulfilling, guilt-free life.   John Bradshaw, author of the New York Times bestselling book, Healing the Shame that Binds You, explains that there are two kinds of shame - healthy shame and toxic shame.  Healthy shame is what helps us get along with other people, prevents us from going through life as a total narcissist and, used properly, can be a force for positive growth. We need a little of this in our lives.

Toxic shame, on the other hand is often guilt-based and makes us feel bad about how we look or feel, where we were born, how we were raised, our religion, or our sexuality. When the baby boomers ushered in the self-esteem movement, they were right to try to rid society of toxic shame.  Whether it's imposed by others or self-imposed, it has no useful function and indeed, paralyzes many sufferers well into adulthood. The problem is, in attempting to rid ourselves of the pain of toxic shame, we threw the baby out with the bathwater and ditched healthy shame at the same time.  The pendulum has swung too far and we're now living in an age of self-revelation where doing anything in public is acceptable.  Rather than take accountability for their actions, criminals blame their childhood, their stress level, the economy, Wall Street.  Fame-hungry reality stars compete in lewd and degrading competitions desperate to extend their 15 minutes of infamy.  Teenagers videotape themselves or others behaving badly and then share it on Facebook for all to see.

I think it's time to embrace a return to healthy shame for the good of society.  Just imagine, in a world where people are shamed for their embarrassing behaviour, there would be no Keeping Up With the Kardashians, no Wall Street banking tycoons still holding jobs, no people having loud inane cell phone conversations in public and no politicians emailing photos of their genitalia to interns.  This is something I can get behind.

Why You Need to Stop Being Late for Everything

While browsing at a small-town thrift store last week, something shiny caught my eye. Hanging on the wall behind the cash register, was a large, cartoonish costume that looked like a burlesque dancer, complete with a garish gold bikini and tassles on the nipples. It was crudely made - white fabric haphazardly stuffed, and an apron-like hook to go over the wearer's head. Sewed to the midriff was a paper sign that read: "I was late for work today".

I asked a staff member about it and she explained that if an employee is late for work, the store owner makes them wear it all day. "Does she really enforce it," I said? When the cashier nodded, I asked if she had ever had to wear it. "Only once," she said, "It was so embarrassing that I started to set my alarm 15 minutes earlier."

As I left the store, I did a small fist pump for the employer who had managed to teach her staff the importance of showing up on time in a way that actually worked but still had an element of fun.  Obviously this tactic lends itself to the atmosphere of a funky thrift shop and would probably be inappropriate in a law office or any other environment where the tardy employee would be meeting with clients.  But the notion that you could shame people into being on time was intriguing.


I have worked with, and employed, people who have been habitually late for work and meetings and while I have attempted to help them understand that their behaviour is disrespectful, disruptive and will decrease their opportunities for promotion, I have not been as successful as the thrift store owner.  


While some of the chronically tardy accept responsibility and are truly apologetic, most believe they are innocent victims of circumstance when in actual fact, being late is the result of many choices that are within their control.  They all have excuses and they're not even good ones: My husband takes a long time in the bathroom. I got caught up watching TV. I forgot I had no clean clothes. My mother called.  I was reviewing my stocks online. I like to eat breakfast slowly. I was having a great dream. It's snowing. 


Obviously I understand that in our fast-paced society, we are all late sometimes.  A kid's meltdown, unexpected road construction or a subway outage can derail event the most organized among us.  But occasional lateness is quite different from chronic tardiness characterized by a complete inability to arrive anywhere on time that is generally part of a lifelong pattern.  


Psychologists have difficulty pinpointing if always-late people are deliberately disrespectful or if they are actually unable to estimate time.  Those of us who generally arrive on time go through a mental process when we are faced with a deadline.  We determine the number of minutes between where we are now and where we need to be and develop a work-back schedule that includes an inventory of everything we need and/or want to do in the ensuing time.  Using past experience, we note how long it will take to complete each thing and if it's obvious we don't have enough time for everything, we eliminate things from the list or do things less "perfectly" than we would like.  As the time ticks down, we check the clock frequently, don't start things we can't finish and look for efficiencies along the way. We may repeat this process several times as we navigate our day.  


Unsurprisingly, people who are always late, don't activate this process and no one can say with certainty whether it's deliberate or innate.  They really believe they can sleep another fifteen minutes, watch ten more minutes of TV or stop at that trendy coffee shop with the huge lineup.  Despite the fact that it has taken them 20 minutes to style their hair every day for the past ten years, they will allot 15 minutes today, thinking they will somehow defy gravity and do it faster.   

