10 surprising lessons from entrepreneurship

For eight years, I co-owned a successful Toronto PR agency.  At its peak, we had 13 employees and a nice portfolio comprising global brands and local start-ups.  I’m now a full-time employee and an occasional freelancer 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 doesn’t care if you had too much wine the night before or if you are already exhausted from taking care of other children. 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 your agency, it’s tempting to eschew boring, restrictive things like time sheets, office hours and signed contracts. But, if you’re successful, you will eventually need them and they are much harder to introduce later on.  Take the time to develop processes for your office, your employees, sub-contractors and clients.  You won’t always look at them when things are good but you’ll rely on them if 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 yet another low-paying account.  And when you’re a sole practitioner, you have the freedom to make these decisions.  But when you have employees relying on you for their livelihood, you will sometimes compromise to keep the cash flowing and avoid unpleasant discussions or even layoffs.
4. Management theorists are not always right – There is no shortage of business gurus peddling their books, preaching about swimming with sharks and telling you to get of your comfort zone.  The thing is, most of them aren’t actually running a business and some are academics who have never even worked in a corporate setting.  By all means, read the books and stay abreast of the trends but remember, the concepts are theoretical. You know what’s best for your business. Even Sheryl Sandberg has now admitted she was wrong about some parts of her much-touted book, Lean in.
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 build.  If you don’t have a road map for growing your business, someone else (usually a client) 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 wear many hats – CEO, HR director, accountant, procurement officer, community manager, 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 a purchase order has been issued and even then, it could be months before you see a penny.  Potential employees will accept your job offer and then change their minds.  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 and never confuse a memo with reality.
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 glacial and there can be a few months from a first meeting to winning the business to working on the account to seeing that first payment.  To quote Alec Baldwin in Glengarry Glen Ross, “always be closing”.
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 have to.  Never be afraid to follow your instincts.  They’re what got you where you are.

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