Diana Delonzor, author of Never Be Late Again: 7 Cures for the Punctually Challenged, is a reformed late person who retrained herself and now helps others.  Delonzor says that being chronically late goes well beyond poor time management and different people have different reasons, although they're not always conscious.  Some use it as a form of control and rebellion against authority, others lack the willpower and discipline to follow through on actions.  Some people just have an 'absent-minded professor' personality and are always getting lost in their thoughts and activities. She says that being ten minutes late for work everyday for a year amounts to one week's paid vacation.


So are they just irresponsible or do they suffer from an inherent lack of self-discipline?  Well, if they're looking for an office job, it doesn't really matter.  In order for a workplace (and society in general) to function, we need some kind of order and one of the simplest ways to maintain that is to organize our time.  While DeLonzor is proof that a habitually late person can be reformed, it's very hard to change lifelong patterns and once you have the reputation for being unreliable, you can lose friends, get skipped over for promotions and even get fired.


None of us has the luxury of a job that only calls on us to do things we find easy and conveniently overlooks our weaknesses.  For some, tardiness is a weakness, for others it might be teamwork or providing feedback.  We all have to work at overcoming the stuff that just doesn't come naturally.  If you're unable or unwilling to do that, then you're probably sentenced to a life of working on your own, which is not necessarily a bad thing but even then, you will not be able to avoid the odd meeting, wedding or dinner with friends.

Weigh the options before you pull a Johnny Paycheck

Take this Job and Shove It...If you're over 40, you probably remember that old Johhny Paycheck song. It's a sad tale about a man who worked long and hard for no reward. It struck such a chord with disgruntled workers in America, that it spent 18 weeks at Number 1, was the basis for a movie of the same name and has become an anthem for overworked and under-appreciated employees everywhere.

I found myself humming this song as I read about Kai Nagata, a 24-year-old CTV correspondent who became so disillusioned with what he termed the "Barbie and Ken" style of TV news that he felt he had no choice but to resign. But he didn't just hand in his letter, eat his farewell cake, clear his desk and leave. Instead, he chose to vent his frustration in a 3,000-word missive about everything that's wrong with the business. The essay went on to receive widespread attention from journalists across Canada and was even lauded by Roger Ebert.

Before I go any further, let me say that his parting words, admittedly well-written, are much more eloquent than the words in the Johnny Paycheck song and he makes some valid points. Among other claims, Nagata bemoans the "unspoken ratio of talent to attractiveness" and the focus on the recent royal visit when "there was real news happening". And, in a world where few people act with integrity, I admire his decision not only to resign from a position which doesn't align with his personal values but also to have the courage to outline the reason for his departure in so candid a manner.

From a business etiquette viewpoint however, I don't believe it's a good idea to burn your bridges so spectacularly at such a young age. I'm not totally against the burning of bridges and I've torched a few myself but in each case, I weighed the pros and cons of the consequences and really asked myself if my discomfort, dislike or disgust of the person or organization was so great that I was comfortable knowing I could never count on them for support again On the few cases, I decided to burn a bridge, I shared my opinions freely but only with my direct supervisor, in person and in private and without any desire to gain fame or notoriety from it.

Although he may be one of the few to act on his impulses, Nagata is simply the latest in a long line of young people (myself included) who have chosen a profession, studied it and dreamed of all the wonderful things we would do with it, only to find out that, once we were finally working in our chosen field, it didn't live up to our expectations. This is a huge disappointment for an idealistic young person and sadly, remains a source of frustration for many people who have been toiling away for decades.

We are all tested in the workplace and we all face times when we have to decide whether or not we should continue working at a job which has become unpleasant, that is, assuming we have the freedom to do so. If such freedom exists then we need to establish our personal threshold for frustration. How important it is that the way we pay our bills match our personal values, that the role we have is the one we signed up for, that the business operations of our employer match the values on its mission statement, that we feel comfortable with the state of the industry in which we toil?

And if it's unbearable, then we leave, and etiquette dictates that we do it in as gracious a manner as possible, not only because it's the professional thing to do, but also because it's a small world and we need all the friends we can get.

I'm not sure how the future will unfold for this young man. Perhaps the infamy he has achieved from his farewell letter will catapult him to a much more rewarding position and his risk will have been well worth it. But he's very young and has a lot of working years left. Let's hope he never has to ask his former employers for a reference.

Have you ever told someone to "take this job and shove it?" I'd love to hear about it.